CUMULUS MEDIA INC
S-3/A, 1999-11-17
RADIO BROADCASTING STATIONS
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<PAGE>   1


   AS FILED WITH THE SECURITIES AND EXCHANGE COMMISSION ON NOVEMBER 17, 1999.

                                            REGISTRATION STATEMENT NO. 333-89825
- --------------------------------------------------------------------------------
- --------------------------------------------------------------------------------
                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549
                      ------------------------------------

                                   AMENDMENT

                                    NO. 2 TO

                                    Form S-3
                             REGISTRATION STATEMENT
                                   UNDER THE
                             SECURITIES ACT OF 1933
                      ------------------------------------
                               CUMULUS MEDIA INC.
             (Exact name of Registrant as specified in its charter)

<TABLE>
<S>                                     <C>                                     <C>
              ILLINOIS                                  4832                                 36-4159663
  (State or Other Jurisdiction of           (Primary Standard Industrial                  (I.R.S. Employer
   Incorporation or Organization)           Classification Code Number)                 Identification No.)
</TABLE>

   111 EAST KILBOURN AVENUE, SUITE 2700, MILWAUKEE, WI 53202, (414) 615-2800
   (Address, Including Zip Code and Telephone Number, Including Area Code, of
                   Registrant's Principal Executive Offices)

                      ------------------------------------
                     RICHARD W. WEENING, EXECUTIVE CHAIRMAN
                 LEWIS W. DICKEY, JR., EXECUTIVE VICE CHAIRMAN
                               CUMULUS MEDIA INC.
                      111 EAST KILBOURN AVENUE, SUITE 2700
                              MILWAUKEE, WI 53202
                                 (414) 615-2800
 (Name, address, including zip code, and telephone number, including area code,
                             of agent for service)
                                   COPIES TO:

<TABLE>
<S>                                                       <C>
               WILLIAM F. SCHWITTER, ESQ.                                GEORGE R. KROUSE, JR., ESQ.
          PAUL, HASTINGS, JANOFSKY & WALKER LLP                          SIMPSON THACHER & BARTLETT
                     399 PARK AVENUE                                        425 LEXINGTON AVENUE
                NEW YORK, NEW YORK 10022                                  NEW YORK, NEW YORK 10017
                     (212) 318-6000                                            (212) 455-2000
</TABLE>

                      ------------------------------------
    Approximate date of proposed sale to the public: As soon as practicable
after this Registration Statement becomes effective.
    If the only securities being registered on this Form are being offered
pursuant to dividend or interest reinvestment plans, please check the following
box. [ ]
    If any of the securities being registered on this Form are to be offered on
a delayed or continuous basis pursuant to Rule 415 under the Securities Act of
1933, other than securities offered only in connection with dividend or interest
reinvestment plans, check the following box. [ ]
    If this Form is filed to register additional securities for an offering
pursuant to Rule 462(b) under the Securities Act, please check the following box
and list the Securities Act registration statement number of the earlier
effective registration statement for the same offering. [ ]
    If this Form is a post-effective amendment filed pursuant to Rule 462(c)
under the Securities Act, check the following box and list the Securities Act
registration statement number of the earlier effective registration statement
for the same offering. [ ]
    If delivery of the prospectus is expected to be made pursuant to Rule 434,
please check the following box. [ ]

                      ------------------------------------
                        CALCULATION OF REGISTRATION FEE


<TABLE>
<CAPTION>
- -----------------------------------------------------------------------------------------------------------------------------
                                                            PROPOSED MAXIMUM       PROPOSED MAXIMUM          AMOUNT OF
                                        AMOUNT TO            OFFERING PRICE       AGGREGATE OFFERING        REGISTRATION
TITLE OF SHARES TO BE REGISTERED      BE REGISTERED          PER SHARE (1)            PRICE (1)                 FEE
- -----------------------------------------------------------------------------------------------------------------------------
<S>                               <C>                    <C>                    <C>                    <C>
  Class A common stock, par
value $0.01 per share.........     4,600,000 shares (2)         $36,375              $167,325,000           $46,517 (3)
- -----------------------------------------------------------------------------------------------------------------------------
</TABLE>


(1) Estimated solely for the purpose of calculating the registration fee
    pursuant to Rule 457.
(2) Includes 600,000 shares issuable upon exercise of the Underwriters'
    over-allotment option.

(3) $43,399 of the registration fee was previously paid in connection with the
    Company's filings on October 28, 1999 and November 4, 1999.


    THE REGISTRANT HEREBY AMENDS THIS REGISTRATION STATEMENT ON SUCH DATE OR
DATES AS MAY BE NECESSARY TO DELAY ITS EFFECTIVE DATE UNTIL THE REGISTRANT SHALL
FILE A FURTHER AMENDMENT WHICH SPECIFICALLY STATES THAT THIS REGISTRATION
STATEMENT SHALL THEREAFTER BECOME EFFECTIVE IN ACCORDANCE WITH SECTION 8(A) OF
THE SECURITIES ACT OF 1933 OR UNTIL THIS REGISTRATION STATEMENT SHALL BECOME
EFFECTIVE ON SUCH DATE AS THE COMMISSION, ACTING PURSUANT TO SAID SECTION 8(A),
MAY DETERMINE.
- --------------------------------------------------------------------------------
- --------------------------------------------------------------------------------
<PAGE>   2

                PART II. INFORMATION NOT REQUIRED IN PROSPECTUS

ITEM 14. OTHER EXPENSES OF ISSUANCE AND DISTRIBUTION.

     The expenses in connection with the distribution of the securities being
registered are set forth in the following table (all amounts except the
registration fee, the NASD fee and the Nasdaq National Market fee are
estimated):


<TABLE>
<S>                                                             <C>
Registration fee............................................    $   46,517
NASD fee....................................................        15,680
Nasdaq National Market fee..................................        17,500
Printing expenses...........................................       150,000
Legal fees and expenses.....................................       250,000
Accounting fees and expenses................................       250,000
Blue sky fees and expenses (including attorneys' fees)......        50,000
Transfer agent fee..........................................        25,000
Miscellaneous...............................................       447,500
                                                                ----------
       TOTAL................................................    $1,252,197
                                                                ==========
</TABLE>


- ------------
* To be completed by amendment.

     All expenses in connection with the issuance and distribution of the Class
A common stock being offered will be borne by the Company (other than selling
commissions).

ITEM 15. INDEMNIFICATION OF DIRECTORS AND OFFICERS.

     The Company maintains officers' and directors' liability insurance which
will insure against liabilities that officers and directors of the Company may
incur in such capacities. The Company has also entered into indemnification
agreements with its directors and officers.

     Reference is made to the Proposed Form of Underwriting Agreement filed as
Exhibit 1.1 which provides for indemnification of the directors and officers of
the Company signing the Registration Statement and certain controlling persons
of the Company against certain liabilities, including those arising under the
Securities Act in certain instances, of the Underwriters.

ITEM 16. EXHIBITS.

     There are filed with the Registration Statement the following exhibits:


<TABLE>
<CAPTION>
EXHIBIT NO.                          DESCRIPTION
- -----------                          -----------
<S>          <C>
1.1**        Form of Underwriting Agreement between the Registrant and
             the Underwriters.
2.1*         Asset Purchase Agreement and Plan of Reorganization by and
             between Cumulus Media Inc., Broadcast Software International
             Inc. and Ron Burley, dated as of September 15, 1999.
2.2*         Option Agreement by and between Cumulus Broadcasting
             Company, Inc., Cumulus Licensing Corp., Cumulus Wireless
             Services Inc. and Green Bay Broadcasting Company, Inc.,
             dated as of September 15, 1999.
2.3****      Asset Purchase Agreement by and between Cumulus
             Broadcasting, Inc., Cumulus Licensing Corp., Cumulus
             Wireless Services Inc., C.F. Radio, Inc., Cape Fear Radio,
             LLC, Cape Fear Broadcasting Company and Cape Fear Tower
             Systems, LLC dated as of September 23, 1999.
2.4****      Asset Purchase Agreement dated as of April 2, 1999, by and
             between Cumulus Broadcasting, Cumulus Licensing, Cumulus
             Wireless and Phillips Broadcasting Company, Inc.
</TABLE>


                                      II-1
<PAGE>   3


<TABLE>
<CAPTION>
EXHIBIT NO.                          DESCRIPTION
- -----------                          -----------
<S>          <C>
2.5****      Asset Purchase Agreement dated as of March 9, 1999 by and
             between Cumulus Broadcasting, Cumulus Licensing, Cumulus
             Wireless, HMH Broadcasting Inc., a Kentucky corporation and
             HMH Realty, LLC.
2.6****      Stock Purchase Agreement dated June 15, 1999, among the
             Company and M&F Calendar Holdings, L.P., Kevin C. Whitman,
             nassau Capital Partners L.P., NAS Partners I L.L.C., and
             Philip J. Giordano.
2.7****      Asset Purchase Agreement dated as of June 29, 1999, by and
             among Cumulus Broadcasting, Cumulus Licensing and Coast
             Radio, L.L.C., a Florida limited liability company.
4.1***       Form of Certificate of Designation with respect to Series A
             Cumulative Exchangeable Redeemable Preferred Stock due 2009.
4.2***       Form of Exchange Debenture Indenture between Cumulus Media
             Inc. and U.S. Bank Trust National Association, as Trustee.
4.3***       Form of Indenture between Cumulus Media Inc. and Firstar
             Bank of Minnesota, N.A., as Trustee.
5.1**        Opinion of Holleb & Coff as to the validity of the Class A
             common stock.
10.1*        Amended and Restated Credit Agreement among Cumulus Media
             Inc., Lehman Brothers Inc., Barclays Capital and Lehman
             Commercial Paper.
10.2*        Cumulus Media Inc. 1999 Employee Stock Incentive Plan.
10.3*        Cumulus Media Inc. 1999 Executive Stock Incentive Plan.
21.1*        Subsidiaries of Cumulus Media Inc.
23.1*        Consent of PricewaterhouseCoopers LLP.
23.2**       Consent of Holleb & Coff (included in Exhibit 5.1).
23.3*        Consent of Wipfli Ullrich Bertelson LLP.
23.4*        Consent of KPMG LLP.
24.1*        Powers of Attorney, included on page II-4.
</TABLE>


- ------------
*      Previously filed.


**     Filed herewith.



***   Incorporated by reference to our Registration Statement on Form S-1
      (Registration Statement No. 333-48849) declared effective on June 26,
      1998.



****  Incorporated by reference to our Current Report on Form 8-K filed with SEC
      on November 3, 1999.


ITEM 17. UNDERTAKINGS.

(a) The undersigned registrant hereby undertakes:

          (1) To file, during any period in which offers or sales are being
     made, a post-effective amendment to this registration statement:

             (i) To include any prospectus required by Section 10(a)(3) of the
        Securities Act of 1933;

             (ii) To reflect in the prospectus any acts or events arising after
        the effective date of the registration statement (or the most recent
        post-effective amendment thereof) which, individually or in the
        aggregate, represent a fundamental change in the information set forth
        in the registration statement. Notwithstanding the foregoing, any
        increase or decrease in volume of securities offered (if the total
        dollar value of securities offered would not exceed that which was
        registered) and any deviation from the low or high end of the estimated
        offering range may be reflected in the form of prospectus filed with the
        Commission pursuant to Rule 424(b) if, in the aggregate, the changes in

                                      II-2
<PAGE>   4

        volume and price represent no more than a 20% change in the maximum
        aggregate offering price set forth in the "Calculation of Registration
        Fee" table in the effective registration statement; and

             (iii) To include any material information with respect to the plan
        of distribution not previously disclosed in the registration statement
        or any material change to such information in the registration
        statement;

       provided, however, that paragraphs (a)(1)(i) and (a)(1)(ii) herein do not
       apply if the Registration Statement is on Form S-3 or Form S-8, and the
       information required to be included in a post-effective amendment by
       those paragraphs is contained in periodic reports filed with or furnished
       to the Commission by the registrant pursuant to Section 13 or Section
       15(d) of the Securities Exchange Act of 1934 that are incorporated by
       reference in this registration statement;

          (2) That, for the purpose of determining any liability under the
     Securities Act, each such post-effective amendment shall be deemed to be a
     new registration statement relating to the securities offered therein, and
     the offering of such securities at that time shall be deemed to be the
     initial bona fide offering thereof; and

          (3) To remove from registration by means of a post-effective amendment
     any of the securities being registered which remain unsold at the
     termination of the offering.

             (a) The undersigned registrant hereby undertakes that, for purposes
        of determining any liability under the Securities Act of 1933, each
        filing of the registrant's annual report pursuant to Section 13(a) or
        15(d) of the Securities Exchange Act of 1934 (and, where applicable,
        each filing of an employee benefit plan's annual report pursuant to
        Section 15(d) of the Securities Exchange Act of 1934) that is
        incorporated by reference in the Registration Statement shall be deemed
        to be a new registration statement relating to the securities offered
        therein, and the offering of such securities at that time shall be
        deemed to be the initial bona fide offering thereof.

             (b) Insofar as indemnification for liabilities arising under the
        Securities Act of 1933, as amended, may be permitted to directors,
        officers and controlling persons of the registrant pursuant to the
        foregoing provisions, or otherwise, the registrant has been advised that
        in the opinion of the Securities and Exchange Commission such
        indemnification is against public policy as expressed in the Securities
        Act of 1933, as amended, and is, therefore, unenforceable. In the event
        that a claim for indemnification against such liabilities (other than
        the payment by the registrant of expenses incurred or paid by a
        director, officer or controlling person of the registrant in the
        successful defense of any action, suit or proceeding) is asserted by
        such director, officer or controlling person in connection with the
        securities being registered, the registrant will, unless in the opinion
        of its counsel the matter has been settled by controlling precedent,
        submit to a court of appropriate jurisdiction the question whether such
        indemnification by it is against public policy as expressed in the
        Securities Act of 1933, as amended, and will be governed by the final
        adjudication of such issue.

             (c) The undersigned registrant hereby undertakes to file an
        application for the purpose of determining eligibility of the trustee to
        act under subsection (a) of Section 310 of the Trust Indenture Act in
        accordance with the rules and regulations prescribed by the Securities
        and Exchange Commission under Section 305(b)(2) of the Trust Indenture
        Act.

                                      II-3
<PAGE>   5

                                   SIGNATURES


     Pursuant to the requirements of the Securities Act of 1933, the registrant
has duly caused Amendment No. 1 to the Registration Statement to be signed on
its behalf by the undersigned, thereunto duly authorized, in the City of New
York, State of New York, on November 17, 1999.


                                          CUMULUS MEDIA INC.

                                          By:    /s/ RICHARD W. WEENING
                                            ------------------------------------

                                            Richard W. Weening
                                            Executive Chairman

     Pursuant to the requirements of the Securities Act of 1933, as amended,
this Registration Statement has been signed by the following persons in the
capacities and on the dates indicated.


<TABLE>
<CAPTION>
                  SIGNATURE                                 CAPACITY                      DATE
                  ---------                                 --------                      ----
<S>                                            <C>                                  <C>
           /s/ RICHARD W. WEENING              Executive Chairman, Treasurer and    November 17, 1999
- ---------------------------------------------  Director (Principal Executive
             Richard W. Weening                Officer)

           /s/ RICHARD W. WEENING              Executive Vice Chairman and          November 17, 1999
- ---------------------------------------------  Director
Lewis W. Dickey, Jr., by Richard W. Weening,
              Attorney-in-Fact

           /s/ RICHARD W. WEENING              President and Director               November 17, 1999
- ---------------------------------------------
William M. Bungeroth, by Richard W. Weening,
              Attorney-in-Fact

           /s/ RICHARD W. WEENING              Vice President and Chief Financial   November 17, 1999
- ---------------------------------------------  Officer (Principal Accounting
  Richard J. Bonick, by Richard W. Weening,    Officer)
              Attorney-in-Fact

                                               Director                             November   , 1999
- ---------------------------------------------
Ralph B. Everett

           /s/ RICHARD W. WEENING              Director                             November 17, 1999
- ---------------------------------------------
   Robert H. Sheridan, III, by Richard W.
          Weening, Attorney-in-Fact

                                               Director                             November   , 1999
- ---------------------------------------------
Eric P. Robison
</TABLE>


                                      II-4
<PAGE>   6

                                 EXHIBIT INDEX


<TABLE>
<CAPTION>
EXHIBIT NO.  DESCRIPTION
- -----------  -----------
<C>          <S>
  1.1**      Form of Underwriting Agreement between the Registrant and
             the Underwriters.
  2.1*       Asset Purchase Agreement and Plan of Reorganization by and
             between Cumulus Media Inc., Broadcast Software International
             Inc. and Ron Burley, dated as of September 15, 1999.
  2.2*       Option Agreement by and between Cumulus Broadcasting
             Company, Inc., Cumulus Licensing Corp., Cumulus Wireless
             Services Inc. and Green Bay Broadcasting Company, Inc.,
             dated as of September 15, 1999.
  2.3****    Asset Purchase Agreement by and between Cumulus
             Broadcasting, Inc., Cumulus Licensing Corp., Cumulus
             Wireless Services Inc., C.F. Radio, Inc., Cape Fear Radio,
             LLC, Cape Fear Broadcasting Company and Cape Fear Tower
             Systems, LLC dated as of September 23, 1999.
  2.4****    Asset Purchase Agreement dated as of April 2, 1999, by and
             between Cumulus Broadcasting, Cumulus Licensing, Cumulus
             Wireless and Phillips Broadcasting Company, Inc.
  2.5****    Asset Purchase Agreement dated as of March 9, 1999 by and
             between Cumulus Broadcasting, Cumulus Licensing, Cumulus
             Wireless, HMH Broadcasting Inc., a Kentucky corporation and
             HMH Realty, LLC.
  2.6****    Stock Purchase Agreement dated June 15, 1999, among the
             Company and M&F Calendar Holdings, L.P., Kevin C. Whitman,
             nassau Capital Partners L.P., NAS Partners I L.L.C., and
             Philip J. Giordano.
  2.7****    Asset Purchase Agreement dated as of June 29, 1999, by and
             among Cumulus Broadcasting, Cumulus Licensing and Coast
             Radio, L.L.C., a Florida limited liability company.
  4.1***     Form of Certificate of Designation with respect to Series A
             Cumulative Exchangeable Redeemable Preferred Stock due 2009.
  4.2***     Form of Exchange Debenture Indenture between Cumulus Media
             Inc. and U.S. Bank Trust National Association, as Trustee.
  4.3***     Form of Indenture between Cumulus Media Inc. and Firstar
             Bank of Minnesota, N.A., as Trustee.
  5.1**      Opinion of Holleb & Coff as to the validity of the Class A
             common stock.
 10.1*       Amended and Restated Credit Agreement among Cumulus Media
             Inc., Lehman Brothers Inc., Barclays Capital and Lehman
             Commercial Paper.
 10.2*       Cumulus Media Inc. 1999 Employee Stock Incentive Plan.
 10.3*       Cumulus Media Inc. 1999 Executive Stock Incentive Plan.
 21.1*       Subsidiaries of Cumulus Media Inc.
 23.1*       Consent of PricewaterhouseCoopers LLP.
 23.2**      Consent of Holleb & Coff (included in Exhibit 5.1).
 23.3*       Consent of Wipfli Ullrich Bertelson LLP.
 23.4*       Consent of KPMG LLP.
 24.1*       Powers of Attorney, included on page II-4.
</TABLE>


- ---------------

*      Previously filed.

**     Filed herewith.


***   Incorporated by reference to our Registration Statement on Form S-1
      (Registration Statement No. 333-48849) declared effective on June 26,
      1998.



****  Incorporated by reference to our Current Report on Form 8-K filed with the
      SEC on November 3, 1999.


<PAGE>   1
                                                        EXHIBIT 1.1



                                4,000,000 SHARES

                               CUMULUS MEDIA INC.

                 CLASS A COMMON STOCK, PAR VALUE $.01 PER SHARE








                             UNDERWRITING AGREEMENT



November __, 1999


<PAGE>   2



                                                           November __, 1999



Morgan Stanley & Co. Incorporated
Bear, Stearns & Co. Inc.
Goldman, Sachs & Co.
Prudential Securities Incorporated
Lehman Brothers Inc.
Banc of America Securities LLC,
as Representatives of the several Underwriters,
c/o Morgan Stanley & Co. Incorporated
    1585 Broadway
    New York, New York  10036

Dear Sirs and Mesdames:

         Cumulus Media Inc., an Illinois corporation (the "COMPANY"), proposes
to issue and sell to the several Underwriters named in Schedule II hereto (the
"UNDERWRITERS"), and certain shareholders of the Company (the "SELLING
SHAREHOLDERS") named in Schedule I hereto severally propose to sell to the
several Underwriters, an aggregate of 4,000,000 shares of the Class A Common
Stock, par value $.01 per share, of the Company (the "FIRM SHARES"), of which
3,000,000 shares are to be issued and sold by the Company and 1,000,000 shares
are to be sold by the Selling Shareholders, each Selling Shareholder selling
the amount set forth opposite such Selling Shareholder's name in Schedule I
hereto. Morgan Stanley & Co. Incorporated, Bear, Stearns & Co. Inc., Goldman,
Sachs & Co., Prudential Securities Incorporated, Lehman Brothers Inc. and Banc
of America Securities LLC shall act as representatives (the "REPRESENTATIVES")
of the several Underwriters.

         The Company also proposes to issue and sell to the several
Underwriters, and the Selling Shareholders severally propose to sell to the
several Underwriters not more than an additional 600,000 shares of the Class A
Common Stock, par value $.01 per share, of the Company (the "ADDITIONAL
SHARES"), of which 300,000 shares are to be issued and sold by the Company and
150,000 shares are to be sold by each of the Selling Shareholders if and to the
extent that the Representatives shall have determined to exercise, on behalf of
the Underwriters, the right to purchase such shares of common stock granted to
the Underwriters in Section 3 hereof. The Firm Shares and the Additional Shares
are hereinafter collectively referred to as the "SHARES". The shares of Class A
Common Stock, par value $.01 per



<PAGE>   3



share, of the Company to be outstanding after giving effect to the sales
contemplated hereby are hereinafter referred to as the "COMMON STOCK". The
Company and the Selling Shareholders are hereinafter sometimes collectively
referred to as the "SELLERS".

         The Company has filed with the Securities and Exchange Commission (the
"COMMISSION") a registration statement, including a prospectus, relating to the
Shares. The registration statement as amended at the time it becomes effective,
including the information (if any) deemed to be part of the registration
statement at the time of effectiveness pursuant to Rule 430A under the
Securities Act of 1933, as amended (the "SECURITIES ACT"), is hereinafter
referred to as the "REGISTRATION STATEMENT"; the prospectus in the form first
used to confirm sales of Shares is hereinafter referred to as the "PROSPECTUS".
If the Company has filed an abbreviated registration statement to register
additional shares of Common Stock pursuant to Rule 462(b) under the Securities
Act (the "RULE 462 REGISTRATION STATEMENT"), then any reference herein to the
term "Registration Statement" shall be deemed to include such Rule 462
Registration Statement.

         1.       Representations and Warranties.  The Company represents and
warrants to and agrees with each of the Underwriters and each of the Selling
Shareholders that:

         a.    The Registration Statement has become effective; no stop order
    suspending the effectiveness of the Registration Statement is in effect,
    and no proceedings for such purpose are pending before or threatened by the
    Commission.

         b.    (i) The Registration Statement, when it became effective, did
    not contain and, as amended or supplemented, if applicable, will not
    contain any untrue statement of a material fact or omit to state a material
    fact required to be stated therein or necessary to make the statements
    therein not misleading, (ii) the Registration Statement and the Prospectus
    conform and, as amended or supplemented, if applicable, will conform in all
    material respects to the requirements of the Securities Act and the
    applicable rules and regulations of the Commission thereunder and (iii) the
    Prospectus does not contain and, as amended or supplemented, if applicable,
    will not contain any untrue statement of a material fact or omit to state a
    material fact necessary to make the statements therein, in the light of the
    circumstances under which they were made, not misleading,

<PAGE>   4


    except that the representations and warranties set forth in this paragraph
    do not apply to statements or omissions in the Registration Statement or
    the Prospectus based upon information relating to any Underwriter or
    Selling Shareholder furnished to the Company in writing by such Underwriter
    through the Representatives or by or on behalf of such Selling Shareholder
    expressly for use therein.

         c.    The Company has been duly incorporated, is validly existing as a
    corporation in good standing under the laws of the jurisdiction of its
    incorporation, has the corporate power and authority to own its property
    and to conduct its business as described in the Prospectus and is duly
    qualified to transact business and is in good standing in each jurisdiction
    in which the conduct of its business or its ownership or leasing of
    property requires such qualification, except to the extent that the failure
    to be so qualified or be in good standing would not have a material adverse
    effect on the Company and its subsidiaries, taken as a whole.

         d.    Each subsidiary of the Company has been duly incorporated, is
    validly existing as a corporation in good standing under the laws of the
    jurisdiction of its incorporation, has the corporate power and authority to
    own its property and to conduct its business as described in the Prospectus
    and is duly qualified to transact business and is in good standing in each
    jurisdiction in which the conduct of its business or its ownership or
    leasing of property requires such qualification, except to the extent that
    the failure to be so qualified or be in good standing would not have a
    material adverse effect on the Company and its subsidiaries, taken as a
    whole; all of the issued shares of capital stock of each subsidiary of the
    Company have been duly and validly authorized and issued, are fully paid
    and non-assessable and are owned directly by the Company, free and clear of
    all liens, encumbrances, equities or claims.

         e.    This Agreement has been duly authorized, executed and delivered
    by the Company.

         f.    The authorized capital stock of the Company conforms as to legal
    matters to the description thereof contained in the Prospectus.

         g.    The shares of Common Stock outstanding prior to the


<PAGE>   5


    issuance of the Shares have been duly authorized and are validly issued,
    fully paid and non-assessable.

         h.    The Shares have been duly authorized and, when issued and
    delivered in accordance with the terms of this Agreement, will be validly
    issued, fully paid and non-assessable, and the issuance of such Shares will
    not be subject to any preemptive or similar rights.

         i.    The execution and delivery by the Company of, and the
    performance by the Company of its obligations under, this Agreement will
    not contravene any provision of applicable law or the certificate of
    incorporation or by-laws of the Company or any agreement or other
    instrument binding upon the Company or any of its subsidiaries that is
    material to the Company and its subsidiaries, taken as a whole, or any
    judgment, order or decree of any governmental body, agency or court having
    jurisdiction over the Company or any subsidiary, and no consent, approval,
    authorization or order of, or qualification with, any governmental body or
    agency is required for the performance by the Company of its obligations
    under this Agreement, except for the registration of the Shares under the
    Securities Act and as may be required by the securities or Blue Sky laws of
    the various states or foreign securities laws in connection with the offer
    and sale of the Shares.

         j.    There has not occurred any material adverse change, or any
    development involving a prospective material adverse change, in the
    condition, financial or otherwise, or in the earnings, business or
    operations of the Company and its subsidiaries, taken as a whole, from that
    set forth in the Prospectus (exclusive of any amendments or supplements
    thereto subsequent to the date of this Agreement).

         k.    There are no legal or governmental proceedings pending or, to
    the best knowledge of the Company, threatened to which the Company or any
    of its subsidiaries is a party or to which any of the properties of the
    Company or any of its subsidiaries is subject which, if determined
    adversely to the Company or any of its subsidiaries, might have a material
    adverse effect on the consolidated financial position, stockholders'
    equity, results of operations, business or prospects of the Company and its
    subsidiaries.

         l.    Each preliminary prospectus filed as part of the Registration
    Statement as originally filed or as part of any amendment thereto, or filed
    pursuant to Rule 424 under the



<PAGE>   6


    Securities Act, complied when so filed in all material respects with the
    Securities Act and the applicable rules and regulations of the Commission
    thereunder.

         m.    Each of the Company and its subsidiaries is not and, after
    giving effect to the offering and sale of the Shares and the application of
    the proceeds thereof as described in the Prospectus, will not be an
    "investment company" as such term is defined in the Investment Company Act
    of 1940, as amended, and the rules and regulations of the Commission
    thereunder.

         n.    The Company and its subsidiaries (i) are in compliance with any
    and all applicable foreign, federal, state and local laws and regulations
    relating to the protection of human health and safety, the environment or
    hazardous or toxic substances or wastes, pollutants or contaminants
    ("ENVIRONMENTAL LAWS"), (ii) have received all permits, licenses or other
    approvals required of them under applicable Environmental Laws to conduct
    their respective businesses and (iii) are in compliance with all terms and
    conditions of any such permit, license or approval, except where such
    noncompliance with Environmental Laws, failure to receive required permits,
    licenses or other approvals or failure to comply with the terms and
    conditions of such permits, licenses or approvals would not, singly or in
    the aggregate, have a material adverse effect on the Company and its
    subsidiaries, taken as a whole.

         o.    There are no costs or liabilities associated with Environmental
    Laws (including, without limitation, any capital or operating expenditures
    required for clean-up, closure of properties or compliance with
    Environmental Laws or any permit, license or approval, any related
    constraints on operating activities and any potential liabilities to third
    parties) which would, singly or in the aggregate, have a material adverse
    effect on the Company and its subsidiaries, taken as a whole.

         p.    Except as disclosed in the Prospectus, there are no contracts,
    agreements or understandings between the Company and any person granting
    such person the right to require the Company to file a registration
    statement under the Securities Act with respect to any securities of the
    Company or to require the Company to include such securities with the
    Shares registered pursuant to the Registration


<PAGE>   7



    Statement.

         q.    The statistical and market-related data included in the Prospe
    are based or derived from sources which the Company and its subsidiaries
    believe to be reliable and materially accurate.

         r.    The Company and its subsidiaries validly hold the Federal
    Communications Commission ("FCC") licenses for each of the radio stations
    owned or operated by the Company and its subsidiaries (the "OWNED STATION
    LICENSES"). With respect to each station to which programming or sales
    marketing services are provided by the Company or its subsidiaries, but
    which are not owned by the Company and its subsidiaries, to the Company's
    knowledge, the parties with which the Company and its subsidiaries have
    entered into such programming or marketing arrangements validly hold the
    FCC licenses (the "PROGRAMMED STATION LICENSES") for such stations. Except
    as set forth in the Prospectus, no proceedings that would reasonably be
    expected to jeopardize the validity of the Owned Station Licenses are
    pending before or, to the Company's knowledge, threatened by, the FCC; and
    to the Company's knowledge, no proceedings that would reasonably be
    expected to jeopardize the validity of the Programmed Station Licenses are
    pending before, or threatened by, the FCC. The Company and its subsidiaries
    possess adequate certificates, authorizations, consents, orders, approvals,
    licenses or permits which are in full force and effect issued by other
    appropriate governmental agencies or bodies necessary to the ownership of
    their respective properties and the conduct of the businesses now operated
    by them and have not received any notice of proceedings relating to the
    revocation or modification of any such certificate, authority, consent,
    order, approval, license or permit and the Company and its subsidiaries are
    in compliance in all material respects with the Communications Act of 1934,
    as amended, and the rules, regulations and policies of the FCC.

         s.    Based solely on the Company's actual knowledge, without
    independent investigation, after giving effect to the pending acquisitions
    (as described in the Registration Statement but not including any
    transaction described therein that is the subject of a letter of intent),
    the Company has no reason to believe that any of the representations,
    warranties and agreements contained in Sections 1(b), 1(k), 1(m), 1(n),
    1(o), 1(p), 1(r) and 1(t) would not be true and correct; provided, however,
    that



<PAGE>   8



    nothing in this representation shall change or be deemed to change the
    Company's obligations or liabilities under the federal securities laws.

         t.    The Company has reviewed its operations to the extent and in the
    manner described in the Prospectus to evaluate the extent to which the
    business or operations of the Company will be affected by the Year 2000
    Problem (that is, any significant risk that computer hardware or software
    applications used or relied upon by the Company will not, in the case of
    dates or time periods occurring after December 31, 1999, function at least
    as effectively as in the case of dates or time periods occurring prior to
    January 1, 2000); as a result of such review, the Company does not believe
    that (i) there are any issues related to the Company's preparedness to
    address the Year 2000 Problem that are of a character required to be
    described or referred to in the Registration Statement or Prospectus which
    have not been accurately described in the Registration Statement or
    Prospectus or (ii) the Year 2000 Problem will have a material adverse
    effect on the Company and its subsidiaries, taken as a whole.

         2.    Representations and Warranties of the Selling Shareholders. Each
of the Selling Shareholders, individually and not jointly, represents and
warrants to and agrees with each of the Underwriters that:

         a.    This Agreement has been duly authorized, executed and delivered
    by or on behalf of such Selling Shareholder.

         b.    The execution and delivery by such Selling Shareholder of, and
    the performance by such Selling Shareholder of its obligations under, this
    Agreement, the Custody Agreement signed by such Selling Shareholder and
    Firstar Bank, N.A., as Custodian, relating to the deposit of the Shares to
    be sold by such Selling Shareholder (the "CUSTODY AGREEMENT") and the Power
    of Attorney appointing certain individuals as such Selling Shareholder's
    attorneys-in-fact to the extent set forth therein, relating to the
    transactions contemplated hereby and by the Registration Statement (the
    "POWER OF ATTORNEY") will not contravene any provision of applicable law,
    or the certificate of incorporation or by-laws of such Selling Shareholder
    (if such Selling Shareholder is a corporation), or any agreement or other
    instrument binding upon such Selling Shareholder or any judgment, order or
    decree of any governmental body, agency or court having jurisdiction over
    such Selling




<PAGE>   9



    Shareholder, and no consent, approval, authorization or order of, or
    qualification with, any governmental body or agency is required for the
    performance by such Selling Shareholder of its obligations under this
    Agreement or the Custody Agreement or Power of Attorney of such Selling
    Shareholder, except such as may be required by the securities or Blue Sky
    laws of the various states, Section 13(d) of the Securities Exchange Act of
    1934, as amended (the "EXCHANGE ACT") and all rules and regulations
    promulgated by the Commission thereunder, Section 16 of the Exchange Act
    and all rules and regulations promulgated by the Commission thereunder and
    consents or waivers obtained in connection with the offer and sale of the
    Shares by such Selling Shareholder.

         c.    Such Selling Shareholder has, and on the Closing Date will have,
    valid title to the Shares to be sold by such Selling Shareholder and the
    legal right and power, and all authorization and approval required by law,
    to enter into this Agreement, the Custody Agreement and the Power of
    Attorney and to sell, transfer and deliver the Shares to be sold by such
    Selling Shareholder.

         d.    The Custody Agreement and the Power of Attorney have been duly
    authorized, executed and delivered by such Selling Shareholder and are
    valid and binding agreements of such Selling Shareholder.

         e.    Delivery of the Shares to be sold by such Selling Shareholder
    pursuant to this Agreement will pass title to such Shares free and clear of
    any security interests, claims, liens, equities and other encumbrances.

         f.    (i) The Registration Statement, when it became effective, did
    not contain and, as amended or supplemented, if applicable, will not
    contain any untrue statement of a material fact or omit to state a material
    fact required to be stated therein or necessary to make the statements
    therein not misleading and (ii) the Prospectus does not contain and, as
    amended or supplemented, if applicable, will not contain any untrue
    statement of a material fact or omit to state a material fact necessary to
    make the statements therein, in the light of the circumstances under which
    they were made, not misleading, but, in each case, only with reference to
    information relating to such Selling Shareholder furnished in writing by or
    on behalf of such



<PAGE>   10



    Selling Shareholder expressly for use in the Registration Statement, any
    preliminary prospectus, the Prospectus or any amendments or supplements
    thereto.

         3.    Agreements to Sell and Purchase. Each Seller, severally and not
jointly, hereby agrees to sell to the several Underwriters, and each
Underwriter, upon the basis of the representations and warranties herein
contained, but subject to the conditions hereinafter stated, agrees, severally
and not jointly, to purchase from such Seller at $______ a share (the "PURCHASE
PRICE") the number of Firm Shares set forth in Schedule II hereto opposite the
name of such Underwriter.

         On the basis of the representations and warranties contained in this
Agreement, and subject to its terms and conditions, the Company and the Selling
Shareholders agree to sell to the Underwriters the Additional Shares, and the
Underwriters shall have a one-time right to purchase, severally and not
jointly, up to 600,000 Additional Shares at the Purchase Price. If the
Representatives, on behalf of the Underwriters, elect to exercise such option,
the Representatives shall so notify the Company and/or the Selling
Shareholders, as applicable, in writing not later than 30 days after the date
of the Prospectus, which notice shall specify the number of Additional Shares
to be purchased by the Underwriters and the date on which such shares are to be
purchased. Such date may be the same as the Closing Date (as defined below) but
not earlier than the Closing Date nor later than ten business days after the
date of such notice. In the event that less than the full amount of the option
to purchase Additional Shares is exercised, the Representatives, on behalf of
the Underwriters, will exercise such option pro rata among the Company and the
Selling Shareholders. Additional Shares may be purchased as provided in Section
5 hereof solely for the purpose of covering over-allotments made in connection
with the offering of the Firm Shares. If any Additional Shares are to be
purchased, each Underwriter agrees, severally and not jointly, to purchase the
number of Additional Shares (subject to such adjustments to eliminate
fractional shares as the Representatives may determine) that bears the same
proportion to the total number of Additional Shares to be purchased as the
number of Firm Shares set forth in Schedule II hereto opposite the name of such
Underwriter bears to the total number of Firm Shares.

         Each Seller hereby agrees that, without the prior written consent of
Morgan Stanley & Co. Incorporated on behalf of the Underwriters, it will not,
during the period ending 90 days after the date of the Prospectus, (i) offer,
pledge, sell,




<PAGE>   11

contract to sell, sell any option or contract to purchase, purchase any option
or contract to sell, grant any option, right or warrant to purchase, lend, or
otherwise transfer or dispose of, directly or indirectly, any shares of Common
Stock or any securities convertible into or exercisable or exchangeable for
Common Stock or (ii) enter into any swap or other arrangement that transfers to
another, in whole or in part, any of the economic consequences of ownership of
the Common Stock, whether any such transaction described in clause (i) or (ii)
above is to be settled by delivery of Common Stock or such other securities, in
cash or otherwise. The foregoing sentence shall not apply to (A) the Shares to
be sold hereunder or (B) the issuance by the Company of shares of Common Stock
upon the exercise of an option or warrant or the conversion of a security
outstanding on the date hereof of which the Underwriters have been advised in
writing. In addition, each Selling Shareholder, agrees that, without the prior
written consent of Morgan Stanley & Co. Incorporated on behalf of the
Underwriters, it will not, during the period ending 90 days after the date of
the Prospectus, make any demand for, or exercise any right with respect to, the
registration of any shares of Common Stock or any security convertible into or
exercisable or exchangeable for Common Stock.

         4.    Terms of Public Offering. The Sellers are advised by the
Representatives that the Underwriters propose to make a public offering of
their respective portions of the Shares as soon after the Registration
Statement and this Agreement have become effective as in the Representatives'
judgment is advisable. The Sellers are further advised by the Representatives
that the Shares are to be offered to the public initially at $______ a share
(the "PUBLIC OFFERING PRICE") and to certain dealers selected by the
Representatives at a price that represents a concession not in excess of
$______ a share under the Public Offering Price, and that any Underwriter may
allow, and such dealers may reallow, a concession, not in excess of $_______ a
share, to any Underwriter or to certain other dealers.

         5.    Payment and Delivery. Payment for the Firm Shares to be sold by
each Seller shall be made to such Seller in Federal or other funds immediately
available in New York City against delivery of such Firm Shares for the
respective accounts of the several Underwriters at 10:00 a.m., New York City
time, on _______, 1999, or at such other time on the same or such other date,
not later than _______, 1999, as shall be designated in writing by the
Representatives. The time and date of such payment are hereinafter referred to
as the "CLOSING DATE".



<PAGE>   12




         Payment for any Additional Shares to be sold by each Seller shall be
made to such Seller in Federal or other funds immediately available in New York
City against delivery of such Additional Shares for the respective accounts of
the several Underwriters at 10:00 a.m., New York City time, on the date
specified in the notice described in Section 3 or at such other time on the
same or on such other date, in any event not later than ___________, 1999 as
shall be designated in writing by the Representatives. The time and date of
such payment are hereinafter referred to as the "OPTION CLOSING DATE".

         Certificates for the Firm Shares and Additional Shares shall be in
definitive form and registered in such names and in such denominations as the
Representatives shall request in writing not later than one full business day
prior to the Closing Date or the Option Closing Date, as the case may be. The
certificates evidencing the Firm Shares and Additional Shares shall be
delivered to the Representatives on the Closing Date or the Option Closing
Date, as the case may be, for the respective accounts of the several
Underwriters, with any transfer taxes payable in connection with the transfer
of the Shares to the Underwriters duly paid, against payment of the Purchase
Price therefor.

         6.    Conditions to the Underwriters' and the Selling Shareholders'
Obligations. The obligations of the Sellers to sell the Shares to the
Underwriters and the several obligations of the Underwriters to purchase and
pay for the Shares on the Closing Date are subject to the condition that the
Registration Statement shall have become effective not later than 5:00 p.m.
(New York City time) on the date hereof.

         The several obligations of the Underwriters and the Selling
Shareholders are subject to the following further conditions:

         a.    Subsequent to the execution and delivery of this Agreement and
    prior to the Closing Date:

                        (i)    there shall not have occurred any downgrading,
         nor shall any notice have been given of any intended or potential
         downgrading or of any review for a possible change that does not
         indicate the direction of the possible change, in the rating accorded
         any of the Company's debt securities or preferred stock by any
         "nationally recognized statistical rating organization," as such term
         is defined for purposes of Rule 436(g)(2) under the


<PAGE>   13



         Securities Act; and

                       (ii)    there shall not have occurred any change, or any
         development involving a prospective change, in the condition,
         financial or otherwise, or in the earnings, business or operations of
         the Company and its subsidiaries, taken as a whole, from that set
         forth in the Prospectus (exclusive of any amendments or supplements
         thereto subsequent to the date of this Agreement) that, in the
         Representatives' judgment, is material and adverse and that makes it,
         in the Representatives' judgment, impracticable to market the Shares
         on the terms and in the manner contemplated in the Prospectus.

         b.    The Underwriters shall have received on the Closing Date a
    certificate, dated the Closing Date and signed by an executive officer of
    the Company, to the effect set forth in Section 6(a)(i) above and to the
    effect that the representations and warranties of the Company contained in
    this Agreement are true and correct as of the Closing Date and that the
    Company has complied with all of the agreements and satisfied all of the
    conditions on its part to be performed or satisfied hereunder on or before
    the Closing Date.

         The officer signing and delivering such certificate may rely upon the
    best of his or her knowledge as to proceedings threatened.

         c.    The Underwriters shall have received on the Closing Date
    opinions of Paul, Hastings, Janofsky & Walker LLP, special counsel for the
    Company, and such other counsel for the Company (including, without
    limitation, the General Counsel of the Company) which is reasonably
    satisfactory to the Representatives, dated the Closing Date, to the effect
    that:

                        (i)   the Company has been duly incorporated, is
         validly existing as a corporation in good standing under the laws of
         the jurisdiction of its incorporation, has the corporate power and
         authority to own its property and to conduct its business as described
         in the Prospectus and is duly qualified to transact business and is in
         good standing in each jurisdiction in which the conduct of its
         business or



<PAGE>   14



         its ownership or leasing of property requires such qualification,
         except to the extent that the failure to be so qualified or be in good
         standing would not have a material adverse effect on the Company and
         its subsidiaries, taken as a whole;

                       (ii)   each U.S. subsidiary of the Company has been duly
         incorporated, is validly existing as a corporation in good standing
         under the laws of the jurisdiction of its incorporation, has the
         corporate power and authority to own its property and to conduct its
         business as described in the Prospectus and is duly qualified to
         transact business and is in good standing in each jurisdiction in
         which the conduct of its business or its ownership or leasing of
         property requires such qualification, except to the extent that the
         failure to be so qualified or be in good standing would not have a
         material adverse effect on the Company and its subsidiaries, taken as
         a whole;

                      (iii)   the authorized capital stock of the Company
         conforms as to legal matters to the description thereof contained in
         the Prospectus;

                       (iv)   the shares of Common Stock (including the Shares
         to be sold by the Selling Shareholders) outstanding prior to the
         issuance of the Shares to be sold by the Company have been duly
         authorized and are validly issued, fully paid and non-assessable;

                        (v)   all of the issued shares of capital stock of each
         subsidiary of the Company have been duly and validly authorized and
         issued, are fully paid and non-assessable and, based solely on a
         review of the stock ledger of each subsidiary, are owned of record by
         the Company or one of its subsidiaries; and, except for the collateral
         pledge of all of such shares to Lehman Commercial Paper Inc. as
         Syndication Agent and Administrative Agent for the Lenders to the
         Company's Credit Agreement, and other matters set forth in the
         Prospectus there are no notations in the stock ledger or on the issued
         and outstanding certificates regarding any liens, encumbrances,
         equities or claims on the holder of record's right, title and interest
         in and to such shares;


                       (vi)   the Shares to be sold by the

<PAGE>   15


         Company have been duly authorized and, when issued and delivered in
         accordance with the terms of this Agreement, will be validly issued,
         fully paid and non-assessable, and the issuance of such Shares will
         not be subject to any preemptive or similar rights;

                        (vii)   this Agreement has been duly authorized,
         executed and delivered by the Company;

                        (viii)  the execution and delivery by the Company of,
         and the performance by the Company of its obligations under, this
         Agreement will not contravene any provision of applicable law or the
         certificate of incorporation or by-laws of the Company or, to the best
         of such counsel's knowledge, any agreement or other instrument binding
         upon the Company or any of its subsidiaries that is material to the
         Company and its subsidiaries, taken as a whole, or, to the best of
         such counsel's knowledge, any judgment, order or decree of any
         governmental body, agency or court having jurisdiction over the
         Company or any subsidiary, and no consent, approval, authorization or
         order of, or qualification with, any governmental body or agency is
         required for the performance by the Company of its obligations under
         this Agreement, except for the registration of Shares under the
         Securities Act and as may be required by the securities or Blue Sky
         laws of the various states in connection with the offer and sale of
         the Shares;

                       (ix)     the statements in the Prospectus under the
         captions "Risk Factors--Governmental Regulation of Broadcasting
         Industry," "Business--Federal Regulation of Radio Broadcasting,"
         "Description of Capital Stock," and "Certain United States Tax
         Consequences to Non-U.S. Holders of Class A Common Stock," in each
         case insofar as such statements describe legal documents or federal,
         New York or Illinois statutes, rules and regulations, constitute a
         fair summary thereof;

                        (x)     to such counsel's knowledge and other than as
         set forth in the Prospectus, there are no legal or governmental
         proceedings pending or threatened to which the Company or any of its
         subsidiaries is a party or to which any of the properties of the
         Company
<PAGE>   16
         or any of its subsidiaries is subject which, if determined
         adversely to the Company or any of its subsidiaries, might have a
         material adverse effect on the consolidated financial position,
         stockholders' equity, results of operations, business or prospects of
         the Company and its subsidiaries;

                       (xi)     the Company and its subsidiaries validly hold
         the Owned Station Licenses; and, to such counsel's knowledge without
         investigation, the parties with which the Company and its subsidiaries
         have entered into programming or marketing arrangements validly hold
         the Programmed Station Licenses;

                        (xii)   no proceedings that would reasonably be
         expected to jeopardize the validity of the Owned Station Licenses are
         pending before or, to such counsel's knowledge, threatened by, the
         FCC; and to such counsel's knowledge without investigation, no
         proceedings that would reasonably be expected to jeopardize the
         validity of the Programmed Station Licenses are pending before, or
         threatened by, the FCC, except as set forth in the Prospectus; and

                        (xiii)  such counsel has participated in
conferendirectors, officers and other representatives of the Company, the
Underwriters, counsel to the Underwriters, and representatives of
PricewaterhouseCoopers LLP, the independent public accountants of the Company,
at which conferences the contents of the Registration Statement and the
Prospectus, and related matters were discussed and subject to (a) the
limitation that such counsel did not independently verify the accuracy,
completeness or fairness of the statements contained in the Registration
Statement or the Prospectus, except as otherwise expressly stated in such
counsel's opinion, (b) the limitations inherent in the information available to
such counsel and (c) the nature and extent of such counsel's participation in
such conferences being such that such counsel is unable to assume, and does not
assume, any responsibility for the accuracy, completeness or fairness of such
statements (and such counsel gives the Underwriters no assurance that such
counsel's procedures described in the first sentence of this paragraph would
necessarily reveal matters of significance with respect to such counsel's
comments), no facts have come to such counsel's attention that would lead such
counsel to believe that the Registration Statement as of its


<PAGE>   17


effective date contained an untrue statement of a material fact or omitted to
state a material fact required to be stated therein or necessary in order to
make the statements therein, in light of the circumstances under which they
were made, not misleading, or that the Prospectus contains an untrue statement
of a material fact or omits to state a material fact required to be stated
therein or necessary in order to make the statements therein, in light of the
circumstances under which they were made, not misleading. Such counsel may
indicate that in making the foregoing comments, such counsel does not intend
them to include or cover the financial statements and notes thereto and other
financial, numerical, accounting or statistical data contained therein or
omitted therefrom as to which such counsel need not express comment.

         d.    The Underwriters shall have received on the Closing Date an
    opinion of Moore & Van Allen, PLLC and Quarles & Brady LLP, counsels for
    the Selling Shareholders, dated the Closing Date, to the effect that:

               (i)     this Agreement has been duly authorized, executed and
         delivered by or on behalf of the applicable Selling Shareholder;

               (ii)    the execution and delivery by the applicable Selling
         Shareholder of, and the performance by such Selling Shareholder of its
         obligations under, this Agreement and the Custody Agreement and Powers
         of Attorney of such Selling Shareholder will not contravene any
         provision of applicable law, or the certificate of incorporation or
         by-laws of such Selling Shareholder (if such Selling Shareholder is a
         corporation), or, to such counsel's knowledge, any agreement or other
         instrument binding upon such Selling Shareholder or, to such counsel's
         knowledge, any judgment, order or decree of any governmental body,
         agency or court having jurisdiction over such Selling Shareholder, and
         no consent, approval, authorization or order of, or qualification
         with, any governmental body or agency is required for the performance
         by such Selling Shareholder of its obligations under this Agreement or
         the Custody Agreement or Power of Attorney of such Selling
         Shareholder, except such as may be required by the securities or Blue
         Sky laws of the



<PAGE>   18





         various states, Section 13(d) of the Securities Exchange Act and all
         rules and regulations promulgated by the Commission thereunder,
         Section 16 of the Exchange Act and all rules and regulations
         promulgated by the Commission thereunder and consents or waivers
         obtained in connection with the offer and sale of the Shares by such
         Selling Shareholder;


               (iii)    the applicable Selling Shareholders has valid title to
         the Shares to be sold by such Selling Shareholder and the legal right
         and power, and all authorization and approval required by law, to
         enter into this Agreement and the Custody Agreement and Power of
         Attorney of such Selling Shareholder and to sell, transfer and deliver
         the Shares to be sold by such Selling Shareholder;

               (iv)     the Custody Agreement and the Power of Attorney of the
         applicable Selling Shareholder have been duly authorized, executed and
         delivered by such Selling Shareholder and are valid and binding
         agreements of such Selling Shareholder; and

               (v)      delivery of the Shares to be sold by the applicable
         Selling Shareholder pursuant to this Agreement will pass title to such
         Shares free and clear of any security interests, claims, liens,
         equities and other encumbrances.

         e.    The Underwriters shall have received on the Closing Date an
    opinion of Simpson Thacher & Bartlett, counsel for the Underwriters, dated
    the Closing Date, covering the matters referred to in Sections 6(c)(vi),
    6(c)(vii), 6(c)(ix) (but only as to the statements in the Prospectus under
    "Description of Capital Stock" and "Underwriters") and 6(c)(xiii) above.

         With respect to Section 6(c)(xiii) above, Simpson Thacher & Bartlett
    may state that their opinion and belief are based upon their participation
    in the preparation of the Registration Statement and Prospectus and any
    amendments or supplements thereto and review and discussion of the contents
    thereof, but are without independent check or verification, except as
    specified.

         The opinions of Paul, Hastings, Janofsky & Walker LLP, Moore & Van
    Allen, PLLC and Quarles & Brady LLP described in Sections 6(c) and 6(d)
    above shall be rendered to the



<PAGE>   19



    Underwriters at the request of the Company or one or more of the Selling
    Shareholders, as the case may be, and shall so state therein.

         f.    The Underwriters shall have received, on each of the date hereof
    and the Closing Date, letters dated the date hereof or the Closing Date, as
    the case may be, in form and substance satisfactory to the Underwriters,
    from PricewaterhouseCoopers LLP, KPMG LLP and Wipfli Ullrich Bertelson LLP,
    each independent public accountants, containing statements and information
    of the type ordinarily included in accountants' "comfort letters" to
    underwriters with respect to the financial statements and certain financial
    information contained or incorporated by reference in the Registration
    Statement and the Prospectus; provided that the letters delivered on the
    Closing Date shall use a "cut-off date" not earlier than the date hereof.

         g.    The "lock-up" agreements, each substantially in the form of
    Exhibit A hereto, between the Representatives and certain shareholders,
    officers and directors of the Company relating to sales and certain other
    dispositions of shares of Common Stock or certain other securities,
    delivered to the Representatives on or before the date hereof, shall be in
    full force and effect on the Closing Date.

         h.    The several obligations of the Underwriters to purchase
    Additional Shares hereunder are subject to the delivery to the
    Representatives on the Option Closing Date of such documents as they may
    reasonably request with respect to the good standing of the Company, the
    due authorization and issuance of the Additional Shares and other matters
    related to the issuance of the Additional Shares.

         7.    Covenants of the Company. In further consideration of the agres
of the Underwriters herein contained, the Company covenants with each
Underwriter and each Selling Shareholder as follows:

         a.    To furnish to the Representatives, without charge, seven igned
     copies of the Registration Statement (including exhibits thereto) and for
     delivery to each other Underwriter a conformed copy of the Registration
     Statement (without exhibits thereto) and to furnish to the Representatives
     in New York City, without charge, prior to 10:00 a.m. New York



<PAGE>   20



     City time on the business day next succeeding the date of this Agreement
     and during the period mentioned in Section 7(c) below, as many copies of
     the Prospectus and any supplements and amendments thereto or to the
     Registration Statement as the Representatives may reasonably request.

         b.    Before amending or supplementing the Registration Statement or
    the Prospectus, to furnish to the Representatives a copy of each such
    proposed amendment or supplement and not to file any such proposed
    amendment or supplement to which the Representatives reasonably object, and
    to file with the Commission within the applicable period specified in Rule
    424(b) under the Securities Act any prospectus required to be filed
    pursuant to such Rule.

         c.    If, during such period after the first date of the public
    offering of the Shares as in the opinion of counsel for the Underwriters
    the Prospectus is required by law to be delivered in connection with sales
    by an Underwriter or dealer, any event shall occur or condition exist as a
    result of which it is necessary to amend or supplement the Prospectus in
    order to make the statements therein, in the light of the circumstances
    when the Prospectus is delivered to a purchaser, not misleading, or if, in
    the opinion of counsel for the Underwriters, it is necessary to amend or
    supplement the Prospectus to comply with applicable law, forthwith to
    prepare, file with the Commission and furnish, at its own expense, to the
    Underwriters and to the dealers (whose names and addresses the
    Representatives will furnish to the Company) to which Shares may have been
    sold by the Representatives on behalf of the Underwriters and to any other
    dealers upon request, either amendments or supplements to the Prospectus so
    that the statements in the Prospectus as so amended or supplemented will
    not, in the light of the circumstances when the Prospectus is delivered to
    a purchaser, be misleading or so that the Prospectus, as amended or
    supplemented, will comply with law.

         d.    To endeavor to qualify the Shares for offer and sale under the
    securities or Blue Sky laws of such jurisdictions as the Representatives
    shall reasonably request; provided that in connection therewith the Company
    shall not be required to qualify as a corporation in that jurisdiction or
    to file a general consent to service of process in any jurisdiction.

         e.    To make generally available to the Company's security holders
    and to the Representatives as soon as

<PAGE>   21



    practicable an earning statement covering the twelve-month period ending
    December 31, 2000 that satisfies the provisions of Section 11(a) of the
    Securities Act and the rules and regulations of the Commission thereunder.

         8.    Expenses. Whether or not the transactions contemplated in this
Agreement are consummated or this Agreement is terminated, the Company agrees
to pay or cause to be paid all expenses incident to the performance of its and
the Selling Shareholders' obligations under this Agreement, including: (i) the
fees, disbursements and expenses of the Company's counsel, the Company's
accountants in connection with the registration and delivery of the Shares
under the Securities Act and all other fees or expenses in connection with the
preparation and filing of the Registration Statement, any preliminary
prospectus, the Prospectus and amendments and supplements to any of the
foregoing, including all printing costs associated therewith, and the mailing
and delivering of copies thereof to the Underwriters and dealers, in the
quantities hereinabove specified, (ii) all costs and expenses related to the
transfer and delivery of the Shares to the Underwriters, including any transfer
or other taxes payable thereon, (iii) the cost of printing or producing any
Blue Sky or Legal Investment memorandum in connection with the offer and sale
of the Shares under state securities laws and all expenses in connection with
the qualification of the Shares for offer and sale under state securities laws
as provided in Section 7(d) hereof, including filing fees and the reasonable
fees and disbursements of counsel for the Underwriters in connection with such
qualification and in connection with the Blue Sky or Legal Investment
memorandum, (iv) all filing fees and the reasonable fees and disbursements of
counsel to the Underwriters incurred in connection with the review and
qualification of the offering of the Shares by the National Association of
Securities Dealers, Inc., (v) any applicable listing or other fees, (vi) the
cost of printing certificates representing the Shares, (vii) the costs and
charges of any transfer agent, registrar or depositary, (viii) the costs and
expenses of the Company associated with the production of road show slides and
graphics, fees and expenses of any consultants engaged in connection with the
road show presentations with the prior approval of the Company, and travel and
lodging expenses of such consultants, and (ix) all other costs and expenses
incident to the performance of the obligations of the Company hereunder for
which provision is not otherwise made in this Section. The Company also agrees
to pay or cause to be paid an amount equal to half of the fees, disbursements
and expenses of counsel for each of the Selling Shareholders in



<PAGE>   22



connection with the Offering and the Selling Shareholders shall pay or cause to
be paid the remaining balance of such amount. It is understood, however, that
except as provided in this Section, Section 9 entitled "Indemnity and
Contribution", and the last paragraph of Section 11 below, the Underwriters
will pay all of their costs and expenses, including fees and disbursements of
their counsel, stock transfer taxes payable on resale of any of the Shares by
them and any advertising expenses connected with any offers they may make. It
is also understood that the Underwriters agree to pay 100% of the reasonable
costs of any aircraft chartered for road show participants, travel and lodging
expenses, meals and breakfast and luncheons in connection with the road show
and its venues.

         9.    Indemnity and Contribution. a. The Company agrees to indemnify
and hold harmless each Underwriter and each person, if any, who controls any
Underwriter within the meaning of either Section 15 of the Securities Act or
Section 20 of the Exchange Act from and against any and all losses, claims,
damages and liabilities (including, without limitation, any legal or other
expenses reasonably incurred in connection with defending or investigating any
such action or claim) caused by any untrue statement or alleged untrue
statement of a material fact contained in the Registration Statement or any
amendment thereof, any preliminary prospectus or the Prospectus (as amended or
supplemented if the Company shall have furnished any amendments or supplements
thereto), or caused by any omission or alleged omission to state therein a
material fact required to be stated therein or necessary to make the statements
therein not misleading, except insofar as such losses, claims, damages or
liabilities are caused by any such untrue statement or omission or alleged
untrue statement or omission based upon information relating to any Underwriter
furnished to the Company in writing by such Underwriter through the
Representatives expressly for use therein.

         b.    Each Selling Shareholder agrees, severally and not jointly, to
indemnify and hold harmless the Company, its directors, its officers who sign
the Registration Statement, each Underwriter and each person, if any, who
controls the Company or any Underwriter within the meaning of either Section 15
of the Securities Act or Section 20 of the Exchange Act, from and against any
and all losses, claims, damages and liabilities (including, without limitation,
any legal or other expenses reasonably incurred in connection with defending or
investigating any such action or claim) caused by any untrue statement or




<PAGE>   23



alleged untrue statement of a material fact contained in the Registration
Statement or any amendment thereof, any preliminary prospectus or the
Prospectus (as amended or supplemented if the Company shall have furnished any
amendments or supplements thereto), or caused by any omission or alleged
omission to state therein a material fact required to be stated therein or
necessary to make the statements therein not misleading, but only with
reference to information relating to such Selling Shareholder furnished in
writing by or on behalf of such Selling Shareholder expressly for use in the
Registration Statement, any preliminary prospectus, the Prospectus or any
amendments or supplements thereto.

         c.    Each Underwriter agrees, severally and not jointly, to indemnify
and hold harmless the Company, the Selling Shareholders, the directors of the
Company, the officers of the Company who sign the Registration Statement and
each person, if any, who controls the Company or any Selling Shareholder within
the meaning of either Section 15 of the Securities Act or Section 20 of the
Exchange Act to the same extent as the foregoing indemnity from the Company to
such Underwriter, but only with reference to information relating to such
Underwriter furnished to the Company in writing by such Underwriter through the
Representatives expressly for use in the Registration Statement, any
preliminary prospectus, the Prospectus or any amendments or supplements
thereto.

         d.    In case any proceeding (including any governmental
investigation) shall be instituted involving any person in respect of which
indemnity may be sought pursuant to Section 9(a), 9(b) or 9(c), such person
(the "INDEMNIFIED PARTY") shall promptly notify the person against whom such
indemnity may be sought (the "INDEMNIFYING PARTY") in writing and the
indemnifying party, upon request of the indemnified party, shall retain counsel
reasonably satisfactory to the indemnified party to represent the indemnified
party and any others the indemnifying party may designate in such proceeding
and shall pay the fees and disbursements of such counsel related to such
proceeding. In any such proceeding, any indemnified party shall have the right
to retain its own counsel, but the fees and expenses of such counsel shall be
at the expense of such indemnified party unless (i) the indemnifying party and
the indemnified party shall have mutually agreed to the retention of such
counsel or (ii) the named parties to any such proceeding (including any
impleaded parties) include both the indemnifying party and the indemnified
party and representation of both parties by the same counsel would be
inappropriate due to actual or potential differing interests between them. It
is understood that the indemnifying party shall




<PAGE>   24



not, in respect of the legal expenses of any indemnified party in connection
with any proceeding or related proceedings in the same jurisdiction, be liable
for the fees and expenses of more than one separate firm (in addition to any
local counsel) for all such indemnified parties and that all such fees and
expenses shall be reimbursed as they are incurred. In the case of any such
separate firm for the Underwriters and such control persons of any
Underwriters, such firm shall be designated in writing by Morgan Stanley & Co.
Incorporated. In the case of any such separate firm for the Company, and such
directors, officers and control persons of the Company, such firm shall be
designated in writing by the Company. In the case of any such separate firm for
the Selling Shareholders and such control persons of any Selling Shareholders,
such firm shall be designated in writing by the persons named as
attorneys-in-fact for the Selling Shareholders under the Powers of Attorney.
The indemnifying party shall not be liable for any settlement of any proceeding
effected without its written consent, but if settled with such consent or if
there be a final judgment for the plaintiff, the indemnifying party agrees to
indemnify the indemnified party from and against any loss or liability by
reason of such settlement or judgment. Notwithstanding the foregoing sentence,
if at any time an indemnified party shall have requested an indemnifying party
to reimburse the indemnified party for fees and expenses of counsel as
contemplated by the second and third sentences of this paragraph, the
indemnifying party agrees that it shall be liable for any settlement of any
proceeding effected without its written consent if (i) such settlement is
entered into more than 30 days after receipt by such indemnifying party of the
aforesaid request and (ii) such indemnifying party shall not have reimbursed
the indemnified party in accordance with such request prior to the date of such
settlement. No indemnifying party shall, without the prior written consent of
the indemnified party, effect any settlement of any pending or threatened
proceeding in respect of which any indemnified party is or could have been a
party and indemnity could have been sought hereunder by such indemnified party,
unless such settlement includes an unconditional release of such indemnified
party from all liability on claims that are the subject matter of such
proceeding.

         e.    To the extent the indemnification provided for in Section 9(a),
9(b) or 9(c) is unavailable to an indemnified party or insufficient in respect
of any losses, claims, damages or liabilities referred to therein, then each
indemnifying party under such paragraph, in lieu of indemnifying such
indemnified party thereunder, shall contribute to the amount paid or payable




<PAGE>   25




by such indemnified party as a result of such losses, claims, damages or
liabilities (i) in such proportion as is appropriate to reflect the relative
benefits received by the indemnifying party or parties on the one hand and the
indemnified party or parties on the other hand from the offering of the Shares
or (ii) if the allocation provided by clause 9(e)(i) above is not permitted by
applicable law, in such proportion as is appropriate to reflect not only the
relative benefits referred to in clause 9(e)(i) above but also the relative
fault of the indemnifying party or parties on the one hand and of the
indemnified party or parties on the other hand in connection with the
statements or omissions that resulted in such losses, claims, damages or
liabilities, as well as any other relevant equitable considerations. The
relative benefits received by the Sellers on the one hand and the Underwriters
on the other hand in connection with the offering of the Shares shall be deemed
to be in the same respective proportions as the net proceeds from the offering
of the Shares (before deducting expenses) received by each Seller and the total
underwriting discounts and commissions received by the Underwriters, in each
case as set forth in the table on the cover of the Prospectus, bear to the
aggregate Public Offering Price of the Shares. The relative fault of the
Sellers on the one hand and the Underwriters on the other hand shall be
determined by reference to, among other things, whether the untrue or alleged
untrue statement of a material fact or the omission or alleged omission to
state a material fact relates to information supplied by the Sellers or by the
Underwriters and the parties' relative intent, knowledge, access to information
and opportunity to correct or prevent such statement or omission. The
Underwriters' respective obligations to contribute pursuant to this Section 9
are several in proportion to the respective number of Shares they have
purchased hereunder, and not joint.

         f.    The Sellers and the Underwriters agree that it would not be just
or equitable if contribution pursuant to this Section 9 were determined by pro
rata allocation (even if the Underwriters were treated as one entity for such
purpose) or by any other method of allocation that does not take account of the
equitable considerations referred to in Section 9(e). The amount paid or
payable by an indemnified party as a result of the losses, claims, damages and
liabilities referred to in the immediately preceding paragraph shall be deemed
to include, subject to the limitations set forth above, any legal or other
expenses reasonably incurred by such indemnified party in connection with
investigating or defending any such action or claim. Notwithstanding the
provisions of this Section 9, no Underwriter shall be required to contribute
any amount in excess of the amount by which the total price at which the Shares



<PAGE>   26




underwritten by it and distributed to the public were offered to the public
exceeds the amount of any damages that such Underwriter has otherwise been
required to pay by reason of such untrue or alleged untrue statement or
omission or alleged omission. No person guilty of fraudulent misrepresentation
(within the meaning of Section 11(f) of the Securities Act) shall be entitled
to contribution from any person who was not guilty of such fraudulent
misrepresentation. The remedies provided for in this Section 9 are not
exclusive and shall not limit any rights or remedies which may otherwise be
available to any indemnified party at law or in equity.

         g.    The indemnity and contribution provisions contained in this
Section 9 and the representations, warranties and other statements of the
Company and the Selling Shareholders contained in this Agreement shall remain
operative and in full force and effect regardless of (i) any termination of
this Agreement, (ii) any investigation made by or on behalf of any Underwriter
or any person controlling any Underwriter, any Selling Shareholder or any
person controlling any Selling Shareholder, or the Company, its officers or
directors or any person controlling the Company and (iii) acceptance of and
payment for any of the Shares.

         10.   Termination. This Agreement shall be subject to termination by
notice given by the Representatives to the Company, if (a) after the execution
and delivery of this Agreement and prior to the Closing Date (i) trading
generally shall have been suspended or materially limited on or by, as the case
may be, any of the New York Stock Exchange, the American Stock Exchange, the
National Association of Securities Dealers, Inc., the Chicago Board of Options
Exchange, the Chicago Mercantile Exchange or the Chicago Board of Trade, (ii)
trading of any securities of the Company shall have been suspended on any
exchange or in any over-the-counter market, (iii) a general moratorium on
commercial banking activities in New York shall have been declared by either
Federal or New York State authorities or (iv) there shall have occurred any
outbreak or escalation of hostilities or any change in financial markets or any
calamity or crisis that, in the Representatives' judgment, is material and
adverse and (b) in the case of any of the events specified in clauses 10(a)(i)
through 10(a)(iv), such event, singly or together with any other such event,
makes it, in the Representatives' judgment, impracticable to market the Shares
on the terms and in the manner contemplated in the Prospectus.


<PAGE>   27


         11.   Effectiveness; Defaulting Underwriters. This Agreement shall
become effective upon the execution and delivery hereof by the parties hereto.

         If, on the Closing Date or the Option Closing Date, as the case may
be, any one or more of the Underwriters shall fail or refuse to purchase Shares
that it has or they have agreed to purchase hereunder on such date, and the
aggregate number of Shares which such defaulting Underwriter or Underwriters
agreed but failed or refused to purchase is not more than one-tenth of the
aggregate number of the Shares to be purchased on such date, the other
Underwriters shall be obligated severally in the proportions that the number of
Firm Shares set forth opposite their respective names in Schedule II bears to
the aggregate number of Firm Shares set forth opposite the names of all such
non-defaulting Underwriters, or in such other proportions as the
Representatives may specify, to purchase the Shares which such defaulting
Underwriter or Underwriters agreed but failed or refused to purchase on such
date; provided that in no event shall the number of Shares that any Underwriter
has agreed to purchase pursuant to this Agreement be increased pursuant to this
Section 11 by an amount in excess of one-ninth of such number of Shares without
the written consent of such Underwriter. If, on the Closing Date, any
Underwriter or Underwriters shall fail or refuse to purchase Firm Shares and
the aggregate number of Firm Shares with respect to which such default occurs
is more than one-tenth of the aggregate number of Firm Shares to be purchased,
and arrangements satisfactory to the Representatives, the Company and the
Selling Shareholders for the purchase of such Firm Shares are not made within
36 hours after such default, this Agreement shall terminate without liability
on the part of any non-defaulting Underwriter, the Company or the Selling
Shareholders. In any such case either the Representatives or the relevant
Sellers shall have the right to postpone the Closing Date, but in no event for
longer than seven days, in order that the required changes, if any, in the
Registration Statement and in the Prospectus or in any other documents or
arrangements may be effected. If, on the Option Closing Date, any Underwriter
or Underwriters shall fail or refuse to purchase Additional Shares and the
aggregate number of Additional Shares with respect to which such default occurs
is more than one-tenth of the aggregate number of Additional Shares to be
purchased, the non-defaulting Underwriters shall have the option to (i)
terminate their obligation hereunder to purchase Additional Shares or (ii)
purchase not less than the number of Additional Shares that such non-defaulting
Underwriters would have been obligated to purchase in the absence of such
default. Any action taken under this paragraph shall not relieve any defaulting
Underwriter from


<PAGE>   28



liability in respect of any default of such Underwriter under this Agreement.

         If this Agreement shall be terminated by the Underwriters, or any of
them, because of any failure or refusal on the part of any Seller to comply
with the terms or to fulfill any of the conditions of this Agreement, or if for
any reason any Seller shall be unable to perform its obligations under this
Agreement, the Company will reimburse the Underwriters or such Underwriters as
have so terminated this Agreement with respect to themselves, severally, for
all out-of-pocket expenses (including the fees and disbursements of their
counsel) reasonably incurred by such Underwriters in connection with this
Agreement or the offering contemplated hereunder.

         12.   Counterparts. This Agreement may be signed in two or more
counterparts, each of which shall be an original, with the same effect as if
the signatures thereto and hereto were upon the same instrument.

         13.   Applicable Law. This Agreement shall be governed by and
construed in accordance with the law of the State of New York.

         14.   Headings. The headings of the sections of this Agreement have
been inserted for convenience of reference only and shall not be deemed a part
of this Agreement.


<PAGE>   29

                                         Very truly yours,

Name:                                    CUMULUS MEDIA INC.

                                         By: ______________________________
                                             Name: Richard Weening
                                             Title: Executive Chairman



                                             The Selling Shareholders
                                             named in Schedule I hereto,
                                             acting severally

                                             By:______________________
                                                   Attorney-in-fact


Accepted as of the date hereof

MORGAN STANLEY & CO. INCORPORATED
BEAR, STEARNS & CO. INC.
GOLDMAN, SACHS & CO.
PRUDENTIAL SECURITIES INCORPORATED
LEHMAN BROTHERS INC.
BANC OF AMERICA SECURITIES LLC,

Acting severally on behalf of themselves
  and the several Underwriters
  named in Schedule II hereto.


By: Morgan Stanley & Co. Incorporated



By:
    -------------------------------






<PAGE>   30



                                                                   SCHEDULE I




   SELLING SHAREHOLDER                                         NUMBER OF
                                                              FIRM SHARES
                                                               TO BE SOLD

State of Wisconsin Investment Board                             500,000
BA Capital Company, L.P.                                        500,000

                                                        ------------------
        Total                                                    1,000,000
                                                        ========================

<PAGE>   31

                                                                  SCHEDULE II


        UNDERWRITER                                     NUMBER OF
                                                       FIRM SHARES
                                                     TO BE PURCHASED

Morgan Stanley & Co. Incorporated
Bear, Stearns & Co. Inc.
Goldman, Sachs & Co.
Prudential Securities Incorporated
Lehman Brothers Inc.
Banc of America Securities LLC
                                                  -------------------
                                                          =====================
       Total                                          4,000,000
                                                      ==================



<PAGE>   32


                                                                    EXHIBIT A

                            [FORM OF LOCK-UP LETTER]

                                                             November __, 1999


Morgan Stanley & Co. Incorporated
Bear, Stearns & Co. Inc.
Goldman, Sachs & Co.
Prudential Securities Incorporated
Lehman Brothers Inc.
Banc of America Securities LLC,
as Representatives of the several Underwriters,
c/o Morgan Stanley & Co. Incorporated
    1585 Broadway
    New York, NY  10036


Dear Sirs and Mesdames:

                  The undersigned understands that Morgan Stanley & Co.
Incorporated ("MORGAN STANLEY") proposes to enter into an Underwriting
Agreement (the "UNDERWRITING AGREEMENT") with Cumulus Media Inc., an Illinois
corporation (the "COMPANY") providing for the public offering (the "PUBLIC
OFFERING") by the several Underwriters, including Morgan Stanley (the
"UNDERWRITERS") of 4,000,000 shares (the "SHARES") of the Class A Common Stock,
par value $.01 per share, of the Company (the "COMMON STOCK").

                  To induce the Underwriters that may participate in the Public
Offering to continue their efforts in connection with the Public Offering, the
undersigned hereby agrees that, without the prior written consent of Morgan
Stanley on behalf of the Underwriters, it will not, during the period
commencing on the date hereof and ending 90 days after the date of the final
prospectus relating to the Public Offering (the "PROSPECTUS"), (1) offer,
pledge, sell, contract to sell, sell any option or contract to purchase,
purchase any option or contract to sell, grant any option, right or warrant to
purchase, lend, or otherwise transfer or dispose of, directly or indirectly,
any shares of Common Stock or any securities convertible into or exercisable or
exchangeable for Common Stock, or (2) enter into




<PAGE>   1
                                                                     EXHIBIT 5.1



                              November 15, 1999





Cumulus Media Inc.
111 East Kilbourn Avenue, Suite 2700
Milwaukee, WI  53202

Ladies and Gentlemen:

            We have acted as special counsel for Cumulus Media Inc., an Illinois
corporation (the "Company") in connection with the Company's Registration
Statement on Form S-3, as amended (the "Registration Statement"), being filed by
the Company under the Securities Act of 1933, as amended, relating to the offer
and sale of up to 4,600,000 shares (the "Shares") of the Company's Class A
common stock, par value $.01 per share (the "Common Stock"). Of the Shares,
300,000 are subject to an option granted to the underwriters by the Company and
300,000 are subject to an option granted to the underwriters by selling
shareholders, in each case to cover over-allotments, if any.

            In connection with this letter, we have examined, considered and
relied solely upon the following documents (collectively, the "Documents"): the
Registration Statement; the Company's Amended and Restated Articles of
Incorporation; the Company's Bylaws; certain resolutions of the Company's Board
of Directors; a certificate of the Company's secretary; and such matters of law
as we have considered necessary or appropriate for the expression of the
opinions contained herein.

            In rendering the opinions set forth below, we have assumed without
investigation the genuineness of all signatures and the authenticity of all
documents submitted to us as originals, the conformity to authentic original
documents of all documents submitted to us as copies, and the veracity of the
Documents. As to questions of fact material to the opinions hereinafter
expressed, we have relied upon the representations and warranties of the Company
made in the Documents.

            Based solely upon and subject to the Documents, and subject to the
qualification set forth below, we are of the opinion that the Shares, when duly



<PAGE>   2

delivered against payment therefor, as contemplated by the Registration
Statement, will be duly authorized, validly issued, fully paid and
non-assessable.

            This opinion letter is limited to the matters stated herein and no
opinions may be implied or inferred beyond the matters expressly stated herein.
The opinions expressed herein are as of the date hereof, and we assume no
obligation to update or supplement such opinions to reflect any facts or
circumstances that may hereafter come to our attention or any changes in law
that may hereafter occur.

            We hereby consent to the filing of this opinion as Exhibit 5.1 to
the Registration Statement and to the reference to us under the caption "Legal
Matters" in the prospectus contained in the Registration Statement.



                                            Very truly yours,

                                            /S/ HOLLEB & COFF

                                            HOLLEB & COFF











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