PLAYBOY ENTERPRISES INC
S-8, 1997-06-27
PERIODICALS: PUBLISHING OR PUBLISHING & PRINTING
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<PAGE>
 
     As filed with the Securities and Exchange Commission on June 27, 1997

                                                     Registration No. 333-______
                                                                                
================================================================================

                      SECURITIES AND EXCHANGE COMMISSION

                            WASHINGTON, D.C. 20549

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

                                   FORM S-8
                            REGISTRATION STATEMENT
                                     Under
                          THE SECURITIES ACT OF 1933

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

                           PLAYBOY ENTERPRISES, INC.

            (Exact name of registrant as specified in its charter)

                   Delaware                                36-2258830
(State or Other Jurisdiction of Incorporation)          (I.R.S. Employer
                                                       Identification No.)

                           680 North Lake Shore Drive
                            Chicago, Illinois 60611
                    (Address of principal executive offices)

         Non-qualified Stock Option Agreements dated November 13, 1996
                 between Playboy Enterprises, Inc. and each of
                    Dennis S. Bookshester and Sol Rosenthal
                            (Full title of the Plan)

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


                             Howard Shapiro, Esq.
               Executive Vice President, Law and Administration,
                         General Counsel and Secretary
                           Playboy Enterprises, Inc.
                          680 North Lake Shore Drive
                            Chicago, Illinois 60611
                                (312) 751-8000
                     (Name, address, and telephone number,
                  including area code, of agent for service)

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

                        CALCULATION OF REGISTRATION FEE
<TABLE>
<CAPTION>
 
=======================================================================================================================
                                                                 Proposed            Proposed
                                                                 maximum              maximum
                                           Amount to be       offering price         aggregate            Amount of
Title of securities to be registered        registered          per share         offering price       registration fee
- -----------------------------------------------------------------------------------------------------------------------
<S>                                        <C>                <C>                 <C>                  <C>
Class B Common Stock, $.01 par value          20,000           $11.9375(1)           $238,750              $100.00
                                              Shares
=======================================================================================================================
</TABLE>


(1)  Calculated using the high and low prices of Class B shares in the composite
     reporting system for June 24, 1997.
===============================================================================
<PAGE>
 
                                    PART II


Item 3.  Incorporation of Documents by Reference

          The Annual Report on Form 10-K of Playboy Enterprises, Inc. (the
"Company" or the "Registrant") for the fiscal year ended June 30, 1996, its
Quarterly Reports on Form 10-Q for the quarterly periods ending September 30,
1996, December 31, 1996 (as amended by Form 10-Q/A) and March 31, 1997 and the
description of the Company's Class A and Class B Common Stock contained in the
registration statement on Form 8-A dated May 17, 1990, as amended by Form 8,
dated June 7, 1990, and any amendment or report filed for the purpose of
updating such description, are incorporated by reference into this registration
statement.  Any documents filed by the Company subsequent to the filing of this
registration statement pursuant to Sections 13(a), 13(c), 14 and 15(d) of the
Securities Exchange Act of 1934, as amended (the "Exchange Act"), prior to the
filing of a post-effective amendment which indicates that all securities offered
have been sold or which deregisters all securities then remaining unsold, shall
be deemed to be incorporated by reference in this registration statement and to
be a part hereof from the date of filing of such documents.

Item 5.  Interests of Named Experts and Counsel

          Howard Shapiro, Esq., whose opinion regarding the validity of the
securities offered hereby is filed as Exhibit 5.1 hereto, is an officer and
stockholder of the Company.  Mr. Shapiro is the Company's Executive Vice
President, Law and Administration, General Counsel and Secretary.  As of May 31,
1997, Mr. Shapiro owned beneficially 15 shares of the Company's Class A Common
Stock and 30,145 shares of the Company's Class B Common Stock (including 22,500
shares of restricted stock subject to vesting) and held options to purchase
35,000 shares of Class A Common Stock and 135,000 shares of Class B Common
Stock.

Item 6.  Indemnification of Directors and Officers

          The Company is a Delaware corporation.  Section 145 of the General
Corporation Law of the State of Delaware (the "GCL") provides that a Delaware
corporation has the power to indemnify its officers and directors in certain
circumstances.

          Subsection (a) of Section 145 of the GCL empowers a corporation to
indemnify any director or officer, or former director or officer, who was or is
a party or is threatened to be made a party to any threatened, pending or
completed action, suit or proceeding, whether civil, criminal, administrative or
investigative (other than an action by or in the right of the corporation)
against expenses (including attorney's fees), judgments, fines and amounts paid
in settlement actually and reasonably incurred in connection with such action,
suit or proceeding provided that such director or officer acted in good faith in
a manner reasonably believed to be in or not opposed to the best interests of
the corporation, and, with respect to any criminal action or proceeding,
provided that such director or officer had no reasonable cause to believe his or
her conduct was unlawful.

                                       2
<PAGE>
 
          Subsection (b) of Section 145 of the GCL empowers a corporation to
indemnify any director or officer, or former director or officer, who was or is
a party or is threatened to be made a party to any threatened, pending or
completed action or suit by or in the right of the corporation to procure a
judgment in its favor, against expenses (including attorneys' fees) actually and
reasonably incurred in connection with the defense or settlement of such action
or suit provided that such director or officer acted in good faith and in a
manner reasonably believed to be in or not opposed to the best interests of the
corporation, except that no indemnification may be made in respect of any claim,
issue or matter as to which such director or officer shall have been adjudged to
be liable to the corporation unless and only to the extent that the court in
which such action or suit was brought determines that despite the adjudication
of liability such director or officer is fairly and reasonably entitled to
indemnity for such expenses which such court shall deem proper.

          Section 145 of the GCL further provides that (i) to the extent a
director or officer of a corporation has been successful in the defense of any
action, suit or proceeding referred to in subsections (a) and (b) of Section 145
or in the defense of any claim, issue or matter therein, such director or
officer shall be indemnified against expenses (including attorney's fees)
actually and reasonably incurred by such director or officer in connection
therewith; (ii) expenses may be advanced by the corporation subject to an
undertaking of the person receiving the advance to reimburse such expenses if
the person receiving the advance is ultimately determined not to be entitled to
indemnification; (iii) indemnification provided for by Section 145 shall not be
deemed exclusive of any other rights to which the indemnified party may be
entitled otherwise; and (iv) the corporation may purchase and maintain insurance
on behalf of a director or officer of the corporation against any liability
asserted against him or her or incurred by him or her in any such capacity or
arising out of his or her status as such, whether or not the corporation would
have the power to indemnify him or her against such liabilities under Section
145.

          As permitted by Section 102(b)(7) of the GCL, Article TWELFTH of the
Company's Restated Certificate of Incorporation provides that directors of the
Company will be exempt from monetary liabilities in certain circumstances, as
follows:

          "Directors shall not be personally liable to the corporation or its
          stockholders for monetary damages for breaches of fiduciary duty as a
          director, except for liability (i) for breach of the director's duty
          of loyalty to the corporation or its stockholders; (ii) for acts or
          omissions not in good faith or which involve intentional misconduct or
          a knowing violation of law; (iii) under Section 174 of the Delaware
          General Corporation Law, or (iv) for any transaction from which the
          director derived an improper personal benefit."

          Article VII, Section 6 of the Company's bylaws provides for
indemnification  of officers and directors of the Company, to the fullest extent
permitted by the GCL, for all expense, liability and loss in connection with any
action, suit or proceeding while serving as a director or officer of the Company
or as an officer, director or employee of any other entity at the request of the
Company.  Such indemnification continues as to a person who has ceased to be a
director or officer, and inures to the benefit of his or her heirs, executors

                                       3

<PAGE>
 
and administrators.  The Company is required to indemnify any officer or
director in connection with a proceeding initiated by such officer or director
only if such proceeding was authorized by the Board.  The right to
indemnification includes the right to be paid by the Company the expenses
incurred in defending any such proceeding in advance of its final disposition
subject to receipt by the Company of any required undertaking to repay all
amounts so advanced if it shall ultimately be determined that the director or
officer is not entitled to be indemnified under the Company's bylaws or
otherwise.  If an indemnification claim is not paid in full by the Company
within ninety days after a written claim has been received by the Company, the
claimant may at any time thereafter bring suit against the Company to recover
the unpaid amount of the claim and, if successful in whole or in part, the
claimant is also entitled to be paid the expense of prosecuting that claim.  The
right to indemnification and payment of expenses incurred in defending a
proceeding in advance of its final disposition conferred in the bylaws is not
exclusive of any other rights.  This section of the bylaws provides further that
the Company may maintain insurance to protect any director or officer against
any expense, liability or loss, whether or not the Company would have the power
to indemnify such person against such expense, liability or loss.  The Company
maintains such insurance for its directors and officers.

Item 8.  Exhibits
<TABLE>
<captiion>

Exhibit Number Description
- -------------- -----------
<C>            <S>      
4.1            Form of certificate for shares of the Company's Class B Common
               Stock (incorporated by reference to Exhibit 1.2 of the
               Registration Statement on Form 8-A, dated May 17, 1990, as
               amended by Form 8, dated May 17, 1990; Commission File No. 1-
               6813)

4.2            Restated Certificate of Incorporation of the Company
               (incorporated by reference to Exhibit 3.1 of the Company's annual
               report on Form 10-K for the year ended June 30, 1995; Commission
               File No. 1-6813)

4.3            Restated bylaws of the Company (incorporated by reference to
               Exhibit 3.2 of the Company's annual report on Form 10-K for the
               year ended June 30, 1994; Commission File No. 1-6813)

4.4            Form of Non-qualified Stock Option Agreements dated November 13,
               1996 between Playboy Enterprises, Inc. and each of Dennis S.
               Bookshester and Sol Rosenthal

5.1            Opinion of Counsel

23.1           Consent of Coopers & Lybrand L.L.P.

23.2           Consent of Counsel (included in Exhibit 5.1)
</TABLE>


                                       4

<PAGE>
 
Item 9.  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 (the "Securities Act");

               (ii) To reflect in the prospectus any facts 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 amount would not exceed that which is registered) and any
          deviation from the low or high and of the estimated maximum 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 volume and price represent no more than 20 percent change in the
          maximum aggregate offering price set forth in the "Calculation of
          Registration Fee" table in the effective registration statement.

               (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) do
          not apply if the registration statement is on Form S-3, Form S-8 or
          Form F-3, 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 Exchange Act that are
          incorporated by reference in the 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.

          (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.

     (b) The undersigned registrant hereby undertakes that, for purposes of
determining any liability under the Securities Act, each filing of the
registrant's annual report pursuant to Section 13(a) or 15(d) of the Exchange
Act (and, where applicable, each filing of an employee benefit plan's annual
report pursuant to Section 15(d) of the Exchange

                                       5
<PAGE>
 
Act) 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.

     (c) Insofar as indemnification for liabilities arising under the Securities
Act 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
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 and will be governed by the final
adjudication of such issue.




                                       6

<PAGE>
 
                                   SIGNATURES

          Pursuant to the requirements of the Securities Act of 1933, the
registrant certifies that it has reasonable grounds to believe that it meets all
of the requirements for filing on Form S-8 and has duly caused this registration
statement to be signed on its behalf by the undersigned, thereunto duly
authorized, in the City of Chicago, State of Illinois, on June 27, 1997.

                              PLAYBOY ENTERPRISES, INC.
                                    (Registrant)

                              By: /s/ Howard Shapiro
                                 -------------------------------------
                                    Howard Shapiro, Executive Vice President,
                                    Law and Administration, General Counsel and
                                    Secretary

          Each of the undersigned, by signing his or her name below, does hereby
constitute and appoint Christie Hefner and Howard Shapiro, and each of them, as
his or her true and lawful attorney-in-fact and agent, with full power of
substitution and resubstitution, for him or her and in his or her name, place
and stead, in any and all capacities, to sign any and all amendments to this
registration statement and to file the same, with exhibits and schedules
thereto, and other documents in connection therewith, with the Securities and
Exchange Commission, granting unto said attorney-in-fact full power and
authority to do and perform each and every act and thing necessary or desirable
to be done in and about the premises, as fully to all intents and purposes as he
or she might or could do in person, thereby ratifying and confirming all that
said attorney-in-fact, or his or her substitute, may lawfully do or cause to be
done by virtue hereof.

          Pursuant to the requirements of the Securities Act of 1933, this
registration statement has been signed by the following persons in the
capacities indicated on June 27, 1997.

Signature                                    Title
- ---------                                    -----

/s/ Christie Hefner                Chairman and Chief Executive Officer
- -------------------------          and Director (Principal Executive
Christie Hefner                    Officer)

/s/ Linda Havard                   Chief Financial Officer and
- -------------------------          Executive Vice President, Finance   
Linda Havard                       and Operations (Principal Financial
                                   and Accounting Officer)

/s/ Dennis S. Bookshester
- -------------------------
Dennis S. Bookshester              Director


/s/ David I. Chemerow
- -------------------------
David I. Chemerow                  Director


/s/ Sol Rosenthal
- -------------------------
Sol Rosenthal                      Director


/s/ Richard S. Rosenzweig
- -------------------------
Richard S. Rosenzweig              Director


/s/ Sir Brian Wolfson
- -------------------------
Sir Brian Wolfson                  Director

                                       7
<PAGE>
 
                                 EXHIBIT INDEX
<TABLE>
<CAPTION>
                                                                   Sequentially
Exhibit Number    Description                                      Numbered Page
- --------------    -----------                                      -------------
<S>               <C>                                              <C>
4.1               Form of certificate for shares of the
                  Company's Class B Common Stock (incorporated by
                  reference to Exhibit 1.2 of the Registration
                  Statement on Form 8-A, dated May 17, 1990, as
                  amended by Form 8, dated May 17, 1990;
                  Commission File No. 1-6813)

4.2               Restated Certificate of Incorporation of the
                  Company (incorporated by reference to Exhibit
                  3.1 of the Company's annual report on Form 10-
                  K for the year ended June 30, 1995; Commission
                  File No. 1-6813)

4.3               Restated bylaws of the Company (incorporated
                  by reference to Exhibit 3.2 of the Company's
                  annual report on Form 10-K for the year ended
                  June 30, 1994; Commission File No. 1-6813)

4.4               Form of Non-qualified Stock Option Agreements
                  dated November 13, 1996 between Playboy
                  Enterprises, Inc. and each of Dennis S.
                  Bookshester and Sol Rosenthal

5.1               Opinion of Counsel

23.1              Consent of Coopers & Lybrand L.L.P.

23.2              Consent of Counsel (included in Exhibit 5.1)
</TABLE>

                                       8

<PAGE>
 
                                                                     Exhibit 4.4

                           PLAYBOY ENTERPRISES, INC.

                     NON-QUALIFIED STOCK OPTION AGREEMENT
                     ------------------------------------

          THIS AGREEMENT, dated as of November 13, 1996 is made by and between
Playboy Enterprises, Inc., a Delaware corporation hereinafter referred to as
"Company," and Sol Rosenthal, a non-employee Director of the Company hereinafter
referred to as "Optionee":

          WHEREAS, the Company wishes to afford the Optionee the opportunity to
purchase shares of its Class B Common Stock, par value $.01 per share
(hereinafter referred to as the "Class B Stock"); and

          WHEREAS, the execution of a stock option agreement in the form hereof 
has been duly authorized by a resolution of the Board of Directors of the 
Company duly adopted on November 13, 1996 and incorporated herein by reference;

          NOW, THEREFORE, in consideration of the mutual covenants herein
contained and other good and valuable consideration, receipt of which is hereby
acknowledged, the parties hereto do hereby agree as follows:


                                   ARTICLE I

                                  DEFINITIONS
                                  -----------

          Whenever the following terms are used in this Agreement, they shall 
have the meaning specified below.

Section 1. - "Board" shall mean the Board of Directors of the Company.

Section 1.2 - "Code" shall mean the Internal Revenue Code of 1986, as amended.

Section 1.3 - "Committee" shall mean the Compensation Committee of the Board.

Section 1.4 - "Company" shall mean Playboy Enterprises, Inc.

Section 1.5 - "Director" shall mean a member of the Board.

Section 1.6 - "Option" shall mean the non-qualified option to purchase 10,000 
shares of Class B Stock of the Company granted under this Agreement.
  
<PAGE>
 
Section 1.7 - "Rule 16b-3" shall mean Rule 16b-3 which has been adopted by the 
Securities and Exchange Commission under the Securities Exchange Act of 1934, as
amended, as such rule or its equivalent is then in effect ("Rule 16b-3").

Section 1.8 - "Secretary" shall mean the Secretary of the Company.

Section 1.9 - "Securities Act" shall mean the Securities Act of 1933, as
amended.

Section 1.10 - "Termination of Service" shall mean the time at which the 
Optionee ceases to serve as a Director for any reason, with or without cause, 
which includes termination by resignation, death or retirement.


                                  ARTICLE II

                                GRANT OF OPTION
                                ---------------

Section 2.1 - Grant of Option
    
     In consideration of the Optionee's agreement to continue to serve as a 
Director and for other good and valuable consideration, on the date hereof the 
Company irrevocably grants to the Optionee a non-qualified option to purchase 
any part or all of an aggregate of 10,000 shares of its Class B Stock upon the 
terms and conditions set forth in this Agreement.

Section 2.2 - Purchase Price

     The purchase price of the shares of Class B Stock covered by the Option 
shall be $12.00 per share, which was 100% of the fair market value per share of 
such shares at the end of the business day immediately preceding the day the 
Option was granted, as determined according to the closing price of the Class B
Stock on such business day.

Section 2.3 - No Additional Rights

     Nothing in this Agreement or in the Plan shall confer upon the Optionee any
right to continue to serve as a Director of the Company or shall interfere with
or restrict in any way the right which is hereby expressly reserved, to remove
the Optionee as a Director in accordance with the By-laws and Restated
Certificate of Incorporation of the Company and applicable law.

Section 2.4 - Adjustments in Option

     In the event that the outstanding shares of Class B Stock are changed into
or exchanged for a different number or kind of shares of the Company or other
securities of the Company by reason of merger, consolidation, recapitalization,

                                      2 
<PAGE>
 
reclassification, stock split, stock dividend or combination of shares, the 
Committee shall make an appropriate and equitable adjustment in the number and 
kind of shares as to which the Option, or portions thereof then unexercised, 
shall be exercisable, so that the Optionee's proportionate interest shall be 
maintained. Such adjustment in the Option shall be made without change in the 
total price applicable to the unexercised portion of the Option (except for any 
change in the aggregate price resulting from rounding-off of share quantities or
prices) and with any necessary corresponding adjustment in the Option price per 
share. Any such adjustment made by the Committee shall be final and binding upon
the Optionee, the Company and all other interested persons.

                                  ARTICLE III

                           PERIOD OF EXERCISABILITY
                           ------------------------

Section 3.1 - Commencement of Exercisability

              a.  Subject to Section 3.1(b), the Option shall become exercisable
              in four (4) cumulative installments as follows:

                  (i)  The first installment shall consist of twenty-five
              percent (25%) of the shares covered by the Option and shall become
              exercisable twelve (12) months after November 13, 1996.

                  (ii)  The second installment shall consist of twenty-five
              percent (25%) of the shares covered by the Option and shall become
              exercisable twenty-four (24) months after November 13, 1996.

                  (iii) The third installment shall consist of twenty-five
              percent (25%) of the shares covered by the Option and shall become
              exercisable thirty-six (36) months after November 13, 1996.

                   (iv) The fourth installment shall consist of twenty-five
              percent (25%) of the shares covered by the Option and shall become
              exercisable forty-eight (48) months after November 13, 1996.

              b.   No portion of the Option which is unexercisable at
              Termination of Service shall thereafter become exercisable.

Section 3.2 - Duration of Exercisability

              The installments provided for in Section 3.1 are cumulative. As
each such installment becomes exercisable it shall remain exercisable until it
becomes unexercisable under the terms of Section 3.3.

                                      3 
<PAGE>
 
Section 3.3 - Expiration of Option
 
              The Option may be exercised any time until the first of the 
following events:

              a.  Ten (10) years from the date the Option was granted if the 
              Optionee is still a Director of the Company.

              b.  Three (3) months after the Optionee's Termination of Service
              if such Termination of Service results from (i) Optionee's
              retirement, or (ii) Optionee's removal from the Board other than
              for cause.

              c.  The effective date of (i) removal of Optionee from the Board
              for cause, (ii) the Optionee's resignation from the Board, or
              (iii) a "Change of Control" described in clauses (iv) and (v) of
              the definition of such term set forth in Section 3.4 hereof.
              
              d.  One (1) year after the date on which the Optionee ceases to be
              a Director of the Company by reason of having become disabled
              (within the meaning of Section 22(e)(3) of the Code); provided,
              however, that this subsection (d) shall not apply if the Optionee
              dies prior to the expiration of such one (1) year period.

              e.  One (1) year from the date of the Optionee's death.

Section 3.4 - Acceleration of Exercisability

              In the event there is a "Change of Control" (as hereinafter
defined), the Optionee shall have the right to exercise the Option with respect
to all shares covered by the Option held by Optionee.

              In the event of any Change of Control described in clauses (iv) or
(v) below, if the Option has then neither been fully exercised nor become
unexercisable under Section 3.1, this Option shall be exercisable as to all
shares covered hereby during the period commencing ninety (90) days prior to the
scheduled effective date of any such Change in Control and ending on the day
immediately preceding the effective date of such Change in Control; provided
that any exercise of any Option so accelerated shall be conditioned upon the
consummation of the contemplated corporate transaction.

              For purposes of this Agreement, the term "Change of Control" means
the occurrence of any of the following events:

                  (i)  except pursuant to a transaction described in the proviso
              to Section 3.4(iv) or (v), Hugh M. Hefner and Christie Hefner
              cease collectively to hold over 50% of the combined voting power
              of the then-

                                       4












 













 
<PAGE>
 
             outstanding securities entitled to vote generally in the election 
             of Directors of the Company ("Voting Stock");
 
                  (ii)  except pursuant to a transaction described in the
             proviso to Section 3.4(iv) or (v), a sale, exchange or other
             disposition of PLAYBOY Magazine;

                  (iii) except pursuant to a transaction described in the 
             proviso to Section 3.4(iv) or (v), the liquidation or dissolution
             of the Company;

                  (iv)  The Company is merged, consolidated or reorganized into
             or with another corporation or other legal person; provided,
             however, that no such merger, consolidation or reorganization will
             constitute a Change of Control if (x) the merger, consolidation or
             reorganization is initiated by the Company, (y) as a result of such
             merger, consolidation or reorganization not less than a majority of
             the combined voting power of the then-outstanding securities of the
             surviving, resulting or ultimate parent corporation, as the case
             may be, immediately after such transaction is held in the aggregate
             by persons who held not less than a majority of the combined voting
             power of the outstanding Voting Stock of the Company immediately
             prior to such transaction, and (z) in connection with such a
             transaction, provision is made for an assumption of this Option or
             a substitution hereof with a new option in the surviving, resulting
             or ultimate parent corporation, as the case may be, of
             substantially equivalent value; or

                  (v)  The Company sells or otherwise transfers all or 
             substantially all of its assets to another corporation or other
             legal person; provided, however, that no such sale or transfer will
             constitute a Change of Control if (w) the sale or transfer is
             initiated by the Company, (x) as a result of such sale or transfer
             not less than a majority of the combined voting power of the then-
             outstanding securities of such corporation or other legal person,
             as the case may be, immediately after such sale or transfer is held
             in the aggregate by persons who held not less than a majority of
             the combined voting power of the outstanding Voting Stock of the
             Company immediately prior to such sale or transfer, and (z) in
             connection with such a transaction, provision is made for an
             assumption of this Option or a substitution hereof with a new
             option in such corporation or other legal person, as the case may
             be, of substantially equivalent value.

             For purposes of this Section 3.4, any Voting Stock beneficially
owned (as such term is defined under Rule 13d-3 or any successor rule or
regulation under the Securities Exchange Act of 1934, as amended) by the Hugh M.
Hefner Foundation shall be deemed to be held by Christie Hefner if and so long
as she has sole voting power with respect to such Voting Stock.

                                       5
<PAGE>
 
                                  ARTICLE IV

                              EXERCISE OF OPTION
                              ------------------

Section 4.1 - Person Eligible to Exercise
              ---------------------------

          a.   Except as may be otherwise determined by the Committee, during 
the lifetime of the Optionee, only he or she may exercise the Option or any 
portion thereof. If the Optionee dies, any exercisable portion of the Option 
may, within the time frame allowed, be exercised by his or her personal 
representative or by any person empowered to do so under the Optionee's will or 
under the then applicable laws of descent and distribution.

          b.   Should the Optionee be determined under applicable law to have 
become a disabled person or the equivalent thereof, the Option may, prior to the
time when the Option becomes unexercisable under this Agreement, be exercised by
the Optionee's guardian or by any other person empowered to do so under 
applicable laws of guardianship.

          For purposes of this Section 4.1, "disabled person" shall mean a
person who (i) because of mental deterioration or physical incapacity is not
fully able to manage his person or estate or (ii) is mentally ill and who
because of his mental illness is not fully able to manage his person or estate.

Section 4.2 - Partial Exercise
              ----------------

          Any exercisable portion of the Option may be exercised in whole or in 
part at any time during the time frame allowed; provided, however, that each 
partial exercise shall be for whole shares only.

Section 4.3 - Manner of Exercise
              ------------------

          The Option, or any exercisable portion thereof, must be exercised by 
delivery to the Secretary or his office of:

          a.   Notice in writing signed by the Optionee (or other person then
          entitled to exercise the Option) that the Option or portion thereof is
          being exercised; and

          b.   Payment in full for the exercised shares:

               (i)  In cash or by certified or cashier's check; or

               (ii) In shares of Class B Stock owned by the Optionee, duly
               endorsed for transfer to the Company. Such shares will be
               credited at the fair market value on the date of delivery; or


                                       6


<PAGE>
 
               (iii) Any combination of the consideration provided in the 
          foregoing subparagraphs (i) and (ii); and

          c.   Such representations and documents as are necessary or advisable
          to effect compliance with all applicable provisions of the Securities
          Act and other federal or state securities laws or regulations; and

          d.   Appropriate proof of the right of such person or persons to
          exercise the Option in the event the Option or portion shall be
          exercised pursuant to Section 4.1 by any person or persons other than
          the Optionee; and

          e.   Full payment to the Company of all amounts which, under federal,
          state or local law, it is required to withhold upon exercise of the
          Option.

Section 4.4 - Share Certificates

          The shares of stock deliverable upon the exercise of the Option shall 
be fully paid and non-assessable.

          The Company shall not be required to issue or deliver any certificate 
or certificates for shares for stock purchased upon the exercise of the Option 
or portion thereof prior to fulfillment of all of the following conditions:

          a.   The completion of any registration or other qualification of such
shares under any state or federal law or under rulings or regulations of the 
Securities and Exchange Commission or of any other governmental regulatory body,
which may be necessary or advisable; and

          b.   The obtaining of any approval or other clearance from any state 
or federal governmental agency which may be necessary or advisable; and

          c.   The payment to the Company of all amounts which, under federal, 
state or local law, it is required to withhold upon exercise of the Option.

Section 4.5 - Rights as Stockholder

          The holder of the Option shall not be, nor have any of the rights or 
privileges of, a holder of the Company's Class B Stock in respect of any shares 
purchasable upon the exercise of any part of the Option unless and until 
certificates representing such shares shall have been issued by the Company to 
such holder.

                                       7





<PAGE>
 
                                   ARTICLE V

                               OTHER PROVISIONS
                               ----------------

Section 5.1 - Administration

     The Committee shall have the power to interpret this Agreement and to adopt
rules for its administration. All actions taken and all interpretations and 
determinations made by the Committee in good faith shall be final and binding 
upon the Optionee, the Company and all other interested persons. No member of
the Committee shall be personally liable for any action, determination or
interpretation made in good faith with respect to the Option.

Section 5.2 - Option Not Transferable

     Except as may be determined by the Committee, neither the Option nor any 
interest or right therein or part thereof shall be liable for the debts,
contracts or engagements of the Optionee or his successors in interest or shall
be subject to disposition by transfer, alienation, anticipation, pledge,
encumbrance, assignment or any other means whether such disposition be voluntary
or involuntary or by operation of law by judgment, levy, attachment, garnishment
or any other legal or equitable proceedings (including bankruptcy), and any
attempted disposition thereof shall be null and void and of no effect; provided,
however, that this Section 5.2 shall not prevent transfers by will or by the
applicable laws of descent and distribution.

Section 5.3 - Modification of Option

     The Option is subject in all events to the condition that, if at any time 
the Board shall determine, in its discretion, that the listing, registration or
qualification of any of the Company's securities upon any securities exchange or
under any law, regulation or other requirement of any governmental authority is
necessary or desirable, or that any consent or approval from any governmental
authority or compliance of the Option with any law or regulation of any such
authority is necessary or desirable, then the Board may modify the terms of the
Option, without the consent of the Optionee, in any manner which the Board deems
necessary or desirable in order to improve the Company's ability to obtain such
listing, registration, qualification, consent, approval or compliance. Without
limitation of the foregoing, to the extent required for compliance with the
provisions of Rule 16b-3 promulgated under the Securities Exchange Act of 1934,
as amended, the Board may provide for restrictions on the sale or transfer of
any shares acquired upon exercise of this Option.

Section 5.4 - Notices

     Any notice to be given under the terms of this Agreement will be by 
registered mail, return receipt requested and if to the Company shall be 
addressed in care of its Secretary at 680 N. Lake Shore Drive, Chicago, Illinois
60611, and if to the

                                       8


<PAGE>
 
Optionee shall be addressed to him at the address given beneath his signature
hereto. By a notice given pursuant to the Section 5.4, either party may
hereafter designate a different address for notices to be given him. Any notice
which is required to be given to the Optionee shall, if the Optionee is then
deceased, be given to the Optionee's personal representative if such
representative has previously informed the Company of his status and address
by written notice under this Section 5.4. Any notice shall be deemed duly given
when delivered or, except in connection with notice of exercise under Section
4.3, at such time as delivery is attempted.

Section 5.5 - Construction

          This Agreement shall be administered, interpreted and enforced under 
the laws of the State of Delaware.

Section 5.6 - No Additional Rights

          Nothing in this Option shall confer upon the Optionee any right to 
continue to serve as a Director or shall interfere with or restrict in any way 
the right, which right is hereby expressly reserved, to remove the Optionee as a
Director in accordance with the By-laws and Certificate of Incorporation of the
Company and applicable law.

Section 5.7 - No Obligation to Register

          The Company shall not be deemed, by reason of the granting of this 
Option, to have any obligation to register the shares of Class B Stock subject 
to this Option under the Securities Act or to maintain in effect any 
registration of such shares which may be made at any time under the Securities 
Act.

                                       9
<PAGE>
 
          IN WITNESS WHEREOF, this Agreement has been executed and delivered by 
the parties hereto.

                                              PLAYBOY ENTERPRISES, INC.




                                              By:  /s/ Howard Shapiro
                                                   -----------------------------
                                                   Authorized Representative
                                                   680 N. Lake Shore Drive
                                                   Chicago, Illinois 60611


/s/ Sol Rosenthal
- -----------------------------
    Sol Rosenthal


441 North Barrington Ave.
- -----------------------------
Los Angeles, CA 90049
- -----------------------------
       Address

Optionee's Taxpayer
Identification Number:

###-##-####
- -----------------------------

                                      10

<PAGE>
 
                                                                     Exhibit 5.1


                     [LETTERHEAD OF HOWARD SHAPIRO, ESQ.]


                                 June 27, 1997



SECURITIES AND EXCHANGE COMMISSION
450 Fifth Street, N.W.
Washington, D.C.  20549

Ladies and Gentlemen:

     I am the Executive Vice President, Law and Administration, General Counsel
and Secretary to Playboy Enterprises, Inc., a Delaware corporation (the
"Company"), and have acted as counsel to the Company in connection with the
issuance of up to 20,000 shares (the "Shares") of the Company's Class B Common
Stock, $.01 par value, issuable upon exercise of the Non-qualified Stock Option
Agreements dated November 13, 1996, between the Company and each of Dennis S.
Bookshester and Sol Rosenthal (the "Agreements") pursuant to a Registration
Statement on Form S-8, filed by the Company with the Securities and Exchange
Commission on the date hereof (the "Registration Statement").

     I am familiar with the proceedings taken and to be taken by the Company in
connection with the authorization, issuance and sale of the Shares, and for the
purposes of this opinion, have assumed such proceedings will be timely completed
in the manner presently proposed.  In addition, I have examined such documents
and such questions of law and fact, including an examination of originals or
copies certified or otherwise identified to my satisfaction of such documents,
corporate records and instruments as I have deemed necessary or appropriate for
purposes of this opinion.

     Based on the foregoing, it is my opinion that the Shares to be issued and
sold pursuant to the Agreements have been duly authorized, and that such Shares,
when issued and sold pursuant to any exercise of the Agreements in accordance
with the terms thereof, will be validly issued, fully paid and nonassessable.

     I hereby consent to the filing of this opinion as an exhibit to the
Registration Statement.

                                        Respectfully submitted,

                                        /s/ Howard Shapiro

                                        Howard Shapiro, Esq.


<PAGE>
 
                                                                    Exhibit 23.1


                   CONSENT OF INDEPENDENT PUBLIC ACCOUNTANTS
                   -----------------------------------------


We consent to the incorporation by reference in the registration statement of
Playboy Enterprises, Inc. on Form S-8 relating to the Non-qualified Stock Option
Agreements dated November 13, 1996, between Playboy Enterprises, Inc. and each
of Dennis S. Bookshester and Sol Rosenthal of our report dated August 1, 1996,
on our audits of the consolidated financial statements and financial statement
schedule of Playboy Enterprises, Inc. as of June 30, 1996 and 1995 and for each
of the three years in the period ended June 30, 1996, which report is
incorporated by reference into the Annual Report on Form 10-K.



                                        /s/ COOPERS & LYBRAND L.L.P.


Chicago, Illinois
June 27, 1997


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