Exhibit 10.1

                        AMENDMENT TO DEBENTURE AGREEMENT


     THIS AGREEMENT (this "AGREEMENT"), is made and entered into as of September
29, 2004, by and between HOLLYWOOD MEDIA CORP., a Florida corporation (the
"COMPANY"), and PORTSIDE GROWTH & OPPORTUNITY FUND LTD. ("HOLDER").

                                   WITNESSETH:

     WHEREAS, Holder is the registered holder of the Company's "6% Senior
Convertible Debenture Due May 22, 2005" in the principal amount of $1,000,000
issued under Certificate No. 2, dated as of May 22, 2002 (the "DEBENTURE"),
which Debenture by its terms is convertible into shares of common stock, par
value $0.01, of the Company ("COMMON STOCK").

     WHEREAS, the Debenture Certificate recites that as of the date of issuance
of the Debenture to Holder the Debenture was convertible based on a Conversion
Price of $3.46 per share, however, as a result of certain antidilution
adjustments under the terms of the Debenture in connection with the Company's
private placement in February 2004, the Conversion Price was reduced to $3.30
per share.

     WHEREAS, the Debenture was purchased by the Holder pursuant to a Securities
Purchase Agreement dated as of May 22, 2002 (the "Purchase Agreement") among the
Company, the Holder and other purchasers.

     WHEREAS, the parties hereto desire to hereby amend the Debenture upon the
terms and agreements provided herein.

     NOW, THEREFORE, in consideration of the mutual covenants and agreements
contained herein, the parties, intending to be legally bound, hereby
acknowledge, confirm and agree as follows:

     1.   Notwithstanding anything to the contrary in the Debenture or the
          Purchase Agreement, the Company and Holder hereby agree that:

          a.   The Debenture is hereby amended such that the May 22, 2005
               "Maturity Date" of the Debenture (as defined therein, which date
               is subject to extension as provided therein), is hereby changed
               and extended from May 22, 2005 to May 22, 2006.

          b.   The current Conversion Price of the Debenture, as adjusted, is
               hereby amended and changed from $3.30 per share to $3.20 per
               share as of the date hereof, and the Debenture is hereby amended
               accordingly.

          c.   Sections 24 and 25 of the Debenture (and the related Exhibit A to
               the Debenture) and all of the terms and provisions thereof are
               hereby deleted and removed in their entirety from the Debenture
               and shall cease to have any force and effect; it being agreed
               that the Debenture is hereby amended to remove such portions of


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               the Debenture, and further agreed that the Holder shall promptly
               deliver the existing original Debenture document (or affidavit of
               lost certificate in customary form) to the Company and the
               Company shall thereupon promptly execute and deliver (with
               delivery no later than 5 business days following receipt thereof)
               to Holder a new Debenture containing the amendments thereto as
               agreed in this Agreement (and further agreed that the Holder
               shall not assign or transfer the Debenture prior to receiving
               such amended Debenture).

          d.   The Holder hereby waives Section 4(o) of the Purchase Agreement
               and any and all rights of the Holder and restrictions on the
               Company thereunder, and the parties further agree that the
               Purchase Agreement is hereby amended to remove and delete Section
               4(o) in its entirety from the Purchase Agreement.

     2.   This Agreement shall be governed by and construed and enforced in
          accordance with the laws of the state of New York. This Agreement
          constitutes the entire understanding and agreement between the parties
          hereto with respect to the subject matter hereof.

     3.   This Agreement may be executed in any number of counterparts, each of
          which shall be enforceable against the parties actually executing such
          counterparts, and all of which together shall constitute one
          instrument.

     IN WITNESS WHEREOF, the undersigned parties have executed this AMENDMENT TO
DEBENTURE AGREEMENT as of the day and year first above written.



HOLLYWOOD MEDIA CORP.                   PORTSIDE GROWTH & OPPORTUNITY FUND LTD.


By: /s/ Mitchell Rubenstein             By: /s/ Jeff Solomon
    -----------------------                 ----------------
Name:   Mitchell Rubenstein             Name:   Jeff Solomon
Title:  Chief Executive Officer         Title:  Managing Member


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