AGREEMENT TO CONVERT DEBENTURE
THIS AGREEMENT (this "AGREEMENT"), is made and entered into as of August 30, 2004, by and between
Hollywood Media Corp., a Florida corporation (the "COMPANY"), and Leonardo, L.P. ("HOLDER").
WHEREAS, Holder is the registered holder of the Company's "6% Senior Convertible Debenture Due May 22,
2005" in the principal amount of $3,000,000 issued under Certificate No. 1, 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 parties hereto desire to agree to convert the Debenture upon the terms and agreements
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, it is agreed that the Debenture shall automatically
convert and be converted in full into shares of Common Stock, on the terms provided below, on and as of any
one date to be selected by Holder (as evidenced by delivery of a Conversion Notice in the form attached hereto
I) from among the days in the period commencing with the date hereof through December 31, 2004, provided,
however, that if no such date is selected then such conversion shall automatically occur on and be effective as of
12:00 Noon (EST) on December 31, 2004 assuming that on such date the Company's Registration Statement on
Form S-3 (SEC File No. 333-91090) registering the resale of