THIS IS THE AMENDED AND RESTATED DEBENTURE WHICH HAS BEEN ISSUED PURSUANT
TO AN AMENDMENT TO DEBENTURE AGREEMENT (THE "DEBENTURE AMENDMENT") DATED
SEPTEMBER 29, 2004 BETWEEN HOLLYWOOD MEDIA CORP. AND PORTSIDE GROWTH &
OPPORTUNITY FUND LTD.
THE SECURITIES REPRESENTED HEREBY HAVE NOT BEEN REGISTERED UNDER THE
SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE
SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED IN THE
ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR THE SECURITIES UNDER
THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS OR
(B) AN OPINION OF COUNSEL, REASONABLY SATISFACTORY TO THE COMPANY, THAT
REGISTRATION IS NOT REQUIRED UNDER SAID ACT OR APPLICABLE STATE SECURITIES
LAWS. THE SECURITIES MAY BE PLEDGED IN CONNECTION WITH A BONA FIDE MARGIN
ACCOUNT OR OTHER LOAN SECURED BY THE SECURITIES.
THE FOLLOWING INFORMATION IS PROVIDED SOLELY FOR PURPOSES OF APPLYING THE
U.S. FEDERAL INCOME TAX ORIGINAL ISSUE DISCOUNT ("OID") RULES TO THIS DEBENTURE.
THIS DEBENTURE HAS AN ISSUE PRICE OF $955,491.36, AN AGGREGATE AMOUNT OF OID OF
$44,508.64, AN ISSUE DATE OF MAY 22, 2002 AND A YIELD TO MATURITY OF 7.689%.
No. 2 $1,000,000.00
HOLLYWOOD MEDIA CORP.
6% SENIOR CONVERTIBLE DEBENTURE DUE MAY 22, 2006
THIS DEBENTURE (this "Debenture") is one of a duly authorized issue of Debentures of HOLLYWOOD
MEDIA CORP., a corporation duly organized and existing under the laws of the State of Florida (the
"Company"), designated as its 6% Senior Convertible Debentures Due May 22, 2005 (although this amended
and restated Debenture has been amended such that it is due May 22, 2006, as provided herein), in an aggregate
principal amount of up to Five Million, Seven Hundred Thousand U.S. Dollars (U.S. $5,700,000) (the
FOR VALUE RECEIVED, the Company promises to pay to Portside Growth & Opportunity Fund Ltd., the
holder hereof, or its registered assigns (the "Holder"), the principal sum of One Million