Joe Pesci as Simon Wilder

Brendan Fraser as Montgomery 'Monty' Kessler

Moira Kelly as Courtney Blumenthal

Patrick Dempsey as Everett Calloway

Josh Hamilton as Jeffrey Hawks

Gore Vidal as Prof. Pitkannan

Deborah Lake Fortson as Homeless Woman

Marshall Hambro as Chuck, Security Guard

Melinda Chilton as Helga

Harve Kolzow as Harvard Cop

James Deuter as Judge

Caroline Gibson as Donation Student

Mara Brock Akil as Ms. Moore

Clebert Ford as Homeless Man

M. Lynda Robinson as Newspaper Purchaser #1

Richard Auguste as Newspaper Purchaser #2

Patricia B. Butcher as Librarian

William Ashby King as Church Custodian

Frank J. Tieri as Homeless Man #2

Rick LeFevour as Mailman

Sunshine H. Hernandez as Marilyn Monroe

Monica Rochman as Sophomore

Claudia Haro as Marty

Daniel Blinkoff as Frank Wilder