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