Jason Biggs as Jerry Falk

Christina Ricci as Amanda Chase

Woody Allen as David Dobel

Stockard Channing as Paula Chase

Danny DeVito as Harvey Wexler

Jimmy Fallon as Bob

Anthony Arkin as Pip's Comic

David Conrad as Dr. Phil Reed

Adrian Grenier as Ray Polito

William Hill as Psychiatrist

Erica Leerhsen as Connie

Fisher Stevens as Manager

Joseph Lyle Taylor as Bill

KaDee Strickland as Brooke

Diana Krall as Diana Krall

Maurice Sonnenberg as Movie Theater Patron

Kenneth Edelson as Hotel Desk Clerk

Wynter Kullman as Emily

Zach McLarty as Ralph

Anthony J. Ribustello as Car Thug #1

Ray Garvey as Car Thug #2

Ralph Pope as Cab Driver

James Babbin as Movie Patron (uncredited)

Carson Grant as Ron Keller, Acting Teacher (uncredited)