John Cusack

Roy Dillon

Stephen Tobolowsky

Jeweler

Anjelica Huston

Lilly Dillon

Jeremy Piven

Sailor - Freshman

Pat Hingle

Bobo Justus

Stephen Frears

Director

Gailard Sartain

Joe

Jan Munroe

Guy in bar

Henry Jones

Sims

Jeff Perry

Drunk

Lou Hancock

Nurse

Barbara De Fina

Executive Producer

Gregory Sporleder

Sailor - Spooney

Annette Bening

Myra Langtry

Jon Gries

Drunk's Friend

Micole Mercurio

Waitress

Jimmy Noonan

Bartender

Paul Adelstein

Sailor - Young Paul

Michael Laskin

Irv

Richard Holden

Cop

Eddie Jones

Mintz

Robert Weems

Racetrack Announcer

Sandy Baron

Doctor

Noelle Harling

Nurse Carol Flynn

Ivette Soler

Maid

David Sinaiko

Sailor - Stinky