Anjelica Huston

Lilly Dillon

John Cusack

Roy Dillon

Annette Bening

Myra Langtry

Jan Munroe

Guy in bar

Robert Weems

Racetrack Announcer

Stephen Tobolowsky

Jeweler

Jimmy Noonan

Bartender

Richard Holden

Cop

Henry Jones

Sims

Michael Laskin

Irv

Eddie Jones

Mintz

Sandy Baron

Doctor

Lou Hancock

Nurse

Gailard Sartain

Joe

Noelle Harling

Nurse Carol Flynn

Ivette Soler

Maid

Pat Hingle

Bobo Justus

Paul Adelstein

Sailor - Young Paul

Jeremy Piven

Sailor - Freshman

Gregory Sporleder

Sailor - Spooney

David Sinaiko

Sailor - Stinky

Jeff Perry

Drunk

Jon Gries

Drunk's Friend

Micole Mercurio

Waitress

Charles Napier

Gloucester Hebbing

J.T. Walsh

Cole

Teresa Gilmore

Receptionist 1

Elizabeth Ann Feeley

Receptionist 2

Billy Ray Sharkey

FBI man

Frances Bay

Arizona Motel Clerk

Xander Berkeley

Lt. Pierson

John Gillespie

Bartender (uncredited)

Juliet Landau

Young Lilly (uncredited)

Sy Richardson

Cab Driver (uncredited)

Martin Scorsese

Opening voice-over (uncredited)