Roy Dillon

John Cusack

Lilly Dillon

Anjelica Huston

Myra Langtry

Annette Bening

Guy in bar

Jan Munroe

Irv

Michael Laskin

Bobo Justus

Pat Hingle

Cole

J.T. Walsh

Racetrack Announcer

Robert Weems

Joe

Gailard Sartain

Jeweler

Stephen Tobolowsky

Gloucester Hebbing

Charles Napier

Bartender

Jimmy Noonan

Simms

Henry Jones

Cop

Richard Holden

FBI Man

Ray Sharkey

Mintz

Eddie Jones

Maid

Ivette Soler

Doctor

Sandy Baron

Nurse

Lou Hancock

Mintz

Ed Jones

Nurse Carol Flynn

Noelle Harling

Lieutenant Pierson

Xander Berkeley

Dealer

Michael Greene

Sailor - Young Paul

Paul Adelstein

Shill

Jason Ronard

Sailor - Freshman

Jeremy Piven

Roper

John Drew Barrymore

Sailor - Spooney

Gregory Sporleder

Sailor - Stinky

David Sinaiko

Young Lilly (uncredited)

Juliet Landau

Drunk

Jeff Perry

Drunk's Friend

Jon Gries

Roy (age 5)

Bradley Pierce

Waitress

Micole Mercurio

Roy (age 8)

Ashton Buzamat

Clerk

Jack McGee

2nd Clerk

Ron Campbell

Vickie the Receptionist

Teresa Gilmore

Receptionist 2

Elizabeth Ann Feeley

Kaggs

Steve Buscemi

FBI Man

Billy Ray Sharkey

Arizona Motel Clerk

Frances Bay

3rd Soldier

Gregory Sporlader

Bartender (uncredited)

John Gillespie

Cab Driver (uncredited)

Sy Richardson

Opening voice-over (uncredited)

Martin Scorsese

1st Beachgoer

Trisha King

Racetrack Announcer

Robert J. Weems

Juliet Taylor*

Victoria Thomas

Receptionist 1

Teresa Gilmore Capps