Sean Penn

Henry 'Hopper' Nash

Nicolas Cage

Nicky / Bud

Elizabeth McGovern

Caddie Winger

John Karlen

Mr. Nash

Rutanya Alda

Mrs. Nash

Max Showalter

Mr. Arthur, Piano Teacher

Crispin Glover

Gatsby Boy

Barbara Howard

Gatsby Girl

Bob Maroff

Al

Carol Kane

Annie the Hooker

Dominic Nardini

Soldier with Annie

John Brandon

Mr. Kaiser

Eve Brent

Mrs. Kaiser

Suzanne Adkinson

Sally Kaiser

Shawn Schepps

Gretchen

Charles Miller

Arnie

Patricia Allison

Mrs. Spangler

Al Hopson

Elmer

Ted Grossman

Skating Soldier

Scott McGinnis

Michael

Brian Trumbull

Kid in Skating Rink

Kate Williamson

Mrs. Winger

Julie Philips

Alice Donnelly

Fielding Greaves

Mr. Donnelly

Arnold Johnson

Tattoo Artist

Kevin Fraser

Marine

Gerry Gibson

High School Principal

Page Hannah

High School Girl

Shane Kerwin

R.D.

Jonathan Charles Fox

Arnold Billings

Michael Madsen

Frank

Dana Carvey

Baby Face

Victor Rendina

Mr. Luzzato

Rebecca Pollack

Girl in Bowling Alley

Victor Paul

Pool Hall Barman

Lou Butera

A Pool Player

Michael Talbott

Bill

Phil Adams

Bill's Shipmate

Chuck Picerni Jr.

Bill's Shipmate

Philip Romano

Bill's Shipmate

Arlin Miller

Minister at Funeral (voice)

Jan Rabson

Sailor (voice)

Walter Mathews

Sailor (voice)

Michael Schoeffling

Amputee Soldier (uncredited)

Steven Lambert

Bit Part (uncredited)