Sean Penn

Character: Emmet Ray

Samantha Morton

Character: Hattie

Anthony LaPaglia

Character: Al Torrio

Uma Thurman

Character: Blanche Williams

James Urbaniak

Character: Harry

John Waters

Character: Mr. Haynes

Gretchen Mol

Character: Ellie

Denis O'Hare

Character: Jake

Molly Price

Character: Ann

Brian Markinson

Character: Bill Shields

Tony Darrow

Character: Ben

Daniel Okrent

Character: A.J. Pickman

Brad Garrett

Character: Joe Bedloe

Kaili Vernoff

Character: Gracie

Woody Allen

Character: Himself

Ben Duncan (DJ)

Character: Himself

Nat Hentoff

Character: Himself

Douglas McGrath

Character: Himself

Dan Moran

Character: Boss

Chris Bauer

Character: Ace

Darryl Alan Reed

Character: Don

Constance Shulman

Character: Hazel

Kellie Overbey

Character: Iris

Katie Hamill

Character: Mary

Lola Pashalinski

Character: Blanche's Friend

Steve Bargonetti

Character: Musician Friend

Benjamin Franklin Brown

Character: Musician Friend

Marc Damon Johnson

Character: Omer

Ron Cephas Jones

Character: Alvin

Vince Giordano

Character: Bass Player #1

Emme Kemp

Character: Jam Session Musician

Clark Gayton

Character: Jam Session Musician

Marcus McLaurine

Character: Jam Session Musician

Carolyn Saxon

Character: Phyliss

Drummond Erskine

Character: First Hobo

Joe Ambrose

Character: Second Hobo

Joseph Rigano

Character: Stagehand

Dennis Stein

Character: Dick Ruth

Carole Bayeux

Character: Rita

Paula Parrish

Character: Party Guest

Cory Solar

Character: Party Guest

Lexi Egz

Character: Party Guest

Yvette Mercedes

Character: Party Guest

Peter Leung

Character: Party Guest

William Addy

Character: Master of Ceremonies

Dick Monday

Character: Chester Weems

Mary Stout

Character: Felicity Thomson

Dick Mingalone

Character: Birdman

Mr. Spoons

Character: Spoon Player

Carol Woods

Character: Helen Minton

Josh Mowery

Character: Movie Director

Fred Goehner

Character: William Weston

Eddy Davis

Character: Bass Player #2

Vincent Guastaferro

Character: Sid Bishop

Ralph Pope

Character: Panhandler

Jerome Richardson

Character: Club Musician

Earl P. McIntyre

Character: Club Musician

James Williams

Character: Club Musician

Frank Wess

Character: Club Musician

Al Bryant

Character: Club Musician

Ray Garvey

Character: Club Manager

Sally Placksin

Character: Sally Jillian

Simon Wettenhall

Character: Jam Session Musician

Orange Kellin

Character: Jam Session Musician

Brooks Giles III

Character: Jam Session Musician

Alfred Sauchelli, Jr.

Character: Ned

Michael Peter Bolus

Character: Lynch

Mick O'Rourke

Character: Holdup Man

John P. 'Jack' McLaughlin

Character: Holdup Man

Chuck Lewkowicz

Character: Police Officer

Rick Mowat

Character: Flat Tire Man

Ted Wilkins

Character: Gas Station Proprietor

Michael Sprague

Character: Django Reinhardt