Sean Penn as Emmet Ray

Samantha Morton as Hattie

Anthony LaPaglia as Al Torrio

Uma Thurman as Blanche Williams

James Urbaniak as Harry

John Waters as Mr. Haynes

Gretchen Mol as Ellie

Denis O'Hare as Jake

Molly Price as Ann

Brian Markinson as Bill Shields

Tony Darrow as Ben

Daniel Okrent as A.J. Pickman

Brad Garrett as Joe Bedloe

Kaili Vernoff as Gracie

Woody Allen as Himself

Ben Duncan (DJ) as Himself

Nat Hentoff as Himself

Douglas McGrath as Himself

Dan Moran as Boss

Chris Bauer as Ace

Darryl Alan Reed as Don

Constance Shulman as Hazel

Kellie Overbey as Iris

Katie Hamill as Mary

Lola Pashalinski as Blanche's Friend

Steve Bargonetti as Musician Friend

Benjamin Franklin Brown as Musician Friend

Marc Damon Johnson as Omer

Ron Cephas Jones as Alvin

Vince Giordano as Bass Player #1

Emme Kemp as Jam Session Musician

Clark Gayton as Jam Session Musician

Marcus McLaurine as Jam Session Musician

Carolyn Saxon as Phyliss

Drummond Erskine as First Hobo

Joe Ambrose as Second Hobo

Joseph Rigano as Stagehand

Dennis Stein as Dick Ruth

Carole Bayeux as Rita

Paula Parrish as Party Guest

Cory Solar as Party Guest

Lexi Egz as Party Guest

Yvette Mercedes as Party Guest

Peter Leung as Party Guest

William Addy as Master of Ceremonies

Dick Monday as Chester Weems

Mary Stout as Felicity Thomson

Dick Mingalone as Birdman

Mr. Spoons as Spoon Player

Carol Woods as Helen Minton

Josh Mowery as Movie Director

Fred Goehner as William Weston

Eddy Davis as Bass Player #2

Vincent Guastaferro as Sid Bishop

Ralph Pope as Panhandler

Jerome Richardson as Club Musician

Earl P. McIntyre as Club Musician

James Williams as Club Musician

Frank Wess as Club Musician

Al Bryant as Club Musician

Ray Garvey as Club Manager

Sally Placksin as Sally Jillian

Simon Wettenhall as Jam Session Musician

Orange Kellin as Jam Session Musician

Brooks Giles III as Jam Session Musician

Alfred Sauchelli, Jr. as Ned

Michael Peter Bolus as Lynch

Mick O'Rourke as Holdup Man

John Patrick McLaughlin as Holdup Man

Chuck Lewkowicz as Police Officer

Rick Mowat as Flat Tire Man

Ted Wilkins as Gas Station Proprietor

Michael Sprague as Django Reinhardt