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Sean Penn Emmet Ray Samantha Morton Hattie Anthony LaPaglia Al Torrio Uma Thurman Blanche Williams James Urbaniak Harry John Waters Mr. Haynes Gretchen Mol Ellie Denis O'Hare Jake Molly Price Ann Brian Markinson Bill Shields Tony Darrow Ben Daniel Okrent A.J. Pickman Brad Garrett Joe Bedloe Kaili Vernoff Gracie Woody Allen Himself Ben Duncan (DJ) Himself Nat Hentoff Himself Douglas McGrath Himself Dan Moran Boss Chris Bauer Ace Darryl Alan Reed Don Constance Shulman Hazel Kellie Overbey Iris Katie Hamill Mary Lola Pashalinski Blanche's Friend Steve Bargonetti Musician Friend Benjamin Franklin Brown Musician Friend Marc Damon Johnson Omer Ron Cephas Jones Alvin Vince Giordano Bass Player #1 Emme Kemp Jam Session Musician Clark Gayton Jam Session Musician Marcus McLaurine Jam Session Musician Carolyn Saxon Phyliss Drummond Erskine First Hobo Joe Ambrose Second Hobo Joseph Rigano Stagehand Dennis Stein Dick Ruth Carole Bayeux Rita Paula Parrish Party Guest Cory Solar Party Guest Lexi Egz Party Guest Yvette Mercedes Party Guest Peter Leung Party Guest William Addy Master of Ceremonies Dick Monday Chester Weems Mary Stout Felicity Thomson Dick Mingalone Birdman Mr. Spoons Spoon Player Carol Woods Helen Minton Josh Mowery Movie Director Fred Goehner William Weston Eddy Davis Bass Player #2 Vincent Guastaferro Sid Bishop Ralph Pope Panhandler Jerome Richardson Club Musician Earl P. McIntyre Club Musician James Williams Club Musician Frank Wess Club Musician Al Bryant Club Musician Ray Garvey Club Manager Sally Placksin Sally Jillian Simon Wettenhall Jam Session Musician Orange Kellin Jam Session Musician Brooks Giles III Jam Session Musician Alfred Sauchelli, Jr. Ned Michael Peter Bolus Lynch Mick O'Rourke Holdup Man John P. 'Jack' McLaughlin Holdup Man Chuck Lewkowicz Police Officer Rick Mowat Flat Tire Man Ted Wilkins Gas Station Proprietor Michael Sprague Django Reinhardt