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| Sean Penn | Emmet Ray |
| Samantha Morton | Hattie |
| Uma Thurman | Blanche |
| Brian Markinson | Bill Shields |
| Anthony LaPaglia | Al Torrio |
| Gretchen Mol | Ellie |
| Vincent Guastaferro | Sid Bishop |
| John Waters | Mr. Haynes |
| Constance Schulman | Hazel, Hooker #1 |
| Kellie Overbey | Iris, Hooker #2 |
| James Urbaniak | Harry |
| Mark Damon Johnson | Omer |
| Darryl Alan Reed | Don |
| Dick Monday | Chester Weems |
| Josh Mowery | Movie Director |
| Fred Goehner | William Weston |
| Brad Garrett | Joe Bedloe |
| Woody Allen | Himself |
| Ben Duncan | Himself |
| Nat Hentoff | Himself |
| Douglas McGrath | Himself |
In the 1930s a great jazz guitarist clashes with lovers, gangsters and other musicians.
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