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| Sean Penn | Eddie |
| Kevin Spacey | Mickey |
| Chazz Palminteri | Phil |
| Robin Wright Penn | Darlene |
| Garry Shandling | Artie |
| Anna Paquin | Donna |
| Meg Ryan | Bonnie |
Eddie is a confused and reckless man with a group of equally problematic friends. His roommate, caustic and sleazy Mickey, is sleeping with Eddie's love, Darlene, because he can. His buddy Phil is prone to violent rages that worry Eddie. All of them ruminate on their lives while consuming drugs and alcohol. Another friend, Artie, eventually arrives with a young date who is ready for a fun night.
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