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