Some great choices named so far. Boogie Nights, American Psycho, Swingers, Pulp Fiction, etc., are all among my favorites. But what about: - Fight Club (another favorite, I found it hilarious) - Any of the more recent British imports, especially the gangster flicks, or anything that Guy Ritchie does. Think Snatch, Lock Stock and Two Smoking Barrels, Sexy Beast, etc. Even Trainspotting, in a different sort of way. All clever, all funny, all stylish.