5. Jeffrey Lebowski in The Big Lebowski
I know that Tara Reid's character Bunny in The Big Lebowski was of ill-repute. She partied, owed money to people all over town and starred in the film Logjammin'. She also may or may not have been the one to kidnap herself-- after all, she's gotta feed the monkey. So it seems to make perfect sense that this young girl might find herself with the film's namesake Jeffrey Lebowski. Despite the fact that he has no joy in his heart, and finds himself having to compensate rug-owners citywide whenever one is micturated on, his apparent wealth are the perfect attractant for a girl who's willing to let Brandt "watch" for a mere $100.