Owen Peadman (Mewes) is a Minnesota bartender who arrives in Los Angeles to try to help his father raise money to save his small restaurant. Owen moves in with his gay uncle Earl (David Keith) and tries to integrate himself into the high society of Hollywood, where he has a chance run-in with a wealthy socialite named Lisa Mancini (Hilton) and her uptight actor boyfriend Hayden Field (Brian Hallisay). Owen, using a little influence and blackmail, gets a taste of the scandalous lifestyles of the Hollywood upper crust while dealing with his growing romantic feelings for Lisa.