Bottoms Up (2006)

Owen Peadman is a Minnesota bartender who arrives in Los Angeles to try to help his father raise money to save his small restaurant.

Owen shacks up with his very gay uncle Earl and tries to integrate himself into the high society of Hollywood where a chance run-in with a wealth socialite named Lisa Mancini and her uptight actor boyfriend Hayden Field where Owen, using a little influence and blackmail, gets a taste of the fast and sordid and scandalous lifestyles of the Hollywood upper crust while dealing with his growing romantic feelings he has for Lisa.