Small time celebrity photographer Les Galantine (Steve Buscemi) has a big mouth and big dreams, but he cant quite talk himself into the right parties to get that one great exclusive photo. He meets Toby (Michael Pitt), a homeless kid who is drawn to the bright lights of New York City and hires him as his assistant. Les pays nothing but room and board but the two are drawn to each other and become friends. Although Toby enjoys the glamour and excitement of Les lifestyle he has dreams of his own; to become an actor. Luck intervenes for Toby when he accidentally meets KHarma Leeds (Alison Lohman) a beautiful pop diva. As their unlikely love blossoms Toby finds himself torn between a chance to follow his dream and to fulfill his obligations to Les. This conflict deepens when Toby leaves Les and lands a part on a Reality Show, partly by sleeping with the shows casting director Dana (Gina Gershon). As Tobys fortunes continue to rise, Les tries to reach out, while also maintaining a bitter resentment toward his former protg.