Forced to quit his prep school job after a humiliating incident, would-be dramatist Louis Ives (Paul Dano) heads to New York City, where he rents a room from has-been playwright Henry Harrison (Kevin Kline) -- who earns a living escorting rich dowagers about town. Despite their huge age difference, the two develop a bond as Henry takes Louis under his wing and leads him on a series of wild adventures. Katie Holmes and John C. Reilly also star.