Bobby Dorfman (Jesse Eisenberg) is the youngest son of a Jewish family in New York City in the 1930s; his elder sister Evelyn is a married school teacher, while his elder brother Ben is a gangster. Discontented with working for his father, a jeweler, Bobby decides to move to Hollywood, where he takes a job running menial errands for his uncle Phil (Steve Carell), a powerhouse talent agent.