Chris Colombo, 44, the son of slain mob boss Joseph Colombo, is on home confinement while he's out on bail for federal racketeering charges. The film follows Colombo on some unsavory outings when he is supposed to be on family outings or running errands.

A young Hip Hop star named Summer G falls for a middle to upper class sister while in college. After she rejects him for a fellow social climber, Summer G spends ten years building a Hip Hop empire, then moves to the Hamptons where he finds the object of his affections.