Bennie Upshaw, the head of a Black working class family in Indianapolis, is a charming, well-intentioned mechanic and lifelong mess just trying his best to step up and care for his family and tolerate his sardonic sister-in-law, all without a blueprint for success.

Two men (Pras, Michael Goorjian) in drag purposely get arrested in order to recover their winning lottery-ticket from an inmate at a women's prison.

Will, a street-smart teenager, moves from the tough streets of West Philly to posh Bel-Air to live with his Uncle Philip, Aunt Vivian, his cousins — spoiled Hilary, preppy Carlton and young Ashley — and their sophisticated British butler, Geoffrey. Though Will’s antics and upbringing contrast greatly with the upper-class lifestyle of his extended relatives, he soon finds himself right at home as a loved part of the family.