Based on the true story of Ruben Santiago Jr. and his relationship with his guardian Rachel Crosby, set in 1950's and 1960's Lackawanna, New York. After the separation of his parents, young Ruben "Junior" Santiago, a part-black, part-Hispanic child, is sent to live in a small-scale boarding house run by the kind-hearted Rachel "Nanny" Crosby and her younger husband Bill. Ruben then grows up witnessing the world of soul and blues music and grows to know the various characters that Nanny takes into her household to help out, from disturbed Ol'lem Taylor; one-armed handyman Mr. Lucious; hairdresser Bertha; war veteran Lonnie; ex-convict Mr. Paul; butch cleaner Ricky and many others.
- S. Epatha MerkersonRachel "Nanny" Crosby
- Marcus Carl FranklinRuben Santiago Jr.
- Mos DefThe Bandleader
- Carmen EjogoAlean
- Bill Simms Jr.Himself
- Louis Gossett Jr.Ol'lem Taylor
- Macy GrayPauline
- Terrence HowardBill Crosby
- Ernie HudsonDick Barrymore
- Delroy LindoMr. Lucious
- Rosie PerezBertha
- Ruben Santiago-HudsonFreddie Cobbs