In the 1950s and '60s, young Ruben Santiago Jr. (Marcus Franklin) lives in a lively boardinghouse in the blue-collar town of Lackawanna, New York, with his father (Jimmy Smits) after his parents separate. Run by the motherly Nanny Crosby (S. Epatha Merkerson) and her taciturn husband (Terrance Dashon Howard), the boardinghouse residents, including The Bandleader (Mos Def), singer Pauline (Macy Gray) and cabaret owner Dick Barrymore (Ernie Hudson), teach the young boy about life and art.