In the 1950s and 1960s, Ruben Santiago-Hudson Jr. lives in a lively boardinghouse in the blue-collar town of Lackawanna, New York, with his father after his parents separate. Run by the motherly Nanny Crosby and her taciturn husband, the boardinghouse residents, including The Bandleader, singer Pauline and cabaret owner Dick Barrymore, teach the young boy about life and art.