 After serving in World War II, he joined Tex Beneke's big band, eventually leaving to perform as a pianist and later a comic in nightclubs.Freeman's work as a studio musician included sessions with Frank Sinatra, Peggy Lee, Ella Fitzgerald, Percy Faith, Mabel Mercer, Charlie Parker, and Rosemary Clooney, for whom he played harpsichord on her hit "Come on-a My House.