Once a member of the fames Edison Male Quartet, Jere Mahoney first recorded "When You Were Sweet Sixteen" (James Thornton) on Edison Records in 1900. The vaudeville composer's wife Bonnie first introduced the song in their husband and wife team stage act in 1898.

Former big band crooner and legitimate television star Perry (Pierino) Como covered "When You Were Sweet Sixteen" in 1947 and peaked at number two on Billboard. This was the B side to the number one "Chi-Baba Chi-Baba". The Satisfiers backed Perry on his radio show and this recording.