The son of clothing merchant Sol Frankel, young Harry grew up in Danville, Kentucky, singing in various quartets, moving with his parents to Richmond, Indiana, when he was nine years old. He joined Coburn’s Minstrels in 1908 and later toured with Al G. Field's Minstrels. Frankel and his pal Joe Dunlevy were known as the Two Blackbirds when they performed in vaudeville theaters during the late 1920s.