He returned in 1965, recording soul music for the Okeh label. He took a further break, becoming a barber, and later relocated to Nashville, Tennessee, where he met Stop Records producer Pete Drake, who produced some records with his old backing group The Endeavors, then bet him that he could not make a country music album that sells, causing him to record Otis Williams and the Midnight Cowboys in 1971, claiming a fictitious all-black country band that was really some Nashville musicians including Elvis Presley's guitarist Scotty Moore.
He came back in 1965, recording soul music for the Okeh label. He took another break, becoming a barber, and later relocated to Nashville, Tennessee, where he met Stop Records producer Pete Drake, who produced some records with his old backing group The Endeavors, then wagered him that he could not make a country music album that would sell, prompting him to record Otis Williams and the Midnight Cowboys in 1971, claiming a fictional all-black country band that was actually comprised of some Nashville musicians including Elvis Presley's guitarist Scotty Moore.