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 returned in 1965, recording soul music for Okeh Records. He then took another break, becoming a barber and eventually relocating to Nashville, Tennessee, where he met Pete Drake, a producer at Stop Records, who challenged him to create a country album that would be successful. As a result, Otis Williams and the Midnight Cowboys were recorded in 1971, with Williams claiming to have assembled an all-black country band, although it was actually a group of Nashville musicians, including Elvis's guitarist Scotty Moore.