In September 1963, after Cox was discharged from the Army, he and Hendrix moved to Clarksville, Tennessee, and formed a band called the King Kasuals. Hendrix had watched Butch Snipes play with his teeth in Seattle and by now Alphonso 'Baby Boo' Young, the other guitarist in the band, was performing this guitar gimmick. Not to be upstaged, Hendrix learned to play with his teeth. He later commented: "The idea of doing that came to me...in Tennessee. Down there you have to play with your teeth or else you get shot. There's a trail of broken teeth all over the stage." Although they began playing low-paying gigs at obscure venues, the band eventually moved to Nashville's Jefferson Street, which was the traditional heart of the city's black community and home to a thriving rhythm and blues music scene. They earned a brief residency playing at a popular venue in town, the Club del Morocco, and for the next two years Hendrix made a living performing at a circuit of venues throughout the South that were affiliated with the Theater Owners' Booking Association (TOBA), widely known as the Chitlin' Circuit. In addition to playing in his own band, Hendrix performed as a backing musician for various soul, R&B, and blues musicians, including Wilson Pickett, Slim Harpo, Sam Cooke, Ike & Tina Turner and Jackie Wilson.
In January 1964, feeling he had outgrown the circuit artistically, and frustrated by having to follow the rules of bandleaders, Hendrix decided to venture out on his own. He moved into the Hotel Theresa in Harlem, where he befriended Lithofayne Pridgon, known as "Faye", who became his girlfriend. A Harlem native with connections throughout the area's music scene, Pridgon provided him with shelter, support, and encouragement. Hendrix also met the Allen twins, Arthur and Albert. In February 1964, Hendrix won first prize in the Apollo Theater amateur contest. Hoping to secure a career opportunity, he played the Harlem club circuit and sat in with various bands. At the recommendation of a former associate of Joe Tex, Ronnie Isley granted Hendrix an audition that led to an offer to become the guitarist with the Isley Brothers' back-up band, the I.B. Specials, which he readily accepted.