After his release, Hendrix and army friend Billy Cox moved to nearby Clarksville, Tennessee, where they formed a band called The King Kasuals. Playing in low-paying gigs at obscure venues, the 'band' eventually moved to Nashville. Playing and sometimes living in the clubs along Jefferson Street, the traditional heart of Nashville's black community and home to a lively rhythm and blues scene offered some sort of 'existence'.In November 1962, Hendrix participated in his first studio session, where his wild but still undeveloped playing found him cut from the soundboard.

In 1965, guitar pioneer and producer Les Paul watched Hendrix audition for a nightclub gig in Greenwich Village, NYC, and was awestruck by his performance. An errand forced Les Paul to leave the club before he had the chance to speak with Hendrix. When he returned later to contact and sign Hendrix, Les Paul found that the club owner had turned Hendrix down for being too loud and crazy and that Hendrix had disappeared.[citation needed] That year, Hendrix earned a spot as the new guitarist for the The Isley Brothers' band and joined their national tour, which included the southern Chitlin' circuit. Hendrix played his first successful studio session on the two-part Isley Brothers hit "Testify". In Nashville, he left the Isleys to tour with Gorgeous George Odell. In Atlanta, he earned a spot in the backing band of Little Richard, The Upsetters. Although Hendrix idolized Richard, he clashed frequently with the star over tardiness, wardrobe, and, above all, Hendrix's flashy stage antics. For a short while, Hendrix quit and toured with Ike and Tina Turner, but was quickly fired for playing wild guitar solos and returned to Little Richard's band. Months later, he was banished from The Upsetters after missing the tour bus in Washington, D.C.. Around this time he refined his flamboyant guitar stage style, much of which was influenced by Johnny "Guitar" Watson.

In 1965, Hendrix joined a New York-based band, Curtis Knight and the Squires, after meeting Knight in the lobby of a seedy midtown hotel where both men were living at the time. Hendrix then toured for two months with Joey Dee and the Starliters before rejoining the Squires in New York. On October 15, 1965, Hendrix signed a three-year recording contract with entrepreneur Ed Chalpin, receiving $1 and 1% royalty on records with Curtis Knight. While the relationship with Chalpin was short-lived, his contract remained in force, which caused considerable problems for Hendrix later on in his career. The legal dispute was eventually settled. During a brief excursion to Vancouver in 1965, Hendrix played in Motown band Bobby Taylor & the Vancouvers with Taylor and Tommy Chong (of Cheech and Chong fame).[citation needed]

In 1966, Hendrix formed his own band, Jimmy James and The Blue Flames, composed of various friends he would casually meet at Manny's Music Shop, including a 15-year old runaway from California named Randy Wolfe. Since there were two musicians named "Randy" in the group, Hendrix dubbed Wolfe "Randy California" and the other "Randy Texas". Randy California would later co-found the band Spirit with Ed Cassidy.

Hendrix and his new band quickly gained local attention and played throughout New York City, but their primary spot was a residency at the Cafe Wha? on MacDougal Street in the West Village. During this period, Hendrix met and worked with singer-guitarist Ellen McIlwaine and guitarist Jeff "Skunk" Baxter, who was an employee at Manny's. Hendrix also met Frank Zappa during this time, who is credited as having introduced Hendrix to the newly-invented wah-wah pedal.

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