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Wootton had been a lifelong fan of Cash's and played his songs religiously until he had perfected the boom-chicka-boom style known as Cash's unique sound. The untimely death of Luther Perkins left only Johnny Cash and drummer W.S. Holland onstage, and Wootton approached Cash requesting to fill in for the night. Wootton stunned the audience, particularly Cash himself, with perfect renditions of every song. Cash mentioned in passing that he might one day call on Wootton again, but within days asked him to join the tour as new lead guitarist.
One of the next performances, perhaps the most notable of Wootton's career, was at San Quentin State Prison where Cash's live album was recorded. Wootton continued in the band with only a brief respite until Cash retired in 1997.
From 2006 to 2007, he performed with Cash's original drummer, W.S. Holland, his wife Vicky and daughter, Scarlett Wootton, as The Tennessee Three. In 2006 the band released their first album since Cash's death, a loving tribute titled "The Sound Must Go On."
The Tennessee Three was scheduled to perform at Folsom Prison in January 2008, commemorating the 40th anniversary of Cash's Folsom show. Wootton eventually withdrew from the concert project, which was later scrapped following disputes between prison officials and show promoters. Wootton continued his 2008 touring as the Tennessee Three with drummer Derrick McCullough, Vicky, Scarlett, and Montana Wootton to appreciative crowds across the globe. The band continues to tour throughout 2009.
- Forbish, Lynn (March 10, 1982). "Johnny Cash Special travels with gusto". The Evening Independent. Retrieved 14 August 2011.