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It didn't take Randall long to get in the middle. Shortly after arriving, he met Carl Jackson, a local musician who was friendly with Harris. Jackson passed along one of Randall's tapes to her, and soon, Randall was a member of the Nash Ramblers, which included former Flying Burrito Brother Al Perkins. "I went over to her house, and we sat around and played a couple of songs," Randall recalls. "There was real good blend, so she hired me. That started things rolling for me. I was kind of the rookie, and there were all these hotshot players and artists."
He spent the next six years with Harris, picking up a Grammy along the way for his work on her 1990 album Live at the Ryman. Randall eventually landed his own deal with RCA Nashville, which released his debut, What You Don't Know, in 1995. The record ended his stint in Harris' band, which dissolved shortly after when several other members also decided to branch out on their own, and began Randall's troubles with the music industry. RCA Nashville shelved Randall's follow-up, recorded by legendary Nashville producer Emory Gordy, before cutting him loose. He quickly signed with Asylum Records, realizing too late that he was making a mistake.
But signing with Asylum turned out to be the best thing he could have done, forcing him to the sidelines long enough to come up with a new game plan. He could have sat around and cried in his beer about the sad state his career was in, and he did, until he turned on his television one night and saw friends like Harris and Steve Earle at the Grammy Awards. It finally clicked, and he knew that Willin' was the record he was going to make, whether anyone else cared or not. A decade after moving to Nashville, he was starting over.
"They cut records the way they wanted to cut records, and they were all at the Grammys, nominated for Grammys," Randall says, laughing slightly. "And I'm sitting over here, goofing off with these goofballs at Asylum Records, going, 'What am I doing?' At this point in my career, I figured I would just go in and do what the hell I wanted to do. And if it bombs, it's my fault."