Alan Jackson Confronts Longevity

Alan Jackson performs "Good Time" at "The 42nd Annual CMA Awards," on Wednesday, Nov. 12, 2008, live from the Sommet Center in Nashville on the ABC Television Network. Photographer: Donn Jones / Provided by Country Music Association.

Dec. 1, 2008 — Alan Jackson observes a major milestone in 2009: 20 years since he signed his first recording contract.

With all that time in the spotlight, his relationship with the public has changed dramatically. Ultimately, he feels as if he’s got a lot more choices than he had when he started.

"Early in my career, you did what you had to do," he told The Detroit Free Press. "I hated doing all that TV, all the talk shows. I feel like I don't fit in there. When you're lucky enough to reach a certain level of success, you don't have to sell yourself as much, which is good, because I don't enjoy that part."

What Alan does enjoy about the job is the actual music part of it — writing and recording the material, then singing it live for his fans. The volume of his success, though, creates some dilemmas in figuring out exactly how to fill out the set list every night.

"It's tough," he observed. "I've got 50-something singles. You can't do half of them, hardly, in a couple of hours. I'm not real crazy about medleys, but I have gotten to where I won't do a whole song — I'll leave out a verse so I can get more songs in. I try to pick the songs that had more of an impact over the years and try to squeeze 'em all in there, and it's working pretty good."

While Alan’s not crazy about doinog TV, he has seen his music appear in the movies several times this year. He’s landed songs in the independent picture Billy: The Early Years and the Oliver Stone film W.