Alan Jackson photo courtesy of Sony Music Nashville.

This week is a significant milestone for Alan Jackson: It marks 20 years since “Here In The Real World” climbed into the Top 20 on the Billboard Hot Country Songs chart. Since then he’s landed more than 50 titles in the Top 10, literally taking him from rags to riches.

Alan was one of the first artists to break through after Arista Records opened its country division, and he’s been with the label ever since, although it appears those days are numbered. What the future holds for him remains to be seen.

“This is actually my last album for Arista,” he told Billboard. “My contract is up after this, so I guess I’ll be doing something for somebody or on my own. I don’t know yet. I haven’t really thought about it that much. I guess it’s time to start thinking about it now.”

The world has changed dramatically in the two decades since Alan signed that first deal, so he finds himself at a crossroads he could never have imagined. The Arista label is no longer an upstart, having found success with such acts as Brooks & Dunn, Brad Paisley, Carrie Underwood and Diamond Rio. The rise of the Internet has changed the business model for the music industry: Albums are on the decline while downloaded singles are on an uptick. And numerous recording artists have established their own labels, including Gretchen Wilson, Big Kenny and Alan’s one-time duet partner, Jimmy Buffett.

So Alan has a number of factors to take into consideration as he moves forward. One option that’s not in the mix is retirement. As long as he can keep having hits and draw people to some 50-60 concerts each year, he plans to keep making music.

“I’ve always said there’s not much to retire from,” he observed. “It’s not really hard work. This is a business. This is a job. You have to work, commit and be dedicated. It’s also fun and rewarding, and it’s not near as hard work as most of my fans have to do for a living. It’s hard to complain.”

Alan’s final Arista album, Freight Train, is due March 30.

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