Alan JacksonTwenty years ago, Alan Jackson signed with Arista Records and became one of the fledgling label's first artists to break through into Billboard's Top 20 with 'Here in the Real World.' Over the years since, Alan has scored 50 more Top 10 hits for Arista, 25 of them chart-topping smashes.

But Alan's contract with the only label he's ever recorded for is up ... and the Georgia superstar is now quietly contemplating where the road leads from here.

"This is actually my last album for Arista," Alan tells 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 guess it's time to start thinking about it now."

Taking into consideration the ever-changing face of country music over the past couple of decades -- albums on the decline, downloaded singles on the upswing, and many artists establishing their own labels now -- Alan has a lot to mull over. But he's holding one important factor uppermost in mind: keep making music and keep drawing fans to his concerts each year.

"I've always said there's not much to retire from,"he says. "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 record for Arista, 'Freight Train,' will be released on March 30. The first single is 'It's Just That Way.' Alan's daughter, Mattie, a sophomore at the University of Tennessee, wrote the treatment for the video. Alan's 2010 tour kicks off April 8 in Estero, Fla., with opening acts Josh Turner and Chris Young.