Alan Jackson looks back on 20 years in the rearview mirror

Watch the weekend classifieds: Alan Jackson may be having one hell of a moving sale before too long. Country music's most reliable superstar and his memoir-writing wife, Denise, plan to put their massive Franklin estate, Sweetbriar, on the market and rebuild on a smaller lot nearby.

The infamously massive compound they've occupied for a dozen years may be a honky-tonker's interpretation of Tara. But at their next place, with God as their witness, they will never have to hire that many lawnmowers again. Goodbye to the air-conditioned gym, the horse stalls, the 30-car garage, the log cabin, the 10-acre lake and the airplane landing strip.

"It's just like a Disney World out here," he says. "But we realized, as our girls got older, that they don't really use the property much. Once they get to be teenagers, they're mostly hanging out with their friends and on the iPod and cell phones in their rooms. If I'd had three boys instead of girls, they might be out here fishing and riding four-wheelers or something."

Surely those iPods contain "Chattahoochee," the career-making summer single that helped build the house and all its wonders? Jackson doesn't sound so sure.

"I guess they're a little jaded to the celebrity stuff, because they don't pay any attention to me and what I do. I say 'Hey girls, I'm on this television special tonight.' 'Uh, OK.' Nobody ever watches any of 'em," he says with a chuckle. "If I'm doing some festival and there's some cool young act on there they like, they might perk up a little bit. But they're used to old daddy."

By all rights, the rest of us should be too, right? On rare occasions, apparently, the natural laws of showbiz longevity can be broken. This summer marks the 20th anniversary of Jackson signing to Arista Nashville. And despite a decided lack of Madonna-esque (or even Reba-esque) reinvention on his part—never has an artist looked exactly the same on so many successive album covers—he's continued to captivate country's audience at a spookily consistent level for the last 19 of those 20 years.

He heads into this anniversary with the first three singles off his most recent album, last year's Good Time, all having made the long haul to No. 1 (with the fourth one, "Sissy's Song," possibly still aimed there). It turns out there's more than one generation of country fans that consider "old daddy" their only daddy that'll walk the line. You can't exactly mistake full amphitheaters for empty nests.

On June 10, the eve of the CMA Festival's opening day, Jackson will be feted at a 20th anniversary celebration at Cadillac Ranch on Lower Broad. Reticent guy that he is, there may or may not be a receiving line or industry trade shots. But he will be doing the one thing he's comfortable with at these kinds of functions: performing. Along with invited guests, fans will be allowed into the free show, with the lineup for wristbands starting outside the club at 4:30 p.m., right after the CMA parade. The party is being thrown for him by...which company is that now?

"I don't even know what label I'm on anymore," he says, chuckling. "I can't remember which ones they merged with. It's got a different name about every two or three weeks."

Oh, yeah: That would be Sony Music Nashville—until recently Sony BMG—whose chairman, Joe Galante, inherited Jackson's recording career in one of those mergers 10 years ago.

"I don't think of him as an anomaly, in that he's one of those guys that won't get off the road and doesn't want to go away," Galante says. "He's not gonna take three years off the radio. He knows you've gotta be around the fans to be in their minds. But I do think he's an anomaly in that he doesn't follow any part of the system in the sense of the way the town works creatively."

There's the matter of his relative purism, at a time when it's understood that everybody in country music listens to and absorbs every kind of contemporary music—a given ever since his fellow "Class of '89" alumnus, Garth Brooks, touted his membership in the KISS Army.

"The first time I got on the bus with Alan, he was playing a Vern Gosdin record—and I think it was an LP at that point," Joe Galante says. "Every time you got on the bus after that, it would be John Conlee, or it would be Merle. You never heard anything that wasn't from the '50s, '60s and '70s, and I think '70s was really kind of pushing it."

He's also the anti-Garth when it comes to his personality. When the definitive Alan Jackson biography is finally written, the chapter on marathon meet-'n'-greets will be very, very, very short.

"Obviously everybody's talked about how shy he is, and I think he's kind of explained the fact that there is that gene in him; his dad had it and he has it and I think one of his daughters has it too," Galante says. "He's not one of those guys to make small talk for the sake of just making small talk, unless he gets to know you, and then he'll sit down and talk your ear off. And he's got a great sense of humor—he is a prankster, he is a smart-ass. He's kind of gigging you along the way, kind of pushing your buttons to see what's gonna happen. And it comes off in his songs in certain ways, just the way he turns a phrase."