Alan Jackson looks back on 20 years in the rearview mirror

By Chris Willman

published: June 11, 2009

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."

Galante says that Jackson's lack of interest in the glad-handing that is second nature to every other major-label country artist now makes all his hit singles even more valuable—and there've been 26 No. 1's to date. Those songs got to those positions the old-fashioned way: They earned it, as songs, without undue help from Jackson dropping by every morning show in the country.

"This is no different from politics," the veteran Music Row player says. "Sometimes people vote for those people that show up all the time and kiss their babies and shake their hands. And those people that don't get around all the time, their music has to work a little harder. In Alan's case, people judge the record, and they judge what he does musically. And of course there are people that know him and support him, but not everybody operates the same way in this industry. His music does earn its place."

There are moments when someone might think Alan Jackson's kidding about a decision...and he's not. If there's anything Jackson is less enthusiastic about than actively working a party, it would have to be photo shoots. He tends to want to recycle leftovers from old sessions, which would explain why he once puzzled knowledgeable fans by appearing on the cover of Entertainment Weekly with a long-dead dog. One of his former managers, Nancy Russell, recalls handling the jacket art for his 2000 album When Somebody Loves You.

"I had sent a bunch of photos out to him and said we gotta pick a photo for the cover," Russell remembers. "He picked this black-and-white head shot. I took it to the label, and they said, 'We really want a color photo.' I called Alan and he was like, 'Well, just tell 'em to throw some damn color on it!' And, to this day, Butch (Waugh) and Joe tease me about me calling them up going 'Y'all just throw some damn color on it'—which we did, by the way," she adds, cracking up.

"The point being, he is not this guy that will sit there and meticulously overthink the album packaging, or anything else that's really incidental. He's always hoped it would be about the music."

The fact that it really has been about the music, for 20 years, has inspired a generation—maybe even a generation-and-a-half—of younger artists who've come up behind the 50-year-old star. Sunny Sweeney, an ex-Austinite who moved to Nashville just a month ago, counts him as a hero, as much for his writing as for the way "he makes traditional country stay cool."

"And the songs I know he didn't write, like 'Monday Morning Church,' I still swear he wrote," Sweeney says, "because I just believe every word he sings."

Jack Ingram, another Texan made good in Nashville, used to cover Jackson songs in the early days, back when he had little use for any other mainstream country.

"Maybe if you just listen to my records, you might not see an obvious lineage from a traditional guy like Alan to a kind of barroom brawler like myself," Ingram says. "But when I was going to the bars back in the early '90s as a wanna-be singer-songwriter, I was playing Jackson songs like 'Chasing That Neon Rainbow' right up against my John Prine songs and my Dylan songs and my own stuff I was doing. Songwriters love him: He's right up there with all the greats of just pure, traditional American storytelling.

"And he does hark back to the era of Ray Price, because, especially for a guy that's never been afraid to show his red neck, there's just some kind of dignity about him that you've gotta respect."

Dierks Bentley first fell in love with "Here in the Real World" living back in Phoenix. "There's something awesome in those three minutes of truth," Bentley says, "and not one word of filler in there." When Bentley first moved to town in 1994, the first star he spotted was Jackson, shopping for shoes in Green Hills Mall. He waited by the exit door for 10 minutes and ambushed him, as a fan. He repeated that experience when he went up to Jackson as a fellow star at a CMT Giants taping.

"He's a pretty shy person, and I wasn't real sure what to talk with him about at the soundcheck," says Bentley, who suddenly felt a little introverted himself. "Then he noticed my old Martin guitar that I've been playing forever—a guitar I've worn a hole in the top of from my pinky from just playing it so much—and it immediately caught his eye and he came back over to ask about it. Old guitars, old cars, anything with soul and history to it, he obviously adores. And that's why his music sounds so authentic, because that's who he is."

Vince Gill has some ideas about where Jackson fits amid the traditionalists. "He's always had a great way of writing songs about the common man, not unlike Merle Haggard," says Gill, spontaneously breaking into the refrain of "Little Bitty." "But he reminds me of Don Williams more than anybody. Don was quiet, but he made the best, coolest records, and found great beauty in simplicity, which Alan does today as well as anybody."

Gill never had to worry about Jackson trying to usurp him as CMA Awards host. "I was always the village idiot, and Alan's always been a quiet fellow. He's always friendly, but you never saw him much, because he liked to stay out there with his cars and his kids and didn't wade into the fray very often. He's probably smarter than most," Gill laughs. "You know, the more that life goes on and everybody's yapping and hollering, I like his style more and more."

Galante is right about the politics/entertainment connection: Folks cast their lot with the guy you'd want to have a beer with. In country music, where stars have to go the extra mile, there is often an expectation—certainly among radio people, and possibly among fans—that this theoretical beer-sipping might actually happen. Jackson may be the last relic of a slightly more mysterious previous era who gets a pass on this. For his devotees, it is enough to imagine that this simpatico legend is off enjoying his own drink...that it's 5 o'clock somewhere, as it were.

If anything, the distance he keeps from the usual promotional machine may even endear him more to country listeners—who sense something a little different about the one guy who doesn't seem to be trying too hard, and who's comfortable in his own take-me-or-leave-me skin. You're less likely to think of Jackson as Gene Simmons with a 10-gallon hat instead of makeup than as the laconic grandpa who never wanted to spend too much time bragging about his WWII adventures. He may be the last country superstar we can feel truly relaxed around, just because we don't actually have to watch him sweat to earn our love.

Alan Jackson remembers some nervous moments professionally. But he doesn't remember them real well, because the last one was 20 years ago. He'd spent a few years knocking around town, doing demos with producers who wanted to slicken up his sound.

Then he fell into what would be a career-long partnership with producer Keith Stegall. He knew Stegall would be simpatico, just based on some Randy Travis sides he'd previously cut. Thus began one of country's most charmed careers, but for the bump in the road that was his first single, "Blue Blooded Woman."

"I saw a lot of people come out with one or two songs, and if there wasn't any buzz going, they'd be gone," Jackson says. "So yeah, I thought, when that first single died, 'Well, there goes my shot.' Then to make it worse, Denise got pregnant. We thought, uh-oh, here I am, my wife's pregnant, and now my career is fixing to not take off. It was a scary time. Then the 'Here in the Real World' song came out and changed it all."

The rest is immediate rags-to-riches-to-continued-riches history. It'd be easy for people to resent the seeming effortlessness of a career that has existed on a sort of two-decade plateau, if not for the richness of the hits: the populism of "Little Man," the hilarious carpetbaggery of "Gone Country," the bittersweet existentialism of "That'd Be Alright"...and of course, "Where Were You (When the World Stopped Turning)," the 9/11-inspired ballad that turned heads across musical and cultural divides.

That song became a defining moment for Jackson—the moment when he could have taken a step away from country toward the kind of genre-shifting superstardom Garth Brooks courted. Pop stations wanted to play "Where Were You," so the label requested a remix without the already near-subliminal steel guitar. Jackson said no.

"As frustrated as people could be with him at times," says ex-manager Russell, "everybody always respected him, even when he was saying no. Because it wasn't like he was just saying no to bug everybody." On one of the very rare occasions where someone dared broach the subject of crossover, "somebody was saying something about AC radio, and he said, 'What's that stand for—Ain't Country?' I loved that."

Besides, the massive attention "Where Were You" drew already made Jackson—surprise!—a little bit uncomfortable.

"Everybody wanted to put me up on a pedestal after that song, like I was some kind of saint," Jackson says. "I'm not. You don't want to get in the mind-set that you're some kind of special healer or something, and you have this ability to write songs that are gonna change people's everyday lives. People were emotionally affected by that song, but it just happened to come out of me. A lot of artists start doing all these songs that want to save everything, and it kind of takes away from what brought 'em there. A few years ago, I was just playing smoky bars. And the next thing you know," he adds with a laugh, "I'm not any different."

That last sentence might make for a pretty nifty career summary, if not for the fact that Jackson did seem to be on a "Think Different" streak through the mid-2000s. There was the biggest-selling country gospel album of all time, Precious Memories, a collection of starkly arranged hymns that Jackson originally recorded as a private gift for his mama before Galante convinced him to put it out. That was followed by a less commercial detour, Like Red on a Rose, a gorgeously subdued one-off that had producer Alison Krauss almost taking on the role of a film director, casting Jackson in the lead in a series of reflective ballads. It was the best-reviewed album of his career, and the most modest-selling.

"That's the way it usually goes—if it's critically acclaimed, then it's not commercially acceptable," he says. "It's hard to please the critics and the Wal-Mart shoppers at the same time. They thought I'd lost my mind! I was proud of that, though. In the beginning, I said 'Here's what'll happen: It'll get great reviews, and it won't sell much, and radio will be scared of it.' And that's basically what happened."

Nancy Russell thinks Jackson's never gotten the credit he deserves for some of his more rebellious impulses. "He really has a rock star mentality, in a way," she says. "Not like Tommy Lee—I just mean doing it on his own terms. You remember that song he did, 'Three Minute Positive Not Too Country Up-tempo Love Song'? I was surprised more people did not talk about what a satire that was—and I got a kick out of how many radio stations actually played it.

"And the thing he did on the CMA Awards, honoring George Jones by playing a little bit of 'Choices' when George didn't get to play the show—I don't think anybody else would have had the balls to do that. But here's Alan, one of the quietest guys in the business, doing it. But he doesn't go into the pressroom to thump his chest about it. He just has strong convictions about stuff."

Like Red on a Rose produced only one Top 5 single, and no No. 1's. "We noticed," laughs Galante, who supported the detour—but wasn't so overzealously supportive that he didn't breathe a sigh of relief when Jackson came back in with Good Time, a pendulum swing back toward the format-friendly happy-go-luckiness promised in its title.

"That was the great thing about having that break with the Alison project and the gospel thing," Jackson says. "It had gotten to be a routine with Keith Stegall and me: Every year or two, you go in with the same players, same studio.... Once these other things happened, he and I were both more interested in going back in and doing a real country album."

But he hadn't completely lost his taste for adventure. Though he'd never had a hand in writing every song on an album before, even as a co-writer, Good Time lists him as sole author on all 17 songs. "I don't think we ever said 'Let's just do all my stuff,' " he swears, insisting the sole authorship factor was an unforeseen fluke. And he points out that not everything on the album is as willfully blithe as Good Time's title track.

"There's 'I Wish I Could Back Up'—that's a positive song," Jackson says, "but it's about a negative past, that does kind of go with my and Denise's experience over the years." It's the one song on the album that might serve as a soundtrack for Denise's memoir of their marital troubles, It's All About Him, which topped The New York Times' best-seller list in 2007.

An eye-opening account of their near-breakup and their rocky path to reconciliation, It's All About Him confirmed much of the gossip surrounding the intensely private couple. If anything, the book granted her husband his aforementioned wish—the one about not wanting to be perceived as too much of a saint.

Though her account of their hard times skimps on actual dirty laundry, it still "certainly was dangling him out there for the whole world to see," Denise Jackson says, unabashedly. "But I also feel like most of the world had some idea of what was going on when we were separated, and the infidelity, which was something I did confirm in the book.

"I think for Alan, it was almost a relief for him for me to tell the truth of this story of our lives as I saw it, and for people to realize that he has had regrets in his personal life, and that by the grace of God we were able to live through that and and be better off in the long run. Because it really was about forgiveness and restoration. But yes, it was a lot to ask of him."

"I knew a lot of my fans might be disappointed," Alan says. "I thought it might really hurt my career. But I also thought that Denise was writing it to help people. And it has. I think it did a lot of good for people, and it didn't destroy me. I think if anything it made me look more human to people. And maybe people realized that no matter what you got or who you are, you still got problems sometimes and gotta work through 'em."

The validation on the best-seller list, he says, "was a great thing for her, and it gave her a chance to show that she's a smart person that has a lot to say, and not just some trophy wife that I got when I couldn't afford a trophy wife."

Jackson has just started working on his next album, and he's been playing songs for Denise at night, getting her opinion before he puts them in front of Stegall the next day. Not that he always takes it to heart.

"I remember him playing 'Where I Come From' for me," Denise Jackson says, "and I said, 'Alan, that's just so corny!' And of course it was a huge hit, so what do I know? There've been times where I said 'Ah, that's kind of corny,' and he'll say, 'You know, Denise, you've lost touch with the real people. You've lost touch with the people that shop at Wal-Mart.'

"And not that that's everybody who listens to country music, but a good portion of the buyers of country music I think are just working people that are trying to make it through each day. And to this day, Alan still feels more comfortable going down and talking to the guy that takes care of our cars—whether it's about cars or life in general—than he is at any music-industry shindig. I think that really helps him continue to identify with the bulk of the people who listen to the music."

Gary Overton has known Jackson since before he got his deal in '89, and subsequently became his manager in the mid-'90s, then the administrator of his song catalog this decade, as the head of EMI Publishing. He's seen Jackson unexpectedly charm corporate chieftains, though he admits there can be an interesting moment or two when the star walks in the room and doesn't say anything, which can either be interpreted as awkward silence or Elvis-like presence.

"Because he's so quiet and known for traditional country, some businesspeople who've never met him misjudge him and think he's probably some hillbilly that came down the pike," Overton says. "And he didn't go to Harvard, but he's a very smart man, and you see that take businesspeople back a step."

But in the end, Jackson can only bring himself to care about the gears of industry so much. This is his 20th anniversary in the business—and maybe also his 20th anniversary of not really giving much of a hoot about the business.

"I hadn't been managing him that long," says Overton, "and we were at his lake house up on Center Hill. I remember saying, 'You know, Alan, an artist's career usually for some reason just starts taking a nosedive. The fickle public gets tired of 'em and the records stop going No. 1 and stop selling. That would probably be a hard time for you to get through emotionally.' He just sat there for a second and then he pointed a big, long old finger across the river at the channel and said, 'You see that cove across the lake? When my star starts falling, I'll have time to go across and fish in that thing, and I've never been over there yet. But I will.'

"You just sit there and think, is this guy 800 years old? Is he Solomon? He's very comfortable with himself and not gonna change his music to please anybody. And the day it doesn't make sense anymore, he's gonna be fishing in that cove." It may be telling that the lakefront house is the Tennessee property the Jacksons aren't selling. A guy's gotta have something to look forward to. If there's ever been a song that's autobiographical in Jackson's career—and there've been plenty, really—it'd be the latest album's "I Still Like Bologna," with lines like "Finally gave in and got a cell phone/I never had that much to say."

"Oh, that's fact there," Jackson says. "It's like when we were building this house and they wanted to put a telephone in there by the toilet. I said, 'You know what? If it's that important, they'll just have to wait till I get through in there.' I don't do text messaging. I put off getting a cell phone as long as I could, and now I've got one. But I don't ever use it, you know. Because people call you if you turn it on."

So says 20 years of professional taciturnity. Here's to 20 more, before the cove across the lake beckons.

Email music@nashvillescene.com.