Alan Jackson: The Quiet ‘Super Outlaw’ Endures

Alan Jackson
Manuel Nauta / NurPhoto
– Alan Jackson
Small Town Southern Man Alan Jackson plays the San Antonio Rodeo Feb. 10, 2014.

Alan Jackson stood onstage just before the sun set on Fort Lauderdale beach in a vintage looking Hawaiian shirt, sunglasses and his signature white cowboy hat. Never mind that the long, tall songwriter was well into his third decade as a country superstar, the sea of people at 2017’s fifth annual Tortuga Music Festival were belly-to-belly, shrieking with delight and singing along with complete abandon to “Chattahoochee,” “Don’t Rock The Jukebox,” “Good Times” and his revved up No. 1 take on Charlie McClain’s “Who’s Cheating Who.”

Never mind many of the fans weren’t born when Jackson had his first hits in 1990 and ‘91, they’d come – the same way they do for The Rolling Stones – to exult in the hard country anthems they’d known their whole lives. Girls on boyfriends’ shoulders, clusters of hot bodies in teeny triangle bikinis, groups of sunburned young men wearing ballcaps or cowboy hats, all with their hands in the air, writhing and jumping in time to “I Don’t Even Know Your Name,” swaying to ballads “Remember When,” “Here In The Real World,” “Midnight in Montgomery,” line-dancing on the edges of the crowd to “Drive (For Daddy Gene)” or “Where I Come From” and quietly mouthing the words to his 9/11 rumination “Where Were You (When The World Stopped Turning).” The Newnan, Georgian’s songs seemed to embody pieces of their lives.

Alan Jackson
Keith Griner / Phierce Photography
– Alan Jackson
cover of Pollstar’s March 9, 2020, issue.
“I’ve had 60 some singles,” Jackson offers quietly. “Except for maybe a couple, they were all at least Top 5 or Top 10. So, the 30-year-olds are playing their kids this music, and (the generational thing)’s been going on now for a while … I guess they know the songs. Because, you know, I’ve always been about the songs.”
Beyond being incredibly shy, Jackson is impossibly humble. For a boy growing up poor, he learned there were more things in life than money, including the value of hard work and the power of love to transcend. Those things permeate his music, giving people something that supersedes light shows, video montages, pyrotechnics and other special effects most arena-sized headliners employ.
WME’s Jonathan Insognia, who also RAs Yola, Boy Named Banjo, Amanda Shires and Orville Peck, marvels at the contrast between the decidedly still superstar and so many other high impact entertainers. “He’s a legend and an icon,” he says. “It’s a different touring strategy. He only plays 20 shows a year, so we wanted to get him in places he’s not been – and the response was just crazy.
Alan Jackson
Phierce Photography / Keith Griner
– Alan Jackson
Don’t Rock The Juxebox: Alan Jackson packs ‘em in at PPG Paints Arena in Pittsburg March 24, 2019.
“He needs to be in arenas, because there’s this wide range of fans. There are the ones who were there in the beginning, people in their 30s or 40s who grew up on him, and a massive amount of young folks who don’t know a world where he wasn’t a superstar. To them, this is a chance to see a genuine superstar play all those incredible songs.”
One of those kids is Universal Music Nashville President Cindy Mabe, the woman engineering breakout success for Carrie Underwood, Eric Church, Sam Hunt, Jon Pardi and Chris Stapleton. “To this day, if you ask me my musical North Star, it’s Alan Jackson,” she says. “His songs are authentic and real. He knows who he is, where he came from, what his audience wants – and you cannot change him.
“Who he is and what he represents is sorely missed and needed in a format that is in an identity crisis. Of course, his music will always appeal to all audiences, including teenagers because they, especially, are searching for authenticity … Alan’s become a cornerstone in country music in the way he saw his heroes George Jones, Merle Haggard and Hank Williams, Sr. do it.”
Country Music Association CEO Sarah Trahern concurs. Having worked with him during her tenure as a programming executive at both TNN: The Nashville Network and Great American Country, she’s seen his authenticity translate into a very specific chemistry.
“The very first show I did at TNN in the ‘90s was a ‘Marty Party,’ with Marty Stuart as host, Junior Brown as the new artist, Johnny Cash was the legend and Alan was the superstar,” she recalls. “I had chills when Johnny Cash walked up to the mic and said, ‘Hello, I’m Johnny Cash.’ But Alan, quietly, had the same presence as Cash. He was undeniable.
“And I saw that same presence when we were at the Ryman three weeks ago presenting him the Joe Talbott Award (for outstanding leadership and contributions to the preservation and advancement of Country Music’s values and traditions). Standing on that stage, telling him the last two people to get this award were Merle Haggard and George Jones, there were tears in his eyes. He has that kind of honesty and that authenticity we have less of today. He walks the walk. He always walks the walk.”
Alan Jackson
Courtesy CMA
– Alan Jackson
Way Back Yonder: Alan Jackson at CMA’s 1993 Fan Fest at the Tennessee State Fairgrounds, part of the 1990s country music explosion he helped lead.
Growing up in a small town, concerts were rare – and often a luxury his family couldn’t afford. He had a small band, playing local clubs before he went to his first show. It was The Kendalls at the Music Park in Franklin, Ga., where he would also see “Mickey Gilley, the Oak Ridge Boys, Ricky Skaggs maybe…”
It wasn’t the spectacle that got him, though. “It made me excited when I saw them, and heard the music like that. Seeing them made me know this is what I wanted to do.”
Like a thousand other dreamers, he and his wife Denise moved to Nashville. He delivered mail at TNN, took crummy little gigs to keep playing and worked at writing songs. A flight attendant, Denise gave Glen Campbell his demos, resulting in Jackson’s first break: a publishing deal. “Home,” the first song he wrote when he got to Nashville, spoke volumes about what he valued. He wrote “I’d Love You All Over Again,” missing Denise in a motel room in Pine Bluff, Ark., as well as “Wanted,” inspired by a John Wayne movie on the TV.
“I didn’t have a record deal, just some ol’ club date,” he remembers. “I was old by today’s standards, 25 or 26 years old. I was married, had worked a job for a bunch of years … When I first got to town, that’s when Randy Travis was happening. Everybody said there was somebody already doing (traditional country).”
Leave it to Tim DuBois, a producer/songwriter, charged with starting Arista’s Nashville division. A start-up label, they took a chance on the quiet 6’ 4” classic country songwriter. If “Blue Blooded Woman (Redneck Man)” failed to ignite, “Here In The Real World” topped the charts and earned 1990 CMA Song and Single of the Year nominations, as well as 1991 Academy of Country Music Song and Single nods and a second CMA Song nomination. 
A superstar was emerging, one who couldn’t be denied. 
Bob Romeo, leader of the Romeo Entertainment Group, remembers, “We started getting calls, ‘Who’s that tall guy with the torn jeans, and the hat?’ That was Alan. They would know a song or two, not his name, but they could describe him. Superstars have an image from day one, and you just know. …”
For Romeo, whose company still does over 800 events a year including Cheyenne Frontier Days, the Colorado State Fair and Country Jam, the connection was instant. “I met Alan through Randy and Lib Hatcher. We were doing some dates, and they said, ‘You need to see him.’
“It was Denver at the Stock Show Building, and I thought, ‘Man, this guy’s good.’ We put him on some fair dates, and that was that … Funny thing is, he’s very shy. It’s got nothing to do with his show; his show just keeps coming at you with all those songs. 
“Alan, literally, blows you off the seat with his music.”
That music truly did blow people away. 
Alan Jackson
– Alan Jackson
2017 Country Music Hall of Fame inductee Alan Jackson at the Country Music Hall of Fame and Museum in Nashville, Tenn., April 5, 2017.
T.J. Osborne, the guitar-playing half of the double ACM and CMA Duo of the Year Brothers Osborne, chuckles about the impact Jackson had on him growing up. “I was into grunge music, Seattle, hard rock bands, but then I heard Alan Jackson – and it pulled me right in and peeled back the layers. Realizing how much was going on, for a kid like me who was all consumed with music, his albums just sucked me in.
“I spent more hours sitting in front of my speakers, listening to Alan Jackson records trying to figure out the solos and guitar parts than Jimi Hendrix! Brent Mason was the greatest guitarist – and the stuff he’d play?! I just wanted to hear what he did next, because like Tom Petty and the Heartbreakers’ Mike Campbell, it was so smart and so direct. 
“You’d know those licks the first time you heard them, and the parts are as iconic as anything else in the song, the hook, the lyrics, the melody. My favorite story is when they went to record ‘Chattahoochee,’ Brent had all these ideas, but Alan wanted to replicate the Cajun zydeco accordion. So simple and specific – the hook is two notes, over and over again – but you know it the second you hear it.”
“He can write both working man, heart-tugging stuff,” says John Osborne, the deep-voiced vocalist brother, later that day, “or really funny stuff. When he writes, ‘It gets hotter’n a hoochee coochee?! It’s so clever. And I remember thinking, ‘How can he get away with singing that?’ But nobody seemed to notice.
“Maybe because when he’s singing ‘Small Town Working Man’ or ‘The Little Man,’ if you’re from a small town, you know he understands. He’s not the most acrobatic vocalist, but he has a way of delivering that makes you feel even more than what’s there … He’s amazing that way.”
CMA Album/multiple Vocal Event/Female Vocalist of the Year winner Patty Loveless, who toured with Jackson in the ‘90s, takes Jackson’s connection a step further. The hard country singer from Kentucky says “Alan’s music is the effective beauty of simplicity.
“He’s a classic country gentleman. The songs he sings and writes, they’re all him, but there’s so many people living the same way – and they sense that he’s lived it, too,” Loveless continues. “Alan knows where he comes from, where his roots are, what he loves; he’s country as dirt and he doesn’t forget. To me, he’s as real as Hank Williams, Sr. and Merle (Haggard), those real classic male country artists. I’ve always looked at Hank Sr., the footage and the stories and seen a man who didn’t think of himself as a star, but more a songwriter giving his life to the people. Alan reflects that.”
“Hank Sr. was a lot poorer, and had it rougher than we did,” Jackson responds.  

Alan Jackson
Scott Legato / Getty Images)
– Alan Jackson
Alan Jackson at The Palace of Auburn Hills on February 7, 2013 in Auburn Hills, Michigan.
“He had to be a man. You know, I’m a big fan of Hank Sr. He had a lot of great uptempo things, but he had songs about life. He mixed it up, and that’s what I try to do, too. Those gospel albums I did for my Mama, they sold millions. ‘Sissy’s Song,’ we’d never really had a death in our family, and people tell us it helped ’em through things in their life. It’s all different things in the show.”
That notion of distilling life – the good, the sad and the funny – defines Jackson’s success. Able to keep the fans on their feet – “sometimes they don’t even sit down” – his connection is deeper than his enduring sex appeal or his cascade of tempo leavened by meaningful ballads.
Loveless says of his looks, “He never flaunted it, but he was sexy – and that made him sexier.”
Trahern thinks his songwriting played a part, too. “Like Kris Kristofferson, his songs invoke a presence in time and a moment that is here, right now. Alan can do that, too, and it speaks to grandfathers and little kids without being anything but true to himself.”
Stressing the support of Debbie Doebler, Jackson’s longtime manager, WME’s Insogna, who also grew up in Newnan, Ga., explains, “She’s the only one who’s been there since day one. She’ll go to war for her people, and she goes there for Alan every day. She’s incredibly objective and isn’t easily impressed, so she creates a great team to be part of.”
With the focus on arena plays, they’ve paired with Outback Concerts’ Mike Smardak exclusively. The secret sauce Insogna believes, “is ‘Trust.’ It works well for us. It’s a management/agency/promoter relationship where we all have so much respect for each other and want the same things. More than country music, Alan’s an American icon. No one takes that status lightly. His songs are built into the cultural DNA, so people get two hours of absolute hits – they’re hoarse when they go home. With that, our goals are to keep spreading country music, real country music.”
“We played two shows with him last summer,” John Osborne recalls, clearly delighted by the experience. “We sat sidestage both nights, knowing we were going to see one of the greats do it. Some of those songs are old, but they really moved those young fans; because he wrote them, he can really sing them.
“It’s not a boppy thing for a moment in time. It’s authenticity. He wrote them, because he lived them. It was his life. He’s always stood up for country music, country folk, small town people. 
“And if your songs are good, you don’t have to jump around and do a bunch of stuff onstage. He just stands there, and the people go crazy because it’s not shallow and pandering. People are still hungry for that all these years later… And it’s funny, with all these self-proclaimed ‘outlaws’ and ‘hellraisers,’ he’s always been doing things that were Super Outlaw.”
“Alan’s a quiet rebel,” TJ Osborne agrees. “He was pretty rock and roll without knowing it. When he broke into ‘Choices’ at an awards show – just BOOM! – went into it, because they cut George Jones, then walked offstage?! That’s rock & roll.
“It’s not a sound, it’s a mentality. Johnny Cash, Waylon Jennings, Merle Haggard, it’s the way they carried themselves. It’s weirdly ambiguous: sex is part, not giving a shit, disruption. People think it’s big and bombastic, but Alan, you don’t see coming. He’s unabashed and doesn’t care; he’s going to do what he believes is right. I mean, if you’re gonna be a bear, be a grizzly bear.”
Jackson isn’t so sure he’s buying in. Demuring, he says, “I’m still shy, and nervous onstage. I don’t like the spotlight on me, and everybody staring at me. It’s a little harder, because you reach a level – people put expectations on you.
“When I first got to meet George Jones, he was so nervous and anxious. He had a hard time because people told him he was the greatest singer there was. When people keep telling you you’re special, it takes a toll. 
“I’m still doing what I loved. It’s why I came to town. Gene Watson, John Conlee, George Strait, John Anderson, Ricky Skaggs. That was what I loved, along with George Jones and Merle Haggard, and it’s what I still do. It’s a mixture of everything I’ve done narrowed down to which work better together and keep the crowd from falling asleep. 
“It’s what the crowd wants to hear, really. And I’m just glad it’s not so fine-tuned we can’t change it up. I’ve got a mic on the drum riser, and we change things. In the middle, I sit down on a stool, start a few cold, then the band follows me as best they can. I talk about where the songs come from, what they mean – and people seem to like it. After 30 years, that’s pretty good.”