Alan Jackson’s Career Turns 20 with Free Show

Alan and Denise Jackson arrive on the Red Carpet for "The 42nd Annual CMA Awards," broadcast live from the Sommet Center in Nashville, WEDNESDAY, NOVEMBER 12 (8:00-11:00 p.m., ET) on the ABC Television Network. © Adam Larkey / ABC / Retna Ltd.

June 11, 2009 — Alan Jackson distilled much of what we know about him into a short reaction Wednesday night when the Country Music Association, led by board member Kix Brooks and executive director Tammy Genovese, presented him an over-sized collage of photos documenting the 20 years since he signed his first recording deal.

After saying the attention was "a little overwhelming," he gave an aw-shucks summation of the difference between his 1989 position as a struggling, wannabe singer-songwriter and his current place as a multi-award winner with 50 Top 10 hits on his resume.

"I finally saved up enough money to buy me some blue jeans without holes in ‘em," he deadpanned.

It’s a hallmark of Alan’s approach that he’d address a milestone with sly, self-deprecating humor that greatly understates his wealth, putting it in terms that reflect the average man’s wallet. He certainly aided a lot of wallets by throwing a free concert to recognize the two-decade signing anniversary at Cadillac Ranch on Lower Broadway.

With a capacity of 1,800, the Ranch was a great choice. With a classic Cadillac positioned over the bar, it reflects Alan’s well-known passion for cars, and the club’s layout allowed a significant portion of the crowd to get close.

With the anniversary in mind, Alan cranked out a set list that condensed many of those 50 Top 10 hits to a verse and a chorus in order to cram in as many titles as possible. As a result, he ran through 34 songs, 33 of them from that Top 10 list. And it’s particularly telling that he would characterize one of the old No. 1 songs, 1997’s "There Goes," as "obscure." Plenty of artists with careers that lasted perhaps five or six years would willingly center their touring reputation around a sole, 12-year-old chart-topper. For Alan, it’s a minor title in a long list of hits that individually could be considered career-makers: "Where Were You (When The World Stopped Turning)," "Here In The Real World," "Chattahoochee," "Don’t Rock The Jukebox" and "It’s Five O’Clock Somewhere," among them. Added up, it’s a testament to a phenomenal two decades.

As he sang the reflective "Remember When," Alan seemed to stare into the distance, likely going back over the 20 years, just as the song does, to consider how much things have changed for him and wife Denise. And how his relationship with the world at large is different. In 1989, he could shop at the supermarket without being bothered. Now, they turn people away at the door when he fills a large club.

That club will continue to be hopping throughout the CMA Music Festival, even with Alan’s event completed. After the nightly concerts at LP Field Thursday through Saturday, Cadillac Ranch is one of 17 night spots taking part in CMA Music Festival After Hours. Thursday afternoon, Andy Griggs will host a celebrity poker tournament there Thursday with Bobby Bare, Tracy Byrd and Little Texas’ Duane Propes, among others. And Thursday night, Operation Troop Aid holds a benefit concert with such acts as Katie Armiger, Keni Thomas, Adam Gregory and Stephen Cochran.