If you're ever lucky enough to be plucked from the crowd at a Kenny Chesney concert to join the singer at the foot of the stage—as a small group of fans are at each performance—a bit of advice: Do. Not. Touch. The. Boots. One recent night, as Chesney knelt at the stage's edge signing autographs, "This guy tried to sign my boot," says Chesney, motioning to the black ink stain on his size-8 Justin boots. "Can you believe that?" Then again, that's not so bad compared to a more frequent hazard of the job: "What I really hate is when girls with long nails just grab my hand and squeeze hard," he says. "They don't realize they're digging in!"
It's all in a day's work for Chesney, 38, who has spent the last 13 summers—up to 150 days out of the year—on the road bringing his high-octane, boot-scootin' country rock show across the country. How big is his show? He has drawn more than a million audience members every year for the past five years, making him country's No. 1 overall touring act with $25 million in album sales. Whether he's taking his traditional joy ride aboard a John Deere Gator through the preshow tailgating crowd, chilling backstage in the "Vibe Room" with his band or mixing his signature Bloody Marys (the secret is Zing Zang Bloody Mary Mix) aboard his tour bus, "I'm most at home out here," says Chesney, who wrapped his sold-out "The Road and the Radio" tour last month and just released his first live album, Live Those Songs Again. The road, he says, "really is its own world."
As the tireless ringleader of Kenny's World, Chesney captains a traveling circus that includes as many as 23 buses and 54 semi trucks carrying his 260-person crew and equipment—up from the lone tour bus he started with back in 1993. These days, the singer shares his ride with four longtime pals from Tennessee who help manage his road life and tour. "This is my family, and we have become very close out here," he says. "It's comfortable. I trust it. It's forced me to move on."
Most notably for Chesney, that has meant moving on from his high-profile romance with actress Renée Zellweger, 37, which ended when the pair had their four-month marriage annulled last September. "After the craziness of last year, I didn't think I had the heart to go on the road," says Chesney. "But all of my road family and also my fans, they had the heart for me. All of this"—he gestures around his home away from home—"helped me heal." As for his current romantic status, "No, I'm not in love," he says. "I'm not one of those people who wants to be in love for the sake of being in love—but I believe in it. I know I'm not jaded."
Besides, he's got more than enough to keep him busy. Part rigorous boot camp—his famously intense fitness regimen includes daily workouts with a trainer and a strict low-carb, low-fat diet—part rolling frat party, Chesney's life on the road is by now as consistent as his size XL cowboy hat and those 29-in.-waist Levi's. Aboard his bus, he crashes in a twin bunk bed under a dorm-style black comforter ("I sleep better on this bus than anywhere else"), and cleans up after himself (though most of his meals are prepared by a chef who travels with the tour's catering) and kicks back playing Play Station 2's NCAA college football game on his flat-screen TV.
Then it's showtime, with Chesney hitting the stage for two hours of high-fiving, running, jumping, dancing and, of course, rocking. "You're in front of die-hard country fans," Dierks Bentley has said of opening for Chesney. Onstage, "he tries to give fans more bang for their buck," says fellow country singer Chely Wright. "He puts a lot into it."
Not surprisingly, it takes a lot out of him. Dripping in sweat after each performance, Chesney acknowledges that coming down off the stage can be the biggest challenge of all. "That is the loneliest part of being on the road," he says. "You go from being in front of thousands of people, and within 20 or 30 seconds I'm alone on the bus in complete silence. That is a tough adjustment. It's such a contrast emotionally." Not that he plans to relinquish his road-king crown anytime soon. "It's addictive," he says of the touring life. "To feel that juice—it's amazing."