When Kenny Chesney arrived in Nashville in ’91, he wasn’t yet the rum-gulping, island-hopping millionaire his fans have come to love. An ambitious everyman from small town Tennessee, Chesney began in the music business down on his luck and lovesick, the spitting image of the fellow he’s crooned about in so many of his sweet, stirring songs. A pop culture phenomenon for 15 years running, the unassuming Chesney, who stands all of 5’7” with his boots on, has to do little more than blink his baby blues and twist his baseball hat backwards to capture the adoration of millions. Here, Gibson reveals 10 things you may not know about arguably the most written about man in country music.

1. God gave Kenny Willie Nelson. After the 2005 annulment of his marriage to actress Renee Zellweger, about whom he’d written the hit “You Had Me at Hello” before the two even met, Chesney was plagued by writer’s block and had doubts about mustering the material for his new album Just Who I Am: Poets & Pirates, released September 11. Though Chesney calls the new album his most personal to date, he didn’t pen any of the tracks himself. Instead he relied on industry songwriters and let Willie Nelson helm production of the album. “Every artist feeds off inspiration, and when I needed it the most, God gave me Willie Nelson,” Chesney says. 

2. Kenny does his best thinking in the grimy back alley of a burger joint in St. John. “For some reason or another, I feel so relaxed back here with propane tanks, ice makers, brooms. I know it’s odd. And I love it, man. I mean it’s almost like therapy for me to come back here and just sit.” Chesney, who owns a gated home in the U.S. Virgin Islands and lives there a portion of the year, frequents the area’s beachside watering holes and restaurants, where he’s even said to tend bar from time to time.

3. Kenny’s choice in libations have, ahem, changed over the years. Since Cruzan rum began sponsoring his epic tours, he’s altered a lyric in his song “Old Blue Chair” from “That chair was my bed one New Year’s night/ When I passed out from too much Malibu and diet,” to “When I passed out from too much Cruzan and diet”—a not-so-subtle nod to his endorsee. The country singer and the liquor company have even come out with their own concoction, called Chesney’s Cruzan Confusion. The includes Cruzan Coconut, Cruzan Mango, and pineapple juice and has been widely disseminated on the web. 

4. Kenny makes even Oprah look stingy. Chesney’s many times extolled the generosity of Virgin Islands natives, and has evidently taken their cue. Following his 2003 tour, he gifted his road-weary crew with a vacation to St. John. And he didn’t skimp on the travel arrangements. Chesney chartered the Hooters jet and had it stocked with frosty beer and chicken wings for a sky-high party. The love didn’t stop there. The following year he also wrote each of his 100 crew members a bonus check for $14,000.

5. Kenny’s tractor’s not actually sexy. After the 1999 breakout hit “She Thinks My Tractor’s Sexy” helped ingratiate Chesney to the public, he admitted that he owns not one but two tractors but says they’re “not one bit sexy.” “I knew that a lot of people that grew up just like I did would go crazy over [that song],” Chesney says. “But there was no gray area. Either you loved it or you hated it. I was smart enough to record that song but I was smart enough also not to record another one.”

6. Kenny doesn’t just love football, he really, really loves football. Besides calling Indianapolis Colts quarterback Peyton Manning his best friend, the former high school wide receiver recently signed as a free agent with the New Orleans Saints and spent an afternoon practicing with them, even catching one glorious punt. “It was a great day,” said Chesney. “I worked my tail off but when you get out there with those guys, they have so much heart, man. It’s no wonder they were able to really become a force for the city of New Orleans after Katrina and for the country.”

7. At a whopping 147 lbs., Kenny’s got his diet regimen down to an art, subsisting largely on carrot sticks, Red Bull, protein shakes, and egg whites. Several years ago Chesney shed 40 lbs. with daily workouts and has since developed his penchant for sleeveless muscle shirts.

8. Kenny narrowly missed the 9/11 disaster. His video for the “The Tin Man” was scheduled for filming between the two World Trade Center towers on the afternoon of the attack, but equipment delays meant the crew had to reschedule.

9. Kenny and his guitar didn’t hit it off from the beginning. After taking his first guitar lessons in the fifth grade, Kenny quit, complaining of sore fingers, and didn’t pick the instrument back up until he was a student at East Tennessee State University, from which he graduated with an advertising degree. Today, Kenny favors Les Paul Standards and Les Paul Classics.

10. Kenny and friend Tim McGraw are true outlaws, almost. In 2000, the two singers were arrested after Chesney climbed aboard a police horse named Chico backstage at the George Strait Country Music Festival in Buffalo, New York. According to police, McGraw interfered with officers trying to remove Chesney from the horse, leading to a dozen charges against the singers. Eleven months later both Chesney and McGraw were acquitted of all charges.