As a kid, Tennessee native Kenny Chesney has dreams of becoming a star athlete. But by the time he reaches Gibbs High School, those dreams fall short when he stops growing at 5'8". During his freshman year in college, his hairdresser mom Karen buys him a guitar for Christmas. "I remember making up songs in my head," Chesney tells PEOPLE in 2002. "Just stupid stuff." In three months, he figures out the chords to the Eagles' "Tequila Sunrise" and has a new passion for music.
In between marketing classes at East Tennessee State University, Chesney begins performing in small clubs near campus. "I got $5 an hour plus as many enchiladas as I wanted," he tells PEOPLE. Simultaneously, the budding musician makes a homemade album that sells 1,000 copies. He uses the money to buy a new guitar. After graduation, he moves to Nashville, where he signs with Acuff-Rose as a songwriter.
Chesney appears at a Nashville songwriters' showcase and gets a record deal with Capricorn Records. His debut album In My Wildest Dreams fails on radio, and Capricorn disbands its country division. However, he nabs a new deal with Sony BMG Nashville's BNA, which releases 1995's All I Need To Know (left) and delivers two Top 10 country hits.
After scoring his first gold album with 1996's Me and You, Chesney releases I Will Stand, which produces his first No. 1 single, "She's Got It All." "I went through a lot of stressful nights, wondering which songs to keep and which to let go, because this is a very pivotal album for me," Chesney tells Billboard. In 1998, the Academy of Country Music names Cheney Best New Male Vocalist.
Everywhere We Go sells two million copies with the hit, "You Had Me From Hello," borrowed from Jerry Maguire. "When Renée Zellweger said that line, I thought, 'That could be a great song,'" he says. In 2000, his greatest hits album becomes his second double platinum release.
Chesney and pal Tim McGraw (right) are arrested following a concert in Orchard Park, N.Y., after Chesney mounts a policeman's horse. Afraid that Chesney would fall down, McGraw holds back the officers and is arrested on suspicion of second-degree assault, menacing and resisting arrest. Chesney is arrested for disorderly conduct. When they go to trial the following year, they're acquitted on all charges.
The hardworking Tennessean becomes a Caribbean convert with the release of No Shoes, No Shirt, No Problems (left), which sells more than 3 million copies. He also buys a home in the U.S. Virgin Islands and releases All I Want for Christmas Is a Real Good Tan.
Chesney's "Margaritas & Senoritas" tour draws 1.1 million fans, grossing $40 million. "I can't tell you how many people have come up to me and told me they don't really listen to country music, but they love what I'm doing," he tells Billboard. "I love that we've captured a demographic that can grow with us."
Chesney's When the Sun Goes Down goes triple platinum and is 2004's bestselling country album. He also goes on the "Guitars, Tiki Bars + a Whole Lot of Love" tour with Keith Urban, which grosses $50 million. At the CMAs, Chesney wins top honors: Album of the Year and Entertainer of the Year. "I didn't think I was ever going to get to hold one," Chesney tells Billboard. "I've been through so much in 12 years...When we sold the amount of tickets we sold and the amount of albums we sold...it proved to them that we were connecting with people out there."
At a telethon for victims of the Asian tsunami, Chesney meets Renée Zellweger, whom he has a long nursed crush on. After a quick courtship, Chesney, 37, and Zellweger, 36, get married on May 9 in a surprise, barefoot-on-the-beach wedding at Chesney's cliffside estate in St. John. "I may well be the luckiest man alive," Chesney says in a statement. "To be so in love with someone who is so perfect for me – it's just hard to imagine that I'm not going to wake up." With his new wedding ring, Chesney picks up Entertainer of the Year at the Academy of Country Music Awards.
BIOGRAPHY (top to bottom): Courtesy Kenny Chesney; Jim Smeal/WireImage; amazon.com; Jim Smeal/WireImage; amazon.com; Kevin Mazur/WireImage; amazon.com; Justin Kahn/WireImage; Mark Humphrey/AP