It took him nearly a decade to get there, but in 2002 Kenny Chesney began his ascent to a Garth Brooks-like status in country music when his blockbuster album No Shoes, No Shirt, No Problems rocketed to Number on the country and pop charts and eventually sold more than 4 million copies. In 2008 Chesney won the Academy of Country Music's Entertainer of the Year award for the fourth consecutive year. Chesney's mix of heartland rock, pop and country has earned him more than thirty Top Ten country singles and numerous awards.
Born Kenneth Arnold Chesney on March 26, 1968, in Knoxville, Tennessee, to a hair stylist mother, he was raised in nearby Luttrell. Chesney played football at Gibbs High School in Corryton, Tennessee, but didn't begin playing music until he was in college at East Tennessee State University in Johnson City, where he studied advertising. After graduating, he moved to Nashville and signed with BMI and Opryland Music Group in 1992. His debut album, In My Wildest Dreams, came out in two years later on the newly revived southern rock label Capricorn Records. Though it was more pure country than his later albums, Chesney set the tone of his winning career with his smooth baritone on slick ballads like "When She Calls Me Baby" and the upbeat honky-tonk of "Whatever It Takes," which climbed to Number 59 on Billboard's country singles chart.
Chesney left Capricorn for RCA subsidiary BNA Records and released his breakthrough second album, All I Need to Know (Number 39, 1995), which yielded Top Ten country hits in the pop-country "Fall in Love" (Number Six, 1995) and ballad "All I Need to Know" (Number Eight, 1995). Successive albums — Me and You (Number Nine Country, 1995) and I Will Stand (Number Ten country, 1997) — fared even better, producing the country hits "When I Close My Eyes" (Number Two, 1996), "Me and You" (Number Two), "She's Got it All" (Number One), "A Chance" (Number 11), "I Will Stand" (Number 27) and "That's Why I'm Here" (Number Two).
Chesney became a crossover success with Everywhere We Go (Number Five country, Number 51 Pop, 1999), with its hits "How Forever Feels" (Number One country, Number 27 pop, 1999), "You Had Me from Hello" (Number One country, Number 34 pop), the novelty song "She Thinks My Tractor's Sexy" (Number 11 country, Number 68 pop, 1999), and "What I Need to Do" (Number 8 country, Number 56 pop, 2000). The album sold 2 million copies. He began the next decade of his career with Greatest Hits (Number One country, Number 13 pop, 2000), which featured four new songs including "I Lost It" (Number Three country, Number 34 pop) and "Don't Happen Twice" (Number One country, Number 26 pop).
Chesney's sixth release, 2002's No Shoes, No Shirt, No Problems was barely country at all; aside from his Tennessee twang and the presence of pedal-steel guitar, the songs were more in line with those of such average-guy, heartland rockers as Bob Seger, Tom Petty or John Mellencamp. No Shoes… rocketed to Number One on both the pop and country charts, yielding huge crossover hits in the upbeat rockers "Young" (Number Two country, Number 35 pop) and "Big Star" (Number Two country, Number 28 pop), the ballad "A Lot of Things Different" (Number Six country, Number 55 pop) and mid-tempo "The Good Stuff" (Number One country, Number 22 pop, and the pure pop-country of the title track (Number Two country, Number 28 pop, 2003).
Chesney has continued his momentum with successive platinum and multi-platinum Number One country albums throughout the 2000s: When the Sun Goes Down (Number One country, Number One pop, 2004), Be as You Are (Songs from an Old Blue Chair) (Number One country, Number One pop, 2005), The Road and the Radio (Number One country, Number One pop, 2005), Live: Live Those Songs Again (Number One country, Number Four pop, 2006) and Just Who I Am: Poets & Pirates (Number One country, Number Three pop, 2007).
His string of Top Ten country hits in the 2000s includes, "There Goes My Life" (Number One country, Number 29 pop, 2004), his duet with Uncle Kracker "When the Sun Goes Down" (Number One country, Number 26 pop, 2004), his collaboration with Jimmy Buffett, Clint Black, Alan Jackson, Toby Keith and George Strait on Hank Williams' "Hey Good Lookin'" (Number Eight country, Number 63 pop, 2004), "Anything But Mine" (Number One country, Number 48 pop, 2005), "Living in Fast Forward" (Number One country, Number 48 pop, 2005), "Summertime" (Number One country, Number 34 pop, 2006), "Beer In Mexico" (Number One country, Number 61 pop, 2007), "Never Wanted Nothing More" (Number One country, Number 22 pop, 2007), "Don't Blink" (Number One country, Number 29 pop, 2007) and his duet with Strait on "Shiftwork" (Number Two country, Number 47 pop, 2007).
Chesney has won numerous awards including Academy of Country Music honors for New Male Vocalist of the Year (1997), Top Male Vocalist of the Year (2002) and Entertainer of the Year (2005, 2006, 2007, 2008); Country Music Association nods for Album of the Year (When the Sun Goes Down, 2004) and Entertainer of the Year (2004, 2006, 2007); and American Music Association awards for Artist of the Year (2004) and Entertainer of the Year (2007); as well as several CMT video awards.
In 2005, Chesney's personal life became tabloid news when he married actress Renée Zellweger in the U.S. Virgin Islands and filed for an annulment after only four months of marriage. In 2008, Chesney — who has a home in the Caribbean — was slated to embark on his Corona beer-sponsored "Poets & Pirates" stadium tour with openers LeAnn Rimes and Keith Urban.