Contemporary country star Kenny Chesney didn't have the immediate breakout success that many of his peers enjoyed upon signing with major labels, but gradually built up a significant following via hard work, pop-friendly ballads, and a likable, average-guy persona. Chesney was born in Knoxville, TN, in 1968 and raised in the nearby small town of Luttrell, better known as the home of Chet Atkins. He grew up listening to both country and rock & roll, but didn't get serious about music until college, when he studied marketing at East Tennessee State University. He received a guitar as a Christmas present and set about practicing, and was soon performing with the college bluegrass band. He soon started writing songs as well and played for tips in local venues -- most often a Mexican restaurant -- every night he could; additionally, he managed to sell 1,000 copies of a self-released demo album. After graduation in 1991, he moved to Nashville and became the resident performer at the Turf, a rougher honky tonk in the city's historic district. While he gained experience, it wasn't the sort of place where he'd be discovered, and in 1992, he moved on to a publishing deal with Acuff-Rose. From there he landed a record contract with Capricorn and released his debut album, In My Wildest Dreams, in late 1993.

Unfortunately for Chesney, Capricorn wasn't much of a country label; not only was the album underpromoted, but the label's country division shut down completely not long after its release. Still, it sold 100,000 copies and caught the attention of several big-time major labels. Chesney ended up signing with RCA subsidiary BNA, which released All I Need to Know in 1995. The album gave him his first two Top Ten hits in the title track and "Fall in Love." His follow-up, 1996's Me and You, became his first album to go gold, thanks to two number two singles in the title track and "When I Close My Eyes." 1997's I Will Stand was another gold-selling effort that gave Chesney his first-ever number one hit in "She's Got It All," plus another number two with "That's Why I'm Here." His big-time breakthrough, however, came with 1999's Everywhere We Go, which sold over two million copies and spawned two number one hits with "You Had Me from Hello" and "How Forever Feels"; it also featured another Top Ten single in "What I Need to Do," and another, "She Thinks My Tractor's Sexy," that just missed. In 2000, Chesney issued his first Greatest Hits compilation, and two newly recorded songs -- "I Lost It" and "Don't Happen Twice" -- went to number three and number one, respectively.

Greatest Hits became Chesney's second straight double-platinum release and topped the country LP charts. He followed it with the all-new No Shirt, No Shoes, No Problem in early 2002, which gave him his strongest commercial performance yet. It, too, hit number one on the country album charts and spun off four Top Ten singles in "Young," the number one "The Good Stuff," the Bill Anderson co-write "A Lot of Things Different," and "Big Star." A Christmas album plugged the gap for 2003, and he returned strongly with 2004's When the Sun Goes Down, which won in the Album of the Year category at the Country Music Awards. He repeated the win, this time as Entertainer of the Year, with Be as You Are (Songs from an Old Blue Chair). Chesney found himself the subject of much tabloid fodder in 2005 with his surprise marriage to actress Renée Zellweger (he had composed 1999's "You Had Me from Hello" after watching Zellweger in the 1996 film Jerry Maguire). The pair split that same year, citing irreconcilable differences, and Chesney released the chart-topping The Road and the Radio in November. Live: Live Those Songs Again followed in 2006. ~ Steve Huey, All Music Guide