Kenny Chesney
Flip-flops, a straw hat, and a stadium full of people who had never been to the Caribbean singing about it anyway. Kenny Chesney turned "No Shoes, No Shirt, No Problems" into a brand and the 2000s into one long beach party, winning four ACM Entertainer of the Year awards in a row and building the biggest touring career in Billboard's country ledger.
Chesney, born in 1968, got a songwriter's contract after a five-song audition in Nashville in 1992 and a record deal a year later. His 1994 debut sold about ten thousand copies before the label shut its country division; BNA picked him up in 1995, and "She's Got It All" gave him a first number one in 1997. The sound was fiddle-and-steel neotraditional until 1999's Everywhere We Go, when "How Forever Feels," "You Had Me from Hello," and "She Thinks My Tractor's Sexy" moved him toward the tropical country-pop he became known for. Shooting the "How Forever Feels" video in the Virgin Islands, he fell for St. John and later had a house there.
No Shoes, No Shirt, No Problems, released in April 2002, was the breakout: his first album to top the Billboard 200, with "The Good Stuff" spending seven weeks at number one as Billboard's top country song of 2002 and the title track winning CMT's fan-voted "hottest video" award. When the Sun Goes Down followed in 2004 with "There Goes My Life" and a duet with Uncle Kracker and took CMA Album of the Year; The Road and the Radio, in 2005, added "Summertime" and "Beer in Mexico." The ACM named him Entertainer of the Year every year from 2005 through 2008, and the CMA gave him the same award for a third time in four years in 2007. His 2005 marriage to Renée Zellweger, on St. John, was annulled within months.
The real product was the summer tour. The names tell the story: the No Shoes, No Shirt, No Problems Tour in 2002, Margaritas 'n Senoritas in 2003, Guitars, Tiki Bars and a Whole Lotta Love in 2004, the Flip-Flop Summer Tour in 2007, Poets and Pirates in 2008. Billboard gave him its Top Package Tour award five straight years from 2005 to 2009. Opening the 2008 tour at Williams-Brice Stadium in South Carolina, his boot caught between a hydraulic lift and the lip of the stage and crushed his foot; he pried it free in about thirty seconds, sang the show limping, and canceled nothing, even after X-rays showed several crushed bones.
By Billboard's Boxscore count through 2023 he had grossed $1.17 billion and sold 17.9 million tickets, more than any other country act. He entered the Country Music Hall of Fame in October 2025.
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