Kenny Chesney

September 14

The Chesney-Zellweger Annulment

Zellweger files for an annulment, citing "fraud." Chesney tells PEOPLE in a November 2005 cover story that he has no regrets about marrying Zellweger. "What I did in May, I meant. Isn't it great that kind of love exists?" But he also admits: "I'm sad, I'm angry, and I'm hurt and confused. This is not what I envisioned my life to be six months ago." In response to tabloid rumors about his sexual orientation, Chesney says, "I'm pretty firm in my sexuality and my love for women."

Kenny Chesney

November 08

On the Road Again

"I have engulfed myself with work and music," he tells PEOPLE of his latest release, The Road and the Radio, which debuts at No. 1. Despite the success, the Country Music Awards name Chesney's former opening act, Keith Urban, Entertainer of the Year. Chesney goes back on the road. "After the craziness of last year, I didn't think I had the heart to go on the road," he says. "But all of my road family and also my fans, they had the heart for me." The following year, he takes back the CMA for Entertainer of the Year.


Kenny Chesney


Poets & Pirates

Seventeen trucks move Chesney's "Flip Flop Summer Tour" from arena to arena. His fifth consecutive summer tour draws more than a million fans. "Believe it or not, I want to keep growing my audience," he tells Billboard. That September, Just Who I Am: Poets & Pirates (right) debuts at No. 1 on the country charts.

Kenny Chesney

November 07

CMA's Reigning King

Chesney wins the top award, Entertainer of the Year, at the 2007 CMA Awards. "Guys, I can't believe that I get to stand on the stages I stand on every summer, and get to sing the songs that I sing," he says during his acceptance speech. Chesney is again named Entertainer of the Year at the 2008 CMAs, marking the third consecutive year and fourth time overall he has won the award. The win follows his fourth consecutive Entertainer of the Year award at the Academy of Country Music Awards in May 2008.


Kenny Chesney


Friends Forever

Chesney graces PEOPLE's country music issue alongside pal Tim McGraw, who appears on the country star's latest hit "Feel Like a Rock Star." The longtime pals will also trek across the U.S. for their co-headlining "Brothers of the Sun" tour. "I tell you what we won't be doing on tour – love ballad duets!" Chesney tells PEOPLE. "That time of night, in a football stadium, they want it loud and fast. That's what we'll give them."

Photo Credits

BIOGRAPHY (top to bottom): Scott Gries/Getty Images; amazon.com; Scott Gries/Getty

Edited by Julia Wang

Kenny Chesney

Celebrity Central / Top 25 Celebs