Chesney took home his fourth entertainer of the year trophy Wednesday, tying Garth Brooks for the most wins in the category, considered the night's top honor. He's now won the award the last three years in a row.
"Winning entertainer of year for the fourth time in five years is more than this kid ever dreamed of," Chesney said backstage.
And to his competitors, he issued a challenge: "Come and get me."
Chesney wasn't the night's only big winner. George Straight won single and album of the year, making him the act with the most awards in the history of the Country Music Association Awards, with 22 total.
Strait thanked the songwriters for "letting me sing such a beautiful song" after the poignant "I Saw God Today" won single of the year. He later won album of the year for "Troubadour."
"Everybody says they've got the greatest fans. Well, I've really got the greatest fans," Strait said in accepting the album award.
Also winning two awards was Jennifer Nettles of Sugarland. Sugarland won the award for duo of the year, and earlier, Nettles won song of the year for Sugarland's hit "Stay."
"We have so much to prove songs to write, people to win" over, Nettles said backstage.
The show, which was co-hosted by Carrie Underwood and Brad Paisley, was highlighted by a touching tribute to U.S. troops, a surprise appearance by rapper Lil Wayne and the return of one of country's biggest stars, Shania Twain.
Underwood won her third consecutive female vocalist award and told her mom in her acceptance speech, "It's real hard to sing when you're in the second row crying." It came after her performance of her No. 1 hit "Just a Dream," about a woman who lost her loved one in war. The song was introduced by Leslie Ponder who lost her husband in Afghanistan.
The former "American Idol" champ also thanked country fans. "I got here in an unconventional way, and you guys didn't have to accept me at all."
Paisley, who won video of the year earlier, hugged Keith Urban and kissed the stomach of his pregnant wife, actress Kimberly Williams-Paisley, as he went up to collect his award.
Rascal Flatts won their sixth straight vocal group of the year award, beating out the Eagles, Emerson Drive, Lady Antebellum and Little Big Town for the honor.
Lady Antebellum, a trio that is one of country music's most promising acts, won best new artist. As they picked up their award, their awe-struck guitarist, Dave Haywood, said: "It's not supposed to happen like this."
While the awards may have been the main point of the evening, it was the performances that dominated the show.
Kid Rock performed his hit "All Summer Long," and, perhaps in a nod to his hip-hop roots, brought out top-seller Lil Wayne on stage, though the rapper didn't utter a word he just mimicked playing a guitar onstage. He may have been the first true rap act to perform at the CMAs.
Taylor Swift brought her hit "Love Story," which features characters named Romeo and Juliet, to life with an elaborate set which featured her wearing a medieval-looking purple gown with a castle backdrop: She later shed the gown to reveal a sweeping white dress.
Brooks & Dunn have said that "Cowgirls Don't Cry" was inspired by country great Reba McEntire, and she joined them on the song, an ode to a tough woman.
Chesney performed his reggae-flavored hit "Everybody Wants to Go to Heaven" with the reggae band the Wailers backing him up. They also performed the Bob Marley classic "Three Little Birds."
"You look really good," Chesney remarked to Twain as he accepted his entertainer award. She wore a sexy, low-cut dress as she presented Chesney with his award. Twain is one of country's best-selling artists, but has spent the last several years out of the spotlight. She hadn't been on the show in four years.
The Eagles, whose return to the top of the charts has a lot to do with their recent country leanings, performed "Busy Being Fabulous."
Paisley and Urban opened the show with dueling guitars as they performed their duet, "Start a Band." The song is the first single from Paisley's new mostly instrumental album, "Play." The two incorporated elements of classic rock anthems such as "Layla" and "Smoke on the Water" as they played.
Paisley also performed a musical tribute to singer and guitarist Jerry Reed, who died this year.
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