Chesney won album of the year honors Tuesday for "When The Sun Goes Down," and, at the end of the night, received the coveted entertainer of the year award.
Shortly into his speech, music signaled his time was up during the live broadcast. Chesney protested, but the cameras cut to hosts Brooks & Dunn and the show ended.
Chesney was gracious about it afterward. He said he wanted to convey that artists like Conway Twitty and George Strait had inspired him.
"For a kid in East Tennessee ... they made me think there was something else out there for me," he said.
Tim McGraw (search)'s "Live Like You Were Dying" won song of the year and single of the year.
"Of course the song is special to me, but I think it is special to a lot of people," McGraw said. "The song to me is not about death, it's an affirmation about life."
Written by Tim Nichols and Craig Wiseman, "Live Like You Were Dying" spent eight weeks at No. 1.
The song, about living life to its fullest, was special for McGraw, who lost his father, former New York Mets and Philadelphia Phillies relief pitcher Tug McGraw, to cancer in January.
The lyrics tell of a man in his early 40s who learned he doesn't have long to live and is asked how he handled the news. McGraw sings, "Someday I hope you get the chance to live like you were dying."
Other winners included Keith Urban, Gretchen Wilson, Brad Paisley, Martina McBride and Rascal Flatts.
"Whiskey Lullaby," a duet recorded by Paisley and Alison Krauss, won for musical event of the year and music video of the year. It's a dark tale about a woman who breaks a man's heart, watches him drink himself to death and then is so guilt-stricken that she too "put that bottle to her head and pulled the trigger."
"I want to thank country radio for playing this," Paisley said. "It says a lot about the great people in our format who will take a chance on a double suicide in a drinking song."
In one of the evening's surprises, Urban won the male vocalist award. He was up against veterans Alan Jackson, George Strait, Toby Keith and Chesney.
"I thought I was just rounding out the category," Urban said.
During the show, Keith and his daughter, Krystal, performed "Mockingbird," and Kix Brooks of the duo Brooks & Dunn paid tribute to the late Ray Charles.
"He really was one soulful country singer. Bless you, Ray Charles," Brooks said.
Keith had six nominations for the Country Music Association awards, but was shut out for the second straight year.
"I have the worst record in the history of the CMA," Keith said recently.
Jackson, who led all nominees for the ceremony with seven, also left empty handed.
McBride won female vocalist of the year, her fourth in that category and third in a row.
"When I was a little girl in Kansas I had some big dreams, but I don't think I ever dreamed this big," she said.
Dolly Parton presented the entertainer of the year award to Chesney, joking, "Once upon a time I won the entertainer of the year award, and if any of you out there remember when that was you keep your mouth shut."
Others who've won the award include Johnny Cash, Merle Haggard, Willie Nelson and Loretta Lynn.
Wilson, who has sold 3 million copies of her debut album, "Here For the Party," won the Horizon Award for best new artist. She fought back tears as she accepted.
"I came here last year and sat way back there in the very back and dreamed of standing up here someday. I just had no idea it would happen this fast for me," she said.
Rascal Flatts won the vocal group award for the second consecutive year.
"It's overwhelming," said bass player Jay DeMarcus. "We had big hopes and aspirations when we started out in this business ... to have something like this in hand at the end of the day sort of gives validity to what you want to accomplish."
Singer-songwriter Kris Kristofferson was inducted into the Country Hall of Fame. His friend Willie Nelson introduced him and sang Kristofferson's "For the Good Times." Faith Hill performed his "Help Me Make It Through the Night" and Randy Travis did "Sunday Morning Coming Down."
Kristofferson, who has been outspoken during his career on political and social issues, sang "Me and Bobby McGee," a song made famous by Janis Joplin.
He thanked the late Johnny and June Cash "for endorsing me back when nobody knew me and defending me later when everybody did and for standing up for truth and justice and human rights."