CMA Wins: 10
Memorable CMA Moment: The Dixie Chicks were a country radio staple in 2000, when the trio took home Vocal Group of the Year and Album of the Year for their multi-platinum-selling 'Fly' album, which spawned five Top 20 singles, including 'Goodbye Earl,' which won Video of the Year the same year. But it was the trio's big win for Entertainer of the Year that perhaps had the three ladies gushing most. "It feels so good," an exuberant Martie Maguire effused from stage. "It's fun to win it when you're out on tour, because night after night the audience has been so giving to us ... We hear them in the audience singing 'Wide Open Spaces' at the top of their lungs, and it's just deafening."
J. Kempin, FilmMagic
CMA Wins: 11
Memorable CMA Moment: Garth took home the first of his four Entertainer of the Year trophies in 1991 -- the same year his 'Ropin' the Wind' became the first country album ever to debut at No. 1 on the pop charts. While the Oklahoma native has been known to get choked up while accepting such honors, he instead elicited a lot of laughs upon accepting this CMA trophy, especially from President George H.W. Bush and his wife Barbara, who were in the audience -- something Garth apparently forgot until mid-speech. "This is cool. It's funny how a chubby kid can just be having fun, and they call it entertaining," Garth said from the stage. "I know this embarrasses these two guys every time I say this, but I don't think any entertainer is anything without his heroes. I love my Georges -- George Strait and George Jones -- and I want to thank you guys for being so good to me ... No offense, Mr. President. I didn't think about that. Sorry."
Frederick Breedon, Getty Images
6. Tim McGraw (tie)
CMA Wins: 11
Most Memorable Win: Tim was no stranger to the CMA Awards stage by 2004, having already won a handful of trophies over the years, including one Entertainer of the Year and two Male Vocalist of the Year wins. But it was his powerful song, 'Live Like You Were Dying,' released only six months after the death of his father, baseball great Tug McGraw, which earned the superstar the award for Single of the Year and became a symbol of hope. "Of course, the song is special to me, but I think it is special to a lot of people," he said from the CMA stage. "The song to me is not about death, it's an affirmation about life."
Rick Diamond, Getty Images
CMA Wins: 14
Most Memorable Win: Brad took home his first CMA trophy, the Horizon Award (now Best New Artist), in 2000 and was Male Vocalist of the Year for three consecutive years beginning in 2007. But who can forget his tearful speech after finally earning the Entertainer of the Year honor for the first time in 2010? "Tonight, to me, is about my grandfather," a visibly emotional Brad noted from stage. "He said, 'I want you to learn to play the guitar, because this is going to get you through the lonely times, and you'll never be alone with this' ... I don't think he ever thought it would draw 20,000 people. He died in 1987."
Adele Starr, Getty Images
4. Alan Jackson
CMA Wins: 16
Most Memorable Win: Alan has scored a victory in nearly every CMA category possible throughout his career, including Single of the Year (in 1993) and Song of the Year (in '94) for 'Chattahoochee.' Few were surprised when the soft-spoken Georgia native took home both Song and Single of the Year again in 2002 for the poignant 'Where Were You (When the World Stopped Turning)?,' a song inspired by the aftermath of the September 11 terrorist attacks. Alan's brief acceptance speech for the chart-topping hit still stands out almost a decade later. "I've been very moved since the beginning of this whole song," he admitted. "I have to thank God for sending me the lyrics and the melody to this song. And thanks to America for taking this song into their hearts."
Doug Collier, AFP/Getty Images
CMA Wins: 18
Most Memorable Win: As one of popular music's most awarded individuals, Vince has had to make a lot of acceptance speeches. The usually jovial, quick-witted entertainer handled things quite differently, however, after earning CMA's Song of the Year for the emotional ballad, 'Go Rest High on That Mountain,' in 2006. It was more what he didn't say than what was said as he accepted the award. Acknowledging the tune was written after the death of Keith Whitley, as well as Vince's own brother, the singer-songwriter barely uttered a "thank you" before adding that the song caused him too much grief to say much more.
Rusty Russell, Getty Images
2. Brooks & Dunn
CMA Wins: 19
Most Memorable Win: During their time together, Brooks & Dunn dominated the Vocal Duo of the Year category, winning it every year from 1992 to 2006, with the exception of 2000 when it went to Montgomery Gentry. But it's the pair's 2006 Single of the Year victory for 'Believe' that truly stands out, giving them their only win ever in that category. "I had no idea -- a lot of competition out there, a lot of hot songs that are really happening with the same theme content," Ronnie Dunn shared, before passing the mic to his partner, who sang his praises. "This guy here did the heavy lifting on that song," Kix Brooks conceded. The Ronnie Dunn-Craig Wiseman-penned tune also earned the writers Song of the Year.
Bryan Bedder, Getty Images
1. George Strait
CMA Wins: 22
Most Memorable Win: He's country music's King George for many reasons, not the least of which is the fact that he holds the record for more CMA wins than any other artist in history. So far, he's taken multiple trophies in the Album, Male Vocalist, Single and Entertainer of the Year categories. Yet, his single victory thus far for Vocal Event of the Year (shared with duet partner Alan Jackson) for 'Murder on Music Row' had the iconic entertainer defending the controversial tune, which accuses Nashville of destroying true country music.
"I don't know how seriously this song was written, but it was [recorded] as kind of a joke," he explained, later adding, "I like traditional country music but I think there is a limited market for it."