Who are the biggest winners in CMA Awards history?

It’s not much of a surprise that the reigning king of country music is also the winningest Country Music Association Award winner with 22 trophies. He’s won in the Entertainer of the Year, Album of the Year, Male Vocalist of the Year and Single of the Year categories, some multiple times each! Strait began his reign in 1985 with an Album of the Year win for "Does Fort Worth Ever Cross Your Mind," Strait’s fourth studio album. 

Because Brooks & Dunn dominated the Vocal Duo of the Year category for 14 non-consecutive years, the award has long been jokingly called the “Brooks & Dunn Award." The duo of Ronnie Dunn and Kix Brooks has also taken home four additional trophies, including winning Entertainer of the Year in 1996, resulting in a total of 18 wins. 

Throughout his time of ruling the country airwaves in the 1990s and 2000s, Tim McGraw has won 14 CMA Awards. His most recent came in 2012, for "Feel Like a Rock Star," a collaboration with Kenny Chesney, in the Vocal Event of the Year category. 

With 18 CMA Awards wins, it’s easy to see why Gill is one of country music’s most enduring figures. Gill began his historic CMA Awards trajectory in 1990 with a win in the Single of the Year category for “When I Call Your Name,” the title track of the album that really launched Gill’s decades-long career. 

For more than two decades, Alan Jackson was one of the most dominant award winners in CMA history. He won the first of his 16 CMA Awards in 1992 in the Music Video of the Year category with “Midnight in Montgomery,” and he is one of only two country artists to win five CMA Awards in the same night, which he did in 2002 thanks in large part to his emotional 9/11 tribute “Where Were You (When the World Stopped Turning).” 

Arguably one of country music’s most successful artists of all time, Garth Brooks has won 14 CMA Awards in his record-shattering career. Six of those wins have come in the coveted Entertainer of the Year category, and in 2005 Brooks was the first recipient of the Pinnacle Award, which recognizes an artist’s global achievements in record and concert ticket sales. 

Also one of the CMA Awards’ most popular hosts, Brad Paisley is a frequent winner with 14 trophies. Paisley took home his first CMA Award in 2002, winning in the Best New Artist category. Since then he’s scored multiple wins in the Male Vocalist of the Year and Music Video of the Year categories, the latter of which can be credited to his cheeky, often hilarious music videos. 

Miranda Lambert has won armfuls of awards in her storied career so far, including 13 CMA Awards. She’s won in the Female Artist of the Year category seven times, and she took home Album of the Year in 2014 for her fifth studio album, "Platinum."

In 2001 Keith Urban burst onto the scene and won the Country Music Association’s Horizon Award, presented to the year’s best new artist. Four years later, Urban took home the Awards’ highest honor, Entertainer of the Year, cementing his status as one of the genre’s biggest acts of the 2000s. Since then he’s racked up 12 wins, and he is nominated for two more at the 2019 CMA Awards. 

Before this powerhouse country trio effectively dropped out of the genre in 2002 after frontwoman Natalie Maines' controversial political comments, the Dixie Chicks were the biggest group in country music. Between 1998 and 2000, the Dixie Chicks won 10 CMA Awards, and they took home their final trophy to date in 2002 in the Vocal Group of the Year category. 

With nine CMA Award wins, Kenny Chesney shares a pretty special milestone with Garth Brooks. In 2008 Chesney tied Brooks’ record four wins in the Entertainer of the Year category. In 2016 Chesney became the third artist ever to win the Pinnacle Award, an honor he also shares with Brooks.

Johnny Cash won the first six of his nine total CMA Awards in the late 1960s, but the final three didn’t come until four decades later. After the release of "American IV: The Man Comes Around" in 2002, Cash won Album of the Year in 2003. He also won in the Single of the Year, and Music Video of the Year categories for his heart-wrenching cover of Nine Inch Nails’ “Hurt.” 

Considering that she’s one of the most successful solo artists of all time, Dolly Parton’s first CMA Awards wins were in the Vocal Duo of the Year category in 1970 and 1971 alongside Porter Wagoner. Since, she’s won seven more trophies on her own, including a Lifetime Achievement Award in 2016. 

One of country music’s most iconic duos, mother-daughter pair Wynonna and Naomi Judd stormed onto the scene in 1984 and took home the New Artist of the Year trophy, their first of nine. After that, the Judds won in the Vocal Group or Vocal Duo of the Year categories seven times, including six consecutive victories. 

Before veering firmly into pop territory, Taylor Swift won an impressive 10 CMA Awards. She’s taken home trophies in the Female Artist of the Year, Entertainer of the Year and Music Video of the Year categories. Swift’s most recent CMA win came in 2017 for Song of the Year “Better Man,” written by Swift and recorded by Little Big Town. 

He may not have the same celebrity status as other artists on this list, but nine-time CMA Award winner and prolific session musician Mac McAnally is a Nashville icon. In the last 10 years, McAnally has won Musician of the Year at the CMA Awards nine times, eight of those consecutively. 

Since winning her first Female Vocalist of the Year award in 1995, Alison Krauss has become one of country music’s most awarded artists. In addition to her eight CMA Awards Krauss has also won a record-shattering 27 Grammy Awards, making her the most awarded country artist in Grammys history.  

Considering how iconic “He Stopped Loving Her Today” is, it’s no surprise that Jones won his first CMA Award in 1980 in the Single of the Year Category and was named Male Vocalist of the Year. He’d go on to win five more CMA Awards, the most recent in 2001 for “Too Country,” a collaboration with Brad Paisley and Bill Anderson. 

This country powerhouse has racked up six wins in the Vocal Group of the Year category, dominating it from 2012 to 2016. The band also won Single of the Year in 2015 for “Girl Crush,” its controversial crossover hit. 

Chris Stapleton came out swinging at the 2015 CMA Awards, where he took home trophies for Album of the Year, Male Vocalist of the Year and New Artist of the Year on the heels of his wildly successful solo debut album, "Traveller." Since, he's racked up several more, bringing his total to 14. 

Hank Williams Jr. won the first of his seven CMA Awards in 1985, in the Music Video of the Year category for the iconic “All My Rowdy Friends Are Comin’ Over Tonight” video, which featured cameos from Willie Nelson, Waylon Jennings, Kris Kristofferson and more country icons. In 1989, Williams took home two awards for his reprisal of his father, Hank Williams Sr.’s classic “There’s a Tear in My Beer.”