These Country Music Stars Have Won at Least 10 Grammy Awards
Their trophy shelves are getting crowded!
Winning a Grammy Award is a top-shelf achievement in music. The gramophone is the most coveted trophy you can get across all genres, and it's not easy to earn them.
Since their inception in 1959, the Recording Academy's Grammy Awards have maintained their prestige, because nominations and wins are awarded not based on popularity, but art. That's rare these days! Members of the Academy vote on the best works of the previous year by looking at artistic merit, not chart position. Grammy voters are made up of professionals in music, including engineers, artists and producers, and they're only allowed to vote in the fields they work in (you can read more about the voting process here, if you're curious).
To get just one Grammy is a bucket-list item, but ten? We'd say it's unheard of, but the country and country-fringe artists below have all done it. Some have blown way past that number!
Alison Krauss: 27 Grammys
Alison Krauss is the most Grammy-decorated artist in country music. She picked up her first Grammy as a solo artist in 1990, earning Best Bluegrass Recording for "I've Got That Old Feeling." Her most recent win was in 2012, when her Paper Airplane project scored Bluegrass Album of the Year.
Vince Gill: 22 Grammys
Like Alison Krauss, Vince won his first-ever Grammy as a solo artist in 1990, for Best Country Vocal Performance, Male ("When I Call Your Name"). Decades later, Vince is closing in on two dozen Grammys. The country star is also a big supporter of the Recording Academy's MusiCares initiative.
Taylor Swift: 14 Grammys
Taylor has remained a Grammy darling since switching from country music to pop in 2014. To date, she is the only artist to win Grammy Album of the Year four times (Midnights, Folklore, 1989 and Fearless).
Ricky Skaggs: 14 Grammys
Ricky Skaggs has 14 Grammys as a soloist (he also has 7 wins as Ricky Skaggs and Kentucky Thunder). He's been earning nominations since the early 1980s!
Alison Krauss & Union Station: 14 Grammys
Oh, there's Alison again! When she's not making music solo, she's leading her band toward Grammy enshrinement. They've got 14 wins as Union Station, with the first coming in 1992 (Every Time You Say Goodbye, Best Bluegrass Album).
Emmylou Harris: 13 Grammys
Emmylou Harris won her first Grammy Award in 1976 for Best Country Vocal Performance, Female for "Elite Hotel." Her most recent came in 2014: Best Americana Album for Old Yellow Moon.
Johnny Cash: 13 Grammys
During his career, Johnny Cash was nominated for a whopping 35 Grammys, 13 of which he won.
Bonnie Raitt: 13 Grammys
Grammy voters love Bonnie Raitt, to the tune of 31 lifetime nominations and 13 wins. She picked up her first trophy in 1989, and she had to juggle it with the others she won that year: Album of the Year for Nick of Time, Best Rock Performance, Female and Best Pop Vocal Performance, Female. She earned Best Traditional Blues Recording for "I'm in the Mood" with John Lee Hooker that year, too. It was a big year!
The Chicks: 13 Grammys
One of country music's most controversial trios are also one of the most Grammy-decorated. Their first win(s) came in 1998, and they took home two: Best Country Performance by a Duo or Group With Vocal for "There's Your Trouble" and Best Country Album for the critic-celebrated Wide Open Spaces.
Willie Nelson: 12 Grammys
Willie's first Grammy win was for one of his all-time greatest songs, "Blue Eyes Crying in the Rain" (Best Male Country Vocal Performance, 1975). He last picked up trophies in 2023, when he took home Best Country Solo Performance and Best Country Album wins.
Related: Willie Nelson, 92, Earns Two Grammy Nods—and His Sons Are Nominated Too!
Linda Rondstadt: 11 Grammys
Linda Rondstadt remains one of the top Grammy earners across genres, though she is no longer making music. She was nominated 27 times in her career, earning 11 trophies in total. The most recent was Best Music Film in 2021 for Linda Ronstadt: The Sound of My Voice, which is a documentary about her life.
Roger Miller: 11 Grammys
It's been quite awhile since Roger Miller last won a Grammy (1966), but he's held his title as one of country music's most-awarded even 30-plus years after his death. He also has two songs in the Grammy Hall of Fame ("King of the Road" and "Dang Me").
Chris Stapleton: 11 Grammys
It seems all awards shows love Chris Stapleton — he's a staple (get it?) at the big country-specific shows, in addition to the Grammys. He scored his first Grammy wins in 2015, and he's still earning nominations. He's up for four in 2026!
Related: How Chris Stapleton Made Country Music History with "Tennessee Whiskey"
Dolly Parton: 10 Grammys
You had to know Dolly would be here, right? She's actually a Grammy Lifetime Achievement Award winner, which is a special one that only goes to artists who have, per the Recording Academy, "have made creative contributions of outstanding artistic significance to the field of recording." That's her, for certain.
Related: Fans Call Dolly Parton's Remake of 1977 Song a "Blessing"
Amanda Hensel Jermstad is a skilled writer based in Austin, Texas. She spent 14 years as Editor-in-Chief of Taste of Country, where she led coverage of the artists, stories and trends shaping country music. With a career deeply rooted in the genre, Amanda has built a reputation for sharp editorial insight and authentic storytelling. Outside of work, she’s a proud mom of three.
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