CMA Awards: Artists with Multiple Wins in Every Award Category

The 58th Annual Country Music Awards saw a few first-time winners, records broken and even extended. Some of the highlights of the night included Chris Stapleton taking home three awards, extended his hold over the most “Male Vocalist of the Year” award totals and breaking an eight-artist tie for the most “Single of the Year” awards.

With Stapleton now leading in two of the CMA’s major award categories, here’s a look at which artists have won a category multiple times, starting with the most:

Entertainer of the Year:

Morgan Wallen managed to secure his second CMA award by winning “Entertainer of the Year” on Wednesday night, after what some may have perceived as years of snubs. While Wallen is the reigning “Entertainer of the Year,” he won’t be appearing on this list due to his single win. Here are the artists with multiple wins in the category:

1. Garth Brooks – 7 wins
2. Kenny Chesney – 4 wins
3. Alabama – 3 wins
4. Alan Jackson – 3 wins
5. George Strait – 3 wins
6. Barbara Mandrell – 2 wins
7. Hank Williams Jr. – 2 wins
8. Vince Gill – 2 wins
9. Taylor Swift – 2 wins
10. Luke Bryan – 2 wins
11. Keith Urban – 2 wins
12. Luke Combs – 2 wins

Album of the Year:

Cody Johnson took home the “Album of the Year” award Wednesday for his album Leather. It was his first time being nominated for the award, meaning he won’t be appearing on this list either. Here are the artists with multiple “Album of the Year” wins:

1. George Strait – 5 wins
2. Ronnie Milsap – 4 wins
3. Johnny Cash – 3 wins
4. Chris Stapleton – 3 wins
5. Merle Haggard – 2 wins
6. Charlie Rich – 2 wins
7. Willie Nelson – 2 wins
8. Vince Gill – 2 wins
9. Tim McGraw – 2 wins
10. Alan Jackson – 2 wins
11. Miranda Lambert – 2 wins
12. Eric Church – 2 wins
13. Luke Combs – 2 wins

Male Vocalist of the Year:

Heading into Wednesday night, Stapleton led the “Male Vocalist of the Year” category with seven wins. By the time the 58th Annual CMA Awards ended, Stapleton walked away with his eighth (and fourth consecutive) win, forever immortalized by the broadcast catching an inaudible Combs saying “His eighth?” in disbelief. With Stapleton at the top of the list, here are the artists that have won the award multiple times:

1. Chris Stapleton – 8 wins
2. Vince Gill – 5 wins
3. George Strait – 5 wins
4. Blake Shelton – 5 wins
5. Ronnie Milsap – 3 wins
6. Keith Urban – 3 wins
7. Brad Paisley – 3 wins
8. Charley Pride – 2 wins
9. George Jones – 2 wins
10. Lee Greenwood – 2 wins
11. Randy Travis – 2 wins
12. Tim McGraw – 2 wins
13. Alan Jackson – 2 wins
14. Luke Combs – 2 wins

Female Vocalist of the Year:

New CMAs host Lainey Wilson picked up her third “Female Vocalist of the Year” award Wednesday night, building on her growing legacy in country music and working her way higher up the list. Here’s the artists with multiple wins in the category:

1. Miranda Lambert – 7 wins
2. Carrie Underwood – 5 wins
3. Reba McEntire – 4 wins
4. Martina McBride – 4 wins
5. Tammy Wynette – 3 wins
6. Loretta Lynn – 3 wins
7. Lainey Wilson – 3 wins
8. Dolly Parton – 2 wins
9. Crystal Gayle – 2 wins
10. Barbara Mandrell – 2 wins
11. Janie Fricke – 2 wins
12. Kathy Mattea – 2 wins
13. Trisha Yearwood – 2 wins

Vocal Group of the Year:

Old Dominion won their seventh consecutive “Vocal Group of the Year” award Wednesday; a CMAs record. Along with fellow 2024 nominees Lady A and Little Big Town, the three groups have had a stranglehold over the category, with Rascal Flatts’ 2008 win being the last of any group not previously named in the category. Here’s the list of groups that have won the award the most times:

1. The Statler Brothers – 9 wins
2. Old Dominion – 7 wins
3. Rascal Flatts – 6 wins
4. Little Big Town – 6 wins
5. Diamond Rio – 4 wins
6. The Chicks – 4 wins
7. Alabama – 3 wins
8. The Judds – 3 wins
9. Lady A – 3 wins
10. Highway 101 – 2 wins
11. Kentucky Headhunters – 2 wins
12. The Mavericks – 2 wins

Vocal Duo of the Year:

Brooks & Dunn brought thousands to their feet at Bridgestone Arena on Wednesday upon winning a CMA-record 15th “Vocal Duo of the Year” award, as the pair hadn’t won the award since 2006. With Brooks & Dun continuing to build on their legendary career over 30 years after it began, here’s a list of duos that’ve won the award multiple times:

1. Brooks & Dunn – 15 wins
2. Brothers Osborne – 6 wins
3. Sugarland – 5 wins
4. Conway Twitty & Loretta Lynn – 4 wins
5. The Judds – 4 wins
6. Willie Nelson – 3 wins*
7. Florida Georgia Line – 3 wins
8. Dolly Parton & Porter Wagoner – 2 wins
9. Kenny Rogers & Dottie West – 2 wins
10. David Frizzle & Shelly West – 2 wins
11. Dan + Shay – 2 wins

* Nelson has won as part of a duo three different times; in 1976 with Waylon Jennings, 1983 win Merle Haggard and 1984 with Julio Iglesias.

Single of the Year:

Stapleton made CMAs history Wednesday by breaking an eight-artist tie for the most “Single of the Year” award wins, standing alone with three thanks to his hit song White Horse. Here’s the artists with multiple wins in the category:

1. Chris Stapleton – 3 wins
2. Willie Nelson – 2 wins
3. Alan Jackson – 2 wins
4. Johnny Cash – 2 wins
5. Lee Ann Womack – 2 wins
6. George Strait – 2 wins
7. Lady A – 2 wins
8. Little Big Town – 2 wins

Song of the Year:

Often confused with the “Single of the Year” award, the “Song of the Year” award goes to the songwriters behind the song, which doesn’t always involved the artist credited with the track under their discography. Stapleton earn his second win in this category on Wednesday night for White Horse, joining several other artists with multiple wins in the category:

1. Vince Gill – 4 wins
2. Don Schlitz – 3 wins
3. Freddie Hart – 2 wins
4. Paul Overstreet – 2 wins
5. Bill Anderson – 2 wins
6. Lori McKenna – 2 wins
7. Mike Henderson – 2 wins
8. Chris Stapleton – 2 wins

Musician of the Year:

Guitarist Charlie Worsham, a member of Dierks Bentley’s touring band, won the “Musician of the Year” award Wednesday night; his first. Here’s a list of musicians that’ve won the award multiple times:

1. Chet Atkins – 10 wins
2. Mac McAnally – 10 wins
3. Johnny Gimble – 6 wins
4. Mark O’Connor – 5 wins
5. Jenee Eleanor – 5 wins
6. Dann Huff – 3 wins
7. Jerry Douglas – 3 wins
8. Roy Clark – 3 wins
9. Jerry Reed – 2 wins
10. Charlie McCoy – 2 wins
11. Brent Mason – 2 wins
12. Hargus “Pig” Robbins – 2 wins
13. Randy Scruggs – 2 wins

Music Video of the Year:

Wilson took home her second consecutive “Music Video of the Year” award Wednesday for the music video of Wildflowers and Wild Horses. Here’s other artists who’ve won the award multiple times:

1. Brad Paisley – 4 wins
2. Hank Williams Jr. – 3 wins
3. Garth Brooks – 2 wins
4. Alan Jackson – 2 wins
5. The Chicks – 2 wins
6. Toby Keith – 2 wins
7. Taylor Swift – 2 wins
8. Miranda Lambert – 2 wins
9. Kenny Chesney – 2 wins

Musical Event of the Year:

First-time CMA Awards nominees Ella Langley and Riley Green took home the “Musical Event of the Year award for their song You Look Like You Love Me on Wednesday, which they would go on to perform during the ceremony that same night. While they won’t appear on this list, they just might in thew future. Here’s the artists with multiple wins in the category:

1. Vince Gill – 4 wins
2. Brad Paisley – 4 wins
3. Tim McGraw – 4 wins
4. Keith Urban – 4 wins
5. Kenny Chesney – 4 wins
6. Patty Loveless – 3 wins
7. George Jones – 3 wins
8. Alan Jackson – 3 wins
9. Dolly Parton – 3 wins
10. Alison Krauss – 3 wins
11. Travis Tritt – 2 wins
12. Lee Ann Womack – 2 wins
13. George Strait – 2 wins
14. Willie Nelson – 2 wins
15. Carly Pearce – 2 wins