| 100% | BILLIEEILISH | 12 | "What Was I Made For?" singer/co-songwriter who won Song of the Year at the 2024 Grammy Awards (2 wds.) |
| 61% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 58% | TRACYCHAPMAN | 12 | "Fast Car" songwriter who won Song of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 58% | JASONALDEAN | 11 | "You Make It Easy" singer who won Entertainer of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 58% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 56% | MIRANDALAMBERT | 14 | "Settling Down" singer who won Entertainer of the Year at the 2022 ACM Awards: 2 wds. |
| 56% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 56% | CAROLEKING | 10 | "You've Got a Friend" singer/pianist who was the first woman to win a Grammy for Song of the Year (2 wds.) |
| 53% | TAYLORSWIFT | 11 | "Better Man" songwriter who won the 2017 CMA Award for Song of the Year (2 wds.) |
| 53% | THOMASRHETT | 11 | "Country Again" singer who won Entertainer of the Year at the 2020 Academy of Country Music Awards: 2 wds. |
| 53% | JASONALDEAN | 11 | "Burnin' It Down" singer who won Entertainer of the Year at the 2016, 2017, and 2018 ACM Awards: 2 wds. |
| 52% | BRUNOMARS | 9 | "24K Magic" singer who won the award for R&B Song, "That's What I Like" in Billboard 2018: 2 wds |
| 51% | GARTHBROOKS | 11 | "Ask Me How I Know" singer who won the 2017 CMA Award for Entertainer of the Year (2 wds.) |
| 51% | GARTHBROOKS | 11 | "That Girl Is a Cowboy" singer who won the 2019 CMA Award for Entertainer of the Year (2 wds.) |
| 51% | LILNASX | 7 | Singer whose 2021 hit song "Montero (Call Me by Your Name)" is nominated for three Grammy Awards, including Record of the Year (3 wds.) |
| 50% | BRANDICARLILE | 13 | Singer whose 2021 hit song "Right on Time" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 50% | DOJACAT | 7 | Singer whose 2021 hit single "Kiss Me More" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 50% | BRUNOMARS | 9 | "24K Magic" singer who won six awards, including Record of the Year, at the 2018 Grammy Awards (2 wds.) |
| 49% | CAELEBDRESSEL | 13 | Seven-time Olympic swimming gold medalist who won Athlete of the Year at the Golden Goggle Awards three times: 2 wds. |
| 49% | MICHAELPHELPS | 13 | 23-time Olympic swimming gold medalist who won Athlete of the Year at the Golden Goggle Awards seven times: 2 wds. |
| 49% | GARTHBROOKS | 11 | "The Dance" singer who won the 2016 CMA Award for Entertainer of the Year: 2 wds. |
| 49% | CHRISSTAPLETON | 14 | "Starting Over" singer/songwriter who won the 2021 CMA Awards for Male Vocalist of the Year, Album of the Year, Single of the Year, and Song of the Year (2 wds.) |
| 49% | BRUNOMARS | 9 | Grammy Award winner for "That's What I Like" who was the halftime headliner at the Super Bowl in 2014 (2 wds.) |
| 49% | CARLYPEARCE | 11 | "I Hope You're Happy Now" singer/songwriter who won the 2021 Country Music Association Award for Female Vocalist of the Year (2 wds.) |
| 49% | ADELE | 5 | Singer who won a Grammy Award for Song of the Year winner for "Hello" |
| 49% | RAISINGSAND | 11 | Bluegrass album by Robert Plant and Alison Krauss that won Album of the Year at the 2009 Grammy Awards (2 wds.) |
| 49% | SMOKEYROBINSON | 14 | "I Second That Emotion" singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 49% | BILLIEEILISH | 12 | Singer-songwriter who sings "What Was I Made For?" on "Barbie: The Album" (2 wds.) |
| 48% | TAYLORSWIFT | 11 | Singer-songwriter whose "1989" won 2016's Grammy Award for Album of the Year (2 wds.) |
| 48% | MILEY | 5 | With 32-Across, singer-songwriter who exclaimed "I just won my first Grammy!" during her performance of "Flowers" at the 2024 Grammy Awards |