| 100% | TAYLORSWIFT | 11 | Singer-songwriter whose "1989" won 2016's Grammy Award for Album of the Year (2 wds.) |
| 69% | CELINEDION | 10 | Singer whose 1996 album "Falling into You" won Grammy Awards for Album of the Year and Best Pop Album (2 wds.) |
| 59% | GARTHBROOKS | 11 | "The Dance" singer who won the 2016 CMA Award for Entertainer of the Year: 2 wds. |
| 59% | MARENMORRIS | 11 | "Girl" singer who won the 2019 CMA Award for Album of the Year (2 wds.) |
| 58% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 2 wds. |
| 54% | ADELEADKINS | 11 | British singer whose third studio album fetched her the Album of the Year in the 2017 Grammy Awards : 2 wds. |
| 53% | JON | 3 | ___ Batiste, "We Are" singer who won the Grammy Award for Album of the Year in 2022 |
| 52% | MAREN | 5 | Country singer Morris whose "Girl" won the 2019 CMA Award for Album of the Year |
| 51% | BADGUY | 6 | 2019 song by Billie Eilish that won the Grammy Award for Record of the Year in 2020: 2 wds. |
| 51% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 51% | GARTHBROOKS | 11 | "The River" singer who won the CMA Award for Entertainer of the Year seven times: 2 wds. |
| 51% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 51% | ALANJACKSON | 11 | "Country Boy" singer who won the CMA Award for Entertainer of the Year three times: 2 wds. |
| 51% | KENNYCHESNEY | 12 | "Come Over" singer who won the CMA Award for Entertainer of the Year four times: 2 wds. |
| 51% | ADELE | 5 | Singer who won a Grammy Award for Song of the Year winner for "Hello" |
| 50% | TAYLORSWIFT | 11 | "Better Man" songwriter who won the 2017 CMA Award for Song of the Year (2 wds.) |
| 49% | MIRANDALAMBERT | 14 | Singer whose "Wildcard" won the Grammy for Best Country Album in 2021: 2 wds. |
| 49% | MARENMORRIS | 11 | Her "Girl" won the 2019 CMA for Album of the Year: 2 wds. |
| 49% | BEYONCE | 7 | Singer who won the Album of the Year Grammy for "Cowboy Carter" |
| 49% | AIMEEMANN | 9 | Grammy award winning female bassist who has been named one of the world's top ten greatest living songwriters by NPR: 2 wds. |
| 49% | BILLIEEILISH | 12 | "What Was I Made For?" singer/co-songwriter who won Song of the Year at the 2024 Grammy Awards (2 wds.) |
| 49% | OLIVIARODRIGO | 13 | Singer whose 2021 hit single "Drivers License" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 49% | LEONARDCOHEN | 12 | Singer-songwriter in the Canadian Music Hall of Fame who won the 2017 Album of the Year Juno Award for "You Want It Darker" (2 wds.) |
| 48% | PERCYFAITH | 10 | Bandleader/orchestrator whose instrumental version of "Theme from 'A Summer Place'" won a Grammy Award for Record of the Year in 1961 (2 wds.) |
| 48% | DOJACAT | 7 | Singer whose 2021 hit single "Kiss Me More" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 48% | BRANDICARLILE | 13 | Singer whose 2021 hit song "Right on Time" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 47% | MARENMORRIS | 11 | "My Church" singer who won the 2016 CMA New Artist of the Year award: 2 wds. |
| 47% | STEVIEWONDER | 12 | American artist who has won the Grammy thrice for "Best Album of the Year," including one for "Innervisions": 2 wds. |
| 47% | JASONALDEAN | 11 | "Burnin' It Down" singer who won Entertainer of the Year at the 2016, 2017, and 2018 ACM Awards: 2 wds. |
| 47% | JONIMITCHELL | 12 | Singer-songwriter in the Canadian Music Hall of Fame who won the 2001 Vocal Jazz Album of the Year Juno Award for "Both Sides Now" (2 wds.) |