| 100% | BECK | 4 | He won Album of the Year at the 2015 Grammys |
| 71% | KACEYMUSGRAVES | 14 | Artist whose album "Golden Hour" won Album of the Year at the 2019 Grammys: 2 wds. |
| 61% | FLOWERS | 7 | Miley Cyrus song that won Record of the Year at the 2024 Grammys |
| 58% | BRUNOMARS | 9 | Winner of Album, Record, and Song of the Year at the 2018 Grammys: 2 wds. |
| 58% | RAISINGSAND | 11 | Bluegrass album by Robert Plant and Alison Krauss that won Album of the Year at the 2009 Grammy Awards (2 wds.) |
| 57% | BEYONCE | 7 | 14-Across, 8-Down, and 49-Across singer whose "Cowboy Carter" won Album of the Year at the Grammy Awards in 2025 |
| 55% | BECK | 4 | His "Morning Phase" won the Album of the Year Grammy in February 2015 |
| 53% | REHAB | 5 | Song of the Year at the 2008 Grammys |
| 52% | MARS | 4 | Singer Bruno who won Grammys for Record, Album, and Song of the Year in 2018 |
| 52% | BECK | 4 | Rocker whose "Morning Phase" won the 2015 Album of the Year |
| 51% | ROAR | 4 | Katy Perry song that lost Song of the Year at the 2013 Grammys |
| 49% | ADELE | 5 | She won Album of the Year honors in 2012 and 2017 |
| 49% | KACEYMUSGRAVES | 14 | 19-Across and 46-Across singer who won four 2019 Grammys, including Album of the Year and Best Country Album for "Golden Hour" (2 wds.) |
| 49% | MIRANDALAMBERT | 14 | "Settling Down" singer who won Entertainer of the Year at the 2022 ACM Awards: 2 wds. |
| 48% | TIMEAFTERTIME | 13 | 1984 Cyndi Lauper hit nominated for Song of the Year at the Grammys |
| 48% | SUNDAY | 6 | "___ Mornin' Comin' Down," 1969 song cover by Johnny Cash that won Song of The Year at the CMAs |
| 48% | TRACYCHAPMAN | 12 | "Fast Car" songwriter who won Song of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 48% | BECK | 4 | Artist who won the 2014 Album of the Year Grammy |
| 48% | BARENAKED | 9 | __ Ladies; won 2001 Juno for Pop Album of the Year |
| 48% | THOMASRHETT | 11 | "Country Again" singer who won Entertainer of the Year at the 2020 Academy of Country Music Awards: 2 wds. |
| 48% | FASTCAR | 7 | 1988 Tracy Chapman hit that won Song of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 47% | IVAN | 4 | Cornejo who won New Artist of the Year at the 2022 Billboard Latin Music Awards |
| 47% | ADELE | 5 | One-named singer who won the 2016 Album of the Year |
| 47% | JASONALDEAN | 11 | "Burnin' It Down" singer who won Entertainer of the Year at the 2016, 2017, and 2018 ACM Awards: 2 wds. |
| 47% | SONG | 4 | ___ of the Year (major category at the Grammys) |
| 47% | MARENMORRIS | 11 | "The Bones" country singer who won Female Vocalist of the Year at the 2020 CMAs: 2 wds. |
| 47% | MIRANDALAMBERT | 14 | "Bluebird" country singer who won Music Video of the Year at the 2020 CMAs: 2 wds. |
| 47% | RAITT | 5 | Her "Nick of Time" won the Grammy for Album of the Year |
| 47% | BEYONCE | 7 | Singer who won the Album of the Year Grammy for "Cowboy Carter" |
| 47% | JASONALDEAN | 11 | "You Make It Easy" singer who won Entertainer of the Year at the 2018 Academy of Country Music Awards: 2 wds. |