| 100% | IGOR | 4 | Album for which Tyler, the Creator won the Best Rap Album Grammy in 2020 |
| 84% | IGOR | 4 | 2019 studio album by American rapper Tyler, the Creator which won a Grammy for the Best Rap Album in 2020 |
| 75% | IGOR | 4 | Tyler, the Creator release that won the 2020 Grammy for Best Rap Album |
| 69% | LOST | 4 | "Call Me If You Get ___," album by Tyler, the Creator that won the Grammy Award for Best Rap Album in 2022 |
| 68% | IGOR | 4 | Tyler, the Creator work that won the 2019 Grammy for Best Rap Album |
| 65% | IGOR | 4 | Tyler, the Creator album that won Best Rap Album at the 2020 Grammy Awards |
| 64% | IGOR | 4 | 2019 album for which Tyler, the Creator won his first Grammy |
| 59% | IGOR | 4 | Tyler, the Creator album that won Best Rap Album at the 2020 Grammys |
| 57% | THEWARONDRUGS | 13 | Band which won the Grammy for Best Rock Album in 2018: 4 wds. |
| 55% | LIVIN | 5 | "While I'm ___," album by Tanya Tucker that won the Grammy Award for Best Country Album in 2020 |
| 54% | VAMPIREWEEKEND | 14 | Indie rock band that won a Best Alternative Music Album Grammy in 2020 for "Father of the Bride": 2 wds. |
| 54% | MIDDLECHILD | 11 | J. Cole single from the album "Revenge of the Dreamers III" that was nominated for a Best Rap Performance Grammy Award in 2020 (2 wds.) |
| 53% | OLDTOWNROAD | 11 | Song for which Lil Nas X and Billy Ray Cyrus won the Grammy for Best Pop Duo/Group Performance in 2020: 3 wds. |
| 52% | STEVEMARTIN | 11 | "L.A. Story" actor whose "The Crow: New Songs for the 5-String Banjo" won the Best Bluegrass Album Grammy in 2010: 2 wds. |
| 51% | FOLKLORE | 8 | Album by Taylor Swift which won the Grammy for Album of the Year in 2021 |
| 51% | IGOR | 4 | Grammy-winning album for Tyler, the Creator |
| 51% | STRESSEDOUT | 11 | Song for which Twenty One Pilots won the Grammy for Best Pop Duo/Group Performance in 2017: 2 wds. |
| 50% | LYLE | 4 | Musician Lovett who won the Best Country Album Grammy in 1996 |
| 50% | SHEERAN | 7 | Ed who won the Grammy for Best Pop Vocal Album in 2018 |
| 50% | ELVISCOSTELLO | 13 | "Look Now" singer who won the Best Traditional Pop Vocal Album Grammy Award in 2020 (2 wds.) |
| 49% | OPUS | 4 | Marc Anthony release that won the 2020 Grammy for Best Tropical Latin Album |
| 49% | CARDI | 5 | ___ B, hip hop star who became the first female rapper to win a Grammy for Best Rap Album |
| 49% | SOUR | 4 | Album by Olivia Rodrigo that won the Grammy Award for Best Pop Vocal Album in 2022 |
| 49% | TRUTH | 5 | "___ Hurts," song by Lizzo which won the 2020 Grammy for Best Pop Solo Performance |
| 49% | JEROME | 6 | Song by Lizzo which won the 2020 Grammy for Best Traditional R&B Performance |
| 49% | MIRANDALAMBERT | 14 | Singer whose "Wildcard" won the Grammy for Best Country Album in 2021: 2 wds. |
| 49% | DRAKE | 5 | Rapper who won the Grammy Award for Best Rap Song in 2017 for "Hotline Bling" |
| 49% | LAMAR | 5 | Kendrick ___, rapper who won the Grammy Award for Best Rap Song in 2016 for "Alright" |
| 49% | EMINEM | 6 | Rapper who won the Grammy Award for Best Rap Song in 2004 for "Lose Yourself" |
| 49% | CHRISSTAPLETON | 14 | Singer whose "Starting Over" won the Grammy for Best Country Album in 2022: 2 wds. |