| 100% | IGOR | 4 | Tyler, the Creator work that won the 2019 Grammy for Best Rap Album |
| 82% | IGOR | 4 | Tyler, the Creator release that won the 2020 Grammy for Best Rap Album |
| 66% | IGOR | 4 | 2019 studio album by American rapper Tyler, the Creator which won a Grammy for the Best Rap Album in 2020 |
| 65% | IGOR | 4 | Tyler, the Creator album that won Best Rap Album at the 2020 Grammy Awards |
| 65% | LOST | 4 | "Call Me If You Get ___," album by Tyler, the Creator that won the Grammy Award for Best Rap Album in 2022 |
| 63% | IGOR | 4 | Album for which Tyler, the Creator won the Best Rap Album Grammy in 2020 |
| 58% | FROMTHEFIRES | 12 | Greta Van Fleet album that won the Grammy Award for Best Rock Album in 2019 (3 wds.) |
| 58% | IGOR | 4 | Tyler, the Creator album that won Best Rap Album at the 2020 Grammys |
| 56% | IGOR | 4 | 2019 album for which Tyler, the Creator won his first Grammy |
| 55% | OPUS | 4 | Marc Anthony release that won the 2020 Grammy for Best Tropical Latin Album |
| 54% | BUTTERFLIES | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Solo Performance |
| 54% | SPACECOWBOY | 11 | Kacey Musgraves single that won the 2019 Grammy for Best Country Song: 2 wds. |
| 54% | SPACECOWBOY | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Song (2 wds.) |
| 53% | HER | 3 | Artist whose self-titled debut won the 2019 Grammy for Best R&B Album |
| 52% | JAIL | 4 | Song by Kanye featuring Jay-Z that won the Grammy Award for Best Rap Song in 2022 |
| 51% | LIVIN | 5 | "While I'm ___," album by Tanya Tucker that won the Grammy Award for Best Country Album in 2020 |
| 51% | SOUR | 4 | Album by Olivia Rodrigo that won the Grammy Award for Best Pop Vocal Album in 2022 |
| 50% | CARDI | 5 | ___ B, hip hop star who became the first female rapper to win a Grammy for Best Rap Album |
| 49% | MORNINGPHASE | 12 | Beck album that won the 2015 Grammy Award for Best Rock Album: 2 wds. |
| 49% | THERESISTANCE | 13 | Muse album that won the 2011 Grammy Award for Best Rock Album: 2 wds. |
| 49% | WASTINGLIGHT | 12 | Foo Fighters album that won the 2012 Grammy Award for Best Rock Album: 2 wds. |
| 49% | ITISWHATITIS | 12 | Album by 41-Across featuring 17-Across that won the Grammy Award for Best Progressive R&B Album in 2021 (5 wds.) |
| 49% | COME | 4 | "The Best is Yet to ___," album by Ella Fitzgerald that won her the Grammy for Best Jazz Vocal Performance in 1984 |
| 48% | HADESTOWN | 9 | Anaïs Mitchell work based on Orpheus and Eurydice that won the 2019 Tony Award for Best Musical |
| 48% | HER | 3 | One-named artist whose self-titled album won the Grammy Award for Best R & B album in 2019 |
| 47% | DURURAN | 7 | Group that won the first Grammy for Best Music Video |
| 47% | MACKLEMORE | 10 | Artist on NBC's "Songland" whose "The Heist," with Ryan Lewis, won a 2014 Grammy for best rap album |
| 47% | IGOR | 4 | Grammy-winning album for Tyler, the Creator |
| 47% | IGOR | 4 | Tyler, the Creator's 2019 Grammy-winning album |
| 47% | IGOR | 4 | 2019 Grammy-winning album from Tyler, the Creator |