| 100% | IGOR | 4 | 2019 Grammy-winning album from Tyler, the Creator |
| 82% | IGOR | 4 | Tyler, the Creator work that won the 2019 Grammy for Best Rap Album |
| 78% | IGOR | 4 | 2019 album from Tyler, the Creator |
| 77% | IGOR | 4 | Tyler, the Creator's 2019 Grammy-winning album |
| 76% | IGOR | 4 | 2019 album for which Tyler, the Creator won his first Grammy |
| 76% | IGOR | 4 | Grammy-winning 2019 album by Tyler, the Creator |
| 70% | IGOR | 4 | Tyler, the Creator release that won the 2020 Grammy for Best Rap Album |
| 69% | IGOR | 4 | Tyler, the Creator album that won Best Rap Album at the 2020 Grammy Awards |
| 69% | IGOR | 4 | Grammy-winning album for Tyler, the Creator |
| 68% | IGOR | 4 | 2019 studio album by American rapper Tyler, the Creator which won a Grammy for the Best Rap Album in 2020 |
| 66% | IGOR | 4 | Grammy-winning Tyler, the Creator album |
| 65% | IGOR | 4 | Tyler, the Creator's Grammy-winning album with the song "Earfquake" |
| 64% | IGOR | 4 | Album for which Tyler, the Creator won the Best Rap Album Grammy in 2020 |
| 63% | IGOR | 4 | Grammy-winning Tyler, the Creator album with the hit "Earfquake" |
| 61% | IGOR | 4 | 2019 #1 album by Tyler, the Creator |
| 61% | IGOR | 4 | 2019 #1 album for Tyler, the Creator |
| 61% | IGOR | 4 | 2019 Tyler, the Creator album |
| 58% | IGOR | 4 | Tyler, the Creator album that won Best Rap Album at the 2020 Grammys |
| 53% | LOST | 4 | "Call Me If You Get ___," album by Tyler, the Creator that won the Grammy Award for Best Rap Album in 2022 |
| 52% | BUTTERFLIES | 11 | Single from the album "Golden Hour" that won Best Country Solo Performance at the 2019 Grammys |
| 52% | FROMTHEFIRES | 12 | Greta Van Fleet album that won the Grammy Award for Best Rock Album in 2019 (3 wds.) |
| 52% | SPACECOWBOY | 11 | Single from the album "Golden Hour" that won Best Country Song at the 2019 Grammys: 2 wds. |
| 51% | HER | 3 | One-named artist whose self-titled album won the Grammy Award for Best R & B album in 2019 |
| 50% | BEAT | 4 | "___ It," a hit single from Michael Jackson's album in 16a that won a Grammy for "Record of the Year" |
| 49% | IGOR | 4 | Tyler, the Creator album with the hit "Earfquake" |
| 49% | OBAMA | 5 | Former U.S. president who won a Best Spoken Word Album Grammy Award for the audiobook of "Dreams from My Father" |
| 48% | JUICE | 5 | Song from 46-Across's album "Cuz I Love You" that won the 2019 Soul Train Music Award for Video of the Year |
| 47% | NEWKIDINTOWN | 12 | Grammy-winning song by the Eagles which was the first single from the same album as 15a: 4 wds. |
| 47% | HARMONYHALL | 11 | Hit single on the 2019 Grammy-winning album by 33-Across (2 wds.) |
| 46% | BLUEBIRD | 8 | 2019 song by Miranda Lambert from the album "Wildcard" |