| 100% | TOPIMPA | 7 | With 48-Across, Kendrick Lamar album that won Best Rap Album at the 2016 Grammys: 3 wds. |
| 69% | ALRIGHT | 7 | Kendrick Lamar single that won Best Rap Song at the 2016 Grammys |
| 55% | IGOR | 4 | Tyler, the Creator album that won Best Rap Album at the 2020 Grammys |
| 50% | SPACECOWBOY | 11 | Single from the album "Golden Hour" that won Best Country Song at the 2019 Grammys: 2 wds. |
| 48% | IGOR | 4 | Tyler, the Creator album that won Best Rap Album at the 2020 Grammy Awards |
| 42% | WHATWASI | 8 | With 48-Across, Billie Eilish hit from "Barbie" that won an Oscar for Best Original Song: 3 wds. |
| 41% | KISSMEKATE | 10 | 1948 Broadway show, with music and lyrics by 41-Across, that won the first Tony for Best Musical: 3 wds. |
| 41% | MENATWORK | 9 | 15-Across and 33-Across rock band from Australia that won Best New Artist at the 1983 Grammy Awards (3 wds.) |
| 40% | BUTTERFLIES | 11 | Single from the album "Golden Hour" that won Best Country Solo Performance at the 2019 Grammys |
| 40% | DAMN | 4 | Kendrick Lamar album that won the Pulitzer Prize for Music |
| 39% | BLACKER | 7 | “The ___ the Berry” (song that opened Kendrick Lamar’s performance at the 2016 Grammys) |
| 39% | KISSMEKATE | 10 | 1948 show with music and lyrics by 39-Across that won the first Tony Award for Best Musical (3 wds.) |
| 39% | DAMN | 4 | 2017 Kendrick Lamar album that won the Pulitzer Prize for Music |
| 39% | NEEDTOKNOW | 10 | Hit single by 50-Across that was nominated for Best Melodic Rap Performance at the 2022 Grammy Awards (3 wds.) |
| 39% | KISSMEMORE | 10 | 50-Across and SZA hit single that won Best Pop Duo/Group Performance at the 2022 Grammy Awards (3 wds.) |
| 38% | DONTWANNAFIGHT | 14 | Alabama Shakes song that won the Grammy Award for Best Rock Song in 2016: 3 wds. |
| 38% | BAD | 3 | With 35-Across, Taylor Swift hit that won the 2016 Best Music Video Grammy |
| 38% | THEGREATEST | 11 | With 42-Across, 1952 circus film that won the Best Picture Oscar: 2 wds. |
| 38% | ZACBROWNBAND | 12 | American country music band with the hit song "Colder Weather", that won the 2010 Grammy for Best New Artist: 3 wds. |
| 38% | THEWEEKND | 9 | Singer with an oddly spelled name whose "Starboy" won Best Urban Contemporary Album at the 2018 Grammy Awards (2 wds.) |
| 37% | FROMTHEFIRES | 12 | Greta Van Fleet album that won the Grammy Award for Best Rock Album in 2019 (3 wds.) |
| 37% | VICTORIAMONET | 13 | "On My Mama" R&B singer who won Best New Artist at the 2024 Grammys: 2 wds. |
| 37% | TRUTHHURTS | 10 | 1-Across hit that won Best Pop Solo Performance at the 2020 Grammy Awards: 2 wds. |
| 37% | LAINEYWILSON | 12 | "Bell Bottom Country" singer who won Best Country Album at the 2024 Grammy Awards (2 wds.) |
| 37% | THESHAPEOF | 10 | With 55-Across, 2017 Guillermo del Toro sci-fi/fantasy film that won Best Picture and three other Oscars: 3 wds. |
| 37% | BODYLIKEA | 9 | With 48-Across, Sam Hunt song that spent 34 weeks atop the Hot Country charts in 2017: 3 wds. |
| 36% | AIMEEMANN | 9 | Former 'Til Tuesday lead singer whose "Mental Illness" won Best Folk Album at the 2018 Grammy Awards (2 wds.) |
| 36% | GIRLONFIRE | 10 | Album by 40-Across that won a Grammy for Best R&B Album (3 wds.) |
| 36% | MADEINAMERICA | 13 | "O.J.:___," documentary series, based on the life of O. J. Simpson, that won the Oscar for Best Documentary Feature in 2016: 3 wds. |
| 36% | LETSMAKELOVE | 12 | Duet by Faith Hill and Tim McGraw, released in 2000, that won the couple a Grammy for Best Country Collaboration with Vocals: 3 wds. |