| 100% | BUTTERFLIES | 11 | Single from the album "Golden Hour" that won Best Country Solo Performance at the 2019 Grammys |
| 85% | SPACECOWBOY | 11 | Single from the album "Golden Hour" that won Best Country Song at the 2019 Grammys: 2 wds. |
| 48% | KACEYMUSGRAVES | 14 | Artist whose album "Golden Hour" won Album of the Year at the 2019 Grammys: 2 wds. |
| 48% | TRUTHHURTS | 10 | 1-Across hit that won Best Pop Solo Performance at the 2020 Grammy Awards: 2 wds. |
| 47% | BUTTERFLIES | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Solo Performance |
| 46% | 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.) |
| 43% | ALRIGHT | 7 | Kendrick Lamar single that won Best Rap Song at the 2016 Grammys |
| 43% | IGOR | 4 | Tyler, the Creator album that won Best Rap Album at the 2020 Grammys |
| 41% | TOPIMPA | 7 | With 48-Across, Kendrick Lamar album that won Best Rap Album at the 2016 Grammys: 3 wds. |
| 41% | SPACECOWBOY | 11 | Kacey Musgraves single that won the 2019 Grammy for Best Country Song: 2 wds. |
| 40% | KISSMEMORE | 10 | 50-Across and SZA hit single that won Best Pop Duo/Group Performance at the 2022 Grammy Awards (3 wds.) |
| 40% | 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.) |
| 39% | JEAN | 4 | "Billie ___," the second single from Michael Jackson's album in 16a, that won two Grammys and one American Music Award |
| 38% | ROMA | 4 | Movie that won Best Director at the 2019 Oscars |
| 38% | ROLLING | 7 | With 18-Across, Adele single from the album "21" that won the Grammy Award for Record of the Year for 2011 |
| 36% | IGOR | 4 | Tyler, the Creator album that won Best Rap Album at the 2020 Grammy Awards |
| 36% | GIRL | 4 | 2019 album by 44-Across that won the Country Music Association's Album of the Year Award |
| 36% | LAINEYWILSON | 12 | "Bell Bottom Country" singer who won Best Country Album at the 2024 Grammy Awards (2 wds.) |
| 35% | IGOR | 4 | Tyler, the Creator work that won the 2019 Grammy for Best Rap Album |
| 35% | BROKENHALOS | 11 | Chris Stapleton single that won the 2018 Grammy for Best Country Song: 2 wds. |
| 35% | HUMBLEANDKIND | 13 | Tim McGraw single that won the 2017 Grammy for Best Country Song: 3 wds. |
| 34% | SPACECOWBOY | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Song (2 wds.) |
| 34% | NEEDTOKNOW | 10 | Hit single by 50-Across that was nominated for Best Melodic Rap Performance at the 2022 Grammy Awards (3 wds.) |
| 34% | TRUTH | 5 | "___ Hurts," song by Lizzo that won the Grammy Award for Best Pop Solo Performance in 2020 |
| 34% | THE | 3 | "___ Americans," FX show that won the 2019 Golden Globe Award for Best Television Series in Drama |
| 34% | HEARTBREAKER | 12 | 1978 Dolly Parton song from the eponymous album that topped the U.S. country singles chart |
| 34% | MENATWORK | 9 | 15-Across and 33-Across rock band from Australia that won Best New Artist at the 1983 Grammy Awards (3 wds.) |
| 34% | STAR | 4 | "A ___ Is Born," film with the song "Shallow" that won the 2019 Golden Globe Award for Best Original Song |
| 34% | FROMTHEFIRES | 12 | Greta Van Fleet album that won the Grammy Award for Best Rock Album in 2019 (3 wds.) |
| 34% | PONTOON | 7 | #1 country hit for 48-Across that won the 2013 Grammy for Best Country Duo/Group Performance |