| 100% | ITISWHATITIS | 12 | Album by 41-Across featuring 17-Across that won the Grammy Award for Best Progressive R&B Album in 2021 (5 wds.) |
| 53% | CRANESINTHESKY | 14 | Song by 49-Across that won a Grammy Award for Best R&B Performance in 2017 (4 wds.) |
| 53% | JAIL | 4 | Song by Kanye featuring Jay-Z that won the Grammy Award for Best Rap Song in 2022 |
| 53% | HER | 3 | One-named artist whose self-titled album won the Grammy Award for Best R & B album in 2019 |
| 52% | STAYHIGH | 8 | Brittany Howard song that won the Grammy Award for Best Rock Song in 2021: 2 wds. |
| 52% | FROMTHEFIRES | 12 | Greta Van Fleet album that won the Grammy Award for Best Rock Album in 2019 (3 wds.) |
| 52% | TOWN | 4 | "Old ___ Road," song by Lil Nas X featuring Billy Ray Cyrus that won the Grammy Award for Best Pop Duo/Group Performance in 2020 |
| 48% | GIRLONFIRE | 10 | Album by 40-Across that won a Grammy for Best R&B Album (3 wds.) |
| 48% | TRUTH | 5 | "___ Hurts," song by Lizzo that won the Grammy Award for Best Pop Solo Performance in 2020 |
| 48% | DONTWANNAFIGHT | 14 | Alabama Shakes song that won the Grammy Award for Best Rock Song in 2016: 3 wds. |
| 47% | THISLAND | 8 | Gary Clark Jr. song that won the Grammy Award for Best Rock Song in 2020: 2 wds. |
| 47% | MAKING | 6 | "___ a Fire," song by Foo Fighters that won the Grammy Award for Best Rock Performance in 2022 |
| 47% | WAITING | 7 | "___ on a War," song by Foo Fighters that won the Grammy Award for Best Rock song in 2022 |
| 47% | SOUR | 4 | Album by Olivia Rodrigo that won the Grammy Award for Best Pop Vocal Album in 2022 |
| 47% | THEWAYIMLIVIN | 13 | Album by 29-Across/32-Across nominated for the Best Country Album Grammy Award in 2015 (4 wds.) |
| 46% | JEAN | 4 | "Billie ___," song by from 14a that won the Grammy for Best R&B Song in 1984 |
| 46% | BADGUY | 6 | 2019 song by Billie Eilish that won the Grammy Award for Record of the Year in 2020: 2 wds. |
| 46% | AINTITFUN | 9 | Hit single by Paramore that won a Grammy Award for Best Rock Song in 2015 (3 wds.) |
| 46% | LIVIN | 5 | "While I'm ___," album by Tanya Tucker that won the Grammy Award for Best Country Album in 2020 |
| 46% | BLACK | 5 | "___ Parade," single by Beyonce which won the Grammy for Best R&B Performance in 2021 |
| 45% | MORE | 4 | "Kiss Me ___," song by Doja Cat ft. SZA that won the Grammy Award for the Best Pop Duo/Group Performance in 2022 |
| 45% | SONGSIHEARD | 11 | 33-Across album that won a Grammy Award for Best Traditional Pop Vocal Album (3 wds.) |
| 45% | TIFFANYHADDISH | 14 | "Black Mitzvah" comedian who won a Grammy Award for Best Comedy Album in 2021 (2 wds.) |
| 45% | LOST | 4 | "Call Me If You Get ___," album by Tyler, the Creator that won the Grammy Award for Best Rap Album in 2022 |
| 45% | HORSE | 5 | "Dark ___," song by Katy Perry featuring Juicy J that won the MTV Video Music Award for Best Female Video in 2014 |
| 44% | IFIAINTGOTYOU | 13 | Song by 40-Across that won a Grammy for Best Female R&B Vocal Performance (5 wds.) |
| 44% | IHOPEYOUDANCE | 13 | Song by 29-Across/32-Across that won the Best Country Song Grammy Award in 2001 (4 wds.) |
| 44% | ONTHEROADAGAIN | 14 | Song by 30-Across/33-Across that won a Grammy Award for Best Country Song and was inducted into the Grammy Hall of Fame (4 wds.) |
| 44% | THEAMERICANS | 12 | Spy drama starring 17-Across and 41-Across that won the 2019 Golden Globe Award for Best Television Series - Drama (2 wds.) |
| 43% | MORNINGPHASE | 12 | Beck album that won the 2015 Grammy Award for Best Rock Album: 2 wds. |