| 100% | FOOLFORYOU | 10 | Best R&B Song Grammy winner for 39-Across: 3 wds. |
| 57% | MUNILONG | 8 | 2023 Best R&B Performance Grammy winner for "Hrs & Hrs": 2 wds. |
| 50% | BEYONCE | 7 | 2021 Best R&B Performance Grammy winner for "Black Parade" |
| 49% | IFIAINTGOTYOU | 13 | Song by 40-Across that won a Grammy for Best Female R&B Vocal Performance (5 wds.) |
| 46% | CRANESINTHESKY | 14 | Song by 49-Across that won a Grammy Award for Best R&B Performance in 2017 (4 wds.) |
| 43% | SPACECOWBOY | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Song (2 wds.) |
| 42% | GIRLONFIRE | 10 | Album by 40-Across that won a Grammy for Best R&B Album (3 wds.) |
| 41% | ALWAYSONMYMIND | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1983: 4 wds. |
| 41% | ONTHEROADAGAIN | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1981: 4 wds. |
| 41% | RAPGOD | 6 | 37-Across song that was nominated for the 2015 Best Rap Performance Grammy Award (2 wds.) |
| 40% | IFIAINTGOTYOU | 13 | 2004 18-Across hit that won a Grammy for Best Female R&B Vocal Performance: 5 wds. |
| 39% | DONTWANNAFIGHT | 14 | Alabama Shakes song that won the Grammy Award for Best Rock Song in 2016: 3 wds. |
| 38% | FOOFIGHTERS | 11 | Band whose "Run" won the 2018 Grammy for Best Rock Song: 2 wds. |
| 38% | DEAREVANHANSEN | 14 | 2017 Tony Award winner for Best Musical (3 wds.) |
| 38% | JAZMINE | 7 | With 50-Across, 2022 Best R&B Performance Grammy co-winner for "Pick Up Your Feelings" |
| 38% | FOUROUTOFFIVE | 13 | Arctic Monkeys song nominated for the 2019 Grammy for Best Rock Performance (4 wds.) |
| 38% | JEROME | 6 | Song by Lizzo which won the 2020 Grammy for Best Traditional R&B Performance |
| 38% | BROKENHALOS | 11 | Chris Stapleton single that won the 2018 Grammy for Best Country Song: 2 wds. |
| 38% | SPACECOWBOY | 11 | Kacey Musgraves single that won the 2019 Grammy for Best Country Song: 2 wds. |
| 38% | PATBENATAR | 10 | 1981 Grammy winner for "Fire and Ice" (Best Rock Vocal Performance, Female): 2 wds. |
| 38% | MACYGRAY | 8 | R&B singer best known for the song I Try |
| 38% | NAS | 3 | Grammy winner for Best Rap Album in 2021 |
| 38% | NEWKIDINTOWN | 12 | 1976 Eagles song that won the Best Arrangement for Voices Grammy in 1977: 4 wds. |
| 38% | INCHNAILS | 9 | Nine ___, band whose song "Wish" won the 1993 Grammy for Best Metal Performance: 2 wds. |
| 37% | RIVERDANCE | 10 | 1997 Grammy winner for Best Musical Show |
| 37% | IRONMAIDEN | 10 | *2010 Grammy winner for Best Metal Performance |
| 37% | ADELE | 5 | 2009 Grammy winner for Best New Artist |
| 37% | CHOPSUEY | 8 | 2001 song that earned 30-Across its first Grammy nomination, for Best Metal Performance: 2 wds. |
| 37% | ALABAMASHAKES | 13 | Band whose "Don't Wanna Fight" won the 2016 Grammy for Best Rock Song: 2 wds. |
| 37% | LITTLEBIGTOWN | 13 | Winner of the 2016 Grammy for Best Country Duo/Group Performance: 3 wds. |