| 100% | CHOPSUEY | 8 | 2001 song that earned 30-Across its first Grammy nomination, for Best Metal Performance: 2 wds. |
| 43% | RAPGOD | 6 | 37-Across song that was nominated for the 2015 Best Rap Performance Grammy Award (2 wds.) |
| 42% | NEEDEDME | 8 | 2016 Rihanna hit that received a Grammy nomination for Best R&B Performance: 2 wds. |
| 39% | INCHNAILS | 9 | Nine ___, band whose song "Wish" won the 1993 Grammy for Best Metal Performance: 2 wds. |
| 37% | TRUTHHURTS | 10 | Viral 46-Across song that won the 2020 Grammy Award for Best Pop Solo Performance (2 wds.) |
| 35% | BETTERNOW | 9 | Top 10 song by 42-Across that was nominated for a Best Pop Solo Performance Grammy Award (2 wds.) |
| 35% | CRANESINTHESKY | 14 | Song by 49-Across that won a Grammy Award for Best R&B Performance in 2017 (4 wds.) |
| 34% | YOULLTHINKOFME | 14 | First song by 49-Across to win the Grammy Award for Best Male Country Vocal Performance (4 wds.) |
| 34% | STAYHIGH | 8 | Brittany Howard song that won the Grammy Award for Best Rock Song in 2021: 2 wds. |
| 34% | IFIAINTGOTYOU | 13 | Song by 40-Across that won a Grammy for Best Female R&B Vocal Performance (5 wds.) |
| 34% | DRSTRANGELOVE | 13 | 1964 comedy that earned Peter Sellers a Best Actor Oscar nomination for playing three roles: 2 wds. |
| 34% | IMNOT | 5 | With 49-Across, song that won 14-Across his Best Country Song Grammy: 2 wds. |
| 34% | IHOPEYOUDANCE | 13 | Song by 29-Across/32-Across that won the Best Country Song Grammy Award in 2001 (4 wds.) |
| 33% | YOURWOMAN | 9 | "Touch ___," 1972 Dolly Parton song that was nominated for a Grammy: 2 wds. |
| 32% | NEWKIDINTOWN | 12 | 1976 Eagles song that won the Best Arrangement for Voices Grammy in 1977: 4 wds. |
| 32% | THISLAND | 8 | Gary Clark Jr. song that won the Grammy Award for Best Rock Song in 2020: 2 wds. |
| 32% | BROKENHALOS | 11 | Chris Stapleton single that won the 2018 Grammy for Best Country Song: 2 wds. |
| 32% | SPACECOWBOY | 11 | Kacey Musgraves single that won the 2019 Grammy for Best Country Song: 2 wds. |
| 32% | HERE | 4 | "___ You Come Again," 1977 Dolly Parton song that won a Grammy for Best Female Country Vocal Performance |
| 32% | ISME | 4 | "This ___," Keala Settle song that won the 2018 Golden Globe Award for Best Original Song: 2 wds. |
| 31% | METALLICA | 9 | Heavy metal band whose song "One" won the first ever Grammy for Best Metal Performance in 1990 |
| 31% | IRONMAIDEN | 10 | *2010 Grammy winner for Best Metal Performance |
| 31% | LUSTFORLIFE | 11 | 1956 movie that earned 46-Across an Oscar nomination for Best Actor: 3 wds. |
| 31% | NELLIEFORBUSH | 13 | "South Pacific" role that earned Mary Martin a Best Actress Tony for playing a WWII Navy nurse: 2 wds. |
| 31% | PETERPAN | 8 | Title role that earned Mary Martin a Best Actress Tony for playing a boy who could fly: 2 wds. |
| 31% | SPACECOWBOY | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Song (2 wds.) |
| 31% | ALMOSTTHERE | 11 | "The Princess and the Frog" song that was nominated for an Oscar for Best Original Song of 2009: 2 wds. |
| 30% | STRESSEDOUT | 11 | Song for which Twenty One Pilots won the Grammy for Best Pop Duo/Group Performance in 2017: 2 wds. |
| 30% | 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.) |
| 30% | BETTERMAN | 9 | 2016 song written by Taylor Swift and performed by 33-Across that won a Grammy Award for Best Country Duo/Group Performance (2 wds.) |