| 100% | CHAINOFFOOLS | 12 | Aretha Franklin's 1967 single that won her a Grammy for Best Female R&B Vocal Performance and later a Grammy Hall Of Fame Award: 3 wds. |
| 40% | 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.) |
| 38% | MYFAITHINYOU | 12 | "If I Ever Lose ___," single that won Sting a Grammy Award for Best Pop Vocal Performance (Male) in 1994: 4 wds. |
| 38% | IFIAINTGOTYOU | 13 | 2004 18-Across hit that won a Grammy for Best Female R&B Vocal Performance: 5 wds. |
| 38% | IFIAINTGOTYOU | 13 | Song by 40-Across that won a Grammy for Best Female R&B Vocal Performance (5 wds.) |
| 37% | SUPERWOMAN | 10 | Song from 17a which won Alicia Keys a Grammy for Best Female R&B Vocal Performance in 2009 |
| 36% | CRANESINTHESKY | 14 | Song by 49-Across that won a Grammy Award for Best R&B Performance in 2017 (4 wds.) |
| 35% | MAN | 3 | "___! I Feel Like a Woman!" 1999 Shania Twain song that won a Grammy Award for Best Female Country Vocal Performance |
| 33% | 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.) |
| 33% | SONGSIHEARD | 11 | 33-Across album that won a Grammy Award for Best Traditional Pop Vocal Album (3 wds.) |
| 33% | AINTITFUN | 9 | Hit single by Paramore that won a Grammy Award for Best Rock Song in 2015 (3 wds.) |
| 33% | WEFOUNDLOVE | 11 | Single from Rihanna's 6th studio album, a collaboration with DJ Calvin Harris, that won her a Grammy and was featured in "Sherlock" : 3 wds. |
| 32% | 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. |
| 31% | KISSMEMORE | 10 | 50-Across and SZA hit single that won Best Pop Duo/Group Performance at the 2022 Grammy Awards (3 wds.) |
| 31% | KENNYROGERS | 11 | Country Music Hall of Fame singer who's won the American Music Award for Favorite Country Single a record five times (2 wds.) |
| 31% | VISIONOF | 8 | "___ Love," song by Mariah Carey for which she won the Grammy for Best Female Pop Vocal Performance: 2 wds. |
| 31% | REBAMCENTIRE | 12 | Country Music Hall of Fame singer who's won the American Music Award for Favorite Female Country Artist a record 11 times (2 wds.) |
| 31% | ICANTBREATHE | 12 | H.E.R. single that won the 2021 Grammy for Song of the Year: 3 wds. |
| 31% | 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.) |
| 30% | INDUSTRYBABY | 12 | 2021 #1 song by Lil Nas X and 36-Across that was nominated for a Best Melodic Rap Performance Grammy Award and won three MTV Video Music Awards (2 wds.) |
| 30% | HUMBLEANDKIND | 13 | Tim McGraw single that won the 2017 Grammy for Best Country Song: 3 wds. |
| 30% | WEAREINLOVE | 11 | 33-Across album that won a Grammy for Best Jazz Vocal Performance, Male (4 wds.) |
| 30% | GIRLONFIRE | 10 | Album by 40-Across that won a Grammy for Best R&B Album (3 wds.) |
| 30% | ITISWHATITIS | 12 | Album by 41-Across featuring 17-Across that won the Grammy Award for Best Progressive R&B Album in 2021 (5 wds.) |
| 30% | ACTAFOOL | 8 | Single from Ludacris that was part of the soundtrack for "2 Fast 2 Furious," and was also nominated for a Grammy: 3 wds. |
| 29% | HERE | 4 | "___ You Come Again," 1977 Dolly Parton song that won a Grammy for Best Female Country Vocal Performance |
| 29% | NEEDEDME | 8 | 2016 Rihanna hit that received a Grammy nomination for Best R&B Performance: 2 wds. |
| 29% | IRENE | 5 | Singer Cara who won a Grammy for best female pop vocal performance for "Flashdance ... What a Feeling" |
| 29% | JUSTLIKETHAT | 12 | Bonnie Raitt single that won the 2023 Grammy for Song of the Year: 3 wds. |
| 29% | ABOUTDAMNTIME | 13 | 2022 Lizzo hit single that won a Grammy for Record of the Year (3 wds.) |