| 100% | IFIAINTGOTYOU | 13 | 2004 18-Across hit that won a Grammy for Best Female R&B Vocal Performance: 5 wds. |
| 75% | IFIAINTGOTYOU | 13 | Song by 40-Across that won a Grammy for Best Female R&B Vocal Performance (5 wds.) |
| 59% | 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. |
| 55% | WEAREINLOVE | 11 | 33-Across album that won a Grammy for Best Jazz Vocal Performance, Male (4 wds.) |
| 53% | HERE | 4 | "___ You Come Again," 1977 Dolly Parton song that won a Grammy for Best Female Country Vocal Performance |
| 53% | CRANESINTHESKY | 14 | Song by 49-Across that won a Grammy Award for Best R&B Performance in 2017 (4 wds.) |
| 52% | SUPERWOMAN | 10 | Song from 17a which won Alicia Keys a Grammy for Best Female R&B Vocal Performance in 2009 |
| 51% | GIRLONFIRE | 10 | Album by 40-Across that won a Grammy for Best R&B Album (3 wds.) |
| 50% | NEEDEDME | 8 | 2016 Rihanna hit that received a Grammy nomination for Best R&B Performance: 2 wds. |
| 47% | FAMILYTIES | 10 | 2021 Baby Keem and Kendrick Lamar hit that won a Grammy for Rap Performance: 2 wds. |
| 47% | IRENE | 5 | Singer Cara who won a Grammy for best female pop vocal performance for "Flashdance ... What a Feeling" |
| 46% | SONGSIHEARD | 11 | 33-Across album that won a Grammy Award for Best Traditional Pop Vocal Album (3 wds.) |
| 45% | MYFAITHINYOU | 12 | "If I Ever Lose ___," single that won Sting a Grammy Award for Best Pop Vocal Performance (Male) in 1994: 4 wds. |
| 44% | HERO | 4 | Hit song by Mariah Carey that was nominated for a Grammy for Best Female Pop Vocal Performance in 1995 |
| 42% | MAROONED | 8 | 1994 Pink Floyd instrumental track that won a Grammy for Best Rock Instrumental Performance |
| 42% | AINTITFUN | 9 | Hit single by Paramore that won a Grammy Award for Best Rock Song in 2015 (3 wds.) |
| 41% | TLC | 3 | Girl group that won a Best R&B Album Grammy for "FanMail" |
| 41% | TRUTHHURTS | 10 | 1-Across hit that won Best Pop Solo Performance at the 2020 Grammy Awards: 2 wds. |
| 40% | 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.) |
| 40% | NAME | 4 | "You Don't Know My ___," 2003 song by Alicia Keys that won a Grammy Award for Best R&B Song |
| 40% | LITTLEBIG | 9 | ___ Town, country music group that won a Grammy for their hit song "Girl Crush": 2 wds. |
| 39% | MAN | 3 | "___! I Feel Like a Woman!" 1999 Shania Twain song that won a Grammy Award for Best Female Country Vocal Performance |
| 39% | ALWAYSONMYMIND | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1983: 4 wds. |
| 39% | ONTHEROADAGAIN | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1981: 4 wds. |
| 39% | 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.) |
| 38% | TRUTHHURTS | 10 | Viral 46-Across song that won the 2020 Grammy Award for Best Pop Solo Performance (2 wds.) |
| 38% | JOHN | 4 | ___ Legend, American singer who won a Grammy for Best R&B Album in 2006 |
| 38% | HER | 3 | Artist whose self-titled debut won a Grammy for Best R&B Album |
| 38% | SYSTEMOFADOWN | 13 | Group that won a Grammy for 2005's "B.Y.O.B": 4 wds. |
| 37% | BEATIT | 6 | 1983 hit that won a Grammy for Record of the Year |