| 100% | GEORGIAONMYMIND | 15 | 1960 Grammy-winning song by 36-Across |
| 64% | BUTTERFLIES | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Solo Performance |
| 64% | 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.) |
| 63% | SPACECOWBOY | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Song (2 wds.) |
| 62% | IFIAINTGOTYOU | 13 | Song by 40-Across that won a Grammy for Best Female R&B Vocal Performance (5 wds.) |
| 61% | IHOPEYOUDANCE | 13 | Song by 29-Across/32-Across that won the Best Country Song Grammy Award in 2001 (4 wds.) |
| 61% | CRANESINTHESKY | 14 | Song by 49-Across that won a Grammy Award for Best R&B Performance in 2017 (4 wds.) |
| 58% | YOULLTHINKOFME | 14 | First song by 49-Across to win the Grammy Award for Best Male Country Vocal Performance (4 wds.) |
| 58% | OLDTOWNROAD | 11 | 2019 song by 44-Across whose remix version with Billy Ray Cyrus won two Grammy Awards (3 wds.) |
| 57% | JEROME | 6 | Song by Lizzo which won the 2020 Grammy for Best Traditional R&B Performance |
| 57% | ALLEY | 5 | "___ Cat," instrumental song by Bent Fabric which won a Grammy in 1963 |
| 56% | RIVER | 5 | "Cry Me a ___," 2002 song by Justin Timberlake which won a Grammy Award |
| 56% | GRAMMY | 6 | Song of the Year award won by Lorde for 36-Across |
| 55% | DOESHELOVEYOU | 13 | Grammy-winning song re-recorded by Dolly Parton and 43-Across for 18-Across (4 wds.) |
| 55% | SWEETLOVE | 9 | Grammy-winning song by Anita Baker |
| 55% | LAYLA | 5 | A hit song by Eric Clapton titled after a lady, that won a Grammy |
| 55% | HELLO | 5 | 2015 song by Adele that won the Grammy Award for Record of the Year |
| 55% | WHAT | 4 | "___ Goes Around...Comes Around," 2006 song by Justin Timberlake which won a Grammy award |
| 55% | TRUTH | 5 | "___ Hurts," song by Lizzo which won the 2020 Grammy for Best Pop Solo Performance |
| 55% | DANI | 4 | "___ California," 2006 song by the Red Hot Chili Peppers that won two Grammy awards |
| 55% | 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.) |
| 54% | JAIL | 4 | Song by Kanye featuring Jay-Z that won the Grammy Award for Best Rap Song in 2022 |
| 54% | INTOTHEWILD | 11 | Debut solo studio album by 36-Across that features the Golden Globe-winning song "Guaranteed" (3 wds.) |
| 54% | TOGETHER | 8 | "We Belong ___," song by Mariah Carey that won the Grammy for Best R&B Song |
| 54% | SINGLE | 6 | "___ Ladies (Put a Ring on It)," 2008 song by Beyonce that won three Grammy Awards |
| 54% | YOU | 3 | "I Will Remember ___," song by Canadian singer Sarah McLachlan that won her a Grammy Award |
| 53% | JEAN | 4 | "Billie ___," song by from 14a that won the Grammy for Best R&B Song in 1984 |
| 53% | HELLO | 5 | Hit song by Adele that won 3 Grammy awards including Record of the Year in 2017 |
| 53% | TRUTH | 5 | "___ Hurts," song by Lizzo that won the Grammy Award for Best Pop Solo Performance in 2020 |
| 53% | THIS | 4 | "___ is America," hit song by Childish Gambino which won the Grammy for Record of the Year |