| 100% | BUTTERFLIES | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Solo Performance |
| 82% | SPACECOWBOY | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Song (2 wds.) |
| 66% | SPACECOWBOY | 11 | Kacey Musgraves single that won the 2019 Grammy for Best Country Song: 2 wds. |
| 59% | YOULLTHINKOFME | 14 | First song by 49-Across to win the Grammy Award for Best Male Country Vocal Performance (4 wds.) |
| 56% | TRUTH | 5 | "___ Hurts," song by Lizzo which won the 2020 Grammy for Best Pop Solo Performance |
| 56% | TRUTHHURTS | 10 | Viral 46-Across song that won the 2020 Grammy Award for Best Pop Solo Performance (2 wds.) |
| 55% | YOU | 3 | "Someone like ___," hit song by Adele that won the Grammy for Best Pop Solo Performance in 2012 |
| 54% | PONTOON | 7 | #1 country hit for 48-Across that won the 2013 Grammy for Best Country Duo/Group Performance |
| 54% | TRUTH | 5 | "___ Hurts," song by Lizzo that won the Grammy Award for Best Pop Solo Performance in 2020 |
| 54% | BROKENHALOS | 11 | Chris Stapleton single that won the 2018 Grammy for Best Country Song: 2 wds. |
| 54% | HUMBLEANDKIND | 13 | Tim McGraw single that won the 2017 Grammy for Best Country Song: 3 wds. |
| 53% | MAKING | 6 | "___ a Fire," song by Foo Fighters that won the Grammy Award for Best Rock Performance in 2022 |
| 52% | JEROME | 6 | Song by Lizzo which won the 2020 Grammy for Best Traditional R&B Performance |
| 51% | IFIAINTGOTYOU | 13 | Song by 40-Across that won a Grammy for Best Female R&B Vocal Performance (5 wds.) |
| 50% | BADGUY | 6 | 2019 song by Billie Eilish that won the Grammy Award for Record of the Year in 2020: 2 wds. |
| 50% | 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.) |
| 50% | ELLAMAI | 7 | Singer whose “Boo’d Up” won the 2019 Grammy for Best R. & B. Song |
| 49% | STRANGER | 8 | "___ in My House," song written by Mike Reid that won the Grammy for Best Country Song in 1984 |
| 49% | CRANESINTHESKY | 14 | Song by 49-Across that won a Grammy Award for Best R&B Performance in 2017 (4 wds.) |
| 49% | JEAN | 4 | "Billie ___," song by from 14a that won the Grammy for Best R&B Song in 1984 |
| 48% | TOGETHER | 8 | "We Belong ___," song by Mariah Carey that won the Grammy for Best R&B Song |
| 48% | IHOPEYOUDANCE | 13 | Song by 29-Across/32-Across that won the Best Country Song Grammy Award in 2001 (4 wds.) |
| 47% | IGOR | 4 | Tyler, the Creator work that won the 2019 Grammy for Best Rap Album |
| 47% | 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.) |
| 47% | ALWAYSONMYMIND | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1983: 4 wds. |
| 47% | ONTHEROADAGAIN | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1981: 4 wds. |
| 46% | 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.) |
| 46% | WAITING | 7 | "___ on a War," song by Foo Fighters that won the Grammy Award for Best Rock song in 2022 |
| 45% | MORE | 4 | "Kiss Me ___," song by Doja Cat ft. SZA that won the Grammy Award for the Best Pop Duo/Group Performance in 2022 |
| 45% | UNCOMFORTABLE | 13 | Halestorm song nominated for the 2019 Grammy for Best Rock Performance |