| 100% | PONTOON | 7 | #1 country hit for 48-Across that won the 2013 Grammy for Best Country Duo/Group Performance |
| 63% | 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.) |
| 63% | BUTTERFLIES | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Solo Performance |
| 59% | TOWN | 4 | "Old ___ Road," song by Lil Nas X featuring Billy Ray Cyrus that won the Grammy Award for Best Pop Duo/Group Performance in 2020 |
| 57% | LITTLEBIGTOWN | 13 | Winner of the 2016 Grammy for Best Country Duo/Group Performance: 3 wds. |
| 56% | SPACECOWBOY | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Song (2 wds.) |
| 55% | ZACBROWNBAND | 12 | American country music band with the hit song "Colder Weather", that won the 2010 Grammy for Best New Artist: 3 wds. |
| 55% | KISSMEMORE | 10 | 50-Across and SZA hit single that won Best Pop Duo/Group Performance at the 2022 Grammy Awards (3 wds.) |
| 55% | ALWAYSONMYMIND | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1983: 4 wds. |
| 55% | ONTHEROADAGAIN | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1981: 4 wds. |
| 54% | MORE | 4 | "Kiss Me ___," song by Doja Cat ft. SZA that won the Grammy Award for the Best Pop Duo/Group Performance in 2022 |
| 54% | TRUTHHURTS | 10 | 1-Across hit that won Best Pop Solo Performance at the 2020 Grammy Awards: 2 wds. |
| 53% | STARTED | 7 | "Let's Get It ___," 2004 song by the Black Eyed Peas that won a Grammy for Best Rap Performance by a Duo or Group |
| 53% | DURURAN | 7 | Group that won the first Grammy for Best Music Video |
| 53% | YOU | 3 | "Someone like ___," hit song by Adele that won the Grammy for Best Pop Solo Performance in 2012 |
| 52% | BROKENHALOS | 11 | Chris Stapleton single that won the 2018 Grammy for Best Country Song: 2 wds. |
| 52% | HUMBLEANDKIND | 13 | Tim McGraw single that won the 2017 Grammy for Best Country Song: 3 wds. |
| 52% | SPACECOWBOY | 11 | Kacey Musgraves single that won the 2019 Grammy for Best Country Song: 2 wds. |
| 51% | YOULLTHINKOFME | 14 | First song by 49-Across to win the Grammy Award for Best Male Country Vocal Performance (4 wds.) |
| 51% | TRUTHHURTS | 10 | Viral 46-Across song that won the 2020 Grammy Award for Best Pop Solo Performance (2 wds.) |
| 51% | CHICKS | 6 | The ___, country music group that won a Grammy for their hit song "Not Ready to Make Nice" |
| 49% | LIVIN | 5 | "While I'm ___," album by Tanya Tucker that won the Grammy Award for Best Country Album in 2020 |
| 49% | 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.) |
| 48% | TRUTH | 5 | "___ Hurts," song by Lizzo that won the Grammy Award for Best Pop Solo Performance in 2020 |
| 48% | WEFOUNDLOVE | 11 | Rihanna hit that won the 2013 Best Music Video Grammy: 3 wds. |
| 48% | IFIAINTGOTYOU | 13 | 2004 18-Across hit that won a Grammy for Best Female R&B Vocal Performance: 5 wds. |
| 48% | MAKING | 6 | "___ a Fire," song by Foo Fighters that won the Grammy Award for Best Rock Performance in 2022 |
| 47% | COME | 4 | "The Best is Yet to ___," album by Ella Fitzgerald that won her the Grammy for Best Jazz Vocal Performance in 1984 |
| 47% | MAN | 3 | "___! I Feel Like a Woman!" 1999 Shania Twain song that won a Grammy Award for Best Female Country Vocal Performance |
| 46% | NEEDTOKNOW | 10 | Hit single by 50-Across that was nominated for Best Melodic Rap Performance at the 2022 Grammy Awards (3 wds.) |