| 100% | IMNOT | 5 | With 49-Across, song that won 14-Across his Best Country Song Grammy: 2 wds. |
| 58% | SPACECOWBOY | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Song (2 wds.) |
| 57% | ALWAYSONMYMIND | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1983: 4 wds. |
| 57% | ONTHEROADAGAIN | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1981: 4 wds. |
| 57% | BROKENHALOS | 11 | Chris Stapleton single that won the 2018 Grammy for Best Country Song: 2 wds. |
| 57% | SPACECOWBOY | 11 | Kacey Musgraves single that won the 2019 Grammy for Best Country Song: 2 wds. |
| 53% | GLENCAMPBELL | 12 | "Rhinestone Cowboy" singer who recently won the Best Country Song Grammy: 2 wds. |
| 53% | ZACBROWNBAND | 12 | American country music band with the hit song "Colder Weather", that won the 2010 Grammy for Best New Artist: 3 wds. |
| 51% | CRANESINTHESKY | 14 | Song by 49-Across that won a Grammy Award for Best R&B Performance in 2017 (4 wds.) |
| 51% | 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.) |
| 51% | IHOPEYOUDANCE | 13 | Song by 29-Across/32-Across that won the Best Country Song Grammy Award in 2001 (4 wds.) |
| 51% | YOULLTHINKOFME | 14 | First song by 49-Across to win the Grammy Award for Best Male Country Vocal Performance (4 wds.) |
| 51% | LEAVETHE | 8 | With 32-Across, Silk Sonic single that won the 2022 Grammy for Song of the Year: 2 wds. |
| 49% | TRUTHHURTS | 10 | Viral 46-Across song that won the 2020 Grammy Award for Best Pop Solo Performance (2 wds.) |
| 49% | STAYHIGH | 8 | Brittany Howard song that won the Grammy Award for Best Rock Song in 2021: 2 wds. |
| 49% | LITTLEBIG | 9 | ___ Town, country music group that won a Grammy for their hit song "Girl Crush": 2 wds. |
| 49% | HUMBLEANDKIND | 13 | Tim McGraw single that won the 2017 Grammy for Best Country Song: 3 wds. |
| 48% | THISLAND | 8 | Gary Clark Jr. song that won the Grammy Award for Best Rock Song in 2020: 2 wds. |
| 48% | SPACECOWBOY | 11 | Single from the album "Golden Hour" that won Best Country Song at the 2019 Grammys: 2 wds. |
| 47% | 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.) |
| 47% | BRANDICARLILE | 13 | 18-Across and 42-Across singer who won a Best Country Song Grammy Award for "Bring My Flowers Now" (2 wds.) |
| 47% | ISLANDSIN | 9 | With 40-Across, song that reached #1 on Billboard's country and Hot 100 charts in 1983: 2 wds. |
| 46% | WHATWASI | 8 | With 48-Across, Billie Eilish hit from "Barbie" that won an Oscar for Best Original Song: 3 wds. |
| 46% | THEGREATEST | 11 | With 42-Across, 1952 circus film that won the Best Picture Oscar: 2 wds. |
| 46% | IFIAINTGOTYOU | 13 | Song by 40-Across that won a Grammy for Best Female R&B Vocal Performance (5 wds.) |
| 45% | CHOPSUEY | 8 | 2001 song that earned 30-Across its first Grammy nomination, for Best Metal Performance: 2 wds. |
| 45% | BUTTERFLIES | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Solo Performance |
| 45% | THEFIGHTER | 10 | 2017 hit song by 17-Across that was inspired by his relationship with 30-Across: 2 wds. |
| 44% | STRANGER | 8 | "___ in My House," song written by Mike Reid that won the Grammy for Best Country Song in 1984 |
| 44% | TRUTHHURTS | 10 | 1-Across hit that won Best Pop Solo Performance at the 2020 Grammy Awards: 2 wds. |