| 100% | DOESHELOVEYOU | 13 | Grammy-winning song re-recorded by Dolly Parton and 43-Across for 18-Across (4 wds.) |
| 48% | 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.) |
| 46% | RIGHTONTIME | 11 | 2021 song by 32-Across nominated for three Grammy Awards, including Record of the Year and Song of the Year (3 wds.) |
| 45% | 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.) |
| 44% | SOLONGSOWRONG | 13 | Grammy-winning album by 39-Across and 18-Across (4 wds.) |
| 44% | CRANESINTHESKY | 14 | Song by 49-Across that won a Grammy Award for Best R&B Performance in 2017 (4 wds.) |
| 44% | BESTFOLKALBUM | 13 | 2012 Grammy won by 44-Across for 18-Across: 3 wds. |
| 44% | YOULLTHINKOFME | 14 | First song by 49-Across to win the Grammy Award for Best Male Country Vocal Performance (4 wds.) |
| 43% | IWANTED | 7 | "Everything ___," song by Billie Eilish which won the Grammy for Record of the Year in 2021: 2 wds. |
| 43% | REACHOUTFORME | 13 | Song by Burt Bacharach and 26-Across that was a hit for 15-Across in 1964: 4 wds. |
| 42% | ALWAYSLOVEYOU | 13 | "I Will ___," number-one hit by Whitney Houston recorded for "The Bodyguard" which is a cover of a Dolly Parton song: 3 wds. |
| 42% | 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.) |
| 42% | BADGUY | 6 | 2019 song by Billie Eilish that won the Grammy Award for Record of the Year in 2020: 2 wds. |
| 42% | ALWAYSONMYMIND | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1983: 4 wds. |
| 42% | ONTHEROADAGAIN | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1981: 4 wds. |
| 41% | SPACECOWBOY | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Song (2 wds.) |
| 41% | ISTILLBELIEVE | 13 | 2020 biopic featuring 43-Across named for a hit song by 18-Across (3 wds.) |
| 41% | DONTLETMEDOWN | 13 | The Chainsmokers song that won the 2017 Grammy Award for Best Dance Recording (4 wds.) |
| 40% | IFIAINTGOTYOU | 13 | Song by 40-Across that won a Grammy for Best Female R&B Vocal Performance (5 wds.) |
| 40% | ABOYNAMEDSUE | 12 | Johnny Cash song for which Shel Silverstein won a Grammy: 4 wds. |
| 40% | PULITZERPRIZE | 13 | Award won by 40-Across for 18-Across (2 wds.) |
| 39% | YOURWOMAN | 9 | "Touch ___," 1972 Dolly Parton song that was nominated for a Grammy: 2 wds. |
| 39% | IFEELFORYOU | 11 | Grammy-winning song written by Prince that was a #1 hit for Chaka Khan in 1984 (4 wds.) |
| 39% | NEWKIDINTOWN | 12 | 1976 Eagles song that won the Best Arrangement for Voices Grammy in 1977: 4 wds. |
| 39% | JUNEIS | 6 | With 4 Down, 26 Across, and 18 Down, "Carousel" song famously slaughtered by Leslie Uggams |
| 38% | HERE | 4 | "___ You Come Again," 1977 Dolly Parton song that won a Grammy for Best Female Country Vocal Performance |
| 38% | CANTBUYMELOVE | 13 | 1964 #1 song for The Beatles written by 46-Across and John Lennon (4 wds.) |
| 38% | UNFORGETTABLE | 13 | 1991 duet between 18- and 43-Across that won a Grammy |
| 38% | PULITZERPRIZE | 13 | Award won by 18-Across for "Beloved" (2 wds.) |