| 100% | ABETTERMAN | 10 | #1 song by 45-Across from 35-Across that won the 1989 Single of the Year Academy of Country Music Award (3 wds.) |
| 65% | KILLINTIME | 10 | Album by 45-Across featuring the singles 18-Across and 26-Across that won the 1989 Album of the Year Academy of Country Music Award (2 wds.) |
| 51% | PIECEOFME | 9 | Song by 32-Across that won three MTV Video Music Awards in 2008, including Video of the Year (3 wds.) |
| 47% | FASTCAR | 7 | 1988 Tracy Chapman hit that won Song of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 46% | GIRL | 4 | 2019 album by 44-Across that won the Country Music Association's Album of the Year Award |
| 45% | LITTLEBIGTOWN | 13 | 15-Across and 54-Across band that won the 2017 Country Music Association Award for Vocal Group of the Year (3 wds.) |
| 44% | KNOWINGYOU | 10 | Top 10 single that 30-Across performed at the Academy of Country Music Awards ceremony in 2021 (2 wds.) |
| 44% | OLDDOMINION | 11 | "Written in the Sand" band that won Vocal Group of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 44% | WASTED | 6 | Carrie Underwood song that won Most Performed Song of the Year in the 2007 ASCAP Country Music Awards |
| 44% | RAIN | 4 | "___ On Me," song by Lady Gaga and Ariana Grande that won the MTV Video Music Award for Song of the Year in 2020 |
| 43% | JUICE | 5 | Song from 46-Across's album "Cuz I Love You" that won the 2019 Soul Train Music Award for Video of the Year |
| 43% | AHARDDAYS | 9 | "___ Night," a musical comedy film starring the Beatles that won 31-Across an Academy Award for scoring of music: 3 wds. |
| 43% | 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.) |
| 43% | JUSTLIKETHAT | 12 | Bonnie Raitt single that won the 2023 Grammy for Song of the Year: 3 wds. |
| 43% | CLINTBLACK | 10 | 18-Across, 26-Across, and 35-Across country singer who won four 1989 Academy of Country Music Awards, including Top Male Vocalist (2 wds.) |
| 42% | ICANTBREATHE | 12 | H.E.R. single that won the 2021 Grammy for Song of the Year: 3 wds. |
| 42% | THOMASRHETT | 11 | "Country Again" singer who won Entertainer of the Year at the 2020 Academy of Country Music Awards: 2 wds. |
| 42% | TRACYCHAPMAN | 12 | "Fast Car" songwriter who won Song of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 42% | HANDSTOMYSELF | 13 | Single from Selena Gomez's album "Revival" that was influenced by the music of American singer Prince: 3 wds. |
| 41% | MIRANDALAMBERT | 14 | "Tin Man" singer who won Female Vocalist of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 41% | COLESWINDELL | 12 | 2015 Academy of Country Music Awards New Artist of the Year who sings 30-Across with 18-Across (2 wds.) |
| 41% | LAINEYWILSON | 12 | 2021 Academy of Country Music Awards New Artist of the Year who sings 30-Across with 40-Across (2 wds.) |
| 41% | HELLO | 5 | Hit song by Adele that won 3 Grammy awards including Record of the Year in 2017 |
| 41% | JASONALDEAN | 11 | "You Make It Easy" singer who won Entertainer of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 41% | TOOMUCHHEAVEN | 13 | Song that was the first of three #1 singles by 42-Across in 1979 (3 wds.) |
| 40% | ROLLING | 7 | "___ in the Deep," hit song by Adele that won 3 Grammy awards including Record of the Year in 2012 |
| 40% | BADGUY | 6 | 2019 song by Billie Eilish that won the Grammy Award for Record of the Year in 2020: 2 wds. |
| 40% | IHOPEYOUDANCE | 13 | Song by 29-Across/32-Across that won the Best Country Song Grammy Award in 2001 (4 wds.) |
| 40% | WEAREYOUNG | 10 | #1 fun. hit released in 2011 that won the Grammy for Song of the Year: 3 wds. |
| 39% | LEAVETHE | 8 | With 32-Across, Silk Sonic single that won the 2022 Grammy for Song of the Year: 2 wds. |