| 100% | OLDTOWNROAD | 11 | Song for which Lil Nas X and Billy Ray Cyrus won the Grammy for Best Pop Duo/Group Performance in 2020: 3 wds. |
| 68% | 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 |
| 60% | SAYSOMETHING | 12 | Song for which A Great Big World and Christina Aguilera won the Grammy for Best Pop Duo/Group Performance in 2015: 2 wds. |
| 51% | OLDTOWNROAD | 11 | Lil Nas X and Billy Ray Cyrus song that won the 2019 American Music Award for Favorite Rap/Hip-Hop Song (3 wds.) |
| 48% | STRESSEDOUT | 11 | Song for which Twenty One Pilots won the Grammy for Best Pop Duo/Group Performance in 2017: 2 wds. |
| 41% | TRUTH | 5 | "___ Hurts," song by Lizzo that won the Grammy Award for Best Pop Solo Performance in 2020 |
| 40% | 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.) |
| 39% | MORE | 4 | "Kiss Me ___," song by Doja Cat ft. SZA that won the Grammy Award for the Best Pop Duo/Group Performance in 2022 |
| 39% | KISSMEMORE | 10 | 50-Across and SZA hit single that won Best Pop Duo/Group Performance at the 2022 Grammy Awards (3 wds.) |
| 39% | TRUTH | 5 | "___ Hurts," song by Lizzo which won the 2020 Grammy for Best Pop Solo Performance |
| 37% | TRUTHHURTS | 10 | Viral 46-Across song that won the 2020 Grammy Award for Best Pop Solo Performance (2 wds.) |
| 37% | YOU | 3 | "Someone like ___," hit song by Adele that won the Grammy for Best Pop Solo Performance in 2012 |
| 37% | VISIONOF | 8 | "___ Love," song by Mariah Carey for which she won the Grammy for Best Female Pop Vocal Performance: 2 wds. |
| 36% | COUNTRYFOROLD | 13 | "No ___ Men," a movie in which Javier Bardem starred in and won the Best Actor Award at the Oscars for his performance: 3 wds. |
| 36% | RAIN | 4 | "___ on Me," 2020 Lady Gaga and Ariana Grande song that won the Best Pop Duo Performance at the 63rd Grammy Awards |
| 35% | LITTLEBIGTOWN | 13 | Winner of the 2016 Grammy for Best Country Duo/Group Performance: 3 wds. |
| 35% | DONTWANNAFIGHT | 14 | Alabama Shakes song that won the Grammy Award for Best Rock Song in 2016: 3 wds. |
| 35% | THISISME | 8 | Song from "The Greatest Showman" which won the Golden Globe Award for Best Original Song in 2017: 3 wds. |
| 35% | THISLAND | 8 | Gary Clark Jr. song that won the Grammy Award for Best Rock Song in 2020: 2 wds. |
| 34% | JEROME | 6 | Song by Lizzo which won the 2020 Grammy for Best Traditional R&B Performance |
| 34% | OLDTOWNROAD | 11 | 2019 song by Lil Nas X which peaked at number one on the Billboard Hot 100 for nineteen consecutive weeks: 3 wds. |
| 34% | FIGHTFORYOU | 11 | H.E.R. song from "Judas and the Black Messiah" that won the Oscar for Best Original Song in 2021: 3 wds. |
| 34% | CITYOFSTARS | 11 | Ryan Gosling and Emma Stone song from "La La Land" that won the Oscar for Best Original Song in 2017: 3 wds. |
| 34% | HARRY | 5 | ___ Styles, "Watermelon Sugar" singer who won the Grammy for Best Pop Solo Performance in 2021 |
| 33% | 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 |
| 33% | 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.) |
| 33% | THEWARONDRUGS | 13 | Band which won the Grammy for Best Rock Album in 2018: 4 wds. |
| 33% | CLUB | 4 | Culture ___, English pop group that won the Grammy for Best New Artist in 1984 |
| 33% | BLACK | 5 | "___ Parade," single by Beyonce which won the Grammy for Best R&B Performance in 2021 |
| 33% | LETSMAKELOVE | 12 | Duet by Faith Hill and Tim McGraw, released in 2000, that won the couple a Grammy for Best Country Collaboration with Vocals: 3 wds. |