| 100% | STRESSEDOUT | 11 | Song for which Twenty One Pilots won the Grammy for Best Pop Duo/Group Performance in 2017: 2 wds. |
| 62% | 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. |
| 57% | 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. |
| 50% | VISIONOF | 8 | "___ Love," song by Mariah Carey for which she won the Grammy for Best Female Pop Vocal Performance: 2 wds. |
| 48% | MORE | 4 | "Kiss Me ___," song by Doja Cat ft. SZA that won the Grammy Award for the Best Pop Duo/Group Performance in 2022 |
| 47% | 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 |
| 46% | CRANESINTHESKY | 14 | Song by 49-Across that won a Grammy Award for Best R&B Performance in 2017 (4 wds.) |
| 45% | YOU | 3 | "Someone like ___," hit song by Adele that won the Grammy for Best Pop Solo Performance in 2012 |
| 44% | TRUTH | 5 | "___ Hurts," song by Lizzo that won the Grammy Award for Best Pop Solo Performance in 2020 |
| 44% | IWANTED | 7 | "Everything ___," song by Billie Eilish which won the Grammy for Record of the Year in 2021: 2 wds. |
| 44% | THISISME | 8 | Song from "The Greatest Showman" which won the Golden Globe Award for Best Original Song in 2017: 3 wds. |
| 43% | STAYHIGH | 8 | Brittany Howard song that won the Grammy Award for Best Rock Song in 2021: 2 wds. |
| 43% | TRUTHHURTS | 10 | Viral 46-Across song that won the 2020 Grammy Award for Best Pop Solo Performance (2 wds.) |
| 43% | THISLAND | 8 | Gary Clark Jr. song that won the Grammy Award for Best Rock Song in 2020: 2 wds. |
| 43% | TRUTH | 5 | "___ Hurts," song by Lizzo which won the 2020 Grammy for Best Pop Solo Performance |
| 41% | INCHNAILS | 9 | Nine ___, band whose song "Wish" won the 1993 Grammy for Best Metal Performance: 2 wds. |
| 41% | HARRY | 5 | ___ Styles, "Watermelon Sugar" singer who won the Grammy for Best Pop Solo Performance in 2021 |
| 41% | 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 |
| 41% | ANDREABOCELLI | 13 | Italian classical singer whose album "Cinema" was nominated for Best Traditional Pop Vocal Album in the 2017 Grammy Awards : 2 wds. |
| 41% | METALLICA | 9 | Heavy metal band whose song "One" won the first ever Grammy for Best Metal Performance in 1990 |
| 40% | STEVEMARTIN | 11 | "L.A. Story" actor whose "The Crow: New Songs for the 5-String Banjo" won the Best Bluegrass Album Grammy in 2010: 2 wds. |
| 40% | THEWARONDRUGS | 13 | Band which won the Grammy for Best Rock Album in 2018: 4 wds. |
| 40% | KISSMEMORE | 10 | 50-Across and SZA hit single that won Best Pop Duo/Group Performance at the 2022 Grammy Awards (3 wds.) |
| 40% | CLUB | 4 | Culture ___, English pop group that won the Grammy for Best New Artist in 1984 |
| 40% | MIRANDALAMBERT | 14 | Singer whose "Wildcard" won the Grammy for Best Country Album in 2021: 2 wds. |
| 40% | BLACK | 5 | "___ Parade," single by Beyonce which won the Grammy for Best R&B Performance in 2021 |
| 40% | TRACYCHAPMAN | 12 | "Fast Car" singer who won the Grammy for Best New Artist in 1989: 2 wds. |
| 40% | CULTURECLUB | 11 | "Karma Chameleon" band that won the Grammy for Best New Artist in 1984: 2 wds. |
| 40% | CHRISSTAPLETON | 14 | Singer whose "Starting Over" won the Grammy for Best Country Album in 2022: 2 wds. |
| 40% | ALWAYSONMYMIND | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1983: 4 wds. |