| 100% | NIPSEYHUSSLE | 12 | "Racks in the Middle" rapper honored posthumously with two Grammy Awards in 2020, including Best Rap Performance (2 wds.) |
| 47% | MIDDLECHILD | 11 | J. Cole single from the album "Revenge of the Dreamers III" that was nominated for a Best Rap Performance Grammy Award in 2020 (2 wds.) |
| 44% | CHARLEYPRIDE | 12 | "Kiss an Angel Good Mornin'" singer who was honored with the 1972 Grammy Award for Best Male Country Vocal Performance (2 wds.) |
| 42% | BILLIEEILISH | 12 | "Bad Guy" singer who won a record five Grammy Awards in 2020, including Best New Artist (2 wds.) |
| 41% | THISLAND | 8 | Gary Clark Jr. song that won the Grammy Award for Best Rock Song in 2020: 2 wds. |
| 41% | RODDYRICCH | 10 | "The Box" rapper who won the BET Award for Best New Artist in 2020: 2 wds. |
| 40% | TRUTHHURTS | 10 | 1-Across hit that won Best Pop Solo Performance at the 2020 Grammy Awards: 2 wds. |
| 40% | ELVISCOSTELLO | 13 | "Look Now" singer who won the Best Traditional Pop Vocal Album Grammy Award in 2020 (2 wds.) |
| 39% | JOCELYNALO | 10 | Softball player who won two National Championships with the Oklahoma Sooners and who was honored with a Best College Athlete, Women's Sports ESPY Award in 2022 (2 wds.) |
| 39% | RAPGOD | 6 | 37-Across song that was nominated for the 2015 Best Rap Performance Grammy Award (2 wds.) |
| 39% | NIPSEYHUSSLE | 12 | Musician/activist honored posthumously with the 2019 BET Award for Best Male Hip Hop Artist (2 wds.) |
| 38% | GLADYSKNIGHT | 12 | Grammy-winning singer honored by the 50-Across with a Lifetime Artistic Achievement Award in 2022 (2 wds.) |
| 37% | JENNIFERLOPEZ | 13 | "If You Had My Love" singer who was honored with the "Billboard" Women in Music Icon Award in 2020 (2 wds.) |
| 37% | TRUTHHURTS | 10 | Viral 46-Across song that won the 2020 Grammy Award for Best Pop Solo Performance (2 wds.) |
| 36% | EDSHEERAN | 9 | "Shape of You" singer who won two awards, including Best Pop Vocal Album, at the 2018 Grammy Awards (2 wds.) |
| 36% | STAYHIGH | 8 | Brittany Howard song that won the Grammy Award for Best Rock Song in 2021: 2 wds. |
| 36% | DRAKE | 5 | Rapper who won the Grammy Award for Best Rap Song in 2017 for "Hotline Bling" |
| 36% | EMINEM | 6 | Rapper who won the Grammy Award for Best Rap Song in 2004 for "Lose Yourself" |
| 36% | CHARLEYPRIDE | 12 | "Kiss an Angel Good Mornin'" singer who received the Willie Nelson Lifetime Achievement Award in 2020: 2 wds. |
| 35% | DANNYBURSTEIN | 13 | "Moulin Rouge!" actor who won the 2020 Tony Award for Best Performance by a Featured Actor in a Musical (2 wds.) |
| 35% | LAMAR | 5 | Kendrick ___, rapper who won the Grammy Award for Best Rap Song in 2016 for "Alright" |
| 35% | GEORGSOLTI | 10 | Hungarian-British artist who holds the record for the most Grammy Awards won in a lifetime, with 31: 2 wds. |
| 35% | WEST | 4 | Kanye ___, rapper who won the Grammy Award for Best Rap Song in 2005 for "Jesus Walks" |
| 35% | TRUTH | 5 | "___ Hurts," song by Lizzo that won the Grammy Award for Best Pop Solo Performance in 2020 |
| 35% | BADGUY | 6 | 2019 song by Billie Eilish that won the Grammy Award for Record of the Year in 2020: 2 wds. |
| 35% | JAY | 3 | ___-Z, rapper who won the Grammy Award for Best Rap Song in 2010 for "Run This Town" |
| 35% | JAROMEIGINLA | 12 | Calgary Flames right wing who was honored with the Best NHL Player ESPY Award twice: 2 wds. |
| 35% | MARIOLEMIEUX | 12 | Pittsburgh Penguins center who was honored with the Best NHL Player ESPY Award three times: 2 wds. |
| 35% | SIDNEYCROSBY | 12 | Pittsburgh Penguins center who was honored with the Best NHL Player ESPY Award eight times: 2 wds. |
| 35% | WIZKHALIFA | 10 | "See You Again" rapper who won the BET Award for Best New Artist in 2011: 2 wds. |