| 100% | TRAVISSCOTT | 11 | Rapper who was nominated for a Grammy for Best Rap Album in 2019 but lost to Cardi B: 2 wds. |
| 66% | JENNIFERLOPEZ | 13 | Singer who was nominated for a Grammy for Best Dance Recording in 2000 but lost to Cher: 2 wds. |
| 66% | TAYLORSWIFT | 11 | Singer who was nominated for a Grammy for Best New Artist in 2008 but lost to Amy Winehouse: 2 wds. |
| 49% | JANELLEMONAE | 12 | Actress in the Best Picture winner "Moonlight" who was nominated for an Album of the Year Grammy in 2019: 2 wds. |
| 49% | MACMILLER | 9 | Artist who was posthumously nominated for a Best Rap Album Grammy in 2019 |
| 46% | CARDI | 5 | ___ B, hip hop star who became the first female rapper to win a Grammy for Best Rap Album |
| 45% | 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% | RICHARDHARRIS | 13 | Actor in the Best Picture winner "Unforgiven" who was nominated for an Album of the Year Grammy in 1968: 2 wds. |
| 43% | HEYMAMA | 7 | 2004 song by the Black Eyed Peas that was nominated for a Grammy for Best Rap Song: 2 wds. |
| 43% | FRANKSINATRA | 12 | Actor in the Best Picture winner "From Here to Eternity" who was nominated for seven Album of the Year Grammys: 2 wds. |
| 42% | NIPSEYHUSSLE | 12 | Late LA hip-hop artist nominated for a 2019 Grammy for Best Rap Album for "Victory Lap": 2 wds. |
| 42% | PATTONOSWALT | 12 | "A.P. Bio" actor who won a Grammy for Best Comedy Album in 2017: 2 wds. |
| 42% | VICTORYLAP | 10 | 2018 studio album by 29-Across that was nominated for a Best Rap Album Grammy (2 wds.) |
| 42% | TIFFANYHADDISH | 14 | "The Last O.G." actress who won a Grammy for Best Comedy Album in 2021: 2 wds. |
| 41% | KATHYGRIFFIN | 12 | "My Life on the D-List" star who won a Grammy for Best Comedy Album in 2014: 2 wds. |
| 40% | CARDIB | 6 | First woman to win a Grammy for Best Rap Album as a solo artist (2 wds.) |
| 39% | ANDERSONPAAK | 12 | LA hip-hop artist who won a 2019 Grammy for Best Rap Performance for "Bubblin": 2 wds. |
| 39% | RACHELWEISZ | 11 | "The Lobster" actress who was nominated for a 2019 Golden Globe Award for her role in 40-Across (2 wds.) |
| 39% | SOFIACOPPOLA | 12 | "Lost in Translation" director who was the third woman nominated for a Best Director Oscar (2 wds.) |
| 38% | IGOR | 4 | 2019 studio album by American rapper Tyler, the Creator which won a Grammy for the Best Rap Album in 2020 |
| 38% | LIVINGHISTORY | 13 | Memoir by 31-Across whose audiobook version was nominated for a Grammy Award for Best Spoken Word Album (2 wds.) |
| 38% | PHOEBEBRIDGERS | 14 | 16-Across and 31-Across singer who was nominated for a 2020 Best New Artist Grammy Award (2 wds.) |
| 38% | NAS | 3 | Rapper who was nominated for a Grammy for "Daughters" |
| 37% | ANDREABOCELLI | 13 | Italian classical singer whose album "Cinema" was nominated for Best Traditional Pop Vocal Album in the 2017 Grammy Awards : 2 wds. |
| 37% | RICHARDJEWELL | 13 | 2019 biographical drama starring Kathy Bates, who was nominated for a Best Supporting Actress Oscar for playing the title character's mother (2 wds.) |
| 37% | DAVIDBOWIE | 10 | Glam rock legend who won a posthumous Best Alternative Music Album Grammy in 2017 for "Blackstar": 2 wds. |
| 37% | DELREY | 6 | Singer Lana whose 2017 album "Lust for Life" was nominated for a Best Pop Vocal Album Grammy (2 wds.) |
| 36% | FIONAAPPLE | 10 | Art pop singer-songwriter who won a Best Alternative Music Album Grammy in 2021 for "Fetch the Bolt Cutters": 2 wds. |
| 36% | ABOUTSCHMIDT | 12 | 2002 dramedy starring Kathy Bates, who was nominated for a Best Supporting Actress Oscar for playing a woman in a memorable hot tub scene (2 wds.) |
| 36% | EDDIEREDMAYNE | 13 | "The Theory of Everything" actor who was nominated for a 2024 Tony for playing the Emcee in "Cabaret": 2 wds. |