| 100% | FIONAAPPLE | 10 | Eight-time, New York-born Grammy Award nominee who won for "Criminal" in 1998 |
| 48% | OLIVIA | 6 | ___ Rodrigo, "Drivers License" singer who won the Grammy Award for Best New Artist in 2022 |
| 43% | ALESSIA | 7 | Cara who won the Grammy for Best New Artist in 2018 |
| 43% | LYNNE | 5 | Shelby who won the Grammy for Best New Artist in 2001 |
| 42% | ROSS | 4 | Diana ___, American singer who won a Grammy for lifetime achievement award in 2012 |
| 42% | WHOOPI | 6 | ___ Goldberg, comedian who won a Grammy Award for Best Comedy Recording in 1986 |
| 42% | PITT | 4 | Brad ___ who won an Academy Award for "Once Upon a Time in Hollywood" |
| 41% | DAVID | 5 | ___ Bowie, English singer who won a Grammy Award for best music video in 1985 |
| 41% | DRAKE | 5 | Rapper who won the Grammy Award for Best Rap Song in 2017 for "Hotline Bling" |
| 41% | LAMAR | 5 | Kendrick ___, rapper who won the Grammy Award for Best Rap Song in 2016 for "Alright" |
| 41% | EMINEM | 6 | Rapper who won the Grammy Award for Best Rap Song in 2004 for "Lose Yourself" |
| 41% | HADDISH | 7 | Tiffany ___, "Black Mitzvah" comedian who won a Grammy Award for Best Comedy Album in 2021 |
| 41% | TRACYCHAPMAN | 12 | "Fast Car" singer who won the Grammy for Best New Artist in 1989: 2 wds. |
| 41% | WEST | 4 | Kanye ___, rapper who won the Grammy Award for Best Rap Song in 2005 for "Jesus Walks" |
| 41% | TIFFANYHADDISH | 14 | "Black Mitzvah" comedian who won a Grammy Award for Best Comedy Album in 2021 (2 wds.) |
| 41% | JON | 3 | ___ Batiste, "We Are" singer who won the Grammy Award for Album of the Year in 2022 |
| 41% | NICKI | 5 | With 33-Across, "Anaconda" rapper who won the BET Award for Best New Artist in 2010 |
| 41% | RODDYRICCH | 10 | "The Box" rapper who won the BET Award for Best New Artist in 2020: 2 wds. |
| 40% | JAY | 3 | ___-Z, rapper who won the Grammy Award for Best Rap Song in 2010 for "Run This Town" |
| 40% | RIHANNA | 7 | One-named singer who won the Grammy Award for Best Urban Contemporary Album for "Unapologetic" in 2014 |
| 40% | KATHYGRIFFIN | 12 | "Calm Down Gurrl" comedian who won a Grammy Award for Best Comedy Album in 2014 (2 wds.) |
| 40% | WHOOPIGOLDBERG | 14 | "Direct from Broadway" comedian who won a Grammy Award for Best Comedy Album in 1986 (2 wds.) |
| 40% | MEGAN | 5 | ___ Thee Stallion, rapper with the hit "Savage" who won the Grammy for Best New Artist in 2021 |
| 40% | WIZKHALIFA | 10 | "See You Again" rapper who won the BET Award for Best New Artist in 2011: 2 wds. |
| 40% | BILLIEEILISH | 12 | "Bad Guy" singer who won a record five Grammy Awards in 2020, including Best New Artist (2 wds.) |
| 40% | CYNDILAUPER | 11 | "Girls Just Wanna Have Fun" singer who won the Grammy for Best New Artist in 1985: 2 wds. |
| 40% | VAMPIREWEEKEND | 14 | New York City rock band whose last two albums each won the Grammy Award for Best Alternative Music Album (2 wds.) |
| 38% | BRAD | 4 | ___ Pitt, actor who won an award for the Best Supporting Actor for "Once Upon a Time in Hollywood" at the 92nd Academy Awards |
| 37% | CARLOSBELTRAN | 13 | Outfielder who won both the Gold Glove and the Silver Slugger awards in 2006 and 2007 while on the New York Mets: 2 wds. |