| 100% | TIFFANYHADDISH | 14 | "The Last O.G." actress who won a Grammy for Best Comedy Album in 2021: 2 wds. |
| 67% | PATTONOSWALT | 12 | "A.P. Bio" actor who won a Grammy for Best Comedy Album in 2017: 2 wds. |
| 66% | KATHYGRIFFIN | 12 | "My Life on the D-List" star who won a Grammy for Best Comedy Album in 2014: 2 wds. |
| 63% | FIONAAPPLE | 10 | Art pop singer-songwriter who won a Best Alternative Music Album Grammy in 2021 for "Fetch the Bolt Cutters": 2 wds. |
| 61% | TIFFANYHADDISH | 14 | "Black Mitzvah" comedian who won a Grammy Award for Best Comedy Album in 2021 (2 wds.) |
| 55% | MIRANDALAMBERT | 14 | Singer whose "Wildcard" won the Grammy for Best Country Album in 2021: 2 wds. |
| 53% | KATHYGRIFFIN | 12 | "Calm Down Gurrl" comedian who won a Grammy Award for Best Comedy Album in 2014 (2 wds.) |
| 53% | WHOOPIGOLDBERG | 14 | "Direct from Broadway" comedian who won a Grammy Award for Best Comedy Album in 1986 (2 wds.) |
| 53% | DAVIDBOWIE | 10 | Glam rock legend who won a posthumous Best Alternative Music Album Grammy in 2017 for "Blackstar": 2 wds. |
| 53% | SARAHPAULSON | 12 | "American Horror Story" actress who won the 2024 Best Leading Actress in a Play Tony for "Appropriate": 2 wds. |
| 52% | CATEBLANCHETT | 13 | Actress who won a Best Supporting Actress Oscar for playing Katharine Hepburn in the 2004 film "The Aviator" (2 wds.) |
| 52% | JASONSUDEIKIS | 13 | "Ted Lasso" actor who won the 2021 Emmy for Outstanding Lead Actor in a Comedy Series: 2 wds. |
| 52% | KATEWINSLET | 11 | "Mare of Easttown" actress who won the 2021 Emmy for Outstanding Lead Actress in a Limited or Anthology Series or Movie: 2 wds. |
| 52% | INGRIDBERGMAN | 13 | Actress who won a Best Supporting Actress Oscar for her 14-minute performance in "Murder on the Orient Express" (2 wds.) |
| 51% | HOLLYHUNTER | 11 | "Broadcast News" star who won a Best Actress Oscar for her role in "The Piano": 2 wds. |
| 51% | VAMPIREWEEKEND | 14 | Indie rock band that won a Best Alternative Music Album Grammy in 2020 for "Father of the Bride": 2 wds. |
| 51% | LOUISEFLETCHER | 14 | Actress who won a Best Actress Oscar for playing 46-Across in the 1975 film "One Flew Over the Cuckoo's Nest" (2 wds.) |
| 50% | BETTYWHITE | 10 | "The Proposal" actress who won a Grammy for the spoken word recording of her book "If You Ask Me": 2 wds. |
| 50% | CHRISTIANBALE | 13 | Actor who won the 2019 Golden Globe Award for Best Actor in a Motion Picture - Musical or Comedy, for the film "Vice": 2 wds. |
| 50% | KATRINALENK | 11 | 30-Across singer/actress who won the 2018 Tony Award for Best Actress in a Musical (2 wds.) |
| 50% | HADDISH | 7 | Tiffany ___, "Black Mitzvah" comedian who won a Grammy Award for Best Comedy Album in 2021 |
| 49% | ALISTROKER | 10 | Actress who won a Tony for her role as Ado Annie in the 2019 Broadway revival of "Oklahoma!": 2 wds. |
| 49% | RACHELMADDOW | 12 | MSNBC host who won a 2021 Grammy for the audiobook of her nonfiction book "Blowout": 2 wds. |
| 49% | LENA | 4 | Dunham who won a 2013 Golden Globe for Best Actress in the TV comedy "Girls" |
| 48% | JODIEFOSTER | 11 | Actress who won a Golden Globe for "The Silence of the Lambs" and won their Cecil B. DeMille Award in 2013: 2 wds. |
| 48% | WHOOPIGOLDBERG | 14 | Actress who won a Best Supporting Actress Oscar for playing 19-Across in 62-Across (2 wds.) |
| 48% | DEBRAMESSING | 12 | Actress who played 17a in the series for which she won a Primetime Emmy Award: 2 wds. |
| 48% | ELAINEMAY | 9 | "The Waverly Gallery" actress who won the Tony Award for Best Performance by a Leading Actress in a Play in 2019 (2 wds.) |
| 48% | VIOLADAVIS | 10 | "The Woman King" actress who won a 2023 Grammy for the audiobook of her memoir "Finding Me": 2 wds. |
| 48% | MERYLSTREEP | 11 | Actress who won a Best Actress Oscar as Margaret Thatcher in "The Iron Lady": 2 wds. |