| 100% | MARCANTHONY | 11 | Ex-husband of Jennifer Lopez who won a Grammy for "Amar Sin Mentiras": 2 wds. |
| 60% | JAMESTAYLOR | 11 | Ex-husband of Carly Simon who won a Grammy for "You've Got a Friend": 2 wds. |
| 56% | MIRANDALAMBERT | 14 | Ex-wife of Blake Shelton who won a Grammy for "The House That Built Me": 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. |
| 49% | JOANRIVERS | 10 | "Fashion Police" host who won a Grammy for a spoken word recording of her book "Diary of a Mad Diva": 2 wds. |
| 48% | RACHELMADDOW | 12 | MSNBC host who won a 2021 Grammy for the audiobook of her nonfiction book "Blowout": 2 wds. |
| 48% | JOANRIVERS | 10 | Late "Fashion Police" host who won a Spoken Word Grammy for "Diary of a Mad Diva": 2 wds. |
| 47% | VIOLADAVIS | 10 | "The Woman King" actress who won a 2023 Grammy for the audiobook of her memoir "Finding Me": 2 wds. |
| 47% | DONCHEADLE | 10 | "Hotel Rwanda" actor who won a 2022 Grammy for the audiobook of John Lewis's "Carry On": 2 wds. |
| 45% | TIFFANYHADDISH | 14 | "The Last O.G." actress who won a Grammy for Best Comedy Album in 2021: 2 wds. |
| 44% | KATHYGRIFFIN | 12 | "My Life on the D-List" star who won a Grammy for Best Comedy Album in 2014: 2 wds. |
| 44% | LADYGAGA | 8 | Singer who won a 2011 Grammy for "Bad Romance": 2 wds. |
| 44% | PATTONOSWALT | 12 | "A.P. Bio" actor who won a Grammy for Best Comedy Album in 2017: 2 wds. |
| 44% | SIDNEYPOITIER | 13 | "Lilies of the Field" actor who won a Grammy for the spoken word recording of his book "The Measure of a Man": 2 wds. |
| 42% | ANDERSONPAAK | 12 | LA hip-hop artist who won a 2019 Grammy for Best Rap Performance for "Bubblin": 2 wds. |
| 42% | DAVIDBOWIE | 10 | Glam rock legend who won a posthumous Best Alternative Music Album Grammy in 2017 for "Blackstar": 2 wds. |
| 42% | JOHNLITHGOW | 11 | "3rd Rock From the Sun" actor who won a Tony Award for "Sweet Smell of Success": 2 wds. |
| 41% | TIFFANYHADDISH | 14 | "Black Mitzvah" comedian who won a Grammy Award for Best Comedy Album in 2021 (2 wds.) |
| 41% | NEWLEY | 6 | Anthony who won a Grammy for "What Kind of Fool Am I?" |
| 41% | FIONAAPPLE | 10 | Art pop singer-songwriter who won a Best Alternative Music Album Grammy in 2021 for "Fetch the Bolt Cutters": 2 wds. |
| 41% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 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% | JASONMOTT | 9 | Author who won the 2021 National Book Award for Fiction for "Hell of a Book": 2 wds. |
| 40% | ALISTROKER | 10 | Actress who won a Tony for her role as Ado Annie in the 2019 Broadway revival of "Oklahoma!": 2 wds. |
| 40% | BRITNEYSPEARS | 13 | Former "All New Mickey Mouse Club" Mouseketeer who won a Grammy Award for her song "Toxic" (2 wds.) |
| 40% | BOB | 3 | ___ Dylan, American singer who won a Grammy for Album of the Year in 1973 |
| 40% | 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. |
| 40% | HELENHAYES | 10 | Actress who won the Emmy, Grammy, Oscar, and Tony (one of her two Oscars was for "Airport"): 2 wds. |
| 40% | IMOGENECOCA | 11 | Comedy partner of Sid Caesar who won a 1952 Emmy for "Your Show of Shows": 2 wds. |