| 100% | JOANRIVERS | 10 | Late "Fashion Police" host who won a Spoken Word Grammy for "Diary of a Mad Diva": 2 wds. |
| 85% | JOANRIVERS | 10 | "Fashion Police" host who won a Grammy for a spoken word recording of her book "Diary of a Mad Diva": 2 wds. |
| 62% | JONSTEWART | 10 | Former "Daily Show" host who won a Spoken Word Grammy for "Earth (The Audiobook)": 2 wds. |
| 54% | BETTYWHITE | 10 | "The Proposal" actress who won a Grammy for the spoken word recording of her book "If You Ask Me": 2 wds. |
| 53% | 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. |
| 52% | RACHELMADDOW | 12 | MSNBC host who won a 2021 Grammy for the audiobook of her nonfiction book "Blowout": 2 wds. |
| 47% | BETTY | 5 | With 33-Across, "The Golden Girls" star who won a Spoken Word Grammy for "If You Ask Me (And of Course You Won't)" |
| 45% | JAMESTAYLOR | 11 | Ex-husband of Carly Simon who won a Grammy for "You've Got a Friend": 2 wds. |
| 45% | MIRANDALAMBERT | 14 | Ex-wife of Blake Shelton who won a Grammy for "The House That Built Me": 2 wds. |
| 45% | VIOLADAVIS | 10 | "The Woman King" actress who won a 2023 Grammy for the audiobook of her memoir "Finding Me": 2 wds. |
| 45% | 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. |
| 45% | MARCANTHONY | 11 | Ex-husband of Jennifer Lopez who won a Grammy for "Amar Sin Mentiras": 2 wds. |
| 43% | OBAMA | 5 | Former U.S. president who won a Best Spoken Word Album Grammy Award for the audiobook of "Dreams from My Father" |
| 42% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 41% | JOHNLITHGOW | 11 | "3rd Rock From the Sun" actor who won a Tony Award for "Sweet Smell of Success": 2 wds. |
| 41% | JEREMYIRONS | 11 | "Reversal of Fortune" actor who'd have an EGOT if he'd won a Grammy for "The Real Thing": 2 wds. |
| 41% | IMOGENECOCA | 11 | Comedy partner of Sid Caesar who won a 1952 Emmy for "Your Show of Shows": 2 wds. |
| 40% | TIFFANYHADDISH | 14 | "Girls Trip" actress who won a 2018 Emmy for hosting "Saturday Night Live": 2 wds. |
| 40% | LADYGAGA | 8 | Singer who won a 2011 Grammy for "Bad Romance": 2 wds. |
| 40% | BETTYWHITE | 10 | "The Golden Girls" actress who won a 2010 Emmy for hosting "Saturday Night Live": 2 wds. |
| 39% | PATTONOSWALT | 12 | "A.P. Bio" actor who won a Grammy for Best Comedy Album in 2017: 2 wds. |
| 39% | HILLARY | 7 | ___ Clinton, former First Lady who won a Grammy for Best Spoken Word album in 1997 |
| 39% | DAVIDBOWIE | 10 | Glam rock legend who won a posthumous Best Alternative Music Album Grammy in 2017 for "Blackstar": 2 wds. |
| 38% | RAYMONDBURR | 11 | Host of the 1959 Primetime Emmy Awards, who won an Emmy himself that evening for "Perry Mason": 2 wds. |
| 38% | ANDERSONPAAK | 12 | LA hip-hop artist who won a 2019 Grammy for Best Rap Performance for "Bubblin": 2 wds. |
| 38% | BRUCEWILLIS | 11 | Host of the 1987 Primetime Emmy Awards, who won an Emmy himself that evening for "Moonlighting": 2 wds. |
| 38% | LORETTADEVINE | 13 | Star of 15-Across who won an Emmy for a guest performance in "Grey's Anatomy": 2 wds. |
| 38% | STEPHENCOLBERT | 14 | Host of "The Late Show" who was once a correspondent on "The Daily Show": 2 wds. |
| 38% | SETHMEYERS | 10 | "Late Night" host who was a cast member on "SNL" for 13 seasons: 2 wds. |