| 100% | 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. |
| 71% | BETTYWHITE | 10 | "The Proposal" actress who won a Grammy for the spoken word recording of her book "If You Ask Me": 2 wds. |
| 65% | 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% | DONCHEADLE | 10 | "Hotel Rwanda" actor who won a 2022 Grammy for the audiobook of John Lewis's "Carry On": 2 wds. |
| 47% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 47% | JOANRIVERS | 10 | Late "Fashion Police" host who won a Spoken Word Grammy for "Diary of a Mad Diva": 2 wds. |
| 46% | SIDNEYPOITIER | 13 | 15-Across, 30-Across, and "Lilies of the Field" star who was the first Black man to win an Academy Award for Best Actor (2 wds.) |
| 45% | JONSTEWART | 10 | Former "Daily Show" host who won a Spoken Word Grammy for "Earth (The Audiobook)": 2 wds. |
| 45% | JEREMYIRONS | 11 | "Reversal of Fortune" actor who'd have an EGOT if he'd won a Grammy for "The Real Thing": 2 wds. |
| 44% | JOHNLITHGOW | 11 | "3rd Rock From the Sun" actor who won a Tony Award for "Sweet Smell of Success": 2 wds. |
| 44% | JEREMYSTRONG | 12 | "Succession" actor who won the 2024 Best Leading Actor in a Play Tony for "An Enemy of the People": 2 wds. |
| 43% | MIRANDALAMBERT | 14 | Ex-wife of Blake Shelton who won a Grammy for "The House That Built Me": 2 wds. |
| 43% | JULIANBARNES | 12 | English author who won the Man Booker Prize for "The Sense of an Ending": 2 wds. |
| 43% | STEPHENKING | 11 | "Carrie" author who won a 1996 O. Henry Award for his short story "The Man in the Black Suit": 2 wds. |
| 42% | VIOLADAVIS | 10 | "The Woman King" actress who won a 2023 Grammy for the audiobook of her memoir "Finding Me": 2 wds. |
| 42% | PATTONOSWALT | 12 | "A.P. Bio" actor who won a Grammy for Best Comedy Album in 2017: 2 wds. |
| 42% | GEORGSOLTI | 10 | Hungarian-British artist who holds the record for the most Grammy Awards won in a lifetime, with 31: 2 wds. |
| 41% | OBAMA | 5 | Former U.S. president who won a Best Spoken Word Album Grammy Award for the audiobook of "Dreams from My Father" |
| 41% | JASONMOTT | 9 | Author who won the 2021 National Book Award for Fiction for "Hell of a Book": 2 wds. |
| 41% | CAROLEKING | 10 | "You've Got a Friend" singer/pianist who was the first woman to win a Grammy for Song of the Year (2 wds.) |
| 41% | COLINFARRELL | 12 | Best Actor Oscar nominee for his portrayal of a man who is suddenly cut out of the life of his best friend in the 2022 film "The Banshees of Inisherin" (2 wds.) |
| 41% | MARCANTHONY | 11 | Ex-husband of Jennifer Lopez who won a Grammy for "Amar Sin Mentiras": 2 wds. |
| 41% | BENKINGSLEY | 11 | Actor born in England who won the Academy Award for Best Actor for his portrayal of Mahatma Gandhi in the movie "Gandhi": 2 wds. |
| 40% | SHEMARMOORE | 11 | "S.W.A.T." actor who won an Emmy for his role on "The Young and the Restless": 2 wds. |
| 40% | DAVIDOYELOWO | 12 | 19-Across and 33-Across actor who won a 2015 NAACP Image Award for his portrayal of Martin Luther King Jr. in "Selma" (2 wds.) |
| 40% | JOSHBROLIN | 10 | Actor from "No Country for Old Men," who plays the role of Cable, a mutant soldier, in "The Untitled Deadpool Sequel": 2 wds. |
| 40% | ALEXNEWELL | 10 | Actor who won a Tony in 2023 for their role as Lulu in the Broadway musical "Shucked": 2 wds. |
| 40% | SIDNEYPOITIER | 13 | Star of 15- and 34-Across who won an Oscar for "Lilies of the Field": 2 wds. |
| 40% | JAMESTAYLOR | 11 | Ex-husband of Carly Simon who won a Grammy for "You've Got a Friend": 2 wds. |