| 100% | MILEYCYRUS | 10 | "Flowers" Record of the Year Grammy nominee who was born on November 23, 1992 (2 wds.) |
| 45% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 43% | PATTILABELLE | 12 | "New Attitude" singer who was the Flower on season 2 of "The Masked Singer": 2 wds. |
| 42% | SETHMACFARLANE | 14 | Five-time Grammy nominee who is also the creator of the animated sitcom "Family Guy" (2 wds.) |
| 42% | MIRANDALAMBERT | 14 | "Wildcard" Best Country Album Grammy winner who was born on November 10, 1983 (2 wds.) |
| 40% | NATERUESS | 9 | Frontman of the band fun. who is featured on 15-/23-Across: 2 wds. |
| 40% | EMINEM | 6 | Record of the Year Grammy nominee for "Lose Yourself" |
| 38% | GETLUCKY | 8 | 2013 Record of the Year Grammy winner by Daft Punk featuring 15-Across/52-Across (2 wds.) |
| 38% | JOHNNYROTTEN | 12 | Punk rock legend who was the Jester on season 6 of "The Masked Singer": 2 wds. |
| 38% | DONNYOSMOND | 11 | Actor who was the Peacock on season 1 of "The Masked Singer": 2 wds. |
| 38% | TORISPELLING | 12 | Actress who was the Unicorn on season 1 of "The Masked Singer": 2 wds. |
| 38% | MARGARETCHO | 11 | Comedian who was the Poodle on season 1 of "The Masked Singer": 2 wds. |
| 37% | NOVAKDJOKOVIC | 13 | Serbian tennis star who's been ATP Player of the Year a record eight times: 2 wds. |
| 37% | DWIGHTHOWARD | 12 | Basketball player who was the Octopus on season 6 of "The Masked Singer": 2 wds. |
| 37% | DANANDSHAY | 10 | "Tequila" Grammy winners who are coaches on season 25 of "The Voice" (2 wds.) |
| 37% | CHRISJERICHO | 12 | Former undisputed WWF champion who was the Bride on season 8 of "The Masked Singer": 2 wds. |
| 37% | RICHARDDAWSON | 13 | "Family Feud" host who was a regular panelist on the 1970s version of "Match Game": 2 wds. |
| 37% | AUDRELORDE | 10 | Revolutionary Black feminist who was an inaugural honoree on the National LGBTQ Wall of Honor: 2 wds. |
| 37% | MALCOLMX | 8 | African-American civil rights leader who is celebrated annually on the third Friday of May: 2 wds. |
| 36% | BRADLEYCOOPER | 13 | "A Star Is Born" actor who guest-starred as himself on season 3 of "Abbott Elementary": 2 wds. |
| 36% | GLADYSKNIGHT | 12 | "Midnight Train to Georgia" singer who was the Bee on season 1 of "The Masked Singer": 2 wds. |
| 36% | ROBSCHNEIDER | 12 | Former "Saturday Night Live" comedian who was the Hamster on season 6 of "The Masked Singer": 2 wds. |
| 36% | FANNIEFLAGG | 11 | Red-headed comic actress who was a regular panelist on the 1970s version of "Match Game": 2 wds. |
| 36% | JOHNLYNCH | 9 | Buccaneers/Broncos safety who will be inducted into the Pro Football Hall of Fame on Sunday: 2 wds. |
| 36% | CALVINJOHNSON | 13 | Lions wide receiver who will be inducted into the Pro Football Hall of Fame on Sunday: 2 wds. |
| 36% | BRIANWILLIAMS | 13 | American journalist who is the chief anchor on MSNBC and host of "The 11th Hour with ___": 2 wds. |
| 36% | MARTHASTEWART | 13 | Entrepreneur and lifestyle guru who was on the cover of the Holiday 2011 issue of Vogue Knitting: 2 wds. |
| 36% | KRYSTENRITTER | 13 | "Jessica Jones" actress who was on the cover of the Late Winter 2018 issue of Vogue Knitting: 2 wds. |
| 36% | NAOMICAMPBELL | 13 | "American Horror Story: Hotel" actress who was the first black model on the cover of French Vogue : 2 wds. |
| 36% | GERALDFORD | 10 | 38th US president (1974-1977) who was on the varsity football team at the University of Michigan: 2 wds. |