| 100% | TOMARNOLD | 9 | Comedian who appeared on "The Best Damn Sports Show Period" in the 2000s (2 wds.) |
| 52% | JONHAMM | 7 | "Mad Men" actor who appeared on the reality dating show "The Big Date" in 1996: 2 wds. |
| 45% | ELLENDEGENERES | 14 | Comedian and daytime talk host who appeared in the "Girls Like You" video: 2 wds. |
| 45% | TIFFANYHADDISH | 14 | Comedian and "Girls Trip" actress who appeared in the "Girls Like You" video: 2 wds. |
| 44% | MICHAELSAM | 10 | Former NFL draft pick who appeared on "Dancing With the Stars" in 2015: 2 wds. |
| 44% | EMOPHILIPS | 10 | High-voiced comedian who appeared in "UHF" and "Meet the Parents": 2 wds. |
| 44% | BILLNYE | 7 | TV "Science Guy" who appeared on "Dancing With the Stars" in 2013: 2 wds. |
| 44% | WARRENSAPP | 10 | Former NFL player who appeared on "Dancing With the Stars" in 2008: 2 wds. |
| 43% | CANDISCAYNE | 11 | "The Magicians" actress who appears in "Disclosure," the 2020 documentary about trans lives on screen: 2 wds. |
| 43% | CHADOCHOCINCO | 13 | Former name of an NFL player who appeared on "Dancing With the Stars" in 2010: 2 wds. |
| 42% | CAROLBURNETT | 12 | Comedian and variety show host who was awarded the Mark Twain Prize in 2013: 2 wds. |
| 42% | WILLIAMSHATNER | 14 | "T.J. Hooker" actor who appeared on "The Twilight Zone" in 1960 and 1963: 2 wds. |
| 42% | MARKMCGWIRE | 11 | Slugger who appeared on the March 23, 1998, cover of Sports Illustrated (2 wds.) |
| 42% | CLORISLEACHMAN | 14 | "Phyllis" actress who appeared on "The Twilight Zone" in 1961: 2 wds. |
| 42% | MAGGIESMITH | 11 | "Gosford Park" actress who appeared in "The Best Exotic Marigold Hotel": 2 wds. |
| 42% | CHARLESBRONSON | 14 | "Death Wish" actor who appeared on "The Twilight Zone" in 1961: 2 wds. |
| 42% | SARAHSILVERMAN | 14 | Comedian and "Ralph Breaks the Internet" actress who appeared in Maroon 5's 2018 "Girls Like You" video: 2 wds. |
| 42% | WANDA | 5 | Comedian ___ Sykes, who appears on the TV shows "Blackish" |
| 41% | LAURAPREPON | 11 | "The Girl on the Train" actress, who played Donna Pinciotti in "That 70's Show": 2 wds. |
| 41% | LEWISBLACK | 10 | Regular ranter on "The Daily Show" who voiced Anger in 47-Across: 2 wds. |
| 41% | JOANRIVERS | 10 | Comedian who was the first woman to host a late-night talk show on a major network: 2 wds. |
| 41% | SINEADOCONNOR | 13 | Irish singer who appeared on the cover of Rolling Stone in its 25th year (1992) (2 wds.) |
| 40% | KATHYGRIFFIN | 12 | "My Life on the D-List" star who won a Grammy for Best Comedy Album in 2014: 2 wds. |
| 40% | CHUCKBERRY | 10 | Rock-and-roll legend who appeared on the cover of Rolling Stone in its 50th year (2017) (2 wds.) |
| 40% | PETEDAVIDSON | 12 | Comedian on 29-Down who plays Scott in "The King of Staten Island": 2 wds. |
| 40% | DALLASCOWBOYS | 13 | Super Bowl champions who appeared on Wheaties boxes four times, starting in 1993: 2 wds. |
| 40% | JOHNSLATTERY | 12 | "Mad Men" actor who appears in one of the stories on 27-Across (2 wds.) |
| 40% | ANNEHATHAWAY | 12 | "Interstellar" actress who appears in one of the stories on 27-Across (2 wds.) |
| 39% | HOWIEMANDEL | 11 | Comedian who is currently the longest-running judge on "America's Got Talent": 2 wds. |
| 39% | KATVOND | 7 | Celebrity tattoo artist who appeared on the TV show "LA Ink": 3 wds. |