| 100% | LEWISBLACK | 10 | Comedian who has been a contributor to 27-Across since 1996 (2 wds.) |
| 53% | NOELFIELDING | 12 | Comedian/actor who has been a co-presenter of "The Great British Bake Off" with 40-Across since 2017 (2 wds.) |
| 50% | SCOTTJUREK | 10 | American ultramarathoner and bestselling author of "Eat & Run" who has been a vegan since 1999: 2 wds. |
| 49% | CELINEDION | 10 | Best-selling Canadian artist who has been a promoter for the Canadian Cystic Fibrosis Foundation (CCFF) since 1982: 2 wds. |
| 47% | STEVEHARVEY | 11 | Comedian who starred in a self-titled sitcom from 1996 to 2002: 2 wds. |
| 46% | JOANRIVERS | 10 | Comedian who was the first woman to host a late-night talk show on a major network: 2 wds. |
| 46% | PAULHOLLYWOOD | 13 | Celebrity chef who has been a judge on "The Great British Bake Off" since 2010 (2 wds.) |
| 46% | PRUELEITH | 9 | South African restaurateur who has been a judge on "The Great British Bake Off" since 2017 (2 wds.) |
| 46% | PAULHOLLYWOOD | 13 | English celebrity chef who has been a judge on "The Great British Bake Off" since 2010 (2 wds.) |
| 45% | QUEENLATIFAH | 12 | "Chicago" actress who has been a spokesperson for Jenny Craig: 2 wds. |
| 45% | SOFIAVERGARA | 12 | Former CoverGirl spokesmodel and "Modern Family" actress who has been a judge on "America's Got Talent" since 2020 (2 wds.) |
| 45% | NORMMACDONALD | 13 | "SNL" actor and comedian who won $500,000 for charity on "Who Wants to Be a Millionaire" in 2000: 2 wds. |
| 44% | ROSIEODONNELL | 13 | "The Flintstones" actress and comedian who won $500,000 for charity on "Who Wants to Be a Millionaire" in 2000: 2 wds. |
| 44% | KELLYCLARKSON | 13 | "American Idol" winner who has been a coach on "The Voice" since season 14 (2 wds.) |
| 44% | LYNNREDGRAVE | 12 | "Gods and Monsters" actress who has been a spokesperson for Weight Watchers: 2 wds. |
| 44% | MARIEOSMOND | 11 | Singer and talk show host who has been a spokesperson for Nutrisystem: 2 wds. |
| 44% | SIMONCOWELL | 11 | Former talent scout and creator of "The X Factor" who has been a judge on "America's Got Talent" since 2011 (2 wds.) |
| 43% | LARRYDAVID | 10 | Brooklyn-born comedian who was an executive producer of 27-Across and 32/38-Across: 2 wds. |
| 43% | REDD | 4 | Comedian Chris who has been a regular on "Saturday Night Live" since 2017 |
| 42% | ANNEHATHAWAY | 12 | "Interstellar" actress who has been a UN Goodwill Ambassador for women: 2 wds. |
| 42% | ANGELINAJOLIE | 13 | "Maleficent" actress who has been a UN Goodwill Ambassador for refugees: 2 wds. |
| 42% | KENANTHOMPSON | 13 | "Fat Albert" star who has been a cast member on "SNL" for a record-breaking 15 seasons: 2 wds. |
| 42% | HOWIEMANDEL | 11 | Former stand-up comedian and "St. Elsewhere" actor who has been a judge on "America's Got Talent" since 2010 (2 wds.) |
| 41% | ALILANDRY | 9 | Winner of Miss USA 1996 who had was also a semi-finalist of Miss Louisiana Teen USA in 1990: 2 wds. |
| 40% | REDSKELTON | 10 | Comedian who got an Honorary Doctorate (said to be in "Foolology") from Ball State: 2 wds. |
| 40% | TINATURNER | 10 | "Private Dancer" singer who has a solo in "We Are the World": 2 wds. |
| 40% | ELLENDEGENERES | 14 | Comedian who starred in a self-titled sitcom from 1994 to 1998: 2 wds. |
| 40% | DIONNEWARWICK | 13 | "Walk On By" singer who has a solo in "We Are the World": 2 wds. |
| 40% | SALVADORDALI | 12 | Spanish surrealist whose home in Port Lligat, Catalonia has been converted to a museum: 2 wds. |
| 40% | LUCILLEBALL | 11 | Early TV comedian who was a charter inductee into the Television Hall of Fame: 2 wds. |