| 100% | SEANPENN | 8 | Two time Academy Award winning actor of "Mystic River" who appeared in a guest role on "Two and a Half Men": 2 wds. |
| 52% | IGLESIAS | 8 | Enrique ___, Spanish singer of "Hero" and "Bailamos" who appeared in a guest role in "Two and a Half Men" |
| 49% | DENISERICHARDS | 14 | Actress who played a Bond Girl in "The World Is Not Enough" and appeared in a guest role in "Two and a Half Men": 2 wds. |
| 48% | SEANPENN | 8 | Actor famous for "Milk" and "Mystic River" who appeared as a guest star on "Friends": 2 wds. |
| 45% | ASHTONKUTCHER | 13 | Actor who replaced Charlie Sheen on "Two and a Half Men": 2 wds. |
| 44% | PAULSCHNEIDER | 13 | Actor who played the role of Mark Brendanawicz in "Parks and Recreation", a character that appeared only in the first two seasons: 2 wds. |
| 42% | ASHTONKUTCHER | 13 | "Two and a Half Men" actor who played Michael Kelso on "That '70s Show": 2 wds. |
| 41% | ASHTONKUTCHER | 13 | Actor who was part of television shows such as "Two and a Half Men" and "That '70s Show": 2 wds. |
| 41% | HOLLANDTAYLOR | 13 | "Two and a Half Men" actress who came out of the closet in 2015 at age 72: 2 wds. |
| 41% | CHARLIESHEEN | 12 | "Two and a Half Men" actor who was a roastee on Comedy Central Roast with Seth MacFarlane as the roast master: 2 wds. |
| 41% | MANDYPATINKIN | 13 | Tony- and Emmy-winning actor who was a guest on the "On Broadway" episode of "Finding Your Roots" in 2021 (2 wds.) |
| 40% | BRADPITT | 8 | Actor famous for "Fight Club" and "Troy" who appeared as a guest star on "Friends": 2 wds. |
| 40% | JAMESEARLJONES | 14 | "Coming 2 America" actor who won two Tony Awards for Best Actor in a Play, for "The Great White Hope" and "Fences" (3 wds.) |
| 39% | MILAKUNIS | 9 | "Friends With Benefits" actress, who made a guest appearance on boyfriend Ashton Kutcher's "Two And A Half Men": 2 wds. |
| 38% | FRANKLANGELLA | 13 | "The Americans" actor who won two Tony Awards for Best Actor in a Play, for "Frost/Nixon" and "The Father" (2 wds.) |
| 38% | BRYANCRANSTON | 13 | "Breaking Bad" actor who won two Tony Awards for Best Actor in a Play, for "All the Way" and "Network" (2 wds.) |
| 37% | CUBAGOODING | 11 | Academy Award-winning actor from "Jerry Maguire", who plays the TV version of 14-Across in "American Crime Story" : 2 wds. |
| 37% | 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.) |
| 37% | JEFFGOLDBLUM | 12 | Actor famous for "Jurassic Park" who appeared as a guest star on "Friends": 2 wds. |
| 37% | JOHNSLATTERY | 12 | "Mad Men" actor who appears in one of the stories on 27-Across (2 wds.) |
| 36% | STANLEYTUCCI | 12 | Two time Emmy winner for his films "Winchell" and "Monk", who plays the role of Merlin, in 30a : 2 wds. |
| 36% | PAULGIAMATTI | 12 | "Cinderella Man" and "Sideways" actor who turned down the role of Michael Scott on "The Office": 2 wds. |
| 36% | 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.) |
| 36% | 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. |
| 36% | NORMMACDONALD | 13 | "SNL" actor and comedian who won $500,000 for charity on "Who Wants to Be a Millionaire" in 2000: 2 wds. |
| 35% | 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. |
| 35% | HOLLANDTAYLOR | 13 | "Two and a Half Men" actress who was nominated for an Emmy Award for "Hollywood" (2 wds.) |
| 35% | BENKINGSLEY | 11 | Actor whose birthday it is today who won an Academy Award for playing Gandhi in the titular film and was knighted in 2002: 2 wds. |
| 35% | KENNETHCHOI | 11 | Actor who played Chester Ming on "The Wolf of Wall Street" and portrays the role of Judge Lance Ito in "American Crime Story" : 2 wds. |
| 35% | KURTWARNER | 10 | Undrafted quarterback who won two MVP awards and led the St. Louis Rams to a win in the 2000 Super Bowl: 2 wds. |