| 100% | TOMSELLECK | 10 | Actor who appeared on "The Dating Game" 15 years before his TV stardom on "Magnum, P.I.": 2 wds. |
| 80% | JOHNRITTER | 10 | Actor who appeared on "The Dating Game" 10 years before his TV stardom on "Three's Company": 2 wds. |
| 67% | FARRAHFAWCETT | 13 | Actress who appeared on "The Dating Game" 7 years before her TV stardom on "Charlie's Angels": 2 wds. |
| 44% | JONHAMM | 7 | "Mad Men" actor who appeared on the reality dating show "The Big Date" in 1996: 2 wds. |
| 41% | TOMSELLECK | 10 | "Blue Bloods" actor who played Magnum on the original "Magnum, P.I." (2 wds.) |
| 41% | JAYHERNANDEZ | 12 | "Scandal" actor who played Magnum on the reboot of "Magnum, P.I." (2 wds.) |
| 41% | JAYHERNANDEZ | 12 | "Scandal" actor who plays Magnum on the 2018 reboot of "Magnum, P.I." (2 wds.) |
| 39% | TIMKANG | 7 | "The Mentalist" actor who played Gordon Katsumoto on "Magnum P.I.": 2 wds. |
| 39% | JAYHERNANDEZ | 12 | "Suicide Squad" actor who played Thomas Magnum on "Magnum P.I.": 2 wds. |
| 38% | LANACONDOR | 10 | "To All the Boys I've Loved Before" actress who guest-starred as Gregory's date on season 3 of "Abbott Elementary": 2 wds. |
| 38% | BILLNYE | 7 | TV "Science Guy" who appeared on "Dancing With the Stars" in 2013: 2 wds. |
| 37% | CHARLESBRONSON | 14 | "Death Wish" actor who appeared on "The Twilight Zone" in 1961: 2 wds. |
| 36% | IANMCSHANE | 10 | The actor who plays Mr. Wednesday on the TV series "American Gods": 2 wds. |
| 36% | BRUCEWILLIS | 11 | Actor who made his mark as an action hero 30 years ago with the hit "Die Hard": 2 wds. |
| 36% | WAGNERMOURA | 11 | "Narcos" actor who plays reporter Dan Velasquez on the Apple TV+ crime thriller "Shining Girls": 2 wds. |
| 36% | WILLIAMSHATNER | 14 | "T.J. Hooker" actor who appeared on "The Twilight Zone" in 1960 and 1963: 2 wds. |
| 36% | TOMSELLECK | 10 | "Blue Bloods" actor who played Magnum in the 1980s "Magnum, P.I." (2 wds.) |
| 35% | GROWINGPAINS | 12 | TV show that cast Leonardo DiCaprio before he got his break on the big screen: 2 wds. |
| 35% | STEVECARELL | 11 | "Foxcatcher" actor who starred on TV's "The Office": 2 wds. |
| 35% | IKEBARINHOLTZ | 13 | "The Afterparty" actor who plays executive Sal Saperstein on 15-Across: 2 wds. |
| 35% | CHUCKBERRY | 10 | Rock-and-roll legend who appeared on the cover of Rolling Stone in its 50th year (2017) (2 wds.) |
| 35% | AMYHILL | 7 | "Just Add Magic" actress who played Teuila "Kumu" Tuileta on the "Magnum P.I." reboot: 2 wds. |
| 35% | SINEADOCONNOR | 13 | Irish singer who appeared on the cover of Rolling Stone in its 25th year (1992) (2 wds.) |
| 35% | TIMROTH | 7 | "Pulp Fiction" actor who played Dr. Cal Lightman on the Fox series "Lie To Me": 2 wds. |
| 34% | JONATHANGROFF | 13 | Actor who originated the role of 15-Across on Broadway (2 wds.) |
| 34% | JOHNLITHGOW | 11 | Actor who won Emmys for his roles on "The Crown," "Dexter," "3rd Rock From the Sun," and "Amazing Stories": 2 wds. |
| 34% | MICHAELHANEKE | 13 | Austrian director who made a Hollywood remake of his original film "Funny Games" in the year 2007: 2 wds. |
| 34% | JOHNSLATTERY | 12 | "Mad Men" actor who appears in one of the stories on 27-Across (2 wds.) |
| 34% | MICHAELKEATON | 13 | "Birdman" actor who appears in the 2015 film "Spotlight": 2 wds. |
| 34% | SHEMARMOORE | 11 | "S.W.A.T." actor who won an Emmy for his role on "The Young and the Restless": 2 wds. |