| 100% | ROBREINER | 9 | "All in the Family" actor who directed "The Princess Bride" and "When Harry Met Sally ...": 2 wds. |
| 58% | ROBREINER | 9 | "When Harry Met Sally... " director who directed "The Princess Bride" (2 wds.) |
| 52% | BILLYCRYSTAL | 12 | "When Harry Met Sally" actor who got to the top of "The $20,000 Pyramid" in a record 26 seconds (2 wds.) |
| 50% | CARRIEFISHER | 12 | "When Harry Met Sally ..." actress who returned as Leia Organa in "Star Wars: The Force Awakens": 2 wds. |
| 49% | ROBERTREDFORD | 13 | "All Is Lost" actor who directed and starred in "The Horse Whisperer": 2 wds. |
| 48% | KENNETHBRANAGH | 14 | Actor who directed and played the title character in 1996's "Hamlet": 2 wds. |
| 47% | BRADLEYCOOPER | 13 | "American Sniper" actor who directed and stars in the "A Star Is Born" remake: 2 wds. |
| 47% | HEATHLEDGER | 11 | Actor who played The Joker in "The Dark Knight," and met an untimely death, aged only 28: 2 wds. |
| 46% | EDWARDNORTON | 12 | "Fight Club" actor who plays Lionel Essrog in "Motherless Brooklyn" and also directed the film: 2 wds. |
| 46% | BILLYCRYSTAL | 12 | "When Harry Met Sally ..." actor who received a 2023 Kennedy Center Honor: 2 wds. |
| 45% | JONFAVREAU | 10 | Actor who plays Happy Hogan in Marvel films, and has directed the pilot for "The Orville": 2 wds. |
| 45% | MANDYPATINKIN | 13 | "The Princess Bride" actor who played the love interest of Barbra Streisand's character in 1983's "Yentl": 2 wds. |
| 45% | WARRENBEATTY | 12 | Actor who directed, wrote, and appears in "Rules Don't Apply": 2 wds. |
| 45% | CARYELWES | 9 | "Glory" actor who played Westley in the 1987 film "The Princess Bride" (2 wds.) |
| 44% | ROBBIECOLTRANE | 14 | Scottish actor who starred in "GoldenEye" and the "Harry Potter" series: 2 wds. |
| 44% | CARROLLOCONNOR | 14 | Actor who starred on "All in the Family," a Norman Lear sitcom: 2 wds. |
| 43% | NICKOFFERMAN | 12 | "Parks and Recreation" actor who plays the US president in "Civil War": 2 wds. |
| 43% | ORSONWELLES | 11 | Actor who directed 17-Across and played the title character: 2 wds. |
| 43% | DAVIDTENNANT | 12 | Scottish actor who played Barty Crouch, Jr. in "Harry Potter and the Goblet of Fire": 2 wds. |
| 43% | ISABELSANFORD | 13 | "All in the Family" actress who played the Bunkers' neighbor Louise Jefferson: 2 wds. |
| 43% | EWANMCGREGOR | 12 | Actor who played 29-/32-Across in the 1990s and 2000s: 2 wds. |
| 43% | ALECGUINNESS | 12 | Actor who played 29-/32-Across in the 1970s and 1980s: 2 wds. |
| 42% | PATRICKHARRIS | 13 | Neil, one of the lead actors in "How I Met Your Mother," who directed the episode "Jenkins" in the show's 5th season: 2 wds. |
| 42% | ISABELSANFORD | 13 | Actress who played Louise on "All in the Family" and 45-Across (2 wds.) |
| 42% | EWANMCGREGOR | 12 | Scottish actor who starred in "Moulin Rouge!" and the "Star Wars" prequels: 2 wds. |
| 42% | OSCARISAAC | 10 | Actor who plays Gomez Addams in the 2019 film "The Addams Family" and in its 2021 sequel (2 wds.) |
| 42% | JOHNCORBETT | 11 | "Sex and the City" actor who plays Rebel's husband Grady in "Rebel": 2 wds. |
| 42% | BURTREYNOLDS | 12 | "Smokey and the Bandit" actor who played filmmaker Jack Horner in "Boogie Nights": 2 wds. |
| 42% | JIMCARREY | 9 | "Dumb and Dumber" actor who played the Riddler in "Batman Forever": 2 wds. |
| 41% | JEANSTAPLETON | 13 | "All in the Family" actress who played Edith Bunker: 2 wds. |