| 100% | BILLYCRUDUP | 11 | "Spotlight" actor who stars with Frances McDormand in "Almost Famous" (2 wds.) |
| 76% | SAMROCKWELL | 11 | "Vice" actor who stars with Frances McDormand in "Three Billboards Outside Ebbing, Missouri" (2 wds.) |
| 68% | CHARLIZETHERON | 14 | "Monster" actress who stars with Frances McDormand in "North Country" (2 wds.) |
| 57% | SETHMACFARLANE | 14 | Actor who starred in and made his directorial debut with 2012's "Ted": 2 wds. |
| 56% | BRADLEYCOOPER | 13 | Actor who starred in and made his directorial debut with 2018's "A Star Is Born": 2 wds. |
| 55% | GEORGECLOONEY | 13 | Actor who starred in and made his directorial debut with 2002's "Confessions of a Dangerous Mind": 2 wds. |
| 54% | KEVINCOSTNER | 12 | "Field of Dreams" actor who starred as the title character in the 1990 film "Dances With Wolves": 2 wds. |
| 51% | GARYBUSEY | 9 | Actor who starred in the biopic "The Buddy Holly Story": 2 wds. |
| 51% | JAKEGYLLENHAAL | 14 | "Zodiac" actor who stars in "Stronger": 2 wds. |
| 51% | MICHAELCERA | 11 | Canadian actor who starred in "Juno": 2 wds. |
| 51% | BENSTILLER | 10 | Actor who starred in "Zoolander" alongside his father Jerry: 2 wds. |
| 51% | IAINARMITAGE | 12 | Child actor who stars in 18-Across: 2 wds. |
| 51% | NOAHWYLE | 8 | "ER" actor who stars in "Falling Skies": 2 wds. |
| 51% | GEORGECLOONEY | 13 | "Gravity" actor who starred in 18-Across: 2 wds. |
| 50% | DAVIDTENNANT | 12 | Scottish actor who starred in "Doctor Who" and "Good Omens": 2 wds. |
| 50% | DWAYNEJOHNSON | 13 | "Baywatch" actor who stars in "Jumanji: Welcome to the Jungle": 2 wds. |
| 50% | NATHANFILLION | 13 | "Firefly" actor who stars in the ABC procedural "The Rookie": 2 wds. |
| 50% | TARONEGERTON | 12 | "Kingsman: The Golden Circle" actor who stars in 41-Across: 2 wds. |
| 50% | MACAULAYCULKIN | 14 | Child actor who starred in 19-Across and 47-Across: 2 wds. |
| 50% | WARRENBEATTY | 12 | "Bugsy" actor who starred as George in the movie "Shampoo": 2 wds. |
| 50% | SCOTTBAKULA | 11 | "Quantum Leap" actor who stars in 33-Across: 2 wds. |
| 50% | JOHNMALKOVICH | 13 | "Dangerous Liaisons" actor who stars in 18-Across: 2 wds. |
| 50% | JOHNSTAMOS | 10 | "Full House" actor who stars in 31-Across: 2 wds. |
| 50% | JUDELAW | 7 | "Cold Mountain" actor who stars in 15-Across: 2 wds. |
| 50% | ETHANHAWKE | 10 | "Training Day" actor who stars in 15-Across: 2 wds. |
| 50% | CHANNINGTATUM | 13 | "Foxcatcher" actor who starred in "22 Jump Street": 2 wds. |
| 50% | TOMHIDDLESTON | 13 | "The Avengers" actor who starred in 44-Across: 2 wds. |
| 50% | HARVEYKEITEL | 12 | "Pulp Fiction" actor who starred in "The Piano": 2 wds. |
| 50% | TYESHERIDAN | 11 | Actor who stars as Wade Owen Watts/"Parzival" in 33-Across: 2 wds. |
| 50% | HARRISONFORD | 12 | Actor who starred in the 1993 movie version of "The Fugitive": 2 wds. |