| 100% | CLINTEASTWOOD | 13 | Oscar-winning actor/director who plays gym owner and boxing trainer Frankie Dunn in "Million Dollar Baby" (2 wds.) |
| 52% | MORGANFREEMAN | 13 | Oscar-winning actor who plays gym assistant and former boxer Eddie "Scrap-Iron" Dupris in "Million Dollar Baby" (2 wds.) |
| 46% | KEVINCOSTNER | 12 | Actor who plays Frank Farmer in 18a and has also won an Oscar for Best Director for "Dances with Wolves": 2 wds. |
| 46% | CLINTEASTWOOD | 13 | Actor and filmmaker who won an Oscar for Best Director at 74 for "Million Dollar Baby": 2 wds. |
| 41% | CLINTEASTWOOD | 13 | "Million Dollar Baby" director who has won 2 Oscars out of 4 nominations for Best Director: 2 wds. |
| 39% | HILARYSWANK | 11 | Oscar-winning actress who plays boxer Maggie Fitzgerald in "Million Dollar Baby" (2 wds.) |
| 37% | MORGANFREEMAN | 13 | "Million Dollar Baby" actor who received the SAG Life Achievement Award in 2017: 2 wds. |
| 36% | MARTINSCORSESE | 14 | New Hollywood director who won an Oscar for "The Departed," and is the most-nominated director alive in terms of Oscars: 2 wds. |
| 36% | CLINTEASTWOOD | 13 | "Million Dollar Baby" and "Unforgiven" actor/director: 2 wds. |
| 36% | ROBERTREDFORD | 13 | Oscar-winning actor/director who played Death on "The Twilight Zone": 2 wds. |
| 35% | ROBERTDUVALL | 12 | Oscar-winning actor who played a man in love with a tiny doll on "The Twilight Zone": 2 wds. |
| 35% | 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.) |
| 34% | BRUCEWILLIS | 11 | Actor who played David Dunn in 38-Across: 2 wds. |
| 34% | ADAMSANDLER | 11 | Actor who played Jill in "Jack and Jill": 2 wds. |
| 34% | WOODYALLEN | 10 | "Midnight in Paris" director who has won 4 Oscars as Director and as Screenwriter, out of 24 total nominations: 2 wds. |
| 34% | HILARYSWANK | 11 | "Million Dollar Baby" actress who plays a journalist whose son was murdered in 31-Across (2 wds.) |
| 34% | MICHAELDOUGLAS | 14 | Oscar-winning actor from "Wall Street" who plays Sandy Kominsky in "The Kominsky Method": 2 wds. |
| 34% | DAVIDLYNCH | 10 | Director who received an honorary Oscar in 2019 for such films as "Blue Velvet" and "Mulholland Drive": 2 wds. |
| 34% | LINAWERTMULLER | 14 | Director who received an honorary Oscar in 2019 for such films as "Seven Beauties" and "Swept Away": 2 wds. |
| 34% | EWANMCGREGOR | 12 | Actor who played 29-/32-Across in the 1990s and 2000s: 2 wds. |
| 34% | ALECGUINNESS | 12 | Actor who played 29-/32-Across in the 1970s and 1980s: 2 wds. |
| 33% | MORGANFREEMAN | 13 | Actor in the Best Picture Oscar films "Driving Miss Daisy," "Unforgiven," and "Million Dollar Baby": 2 wds. |
| 33% | ALANARKIN | 9 | Oscar-winning actor from "Little Miss Sunshine" who plays Norman Newlander in "The Kominsky Method": 2 wds. |
| 33% | SIDNEYPOITIER | 13 | Oscar-winning actor who played 43-Across in a 1997 TV film (2 wds.) |
| 33% | MORGANFREEMAN | 13 | Oscar-winning actor who played 43-Across in the 2009 film "Invictus" (2 wds.) |
| 33% | SIMONPEGG | 9 | Actor who plays technical field agent Benji Dunn in the "Mission: Impossible" series: 2 wds. |
| 33% | ALECGUINNESS | 12 | Oscar-winning actor who played 46-Across in the original "Star Wars" trilogy (2 wds.) |
| 33% | MICHAELGROSS | 12 | Actor who played Burt Gummer in both the movie and TV series "Tremors": 2 wds. |
| 33% | SEANPENN | 8 | Actor who won an Oscar for playing Harvey Milk in "Milk" (2 wds.) |
| 33% | KENNETHBRANAGH | 14 | "Death on the Nile" actor/director who plays Hercule Poirot in and directed "A Haunting in Venice" (2 wds.) |