| 100% | LOUISGOSSETTJR | 14 | "An Officer and a Gentleman" Oscar winner who passed away in 2024 (3 wds.) |
| 50% | LOUGOSSETTJR | 12 | 1982 Best Supporting Actor Oscar winner for "An Officer and a Gentleman" (3 wds.) |
| 48% | DEBRA | 5 | Winger who starred in An Officer and a Gentleman |
| 46% | NICOLEKIDMAN | 12 | "The Hours" Oscar winner who was honored with an AFI Life Achievement Award in 2024 (2 wds.) |
| 46% | ARIANADEBOSE | 12 | "West Side Story" Oscar winner who hosted the Tony Awards in 2022, 2023, and 2024 (2 wds.) |
| 44% | GOSSETT | 7 | Louis ___ Jr. (1983 Oscar winner for An Officer and a Gentleman) |
| 43% | GERE | 4 | Actor Richard who starred in "An Officer and a Gentleman" |
| 42% | ANNEBANCROFT | 12 | Actress who won a Tony and an Oscar for playing Helen Keller's teacher in "The Miracle Worker": 2 wds. |
| 41% | JULIANNEMOORE | 13 | "Still Alice" Oscar winner who plays 50-Across in a 2020 biopic (2 wds.) |
| 41% | OLYMPIADUKAKIS | 14 | "Moonstruck" Oscar winner who starred in 16-Across and 34-Across (2 wds.) |
| 41% | MARLONBRANDO | 12 | "On the Waterfront" Oscar winner who won (and declined) a Best Actor Oscar for playing Vito Corleone in 47-Across (2 wds.) |
| 40% | JKSIMMONS | 9 | "Whiplash" Oscar winner who voices "Yellow" in M&M candy commercials: 3 wds. |
| 40% | TERI | 4 | Actor Garr who passed away in 2024 |
| 40% | GEORGECLOONEY | 13 | "Syriana" Oscar winner who was honored with an AFI Life Achievement Award in 2018 (2 wds.) |
| 40% | JAMIEFOXX | 9 | "Ray" Oscar winner who is a creator and producer of "Alert: Missing Persons Unit": 2 wds. |
| 40% | JULIEANDREWS | 12 | "Mary Poppins" Oscar winner who was honored with an AFI Life Achievement Award in 2022 (2 wds.) |
| 40% | NICOLASCAGE | 11 | "Leaving Las Vegas" Oscar winner who plays twin brothers Charlie and Donald Kaufman in "Adaptation" (2 wds.) |
| 39% | TIMOTHYHUTTON | 13 | "Ordinary People" Oscar winner who plays the father of 50-Across in a 2020 biopic (2 wds.) |
| 39% | JACKPALANCE | 11 | "City Slickers" Oscar winner who plays twin brothers Curly and Duke Washburn in the "City Slickers" films (2 wds.) |
| 39% | MAHERSHALAALI | 13 | Two-time Best Supporting Actor Oscar winner who plays Wayne Hayes in season 3 of 43-Across (2 wds.) |
| 39% | SAMROCKWELL | 11 | "Three Billboards Outside Ebbing, Missouri" Oscar winner who plays a jaded London police inspector in 31-Across (2 wds.) |
| 38% | ADRIENBRODY | 11 | "The Pianist" Oscar winner who plays a Hollywood film director working in a London theater in 31-Across (2 wds.) |
| 38% | CHRISTIANBALE | 13 | "The Fighter" Oscar winner who plays (spoiler alert!) twin brothers Alfred Borden and Bernard Fallon in "The Prestige" (2 wds.) |
| 38% | JKSIMMONS | 9 | "Whiplash" Oscar winner who played 15-Across and 30-Across (3 wds.) |
| 38% | SANDRABULLOCK | 13 | "The Blind Side" Best Actress Oscar winner who starred in 15-Across, 24-Across, 31-Across, and 40-Across (2 wds.) |
| 38% | HALLEBERRY | 10 | "Monster's Ball" Oscar winner who won a Razzie Award for her starring role in the 2004 film "Catwoman" (2 wds.) |
| 38% | ANGELALANSBURY | 14 | British actress honored with Tony, Oscar, BAFTA, and SAG Lifetime Achievement awards who passed away in 2022 (2 wds.) |
| 37% | EARL | 4 | James ___ Jones (actor who passed away in September, 2024) |
| 37% | EMMATHOMPSON | 12 | "Howard's End" Oscar winner who was appointed a Dame Commander of the Order of the British Empire (DBE) in 2018 (2 wds.) |
| 37% | JOEPESCI | 8 | Oscar winner who appeared in a Snickers ad |