| 100% | GARBO | 5 | Four-time Oscar nominee (never a winner) in the 1930s |
| 52% | ENYA | 4 | Oscar nominee for a song in "The Lord of the Rings" |
| 48% | BRADPITT | 8 | Oscar winner for "Once Upon a Time in Hollywood" |
| 48% | BRADPITT | 8 | Best Supporting Actor Oscar winner for the 2019 film "Once Upon a Time in Hollywood": 2 wds. |
| 47% | MVP | 3 | Award won four times in the W.N.B.A. by A'ja Wilson |
| 46% | LEONARDO | 8 | With 52-Across, "The Revenant" Oscar winner who plays actor Rick Dalton in "Once Upon a Time in Hollywood" |
| 46% | CAPRA | 5 | Winner of three directing Oscars in the 1930s |
| 46% | STATELINES | 10 | Borders represented four times in this puzzle — both in the grid and on a map |
| 45% | JACKLEMMON | 10 | Best Actor in a Leading Role Oscar winner for Save the Tiger |
| 45% | LEMMON | 6 | Jack —, Best Actor in a Leading Role Oscar winner for Save the Tiger |
| 45% | BRADPITT | 8 | "Moneyball" Oscar nominee who plays stunt double Cliff Booth in "Once Upon a Time in Hollywood" (2 wds.) |
| 44% | SANS | 4 | Word repeated four times in the last line of Shakespeare's "All the world's a stage" speech |
| 44% | POITIER | 7 | Sidney —, Best Actor in a Leading Role Oscar winner for Lilies of the Field |
| 44% | LEIGH | 5 | Vivien —, Best Actress in a Leading Role Oscar winner for Gone with the Wind |
| 44% | SAINT | 5 | Eva Marie —, Best Actress in a Supporting Role Oscar winner for On the Waterfront |
| 44% | BARRYMORE | 9 | Ethel —, Best Actress in a Supporting Role Oscar winner for None but the Lonely Heart |
| 44% | HURT | 4 | William —, Best Actor in a Leading Role Oscar winner for Kiss of the Spider Woman |
| 44% | CRAWFORD | 8 | Broderick —, Best Actor in a Leading Role Oscar winner for All the King’s Men |
| 43% | BRADLEYCOOPER | 13 | Four-time Oscar nominee who plays Jackson Maine in 29-Across (2 wds.) |
| 43% | NICHOLSON | 9 | Jack —, Best Actor in a Leading Role Oscar winner for One Flew Over the Cuckoo's Nest |
| 43% | TIMOTHYHUTTON | 13 | "Ordinary People" Oscar winner who plays the father of 50-Across in a 2020 biopic (2 wds.) |
| 42% | QID | 3 | Four times a day, in prescriptions |
| 42% | QID | 3 | Four times a day, in an Rx |
| 41% | GEENADAVIS | 10 | Oscar nominee in the role of Thelma Dickinson |
| 41% | THENIGHT | 8 | In the Heat of __; 40th Oscar awards winner |
| 41% | QID | 3 | Four times a day, in an Rx: Abbr. |
| 41% | INGE | 4 | "Splendor in the Grass" Oscar winner |
| 41% | DONUT | 5 | Treat whose varieties appear at the starts of four long answers and are represented a dozen times in this puzzle |
| 41% | ENYA | 4 | Oscar nominee for a "Lord of the Rings" song |