| 100% | BESTACTOR | 9 | Oscar won by 21-Across for "The King's Speech": 2 wds. |
| 52% | GEOFFREYRUSH | 12 | "The King's Speech" actor who has won the Triple Crown of Acting: 2 wds. |
| 46% | FIRTH | 5 | Colin who won an Oscar for "The King's Speech" |
| 45% | THEOVERSTORY | 12 | Novel by 30-Across that won the Pulitzer Prize for Fiction (2 wds.) |
| 44% | SPACECOWBOY | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Song (2 wds.) |
| 44% | THEOVERSTORY | 12 | 2018 novel by 32-Across that won the Pulitzer Prize for Fiction (2 wds.) |
| 43% | COLINFIRTH | 10 | Oscar winner for "The King's Speech" |
| 43% | THEFOGOFWAR | 11 | Documentary film based on Robert S. McNamara that won the Oscar for Best Documentary Feature in 2003: 4 wds. |
| 42% | BESTDIRECTOR | 12 | Oscar won four times by John Ford: 2 wds. |
| 42% | ROBERTREDFORD | 13 | He won the Best Director Oscar for the first film he directed, 1980's "Ordinary People": 2 wds. |
| 42% | COLINFIRTH | 10 | "The King's Speech" actor who plays secret agent Harry Hart in "Kingsman: The Golden Circle": 2 wds. |
| 42% | KEVINCOSTNER | 12 | He won the Best Director Oscar for the first film he directed, 1990's "Dances With Wolves": 2 wds. |
| 42% | PULITZERPRIZE | 13 | Award won by 18-Across for "Beloved" (2 wds.) |
| 41% | AMERICANGODS | 12 | Novel by 39-Across that won the Hugo Award for Best Novel and the Nebula Award for Best Novel (2 wds.) |
| 41% | PULITZERPRIZE | 13 | Award won by 40-Across for 18-Across (2 wds.) |
| 41% | PARISJACKSON | 12 | The King of Pop's daughter who was recently named an ambassador for the Elizabeth Taylor AIDS Foundation: 2 wds. |
| 41% | STANLEYCUP | 10 | Large silver trophy won by the Penguins: 2 wds. |
| 41% | GEORGECLOONEY | 13 | Oscar-winning actor honored by the 50-Across with a Lifetime Artistic Achievement Award in 2022 (2 wds.) |
| 41% | DEBORAHKERR | 11 | "The King and I" actress who was nominated for six Oscars but never won one: 2 wds. |
| 41% | ILLBEGONE | 9 | With 48-Across, 2018 bestseller by 21-Across/37-Across subtitled "One Woman's Obsessive Search for the Golden State Killer" (3 wds.) |
| 41% | THESTONES | 9 | Nickname for the brand fronted by Mick Jagger: 2 wds. |
| 40% | WHITECHRISTMAS | 14 | Irivng Berlin song sung by 53-Across in 16-Across that won an Oscar for Best Original Song (2 wds.) |
| 40% | ELEE | 4 | "Waiting for the Robert ___," song covered by Al Jolson: 2 wds. |
| 40% | THEWILDIRIS | 11 | Collection by 36-Across that won the Pulitzer Prize for Poetry in 1993 (3 wds.) |
| 40% | HAYLEYMILLS | 11 | 17-Across and "The Parent Trap" star who won a Juvenile Oscar for "Pollyanna" (2 wds.) |
| 40% | THEECHOMAKER | 12 | 2006 novel by 32-Across that won the National Book Award for Fiction (3 wds.) |
| 39% | SALMAGLIE | 9 | Losing pitcher for the Dodgers in 15-Across's perfect game: 2 wds. |
| 39% | RULEOFWOLVES | 12 | Novel by 40-Across that won the 2021 Goodreads Choice Award for Young Adult Fantasy (3 wds.) |
| 39% | COLINFIRTH | 10 | "The King's Speech" actor who played Viola's fiancé in "Shakespeare in Love": 2 wds. |
| 39% | THEUNCONSOLED | 13 | 1995 novel by Kazuo Ishiguro for which he won the Cheltenham Prize: 2 wds. |