| 100% | HOUR | 4 | "Darkest ___" (Winston Churchill biopic starring Gary Oldman) |
| 100% | HOUR | 4 | "Darkest ___" (2017 Winston Churchill biopic starring Gary Oldman) |
| 56% | DARKESTHOUR | 11 | 2017 biopic in which Gary Oldman played Prime Minister Winston Churchill: 2 wds. |
| 47% | DARKEST | 7 | "___ Hour," Gary Oldman's movie about Winston Churchill which was released a day prior to Thanksgiving in 2017 |
| 44% | IMMORTAL | 8 | "___ Beloved" (1994 film starring Gary Oldman as Beethoven) |
| 44% | DARKEST | 7 | "___ Hour" (Oscar-winning war film starring Gary Oldman) |
| 44% | SERGEANTYORK | 12 | Biopic starring Gary Cooper as a WWI army soldier (2 wds.) |
| 44% | THESPACE | 8 | 2017 film drama starring Gary Oldman and Asa Butterfield |
| 44% | THEPLAINSMAN | 12 | 1936 biopic starring Gary Cooper as Wild Bill Hickok |
| 43% | DRACULA | 7 | 1992 horror film starring Gary Oldman in the title role |
| 42% | THEKRAYS | 8 | 1990 biopic starring Gary and Martin Kemp in the title roles |
| 41% | KRAYS | 5 | The —, 1990 biopic starring Gary and Martin Kemp in the title roles |
| 41% | OLDMAN | 6 | Gary, played Churchill in Darkest Hour |
| 41% | MANK | 4 | Black-and-white film starring Gary Oldman that won two Oscars in 2021 |
| 40% | TAILOR | 6 | "Tinker ___ Soldier Spy" (John le Carré novel adapted as a film starring Gary Oldman) |
| 39% | OLDMAN | 6 | Actor Gary who plays Winston Churchill in "Darkest Hour" |
| 34% | CHANDLER | 8 | ___ and Monica, fictional couple from "Friends" whose iconic TV wedding featured Gary Oldman as a guest star |
| 33% | TORY | 4 | Winston Churchill, politically |
| 33% | ORATOR | 6 | Winston Churchill, notably |
| 33% | VSIGN | 5 | Winston Churchill gesture |
| 33% | SIR | 3 | ___ Winston Churchill |
| 32% | AFAR | 4 | Winston Churchill's "___ Country" |
| 32% | TORY | 4 | Winston Churchill, e.g. |
| 32% | VSIGN | 5 | Winston Churchill flashed it |
| 32% | SIR | 3 | Winston Churchill's title |
| 32% | RANDOLPH | 8 | Winston Churchill's son |
| 32% | NEVER | 5 | Winston Churchill; ___, ___, ___ give up! |
| 32% | ALI | 3 | Biopic starring Will Smith |
| 32% | ACTOR | 5 | Gary Oldman or Paul Newman |
| 32% | JEROME | 6 | Winston Churchill's mother, Jennie __ |