| 100% | BEN | 3 | Stiller who directed "Zoolander" and "Zoolander 2" |
| 60% | WARRENBEATTY | 12 | Actor who directed, wrote, and appears in "Rules Don't Apply": 2 wds. |
| 59% | PENNYMARSHALL | 13 | "Laverne & Shirley" actress who directed "Big" and "A League of Their Own": 2 wds. |
| 59% | ORSONWELLES | 11 | Actor who directed 17-Across and played the title character: 2 wds. |
| 58% | JODIEFOSTER | 11 | "Panic Room" actress who directed and starred in "Little Man Tate": 2 wds. |
| 58% | ANDYMUSCHIETTI | 14 | Director of "It Chapter Two" who also directed "It" and "Mama": 2 wds. |
| 58% | RONHOWARD | 9 | "Happy Days" actor who directed "Apollo 13" and "A Beautiful Mind": 2 wds. |
| 57% | ROBERTREDFORD | 13 | "All Is Lost" actor who directed and starred in "The Horse Whisperer": 2 wds. |
| 57% | DIANEKEATON | 11 | "Something's Gotta Give" actress who directed and starred in "Hanging Up": 2 wds. |
| 57% | KENNETHBRANAGH | 14 | Actor who directed and played the title character in 1996's "Hamlet": 2 wds. |
| 57% | ANGELINAJOLIE | 13 | Actress who stars in, wrote, directed, and coproduced 16-Across: 2 wds. |
| 57% | HAROLDRAMIS | 11 | Former "SCTV" performer who wrote, produced, and directed "Groundhog Day": 2 wds. |
| 57% | RICHARDDONNER | 13 | "The Goonies" director, who also directed "Superman" and "Lethal Weapon": 2 wds. |
| 57% | BENAFFLECK | 10 | Hollywood star who cowrote, directed, and acted in "The Town": 2 wds. |
| 57% | WOODYALLEN | 10 | Hollywood star who cowrote, directed, and acted in "Annie Hall": 2 wds. |
| 57% | GRETAGERWIG | 11 | "Lady Bird" and "Little Women" director who also directed "Barbie": 2 wds. |
| 56% | ELIZABETHBANKS | 14 | "Pitch Perfect" actress who directed 16-Across and plays Susan Bosley in it: 2 wds. |
| 56% | GEORGECLOONEY | 13 | Hollywood star who cowrote, directed, and acted in "The Monuments Men": 2 wds. |
| 55% | BRADLEYCOOPER | 13 | "American Sniper" actor who directed and stars in the "A Star Is Born" remake: 2 wds. |
| 55% | BEN | 3 | ___ Stiller who directed "Severance" |
| 54% | ROBREINER | 9 | "All in the Family" actor who directed "The Princess Bride" and "When Harry Met Sally ...": 2 wds. |
| 53% | BEN | 3 | Actor Stiller who directs "Severance" |
| 53% | DAVIDFINCHER | 12 | "Gone Girl" director who produces and directs episodes of "House of Cards": 2 wds. |
| 52% | EDWARDNORTON | 12 | "Fight Club" actor who plays Lionel Essrog in "Motherless Brooklyn" and also directed the film: 2 wds. |
| 52% | ANG | 3 | ___ Lee who directed "Sense and Sensibility" |
| 52% | DELPY | 5 | Julie who directed and co-starred in "2 Days in Paris" |
| 51% | TAMRA | 5 | Davis who directed Guncrazy and Billy Madison |
| 51% | GARRYMARSHALL | 13 | Director/producer/actor who created "Happy Days," developed 18-Across, and directed 44-Across: 2 wds |
| 51% | TIMBURTON | 9 | "Frankenweenie" and "Corpse Bride" Oscar nominee who directed 39-Down (2 wds.) |
| 51% | CHLOEZHAO | 9 | "Nomadland" director who directed and co-wrote Marvel's "Eternals" (2 wds.) |