| 100% | NEW | 3 | "Gangs of ___ York" (Oscar-nominated Leonardo DiCaprio film) |
| 55% | TODDFIELD | 9 | Director of Oscar nominated film Tar |
| 53% | TIDES | 5 | "The Prince of ___" (Barbra Streisand film nominated for seven Oscars) |
| 53% | MOON | 4 | "Killers of the Flower ___" (Martin Scorsese film nominated for 10 Oscars) |
| 52% | CINEMA | 6 | ___ For Peace, organization supported by Leonardo DiCaprio that addresses the social relevance of films on society |
| 52% | WOLF | 4 | "The ___ of Wall Street," 2013 Leonardo DiCaprio film |
| 51% | DISTRICT9 | 9 | Oscar-nominated sci-fi film of 2009 |
| 51% | IWO | 3 | Oscar-nominated film "Sands of ___ Jima" |
| 51% | GANGS | 5 | "___ of New York," 2002 historical crime film starring Leonardo DiCaprio |
| 50% | THEBEACH | 8 | Coastal spot; Leonardo DiCaprio film |
| 50% | WALL | 4 | "The Wolf of ___ Street" (2013 Leonardo DiCaprio film) |
| 50% | CATCH | 5 | "___ Me If You Can," 2002 Leonardo DiCaprio film |
| 49% | VALLON | 6 | Amsterdam __; DiCaprio's Gangs of New York role |
| 48% | WOLF | 4 | DiCaprio film, The __ of Wall Street |
| 47% | WOLFOF | 6 | With 37-Across, hit Leonardo DiCaprio film, with "The" |
| 47% | SCORSESE | 8 | Martin __; directed DiCaprio in Gangs of New York |
| 47% | AVA | 3 | Director of 2014 Oscar-nominated film "Selma", ___ DuVernay |
| 47% | WOLF | 4 | Leonardo DiCaprio's "The ___ of Wall Street" |
| 46% | OSCARNODS | 9 | Leonardo DiCaprio received four of them before winning |
| 45% | BROKEBACK | 9 | __ Mountain, most Oscar nominated film in 2006 |
| 45% | THEWHALE | 8 | 2023 Oscar nominated film with Brendan Fraser |
| 45% | LUHRMANN | 8 | Baz, directed 2023 Oscar nominated film Elvis |
| 44% | ULEE | 4 | Oscar nominated title role of Peter Fonda as a beekeeper |
| 44% | GATSBY | 6 | The Great __, 2013 DiCaprio film of 1925 novel |
| 44% | NEWYORK | 7 | Gangs of __; 2002 period drama starring DiCaprio |
| 44% | COCO | 4 | Oscar-winning Pixar film of 2017 |
| 44% | THEREVENANT | 11 | 2015 Leonardo DiCaprio film in which he plays frontiersman Hugh Glass: 2 wds. |
| 44% | THEDEPARTED | 11 | 2006 Leonardo DiCaprio film in which he plays officer Billy Costigan: 2 wds. |
| 44% | MICE | 4 | "Of ___ and Men," 1939 film starring Burgess Meredith that was nominated for multiple Oscars |
| 44% | REV | 3 | The ___anent, movie that gave Leonardo DiCaprio an Oscar |