| 100% | GATSBY | 6 | "The Great ___" (2013 Leonardo DiCaprio starrer) |
| 78% | GATSBY | 6 | The Great __, 2013 DiCaprio film of 1925 novel |
| 64% | WOLF | 4 | "The ___ of Wall Street," 2013 Leonardo DiCaprio film |
| 64% | LEONARDO | 8 | __ DiCaprio, star of Titanic and The Great Gatsby |
| 64% | LEO | 3 | "The Great Gatsby" star DiCaprio's nickname |
| 59% | AVIATOR | 7 | The —, 2004 biopic starring Leonardo DiCaprio as Howard Hughes |
| 58% | GATSBY | 6 | The Great __, DiCaprio's remake of a classic |
| 56% | THEMANINTHE | 11 | & 13D 1998 film drama starring Leonardo DiCaprio in the title role |
| 55% | DIARIES | 7 | The Basketball __; 1995 drama starring DiCaprio |
| 54% | THEDEPARTED | 11 | Leonardo DiCaprio movie also starring Jack Nicholson and Matt Damon: 2 wds |
| 54% | SIRIUS | 6 | Star in the Greater Dog |
| 53% | THEREVENANT | 11 | A Leonardo DiCaprio movie also starring Tom Hardy: 2 wds |
| 53% | JORDANBELFORT | 13 | Real-life stock market manipulator played by Leonardo DiCaprio in 2013's "The Wolf of Wall Street": 2 wds. |
| 53% | CAREYMULLIGAN | 13 | "Never Let Me Go" actress and co-star of Leonardo DiCaprio in "The Great Gatsby" (2 wds.) |
| 53% | WALL | 4 | "The Wolf of ___ Street" (2013 Leonardo DiCaprio film) |
| 53% | TOBEY | 5 | Maguire who starred in 2013's "The Great Gatsby" |
| 53% | TOMCRUISE | 9 | Star of the 2013 movie "Oblivion": 2 wds. |
| 53% | JAMES | 5 | "Oz the Great and Powerful" star Franco |
| 53% | WERE | 4 | "___ the Millers," 2013 film starring Jennifer Aniston |
| 53% | TOMHARDY | 8 | Leonardo DiCaprio's "The Revenant" co-star who also starred in 15-Across, 19-Across, 28-Across, and 42-Across (2 wds.) |
| 52% | WOLF | 4 | "The ___ of Wall Street," 2013 film starring Leonardo DiCaprio with a howling canine in its title |
| 52% | WILLSMITH | 9 | Star of the 2013 film "After Earth": 2 wds. |
| 52% | LOOKOFLOVE | 10 | The —, 2013 biopic starring Steve Coogan as Paul Raymond |
| 52% | CONJURING | 9 | 2013 horror film starring Vera Farmiga, The __ |
| 51% | LOY | 3 | The Great Ziegfeld co-star |
| 51% | TEN | 3 | Great score from a judge on "Dancing with the Stars" |
| 51% | LEO | 3 | A star sign, also the nickname for ___ DiCaprio |
| 51% | FURNACE | 7 | "Out of the___," 2013 film starring Christian Bale that was produced by Leonardo DiCaprio |
| 50% | SHUTTERISLAND | 13 | A Leonardo DiCaprio movie also starring Mark Ruffalo and Ben Kingsley: 2 wds |
| 50% | HER | 3 | 2013 film starring Joaquin Phoenix and the voice of Scarlett Johansson |