| HOWARDHUGHES | Real-life business magnate played by Leonardo DiCaprio in 2004's The Aviator: 2 wds. |
| ALPACINO | He played Shylock in 2004's "The Merchant of Venice" |
| ALANALDA | Oscar nominee for 2004's "The Aviator" |
| JORDANBELFORT | Real-life stock market manipulator played by Leonardo DiCaprio in 2013's The Wolf of Wall Street: 2 wds. |
| JEDGARHOOVER | Real-life FBI director and title character played by Leonardo DiCaprio in a 2011 film: 3 wds. |
| DAWSON | Jack __, character played by Leonardo DiCaprio in Titanic (6) |
| PANAM | Airline featured in "The Aviator" (2 wds.) |
| CATEBLANCHETT | She won a Best Actress Oscar for Blue Jasmine and Best Supporting Actress for The Aviator: 2 wds. |
| MARTINSCORSESE | He directed Leonardo DiCaprio in "The Departed" "Shutter Island" and "The Wolf of Wall Street": 2 wds. |
| ROMEO | Role played by Leonardo DiCaprio on film and Orlando Bloom on stage |
| AVIATOR | The - - -, Howard Hughes biopic directed by Martin Scorsese and starring Leonardo Dicaprio in the title role (7) |
| COBB | "Inception" thief Dom played by Leonardo DiCaprio |
| GROWINGPAINS | 1985-1992 sitcom that featured Leonardo DiCaprio in its final season before he was famous: 2 wds. |
| THEMANINTHE | and 13dn, 1998 film drama starring Leonardo DiCaprio in the title role (3,3,2,3,4,4) |
| IRONMASK | and 13dn, 1998 film drama starring Leonardo DiCaprio in the title role (3,3,2,3,4,4) |
| BILLYZANE | He played the antagonist to Leonardo DiCaprio in |
| WALLSTREET | "The Wolf of ___" (2013 movie where Matthew McConaughey has a memorable scene with Leonardo DiCaprio in a rooftop restaurant) |
| DANES | Who starred opposite Leonardo DiCaprio in Baz Luhrmann's Romeo + Juliet? (5) |
| TESTPILOT | New plane's aviator (2 wds.) |
| HOUR | The 11th ___ 2007 documentary film that was produced and narrated by Leonardo DiCaprio |
