| IRONMASK | and 13dn, 1998 film drama starring Leonardo DiCaprio in the title role (3,3,2,3,4,4) |
| THEMANINTHE | and 13dn, 1998 film drama starring Leonardo DiCaprio in the title role (3,3,2,3,4,4) |
| AVIATOR | The - - -, Howard Hughes biopic directed by Martin Scorsese and starring Leonardo Dicaprio in the title role (7) |
| MARTINSCORSESE | He directed Leonardo DiCaprio in "The Departed" "Shutter Island" and "The Wolf of Wall Street": 2 wds. |
| BLOODDIAMOND | 2006 film drama starring Leonardo DiCaprio and Djimon Hounsou (5,7) |
| TITANIC | 1997 film drama starring Leonardo DiCaprio and Kate Winslet |
| JEDGARHOOVER | Real-life FBI director and title character played by Leonardo DiCaprio in a 2011 film: 3 wds. |
| JOHNNY | and 13dn, 1995 action and sci-fi film starring Keanu Reeves in the title role |
| ELIZABETH | 1998 film drama starring Cate Blanchett in the title role |
| MYNAMEISJOE | 1998 film drama starring Peter Mullan in the title role |
| MEETJOEBLACK | 1998 film drama starring Brad Pitt in the title role |
| HOWARDHUGHES | Real-life business magnate played by Leonardo DiCaprio in 2004's The Aviator: 2 wds. |
| BILLYZANE | He played the antagonist to Leonardo DiCaprio in "Titanic" |
| ROMEO | Role for Leonardo DiCaprio in a '90s romantic tragedy |
| JORDANBELFORT | Real-life stock market manipulator played by Leonardo DiCaprio in 2013's The Wolf of Wall Street: 2 wds. |
| WALLSTREET | "The Wolf of ___" (2013 movie where Matthew McConaughey has a memorable scene with Leonardo DiCaprio in a rooftop restaurant) |
| GROWINGPAINS | 1985-1992 sitcom that featured Leonardo DiCaprio in its final season before he was famous: 2 wds. |
| DAWSON | Jack __, character played by Leonardo DiCaprio in Titanic (6) |
| DANES | Who starred opposite Leonardo DiCaprio in Baz Luhrmann's Romeo + Juliet? (5) |
| LEO | DiCaprio, in the tabloids |
