Even though Leonardo DiCaprio has worked with director/writer Quentin Tarantino multiple times, his 2019 collaboration on “Once Upon a Time in Hollywood” has brought them together to the Oscars for the first time. This year’s bid for Best Actor marks the seventh in his career spread out over the lead, supporting and producer categories.
The 45-year-old actor, whom we first got to know as a child star on the ABC sitcom “Growing Pains,” grew up to become one of the world’s most popular movie stars and accomplished actors, also working with such esteemed directors as Christopher Nolan, Steven Spielberg and particularly, Martin Scorsese, with whom he was worked five times (with two more collaborations possibly in the pipeline).
Beginning with 1993’s “What’s Eating Gilbert Grape,” for which he received his first Academy Award nomination at age 19, he has earned six Oscar nominations before this year, including a win for 2015’s “The Revenant.” DiCaprio has also won three Golden Globe Awards from 13 nominations, as well as a Screen Actors Guild Award (for “The Revenant”) out of 11 nominations (including the ensemble and solo bids for “OUATIH”).
Tour our photo gallery above of his 16 greatest films, ranked from worst to best. Our list includes the movies mentioned above, plus “Titanic,” “Catch Me if You Can,” “Blood Diamond,” “The Aviator,” “The Departed,” “The Wolf of Wall Street” and more.