10 Leonardo DiCaprio Movies Worth Watching!

leonardo dicaprio face movies

Leonardo DiCaprio movies we love

Leonardo DiCaprio is an actor we love to watch. He won an Oscar in 2016 for his role as Hugh Glass in The Revenant, which was one of the most powerful films we’ve ever seen.

While DiCaprio gained much attention for this movie, we’d like to take a moment and remind folks that he’s been appearing on the silver screen for over two decades. Feeling inspired by the body of his work, we decided to create a list of our top 10 Leonardo DiCaprio movies in addition to The Revenant.

Before continuing, we just want to say acknowledge that Leonardo DiCaprio has been a steadfast supporter of LGBT equality over the years. He was one of the first to come right out support same-sex marriage – at a time when being an advocate carried potential risks.

Why not check one out today?

10 signs you are comparing yourself

10. Romeo + Juliet (1996)

Leonardo DiCaprio was already making a name for himself with roles in such movies as The Basketball Diaries and What's Eating Gilbert Grape? when he landed the lead role in Baz Lurhman's modern-day retelling of Shakespeare's romantic tragedy.

DiCaprio and the rest of the cast use the original Shakespearean language as they run around mid-90s L.A. while waving guns each other.

Some people loved it Romeo and Juliet, others not so much. But it remains a unique spin on one of the most enduring stories ever told.

9. Titanic (1997)

This is the movie that cemented DiCaprio's status as a Hollywood megastar. Another romantic tragedy that involved lovers from opposite sides of the track, Titanic paired DiCaprio's poor artist with Kate Winslet's upper-class beauty.

The ship inevitably sinks (spoiler alert!) and another big-screen DiCaprio romance ends in tragedy.

Titanic was a monster hit at the box office, but it divided opinion among critics. Once again, Leo wasn't nominated, and his performance in Titanic wasn't impressive enough to earn him the Best Actor award.

8. The Departed (2006) 

In the mid-90s, Leo was a pretty boy who wouldn't have looked out of place with N-Sync or the Backstreet Boys. Then in the new millennium, Martin Scorsese started casting DiCaprio in roles involving gangsters, guns, and profanity.

DiCaprio would never be seen the same way again. The Departed is the Scorsese/DiCaprio movie that is most similar to the classic gangster movies for which Scorsese is best known. DiCaprio stars alongside a stellar cast, including Jack Nicholson, Matt Damon and Mark Walberg, in a crazily complicated crime story set in Boston.

Scorsese, who suffered a curse similar to DiCaprio's, had never won an Oscar until The Departed, for which he received the Best Director award. However, DiCaprio wasn't even nominated for Best Actor. Well, not for The Departed.

7. Blood Diamond (2006)

Blood Diamond sees Leonardo DiCaprio adopt an African accent for a wild and often brutal adventure wherein he plays a smuggler who teams up with a fisherman, played by Djimon Hounsou, to hunt for an enormous pink diamond. The movie exposes the barbarity of Sierra Leone's diamond mining industry in the context of a big-budget Hollywood action/adventure romp.

Blood Diamond was DiCaprio's second nomination for the Best Actor award, but he was up against heavy competition. The academy loves it when actors play real people, and Forest Whitaker did an outstanding job as Ugandan dictator Idi Amin. Incidentally, 2006 is probably the only year when two of the Best Actor nominees were Americans faking African accents.


6. Gangs of New York (2002)

This is the first movie to pair DiCaprio with Scorsese, and it's clear DiCaprio relished the chance to move past the romances and melodramas that filled his resume in the 1990s. The early days of New York City were wild, violent, and perfectly suited for cinema; it seems odd that more movies weren't set in the same time period as Gangs of New York.

Once again, Leo wasn't even nominated, but one of his co-stars was. Daniel Day-Lewis absolutely steals the show as an anti-immigrant gang leader. Brody was solid in The Pianist, so it's probably fair that he picked up the award.

5. Inception (2010) 

A dream within a dream within a … Inception is famously confusing, but also brilliantly exciting. Director Christopher Nolan was fresh from reinvigorating the Batman series when he made this wild tale of investigators invading dreams. With a highly original premise and a huge budget, Inception is mind-blowing entertainment.

The academy rarely rewards big-budget blockbusters, and Inception was no exception. Once again an actor was recognized for playing a real historical figure.

4. Catch Me If You Can (2002) 

2002 was a rare year in which DiCaprio starred in two movies, and they just happened to be the ones that would establish him as a legitimate acting powerhouse. DiCaprio plays conman Frank Abagnale Jr. in a thrilling cat-and-mouse chase that is all the more engrossing for being based on a true story.

Catch me if You Can was DiCaprio's first time playing a real historical figure, so he might have thought he was in with a shot. However, there were a lot of strong performances on screen in 2002, including Brody's.

3. The Wolf of Wall Street (2013) 

DiCaprio again teamed up with Scorsese and again played a con-man in another movie based on a true story. On screen for almost every second of this greed-fest, DiCaprio's dodgy investment banker is at the center of everything in a crazy tale of excess that takes in dwarf tossing, cousin marrying, and a lot of quaaludes. It's the story of a man who wanted everything and was crazy enough to get it.

Die-hard Leo fans are inclined to say The Wolf of Wall Street was arguably the best film of 2013. He did pick up a nomination, but again, it was not to be.

2. Django Unchained (2012)

Throughout his career, DiCaprio's characters have almost all had some redeeming qualities. Django Unchained gave him his first role as an indefensibly horrible human being. He is both mesmerizing and terrifying as John Candy, a slave trader with a fondness for watching his slaves fight each other to the death.

In one scene, DiCaprio smashes a glass on a dinner table and cuts his hand open — for real — but he continues acting. Surely that must be worth an Oscar?

Jamie Foxx had the lead role, so DiCaprio would only have been eligible for a Best Supporting Actor award. The Academy did hand that award to Django Unchained, but it went to co-star Christoph Waltz. While Waltz put in a good performance, DiCaprio steals the show and probably should have been nominated instead.

1. The Aviator (2004)

DiCaprio stars as real-life Hollywood mogul and amateur pilot Howard Hughes. Hughes was an eccentric character with an interesting life story. He produced some of the biggest-budget movies Hollywood had ever seen, dated movie stars, flew planes for fun, was accused of defrauding the United States government during war time, and spent a long period of time holed up in a room by himself, naked, and terrified of any germs.

This is the nomination that seemed most likely to net Leo that elusive Oscar. He was playing a real person in a movie that involved the film industry, two things Hollywood normally loves. However, Jamie Foxx also played a historical figure — and threw in singing as well.

Still, if Leonardo DiCaprio was ever going to win an Oscar, it probably should have been for The Aviator.