Power Ranking The Six Best Leonardo DiCaprio Movies Of All-Time

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For the first time in a couple years, we are getting a new Leonardo DiCaprio movie. if you don't count Don't Look Up (and it's perfectly ok if you don't), this is the first DiCaprio movie since Once Upon A Time In Hollywood in 2019. He chooses his projects so carefully, it's an event when he has a new film out. Every movie he's been in since The Great Gatsby in 2013 has been nominated for Best Picture. I would think Killers Of The Flower Moon could lock up a nom as well.

Here are my favorite DiCaprio movies. This is entirely my list and I am guessing everybody reading it will disagree. It's tough with someone as talented as him because he is in so many good movies, you're going to leave some off. Titanic is a very good movie but it doesn't crack my Top 6 for him. The first half is just too weak with the dialogue and character buildup. I still really like the movie! I have 72nd on my Top 100 of the 1990's. It's just not good enough to crack his top 6.

6. Catch Me If You Can

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This is DiCaprio's only time working with Steven Spielberg. It's a shame because this is a pretty brilliant movie and they work really well together. The scenes with Christopher Walken and Leo playing father and son alternate between heartwarming and heartbreaking. This is also the last time we really see DiCaprio playing a kid. You could argue he is also young in Gangs Of New York (which also came out in 2002) but his next movie in 2004 has him playing Howard Hughes in The Aviator and it's only adults from there on out. Then again, maybe it's more impressive that Leo was a 28 year old playing a high school kid in this.

5. Gangs Of New York

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It's easy to forget that before 2002, DiCaprio's career was in a weird place. He's in Titanic (which came out at the end of 1997) and put him in the stratosphere of massive stardom instantly. From 1998-01, he was only in three movies. The Man In The Iron Mask (which was made before Titanic came out), Celebrity (a small Woody Allen ensemble piece) and The Beach (which was a box office and critical disappointment). Having this and Catch Me If You Can come out the same year instantly made him a respected actor to go along with being a superstar. 

This isn't a perfect movie but its few flaws are glossed over for me by the incredible set design and performances. I may be alone but I don't think Cameron Diaz is bad at all in this. Daniel Day-Lewis and Leo are fantastic. This is the first time Martin Scorsese and DiCaprio worked together and started a partnership that is now going on six movies.

4. Django Unchained

This is the movie on the list that DiCaprio affected the least. Don't get me wrong, he's perfect as Calvin Candie. Not many movie stars that are that popular would take a role as horrific and evil as Candie. One of the reasons I admire DiCaprio's career so much is his ability to work with the greatest directors and bring a new energy to their work. This movie loses so much of that when DiCaprio gets killed. I love Leo, Jamie Foxx and especially Samuel L. Jackson in this but if we're comparing Waltz/Tarentino movies, Inglorious Basterds holds the crown for me.

3. Inception

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I'd love to see DiCaprio work with Christopher Nolan again. After the box office success of The Dark Knight movies and now the soon to be Oscar love for Oppenheimer, some of Nolan's movies have slipped through the cracks a tiny bit. It's not like Inception is this little forgotten gem, it just keeps getting pushed out of the forefront. Obviously, that's going to happen as movies age but I didn't expect that with something like this that has evergreen themes. 

Things like dreams and regret will never go out of style. Plus, the movie has a timeless look and feel. I am guessing this is one people will still be watching 40-50 years from now. I wouldn't call this Leo's best performance but he is perfect in a confusing movie that relies on bright actors to lead the way.

2. The Departed

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This is my favorite Scorsese/DiCaprio pairing. That means that Wolf Of Wall Street isn't in my Top 5 list which I figure I should explain. I know lots of people love it and would even put it at number 1. To me, it was good but not great. It was an hour too long and felt like it was rehashing a lot of the same territory that Oliver Stone tackled in Wall Street. DiCaprio was great in that he dives head first into all of his roles whether it's in Departed, Wolf Of Wall Street or even The Revenant. It was before he was famous but he jumped into What's Eating Gilbert Grape with the same fervor. These aren't easy roles to play and if performed badly would make him look like an asshole. You have to give him credit for not just doing Marvel movies and resting on his laurels.

The Departed had such a weird trajectory. When it came out, people loved it. When it won the Oscar for Best Picture, it had a sort of backlash that it only won to finally give Scorsese an Oscar. Since then, it's gone from being underrated to being perfectly rated as people seem to love it again. Even the things about it that did annoy me at the time (Jack Nicholson's odd overacting, the rat at the end) don't bother me much anymore. The positive things like DiCaprio's paranoia, Matt Damon's arrogance masking fear and brilliant plot moves (especially at the end) hold up better than ever.

1. Once Upon A Time In Hollywood

This is right there with Belfast, Oppenheimer and 1917 as one of my favorite movies of the past ten years. It's not Tarentino's best movie but it's close for me. I love how it looks with that amazing 1969 set design and how it sounds with the soundtrack that had so many songs I wasn't familiar with. People love The Guardians Of The Galaxy soundtrack but if you had parents of a certain age, you heard all of those songs so many times over your life. The Once Upon A Time In Hollywood soundtrack was almost all songs I didn't have familiarity with.

Add in the great suspense at Spahn Ranch with the dichotomy between the beauty of sun-soaked Hollywood with the dread of the Manson Family lingering around and you get one hell of a great movie. DiCaprio is vulnerable and even annoying as Rick Dalton. It's such an interesting look at middle age and what it means to get older. I've found that the key to getting older is being comfortable with the choices you make. Holding on to the past is a waste of time because the past will never hold you back. It can only vanish. You have to learn how to be content.

For example, I'm content with this list even though I know most (all?) will disagree. If you do disagree, put your top 6 in the comments. I did one of these with Robert De Niro movies and I think roughly the same thing about that list as I do with this one. There really is no wrong answer when making a top Leonardo DiCaprio list. 

Unless you include Don't Look Up.