Top 10 Leonardo DiCaprio Films

From bedraggled teen in This Boy’s Life and The Basketball Diaries to pretty-boy heartthrob in Romeo & Juliet and Titanic to toughened action star in Blood Diamond…Leo has done it all…

Leonardo DiCaprio has made the complete arc of a Hollywood actor – from teen heartthrob to accomplished Oscar-nominated thespian and headline act – seem almost too easy. From the halcyon days of his post-Titanic success, to more recent serious fare, Leo has been blessed with both good looks and extraordinary talent. Nominated for Oscar for his breakout performance in What’s Eating Gilbert Grape, Leo came to major mainstream attention a few years later in Bazz

Luhrmann’s Romeo + Juliet, opposite Claire Danes, before Titanic elevated him to A-list status the following year. Today, we want to celebrate the career (to date) of Leonardo DiCaprio, so here are out suggestions for the ten best films with him in them.

10. Catch Me If You Can (Spielberg, 2002)

catch-me-if-you-can-leonardo-dicaprio
Leo’s first team up with Spielberg resulted in this whimsical, spritely true-story about a man who pretends to be other people. Leo shines opposite Tom Hanks, and easily dazzles his co-stars with that winning smile of his.

9. Romeo + Juliet (Luhrmann, 1996)

Romeo-and-Juliet-leo-dicaprio
The innocence of youth portrayed perfectly by Leo here, as the love-struck Romeo, against Claire Danes’ Juliet, in one of the more raucus version of the famed Shakespeare story. Although he does get lost in amongst the large ensemble cast, DiCaprio more than holds his own each time he’s on the screen.

8. Gangs Of New York (Scorsese, 2002)


The first of three teamings with director Martin Scorsese, Leo plays an Irish migrant in 1850’s New York City, seeking revenge for the death of his father at the hands of the evil Bill The Butcher, played by Daneil Day-Lewis. DDL out-acts Leo in their scenes together, and the film is hampered by an awful performance by Cameron Diaz (miscast badly), but in amongst the confusion Leo’s class and talent shine through.

7. Django Unchained (Tarantino, 2012)


His first real villain role in Tarantino’s slavery epic, Leo plays enigmatic and cruel plantation owner Calvin Candie, a hammer-wielding monster who charms those around him into submission.

6. What’s Eating Gilbert Grape (Hallström, 1993)

WhatsEatingGilbertGrape_dicaprio_depp
DiCaprio’s supporting but memorable role of Johnny Depp’s mentally challenged sibling, in this moving and entertaining dramatic film from Leo’s early career. The role snagged him an Oscar nomination (his first), and gave him the momentum to appear in bigger films, and paving the way for Titanic.

5. Inception (Nolan, 2010)


Leo’s lead role in the ensemble sci-fi actioner from Christopher Nolan, as the fractured and tormented Dom Cobb, remains one of his most iconic thanks to the cult following the film has garnered since release.

4. Titanic (Cameron, 1997)


Regardless of the screechy theme song, the ubiquitous number 1 box office taking ever (for its time) and the thunderous public scorn heaped upon James Cameron’s Best Director speech, Titanic remains a terrific piece of Hollywood entertainment. The fact that Leo is excellent in it is merely icing on the cake.

3. The Aviator (Scorsese, 2004)

leonardo_dicaprio_the_aviator
Leo’s ability to morph into a character was perhaps never more defined as it was in this, Scorsese’s Howard Hughes bio-pic, and a role for which snagged another Oscar nomination. Leo plumbed the darkness of Hughes’ mania with scorching success, and although the film left the mainstream public largely dumbfounded, for critics and fans alike, it was yet another scintillating performance.

2. Blood Diamond (Zwick, 2006)

blood_diamond_dicaprio
Arguably one of the most powerful films in the last 20 years (and I don’t say that lightly), DiCaprio shines alongside Djimon Honsou in this riveting, stunning, shocking film about the illegal diamond trade through Africa. Opposite Jennifer Connelly, Leo is his usual disarming self, but when the going gets tough, Leo stands his ground. Even if you’re not a Leo fan, you owe it to yourself to check this film out.

1. The Departed (Scorsese, 2006)

Leo-Dicaprio-in-The-Departed

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Scorsese’s modern crime masterpiece gave Leo nominations for every award they have a name for (except, strangely, for Oscar) and the ensemble cast made the most of the kudos and acclaim for which this film was justly rewarded.

Alongside the likes of Matt Damon, Jack Nicholson, Martin Sheen, Mark Wahlberg and a host of other Hollywood talent, it could have been too much of too much for DiCaprio to really stand out; yet, stand out he did (and still does), in this, the film I think is the best he’s ever been in.

Honorable Mentions:

The Quick & The Dead

Leo, Russell Crowe, Gene Hackman and Sharon Stone: the cast are excellent in this near-parody of a Western. Pity the film isn’t that great.

The Basketball Diaries

Too depressing for words, the film is excellent and Leo’s very good in it, but I couldn’t sneak it into the top 10.

Revolutionary Road

Leo reunites with Titanic co-star Kate WInslet for Same Mendes’ tragic tale, only to be snubbed come Oscars time again. A great (if depressing) film that highlights DiCaprio’s ability to really get into the skin of a character.

Written and compiled by Rodney Twelftree.

See more great actor lists on Top 10 Films: Caine | De Niro | DiCaprio | Downey Jr. | Hanks | Hoffman | Streep | Roberts | Schwarzenegger | Oldman | Gandolfini | Freeman | Ford | Eastwood | Dreyfuss | Keitel | Woods

About the Author
An Aussie lad with a love of cinema, Rodney Twelftree parlayed his interest in films into a website dedicated to reviewing them. Currently Editor In Chief at fernbyfilms.com, Rodney spends much of his time watching films, television, reading science fiction novels and trawling the internet for news and reviews on all things film.

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  1. Dan Grant Reply

    Really good list. Leo is one of if not the best actor working today. He is definitely one of the biggest draws and his taste is eclectic. He has worked with the best of the best, no doubt.

    I’m glad you included Titanic as it is imo one of the best films of all time. I’m also glad you mentioned Revolutionary RD as an honourable mention. He is simply electric in that film.

    Overall a great list. Nicely done.

    • Rodney Reply

      Thanks Dan, great to hear your thoughts. Titanic was almost a foregone conclusion, it was really only a question of which number it came in at. Such a terrific film, indeed.

  2. Mark Reply

    A great list … although I would have put Blood Diamond at number one. I probably didn’t appreciate the man as much as I should have until I saw it; now I think someone should throw Oscars at him.

    • Dan Reply

      ..similarly, I’ve come to appreciate him as an actor later in his career (after he shed the pretty-boy persona of Romeo + Juliet/Titanic etc.)

    • Rodney Reply

      Anytime anyone asks me for a film recommendation, Blood Diamond comes in in my top 5. A brilliant film regardless of Leo’s involvement, Blood Diamond is utterly superb filmmaking.

  3. Dan Reply

    DiCaprio’s career – in my mind – is one of two halves. There’s the early “scrawny kid” period where he appeared in some very good films and displayed some real potential. He was excellent in The Basketball Diaries and This Boy’s Life. He then went through the “pretty-boy” period with Titanic, Romeo + Juliet and The Beach when I literally couldn’t stand him. My distaste for Titanic has waned over the years as I have, in retrospect, come to admire DiCaprio, but there was a stage in his career when he threatened to become another Paul Walker.

    Since Gangs of New York in 2002 he’s been excellent – consistently choosing the right roles and consistently delivering strong performances. I agree, he’s excellent in Blood Diamond while I’ve also thoroughly enjoyed his work with Scorsese (perfect director to make friends with of course), while Inception and Body of Lies also showed us how good an actor he really is.

    • Rodney Reply

      The difference between Leo and Paul Walker is that Leonardo DiCaprio has the ability to act on camera. Paul Walker lacks this innate ability comprehensively.

  4. Dan Grant Reply

    Imo the fact that he wasnt nominated for REVOLUTIONARY ROAD is criminal. He should have won one by now. I guess his revenge is dating supermodel, making gobs of money and having every director salivating at the thought of working with you.

    • Rodney Reply

      Don’t worry, Dan. I have a sneaking suspicion that he’ll win an Oscar eventually. The law of averages is in his favor – considering his age, and all he’s accomplished until now, I think it’s a given at some point.

      After all, if Sandra Bullock can win a career Oscar, Leo would have to be next in line somewhere…..

  5. Evan Crean Reply

    Great list Rodney. The only one I really take issue with is The Aviator. God I thought that film was awful. And I know DiCaprio is great in it, but my disdain for it would prevent me from including it on my own top DiCaprio countdown. I would have traded the Aviator for Basketball Diaries (which you thankfully included in the Honorable Mentions) or This Boy’s Life.

    • Rodney Reply

      Thanks Evan, glad you thought we did a fair job of this list. The Aviator’s a divisive film when it comes to DiCaprio – a lot of people are either for or against it (no doubt you’ll appreciate that I’m “for” it…) and never the twain shall meet. And as you say, even if you don’t like the film overall, most people agree that DiCaprio’s performance IN it is first rate – which is why I have it in the list.

  6. Dan Grant Reply

    I’m pretty sure you’ll be able to add Wolf of Wall Street to his list of great performances. That films looks like Marty dropped acid, read the stuff about Wall Street and the main character and then got the entire cast to drop acid and then filmed. Can’t wait to see it.

    • Rodney Reply

      Yeah, it looks trippy, doesn’t it! I can’t wait to see it either!

  7. Neal Damiano Reply

    I have to say this is the first list on Top 10 Films I completely disagree with. For starters, not having Basketball Diaries on here is pure blasphemy! Second, including Gangs of New York and Titanic even on the list I can’t see this. Third, having titanic so high up on the list! I would replace Titanic with The Beach and have it high on the list. My final thought not only would I have Basketball Diaries on this list , but I would have is as number two. I agree with The Departed as number one I loved that movie.

    • Rodney Reply

      See, I abhorred The Beach. I thought it was a terrible film (still do) at the time. No way could I include it. I can understand some angst re Titanic placing so high, but c’mon, that’s a terrific film and Leo’s performance is far better than almost everyone elses.

      Just goes to show that not all people have the same taste in film. Which is a good thing!

  8. Neal Damiano Reply

    ^.Oh and I forgot to mention in my little film rant ( all out of love for film) I would have put “Catch Me If You Can ” high up on the list, probably at number 3, Dicaprio was absolutely amazing in this great film. To see it at number 10 hurts!

    • Rodney Reply

      Nothing better than reading a good rant, Neal. As long as we can agree that CMIYC belongs somewhere in the Top 10, I’ll be happy.

  9. Mark Reply

    Mr Grant gave me a great idea – think I’ll watch the Wolf of Wall Street on acid (particularly if Robert Richardson is the DOP … as Oliver Stone showed us, his stuff looks absolutely fantastic when blood infused with arsenic and rat poison is flowing through the brain).

    I think Neal’s self-confessed rant (which I do not entirely disagree with) and some of Rodney’s comment’s post posting his post highlights an interest point about Leo, that being he is pretty damn good in just about everything he is in (could anyone in their right mind do a 10 worst films of Leo list?). Admittedly I’m not the biggest fan of Titanic, but it was a travesty of justice that DiCaprio wasn’t even nominated for an Oscar when he was just as good (if not better) than Kate. Let’s face it – he carried that film.

    I was also a little impartial to Inception (I always kind of miss the point with Nolan, possibly because I don’t ingest enough acid when I watch his films) but, once again, Leo was absolutely terrific in it.

    And yes, I too probably would have put The Bssketball Diaries or A Boy’s Life before The Aviator and Romeo + Juliet. Also MIA is Shutter Island – sure, not the best Scorsese picture, but a great performance in a handsome looking film shot by one of the world’s greatest living DOPs (more acid, anyone?)

    The only way we all would have been happy is if this top ten list was a top 15 list … and even then there would have been conjecture.

    Good work, Rodney ….

    • Rodney Reply

      Thanks Mark! Sounds like we all need to stock up on acid, I guess! LOL!!

      Shutter Island was a very average film (IMHO) and I felt like DiCaprio was cruising through that one a little – again, just my two cents – and not, it’s not one of Scrosese’s better ones. This is why I couldn’t bring myself to include it even in the “honorable mentions” section.

      Inception is flat out brilliant, cast and story alike, and so it was a forgone conclusion that it HAD to be included. Guess that’s one for the neverending fan battles, I think.

      I think what we can take away from all this is that even in a film of mediocre quality, Leo is typically the best part of it; when the actors around him flounder, Leo rises above.

  10. Dan Grant Reply

    Without looking it up, I dont think theres another actor who worked with Spielberg Scorsese Nolan and Tarantino while headlining a movie.

    • Rodney Reply

      I’d say that’s damn close to being correct it’s not even funny. Man, that’s some talent right there.

  11. Raghav Reply

    I would have put Basketball Diaries in the Top 10 in place of Gangs of New York which I think is overrated. Nevertheless, a good list and a reminder how Leo’s acting career has shaped up.

  12. Dan Grant Reply

    His performance in Wolf of Wall Street is one of the best performance I’ve seen.

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