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As Baz Luhrman and Leonardo DiCaprio unveil their second collaborative effort, The Great Gatsby to general audiences this weekend, it’s easy to let the nostalgia take over. It is a beloved story that has been read by teenagers in high schools all across the country for decades and has found a place in all our hearts.

Just like The Great Gatsby, Leonardo DiCaprio has also wormed his way into our hearts throughout his 24-year career. In honor of this remarkable pairing, we thought it would be nice to take a look back at the Leonardo DiCaprio movies that turned the actor into the person we know and love today.

Dom Cobb in ‘Inception’

Leonardo DiCaprio inception

Inception, Chris Nolan’s smash hit from 2010, created one of DiCaprio fans’ favorite and one of the most important roles of his career. In his first film post-The Dark Knight, Nolan made an impression on general audiences, and choosing DiCaprio to lead the film was one of the smartest moves he could have made. Equal parts complicated and endearing, the heart at the center of Inception belongs to the struggle that Leo depicts so effectively as Cobb chooses his own reality.

Jack Dawson in ‘Titanic’

Leonardo DiCaprio HD photo Titanic Jack Dawson

In arguably his most well-known role to date, Leonardo DiCaprio shone through the wide-eyed innocence of Jack Dawson. This character gave life to an event that few people fully understood. History remembers the Titanic as an infamous tragedy, and due reverence is paid to its victims, but Jack Dawson became the face of the many unfortunate victims of unfortunate circumstances in this Oscar-winning film from James Cameron.

Calvin Candy in ‘Django Unchained’

1138856 - Django Unchained

If there’s one thing Tarantino does well, it’s write enchanting villains. Django Unchained was no different. It’s a shame that he didn’t get more recognition, but Calvin Candy is one sickeningly sweet bad guy. The twisted, stringy slaveowner in Tarantino’s spaghetti western is the perfect foil to Django’s hard-edged, street-wise freed slave. If there could be a better dichotomous duo, I would hang up my holster and saunter out of town…

Billy Costigan in ‘The Departed’

The Departed Leonardo DiCaprio Billy Costigan

When an actor lands a partnership with an estimable director like Martin Scorcese, and manages to make an impression enough to land leading roles in four more of his films, you just know that a true talent has found its match. In their third project together, The Departed, DiCaprio tackled the role of Billy Costigan, a young member of a revered mob family in South Boston that becomes a double agent, leaking precious secrets to the Boston police. Most notably, DiCaprio managed to master the tough accent of a South Boston native as well as that of a South African diamond aficionado in the same year. Impressive doesn’t even begin to cover it.

Frank Abagnale Jr. in ‘Catch Me If You Can’

Leonardo DiCaprio Catch Me if You Can

The imaginative tale of a con artist that managed to swindle millions of dollars by posing as a pilot, a doctor, and a legal authority gave Leo an opportunity to play on the light-hearted side of things. More often than not, his choices lean toward the dramatic, and while this role had no shortage of drama, it also demanded playfulness and fun.

Romeo Montague in ‘Romeo + Juliet’

Leonardo DiCaprio Romeo + Juliet

In the world of legendary romances, there is none more well-known than Romeo and Juliet. In their first film together, Baz Luhrman and Leonardo DiCaprio managed to spin this classic tale into one of the most successful re-imaginings of a Shakespeare tale to date. Placing the original dialogue in a modern setting breathed new life into the story without stripping it of its most valuable asset. Leo’s performance raised him to heartthrob status in the mid-late 90s; a distinction he held until his roles of the early 2000s propelled him to the epitome of Hollywood elite.

Jim Carroll in ‘The Basketball Diaries’

Leonardo DiCaprio Basketball Diaries

The Basketball Diaries provided a unique challenge to a young actor on the rise. In a departure from his otherwise squeaky clean image at the time, this horrific tale of a talented basketball player turned drug addict showed the range that DiCaprio could muster, and it proved to any nay-sayers (if there were any) that this fresh faced youngster was a talent to be reckoned with. We include it as a favorite because it’s hard not to be amazed at the talent such a young man can display, especially with such dark, gritty subject matter.

Arnie Grape in ‘What’s Eating Gilbert Grape’


Perhaps the role that established his reputation as a legitimate young actor, Arnie Grape is equal parts charming, challenging, and engaging. It would have been easy to turn the character into a caricature of that level of mental illness, but Leo managed to balance respect and accuracy without falling too far in either direction, and to strike that balance at the rather young age of 19 is the sign of a true talent, and marked him as one to watch.

J. Edgar Hoover in ‘J. Edgar’

Leonardo DiCaprio J Edgar Hoover

While not a fan favorite of his films for sure, no one can deny the talent on display as DiCaprio portrays the man credited with bringing the Federal Bureau of Investigation to prominence during his 50 years of service, J. Edgar Hoover. He managed to bring vulnerability to an otherwise turgid, stodgy man, while also painting him as a strong leader, more than capable of handling the demands of his office.

Danny Archer in ‘Blood Diamond’

Leonardo DiCaprio Danny Archer Blood Diamond

The story surrounding Danny Archer and the controversial diamond business provided the perfect platform for DiCaprio to show off his prestigious talent. While some question the accent he affected to make the role as authentic as possible, even more praise the actor for having the guts to tackle such a momentous obstacle, not to mention also attempting a South Boston accent in a film released the same year. Blood Diamond beautifully displays the dedication that DiCaprio has to his craft.

What is your favorite Leonardo DiCaprio movie and character?

  • http://twitter.com/akacj7 Caroline J.

    no Howard Hughes in the Aviator? “it’s the way of the future… it’s the way of the future… the way of the future… the way of the future….”

  • Gary65

    And still no Oscar :( What is wrong with the world?

    • http://www.facebook.com/profile.php?id=1045615098 Riana-Tiana Menezes

      I just knew someone was going to say that in the comments.:D
      And I don’t know, I really don’t know. Probably because there were better competitors every year he had a chance? :/

      • http://twitter.com/TheAmandaCora Amanda Cora

        While this is true and I can understand times such as when Jamie Foxx won for Ray over him, I also think that sometimes he isn’t even nominated when he deserves it. It is hard to think of a role he hasn’t done well in and many he is exceptional and worthy of recognition.

        I would also point out Revolutionary Road and Shutter Island as some other excellent roles. I was quite sad to see that he was not nominated for RR.

        Hopefully he will have a nomination this year. I think he was the perfect Gatsby but am unsure because of the critique of the film as a whole, that would probably be for supporting. There is also Wolf of Wall Street but we will have to wait and see how he does. However that would be for Best Actor and will have some tough competition already with all the praise Matthew McConaughey is getting for Mud.

    • Grace Tucker❤

      I just can’t believe that he never won one for Arnie Grape.

  • Laura Jones

    Can’t believe he hasn’t won an Oscar! Gatsby better be the one!

  • Sarah

    Leo himself is an icon. Basically everything he touches turns to gold.

    • http://twitter.com/themeels Amelia Brown

      Maybe that’s why they haven’t given him an Oscar yet…

      He’s a modern day Midas. Can’t have him be the only one with a solid gold Oscar.

  • BritBrat

    My favorite has always been and probably will always be Blood Diamond.


  • Saraberry

    so basically all his movies….

  • http://www.facebook.com/profile.php?id=607519910 Catherine Lai

    I love him. I’ll watch anything he’s in.

    • Romina Tare

      me too ^_^

  • http://twitter.com/sarmoso Staci Armoso

    What about Shutter Island?

  • http://www.facebook.com/matthew.weller Matt Weller

    Definately one of the best actors of all time

  • Ashley

    I LOVE him in Revolutionary Road

    • Anon

      yesss.. especially when he gets all angry! so sexy… (weirdly enough)

    • Marie

      Apparently he and Kate Winslet are meant to date and have a doomed relationship. :-p

  • Romina Tare

    Where is Howard Hughes ? You put in this list Jim Carroll and Romeo , but you don’t put Howard Hughes and Teddy Daniels ?!?! WTH !!!

  • Romina Tare

    Cheers up guys Leo will finally get an oscar this year ;) If he doesn’t get it with Great Gatsby , he’ll probably be nominated for The wolf of wall street , and he’ll probably win. Let’s hope and pray for him :)

  • Aidan

    I love Billy Costigan

  • Cassidy Howell

    Howard Hughes !!!

  • Jimmy Rose

    It’s no wonder that “Total Eclipse” is not on this list since it received virtually no attention by anyone. However, I think it like “This Boy’s Life” were critical career milestones, much like “Grape.” Eclipse and Life pitted him against very experienced and lauded actors (Thewlis and DeNiro, respectively), and those films made big directors sit up and take notice of Leo’s ability to hold his own and deliver proficient and emotionally affecting performances.

  • mitchell

    blood diamond, titanic, inception so far as the best movies i think hes done

  • Nilou

    My favorite one is Inception! he’s amazing and it’s not him that cound not get an oscar. it’s oscar that could not get him!

  • anne

    Such an amazing actor. It makes me so sad that he doesn’t have an Oscar. But in my heart you’ve won an Oscar for every single role you’ve ever been in

  • Ani

    What about Gatsby?? It’s in the title but not one of his iconic roles? I protest!

  • Katie

    By far, my favorite role of his is Arnie Grape from ‘What’s Eating Gilbert Grape.’ I have an immense interest in mentally disabled people (especially children, and even further, autistic children), so for an actor to be able to portray such a sensitive subject with such class is an amazing feat in my book. And I say this to anyone who will listen: He should have won the Oscar for which he was nominated for this role. It was his first nomination, and he should have been like Matthew McConaughey this year and won. Also, my mother told me that when she first saw this film (because Leo wasn’t as well known when it came out), she wondered how they got an autistic boy to remember the lines. That’s how good he was.

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