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The 13 Best Leonardo DiCaprio Roles

More than twenty years ago, a fresh-faced teenager captured the hearts of junior-high girls the world over. I don’t think any of us ever imagined at the time that, two decades later, he would be arguably the greatest actor of his generation. With a staggering six Academy Award nominations in his pocket, Leonardo DiCaprio has had an extraordinary career, and only seems to be getting more talented as time goes by. With yet another opportunity to stop being the Susan Lucci of the Oscars, PeelTheOrange.net takes a look at a few great roles he wasn’t nominated for – and here’s hoping he wins tonight:

13. The Basketball Diaries (1995)

DiCaprio had already been acting for a number of years in his early life, so when he decided to try his hand in a more serious coming of age story of Jim Carroll, it was the beginning of his journey to more challenging and character driven roles. The subject of drugs and sexual abuse is a rough one but this small hidden gem was something that truly showed what DiCaprio was capable. It’s a hard film to find but something that should definitely been seen if you want another taste of Dicaprio’s talent in the making. – Mark Salcido

12. Revolutionary Road (2008)

In this writer’s opinion, the fact that he didn’t receive an Oscar nomination for this film is an absolute travesty. He’s heartbreakingly, infuriatingly real as Frank Wheeler, a husband struggling to relate to his fragile wife; an employee bored with his worker-bee status; and a man wrestling with gender roles in the 1950’s.

Reunited with his “Titanic” costar Kate Winslet as his wife April, the two once again have perfect, effortless chemistry, but in a completely different way. As a couple fighting to keep their sinking marriage afloat, they savagely rip open the cracks in the pseudo-perfect façade of those “Leave It To Beaver” marriages so stereotypical of the era. The Wheelers seem to have everything – they’re young, attractive, successful, have two beautiful children, and of course, they’re crazy in love. Or are they?

In the car on the way home from a play in which aspiring actress April has just performed, Frank mercilessly belittles her performance, her appearance, and the significance of her aspirations. Why in the world would a man be so cruel to his wife? Through a series of flashbacks, strewn throughout the current scenes, we begin to understand. This is a couple who both fell in love with the *idea* of who each other could be, rather than the actual person before them. As time goes by, each of them becomes less satisfied, and more bitter. The utter hatred with which they lash out at each other is almost physically painful to watch, and yet you can’t take your eyes off of the unfolding tragedy. When April commits her final act of revenge against Frank, we see just how broken these two people are, and how truly poisonous they are to each other.

This film is one of the great modern dramas. Only watch it if you have several hours of free time, because you’re going to restart it as soon as it’s over. Yes, it’s really that good.

11. The Quick and the Dead (1995)

I generally don’t care for Westerns, but this movie is one of my few exceptions. Sharon Stone’s female gunslinger, Russell Crowe’s preacher with a past, and Gene Hackman’s cold-hearted villain carry the bulk of the plot. But a secondary character, known simply as The Kid, was my introduction to Leo’s work. His amiable charm oozes through the screen in every frame he occupies. The Kid is intent on helping Stone’s Ellen to enter a sharpshooting tournament, in which she hopes to take her revenge on Hackman’s Herod, who killed her father when she was a child. Although it eventually comes out that Herod is The Kid’s father, he makes no effort to stop her, as he knows Herod is a soulless bastard. He has never even acknowledged his son, which is clearly painful for him. Of course, in true Western fashion, The Kid is killed late in the tournament, and Ellen has even more reason to take revenge. She avenges both her father and her fallen friend, who had come to mean a great deal to her in the short time they knew each other. If you like Westerns, or just a good revenge tale, check this one out.

10. The Gangs of New York (2002)

DiCaprio and Daniel Day-Lewis in a film by Martin Scorsese, those words alone are enough to get anyone excited. Gangs of New York as well as Catch Me if You Can earlier in the year are the films in which DiCaprio evolved from teenage heartthrob to fully fledged actor.

The film centers on the titular gangs, each fighting for control of the Five Points neighborhood of New York while at the same time the civil war rages on. The story follows Leonardo DiCaprio’s Amsterdam Vallon as he seeks revenge on gang leader Bill the Butcher played by Daniel Day-Lewis, a violent yet charismatic crime boss responsible for killing Vallon’s father years earlier.

The film currently has the distinction of having the third highest amount of Oscar nominations without scoring a single win, which is surprising given the amount of talent both on and off the screen. Despite this, it led to a five film collaboration between Scorsese and DiCaprio and plenty of future acclaim. Something which I hope to see continue for years to come. – James Hadden

9. The Man In The Iron Mask (1998)

While this movie has its share of cheesy moments, and deviates wildly from the book on which it is based (and even more so from the actual historical events), it’s one of my absolute favorites. It’s such a wonderfully intriguing “what if?” story that we will never have a real answer to. So, all aboard the crazy speculation train, for a big-budget, (almost) perfectly cast Hollywood swashbuckler.

DiCaprio plays two very different roles – the spoiled, selfish, cold-hearted King Louis XIV, who lives in ridiculous opulence while the people of Paris starve; and a quiet, shy, and very kind young man known only as Phillippe. It is soon revealed that Louis and Phillippe are twins, separated at birth to prevent any dispute over who is the rightful heir to the throne. Phillippe lives many years in peaceful ignorance of his birthright, raised in an isolated countryside cottage. However, once Louis learns of the existence of his twin, he does the unthinkable to protect his power and position – Phillippe is taken away from his home and thrown in a lonely cell in the Bastille, his head encased in an iron mask to prevent him from ever being recognized.

Meanwhile, the legendary Musketeers – Athos, Porthos, Aramis, and D’Artagnan – have had enough of King Louis’ cruelty. Aramis has learned of Phillippe’s existence, and has devised a brilliant but daring plan to replace the universally hated Louis with the soft-hearted Phillippe, for the good of all of France.

The escapades of the Musketeers are incredibly entertaining, but with two main roles, DiCaprio is front and center in almost every scene. When these scenes are being shared with the likes of Jeremy Irons, Gabriel Byrne, Gerard Depardieu, and John Malkovich (the one miscast in my opinion, but that’s neither here nor there), you’d better bring your A-game.

Does he succeed? It depends on which scene you’re watching. For me, he was more believable as Louis. The king’s cold, calculating demeanor seeps out of his dispassionate gaze, drips from his every unkind word, and permeates his interactions with everyone, even the Queen Mother. Phillippe, on the other hand, while certainly more likeable, is a bit far-fetched in his extreme innocence and kindness. He seems to harbor no ill will towards those who have lied to him his entire life, or even towards the brother who tried so hard to erase his very existence. While the Musketeers are certainly right to believe that he would be better suited to look out for the best interests of the citizens of France, it’s a bit of a stretch to think he will adapt well to the power, jealousy, and greed that will surround him as monarch.

All in all, it’s DiCaprio’s costars who truly shine in this film, but he plays his roles well enough to keep you entertained. Highly recommended for anyone whole loves period pieces, or glammy Hollywood versions of the classics.

8. Django Unchained (2012)

This film was all about Jamie Foxx and Christoph Waltz but whenever came into scene as Calvin Candie, he almost stole the whole film. The villain was fun and playful and DiCaprio sold every bit of dialogue. His dedication for the character was so strong that even when he injured his hand in an intense interaction with Waltz and Foxx, DiCaprio kept the scene going till the Tarantino yelled “cut”. That take would be the one that ended up in the final cut. – Mark Salcido

7. Romeo + Juliet (1996)

Everyone knows the story. “Two households, both alike in dignity. In fair Verona where we lay our scene. From forth the fatal loins of these two foes, a pair of star-cross’d lovers take their life…………..Never was there a tale of more woe, than this of Juliet and her Romeo.” You probably had to read it in high school English class. But you’ve never seen the tale told in quite such a unique way.

Despite adhering, word for word, to the original Shakespearean dialogue, the setting is the thoroughly modern-day Verona Beach. The warring Capulets and Montagues are essentially rival gangs, each holding onto a bitter vendetta against the other. The blood feud is older than any of its current participants, but none of them seem to question its necessity. Their hatred simply IS, and always will be.

It is under these conditions that Romeo, a Montague, meets Juliet of the House of Capulet. They fall instantly in love, despite the fact that Juliet’s father wants her to marry another man. (She’s only 13, but apparently, that’s just how things were done back in the day.) The pair take their plight to Friar Laurence, a clergyman who has wished for many years to see peace between the two families. To that end, he secretly marries them.

The shit promptly hits the fan, with Romeo being challenged to a duel. He declines, but his friend Mercutio fights in his stead. When Mercutio is wounded, by Juliet’s cousin Tybalt, Romeo takes his revenge and kills Tybalt. Romeo is immediately exiled from Verona, and Juliet’s father moves ahead with his plans to marry her off. She runs to Friar Laurence, pleading for his help. The friar gives her a potion which will slow her breathing and her heartbeat, making her appear dead. He also sends a messenger to Romeo, to inform him of the plan, wherein he will go to Juliet’s crypt, and take her away when she awakens.

Everything goes tits-up when Romeo never receives the message. Believing his love to be truly dead, he does indeed go to her crypt. Taking a bottle of poison from his pocket, he drinks it, and slumps lifeless over her prone body. Of course, that’s when she wakes up, finds him dead, and stabs herself with his dagger. The End.

Taking on one of literature’s most seminal classics is always risky, infinitely more so when your director is as ambitious as Baz Luhrmann. The updated setting juxtaposed against the ancient dialogue should have been ridiculous. But it isn’t, and that’s entirely due to the two leads. DiCaprio and Claire Danes embody the doomed lovers in such an impassioned and believable way, you end up immersed in their plight even though you know exactly how it will end. If you’ve ever thought Shakespeare was boring, this movie will change your mind.



6. Inception (2010)

There’s just so goddamn much going on in Chris Nolan’s dream-invading blockbuster. The scale of the project rewrites Hollywood’s understanding of the word ‘epic’, as it pushes it’s plot downwards as well as forwards. And it’s a movie that might well have failed in its goal were it not for a career best performance from DiCaprio.

His turn as Dom Cobb is the glue that sticks the whole thing together. Every single twist and turn that takes place within the narrative is inexorably linked to Dom’s past and his plans for the future. Leo’s central figure of Cobb is completely focused and driven, coordinating and justifying the noisy and spectacular events that are assaulting the viewer’s senses.

It’s a performance very much like Guy Pearce in ‘Memento’. Or Tom Cruise in ‘Edge Of Tomorrow’. Cobb is a man who is painfully aware of what’s at stake, and what the chances are of it slipping away from him, but he’s prepared to risk and gamble everything on getting the outcome he requires. With a lesser actor, the entire central reason for ‘Inception’ would be secondary to the events taking place. Which would have risked leaving it a shadow of the film it would become. – Simon Andrews

5. Shutter Island (2010)

Well, another Scorsese collaboration and rightfully so.  DiCaprio and Scorsese had already previously worked on three films and they decided to keep the winning streak rolling. The mystery of the role and story were well put together to start with, but DiCaprio added more depth and a ton of emotions that not just any actor could pull off. And when the final reveal of the character’s past is discovered, he goes all out with the water works that put the finally touches on an amazing performance and the continuing legacy of Dicaprio’s acting. – Mark Salcido

4. Titanic (1997)

Speaking of knowing the characters are doomed, but hoping it will somehow end differently………..

While he’d had a few critically acclaimed roles before Titanic, this was the film that introduced the affable charm of Leonardo DiCaprio to the world at large. *Everyone* knew his name within a few weeks of its release. And that is largely because he made Jack Dawson so utterly likeable. That, and his palpable chemistry with Kate Winslet, propelled the film to the title of highest-grossing of all time, which it held for more than a decade.

Jack is a classic starving artist, a drifter who draws whatever catches his eye, eats whatever is available, and sleeps wherever he happens to be tired. It’s a life he has chosen to live, and he’s perfectly happy in it. However, when he wins a ticket for the maiden voyage of the RMS Titanic in a card game, he thinks his luck might be about to change. It is a fine ship, filled to the brim with people of wealth and class. Although he is crammed into steerage with the other destitute passengers, he considers himself fortunate to be there at all.

His first night on board, he is walking the deck when he encounters a young woman on the bow, about to jump into the icy waters below. He manages to talk her down, and is instantly taken with her beauty and her strong spirit. Rose DeWitt Bukater is a high-born lady in every sense of the word, but her family has only their name. In an effort to restore their fortunes, Rose’s mother has convinced her to marry Cal Hockley, a steel magnate who possesses all of the wealth, but none of the grace, of his fellow first-class passengers. They are to be married in Philadelphia, as soon as the ship docks in America. Feeling desperately trapped, Rose saw jumping as her only way out.

Her meeting Jack changes both of their lives forever. Each sees something in the other that they never knew they needed until then. Rose pledges to abandon the life her mother has planned for her, and leave the ship with Jack. Having definitively chosen love over money, they have Cal’s anger and jealousy to deal with. When the ill-fated ship hits its destined iceberg and begins to take on water, Cal has Jack locked up in a lower room, having accused him of being a thief. Rose is able to find and rescue him, and they eventually make their way to the deck of the sinking vessel.




The sinking scenes are terribly sad, knowing that this was a real event that claimed more than a thousand lives. But few things are more heartbreaking than watching Jack realize he’s going to die, and slowly. He has managed to find Rose a broken wooden door to float on, but can’t find anything for himself, and so he is doomed to freeze to death in the frigid sea. Rose loses consciousness at some point, and is awakened by the horn of a rescue boat. The first thing she sees is Jack, dead and gone, with ice forming on his blue face. She is still holding his hands. Finally, she must make the desperate decision to let him go, so that she can wave her arms to get the attention of the lifeboat. His body sinks into the depths, never to be recovered.

On board the rescue ship, she gives her name as Rose Dawson, taking the first concrete step in living a life free of her mother, Cal, and their expectations. She will instead live her life to honor Jack, as he made her promise she would do.

Titanic is an absolutely spectacular film, deserving of every accolade it has received over the years. The production values are second to none, the score is perfect, and the direction is flawless. But it is the acting that truly makes the story. The two doomed lovers are the heart and soul of the movie, giving a real, personal voice to the many victims of this terrible tragedy.

3. Blood Diamond (2006)

Leo’s butchering attempt at a South African accent is arguably the most memorable aspect of his role in Blood Diamond, but let’s be fair, it isn’t the easiest of accents for an actor to turn their hand to. Some of Hollywood’s finest have ruined performances by agreeing to try it. Daniel Craig (Munich). Matt Damon (Invictus). Erm….. Patsy Kensit? (Lethal Weapon 2).

His performance in this movie is notable as it marked the definitive transition point in his career between being cast as a conflicted younger man, and the start of his darker and grittier casting. The whole film is filthily permeated with the dirt and dust of the African Contintent, saturating and enveloping everybody and everything that comes into contact with it.

But Leo’s turn as Bobby Archer is that of a man fully aware of where and who he is. His path to redemption may appear somewhat predictable and obvious, but as his story comes to an end, he is fully self-aware and accepting of what he has achieved, and what it means to all concerned. No more performances as put-upon boys, now it would be for roles of men trying to deal with the consequences and result of their decisions and actions. – Simon Andrews

2. The Departed (2005)

One of the most influential figures behind the evolution of Leo DiCaprio is his work with Martin Scorsese . The Departed marked their third film together, with DiCaprio having become the great director’s latest in a long line of illustrious cinematic muses.

The understanding and respect that the two men have for each other is reflected in Leo’s performance. It’s a noisy movie, packed with heavyweight performers, and it would have been easy for the younger actor to lose himself. With Jack Nicholson, Alec Baldwin, Martin Sheen, Ray Winstone and Mark Whalberg all onscreen, it was a combination of Leo’s developing talents and Scorsese’s clear admiration for him that clearly elevate his performance above that of co-star Matt Damon.

Which hits home all the more with the sudden and shocking end to the movie. Because the plucky and determined young cop has managed to survive and prevail over so much, the conclusion to his tale is so much harder to swallow, sealing it as one of his most memorable performances. – Simon Andrews



1. The Wolf of Wall Street (2013)

Scorsese and DiCaprio decided to continue their chemistry by tackling another factor of America and greed with this true story of wealthy stock-broker Jordan Belfort. No punches were pulled in this sex and drug fueled wild ride that involved crime, corruption and the federal government. DiCaprio definitely deserved his nomination for this role because you got sense that the actor witnessed all the events that this film depicted first hand. But of course, he didn’t win. So, let’s beat our chest in solute for DiCaprio in Wolf of Wall Street. – Mark Salcido

Honorable Mention:

What’s Eating Gilbert Grape (1993)

What are some of your favorite DiCaprio films? Tell us in the comments!

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