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Leonardo DiCaprio’s Movies, Ranked Worst to Best

From ‘Titanic’ to ‘Django Unchained,’ rating the good, bad and WTF ugly of Leo’s big-screen career

Leonardo DiCaprio, Best to Worst

Illustration by Ryan Casey

If the hype is to be believed, Leonardo DiCaprio might finally win an Oscar for his performance in Alejandro Gonzalez Inarritu’s sprawling survival-revenge Western The Revenant. Hidden behind a bushy, Brooklyn hipster-style beard, the actor reportedly put himself through hell and back for the nearly wordless part — from eating raw bison liver to sleeping in animal carcasses on the film’s freezing, remote set up in Calgary. (The movie’s arduous shoot is already becoming the stuff of suffering-for-your-art Hollywood mythology.)

None of the accolades should surprise anyone who’s been following the star since the beginning, however. Over a nearly three decade career, DiCaprio has grown to become one of our most dedicated, intense actors. It was apparent from the start that this was a young man of rare talent –he won acclaim for movies like the rough coming-of-age story This Boy’s Life, and had garnered an Oscar nomination as early as 1993, for playing a mentally disabled teenager in What’s Eating Gilbert Grape? A series of romantic roles in the 1990s – in films like Baz Luhrmann’s MTV-style Shakespeare adaptation of Romeo + Juliet and that little movie about a sinking ship and an iceberg that nobody remembers – turned him into an international heartthrob.

DiCaprio could have easily coasted on that matinee-idol success for the rest of his career; instead, he combined his stardom with ambition and talent to became a first-class leading man, working with directors like Steven Spielberg, Ridley Scott, and – most notably – Martin Scorsese, the latter of whom he’s so far made five movies with. (He also helped Scorsese win his first Oscar, with the gangster epic The Departed.) So with another impressive, sure-to-be-awarded performance upon us, now seems like a good time to go over his marvelous career from stem to stern. Here are all of DiCaprio’s movies — not his roles, mind you, but the actual films — ranked worst to best.

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Illustration by Ryan Casey


‘The Departed’ (2006)

Scorsese finally won that elusive Oscar with this Boston crime thriller – a remake of the terrific Hong Kong thriller Infernal Affairs (2002) — that had DiCaprio as a cop infiltrating the mob and Matt Damon as a mobster infiltrating the police force. It's an intricate, fascinating tale of competing cat-and-mouse games, but the director and his screenwriter, William Monahan, infuse it with so much tragedy that it winds up becoming something almost mythic. And DiCaprio is fantastic here, in a totally unglamorous, grubby role as a desperate man who almost loses his identity. It's one of his all-time greatest performances.

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Illustration by Ryan Casey


‘Inception’ (2010)

Christopher Nolan's sci-fi heist thriller has DiCaprio entering people's dreams and stealing their thoughts — only this time, for that proverbial one last job, he and his team are hired to implant an idea inside someone's mind instead of boosting the usual cerebral data. How did a film with a plot so byzantine, and a set-up so offbeat, ever become such a massive hit? Credit Nolan's dexterity with dialogue and interlocking setpieces, but let's not also forget DiCaprio's remarkable, underrated performance as a brilliant, tormented thief trying – and failing – to keep his own demons at bay. This is one of the saddest blockbusters you'll ever see, and a lot of that is due to to its star, who brings a humanity to what could have easily been a generic brooding hero type.

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Illustration by Ryan Casey


‘Titanic’ (1997)

What's that you say? You don't think this movie is all that? Tough. James Cameron's 1997 box-office record-breaker, Oscar winner, and all-around pop-cultural juggernaut was the most expensive movie of its time — not to mention a years-in-the-making, snidely-dismissed production that sometimes seemed like it would never see the light of day. Then it finally came out … and it was awe-inspiring. As a piece of filmmaking, it does for the vast darkness of the sea what David Lean's Lawrence of Arabia did for the sensuousness of the desert. It also presents a disaster movie extravaganza without ever losing its sense of tragedy (even as it indulges in state-of-the-art effects to show the devastation of the historic shipwreck).

And then there's Leo and Kate. Yes, the logline of their relationship – adventurous drifter falls for frustrated, upper class girl – is pure corn. But the two young stars infuse their earnest back-and-forth with so much genuine emotion that it's hard not to get swept up in their doomed love affair. It's still the highpoint of DiCaprio's career, and one of the greatest old-school movies to come out of Hollywood in the last 20 years.

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