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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

16

‘The Great Gatsby’ (2013)

DiCaprio reunited with his Romeo + Juliet director for this version of F. Scott Fitzgerald's borderline-unfilmable novel, and the results are less dire than might have initially been feared. No, Baz Luhrmann still doesn't "crack" Gatsby – like other directors before him, he can't help but try to make it a love story, even though it's actually the opposite of that – and his all-too-faithful recounting of Fitzgerald's plot works against the overall revisionist spirit the enterprise. (Cue opulent party set to a Fergie song.) But the star himself is such a charmer, and somehow accessible despite his obsessiveness, that it almost doesn't matter. This is the first film in many years that allowed him to showcase a real smile; for a brief moment, it was nice to have Leo the Romantic back in our midst.

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15

‘Celebrity’ (1998)

Woody Allen's homage to Fellini's La Dolce Vita, in which Kenneth Branagh does his best Woody Allen impersonation as a hotshot magazine journalist whose insecurities get the best of him. Once you look beyond Branagh's too-nebbish-by-half performance, the film is actually a pretty funny, semi-cutting portrait of modern celebrity culture. But even its detractors agree that DiCaprio is the best thing in the film, playing an entitled, bratty movie star who invites the writer-hero to witness, and participate in, his debauched shenanigans.You may draw your own conclusions, folks.

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14

‘What’s Eating Gilbert Grape?’ (1993)

In this sharply observed but gently told coming-of-age tale, DiCaprio plays Arnie, the mentally handicapped younger brother of Johnny Depp's titular small-town slacker. The film, based on Peter Hedges' novel, is an offbeat mix of typically quirky elements, and it could have easily been hard to stomach. But the author and director Lasse Hallstrom's affection for these characters shines through. Their greatest asset is the young Leo himself, in his first Oscar-nominated role, bringing great sensitivity and complexity to a part that might have come off as cloying or cynical.

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13

‘Romeo + Juliet’ (1996)

To a generation that came of age with this Shakespeare adaptation, DiCaprio and Clare Danes were the last word in star-crossed pairings, playing the Bard's doomed couple in Baz Luhrmann's histrionic, gang-war-filled modern take on the classic play. The Aussie filmmaker's over-the-top treatment of the material is often laughable — but the chemistry between the leads is undeniably amazing, and Danes gave one of her best early performances in this. DiCaprio, for his part, sounds great and looks even better; his success here helped lay the groundwork for his epochal turn in Titanic a few years later.

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12

‘The Beach’ (2000)

Until it goes off the rails in its final act, Danny Boyle's adaptation of Alex Garland's thriller about a small colony of folks who've settled a remote Southeast Asian island is a moving portrait of generational angst. These Western travelers and backpacking ex-pats are searching for utopia in a highly technologized world, and DiCaprio's charming cockiness comes in handy as his adventurous tourist goes from looking for connections to desperately trying to survive. This highly anticipated film, which was the first project DiCaprio signed on to following his Titanic superstardom, didn't win much love back when it was first released. It's worth another look.

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Leonardo Dicaprio; This boys life; departed; titanic

11

‘Shutter Island’ (2010)

DiCaprio's work with Martin Scorsese has always centered around obsession, and this noirish mystery is their most haunted film yet — as well as the most vulnerable the actor has ever been. He plays an investigator looking into the disappearance of a cryptic inmate at a creepy island insane asylum. As he delves further into the case, however, his own psyche starts being called into question. So DiCaprio not only has to carry the narrative, but he also has to tear down his character as the film proceeds. To keep us watching while fostering such uncertainty is the mark of a truly great actor.

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10

‘This Boy’s Life’ (1993)

This adaptation of Tobias Wolff's memoir gave DiCaprio one of his earliest leading roles: Toby, the loving son of troubled single mom Ellen Barkin. When she shacks up with a seemingly respectable but domineering and abusive Robert De Niro, it's war between the adolescent offspring and his stepfather-to-be. It's an evocative, touching little movie, defined by the powerful bond between Barkin and DiCaprio. And as the young actor's character goes from being a wide-eyed son to a rebellious greaser to an independent, sensitive young man, his performance gains complexity.

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9

‘The Wolf of Wall Street’ (2013)

While this is far from Martin Scorsese's best film, it contains some of DiCaprio's finest work to date, as real-life penny-stock kingpin and financial huckster Jordan Belfort. The director in recent years has alternated between epic fictions and major musical documentaries — and in some strange way, this is an unlikely combination of both. Belfort was famous for his rousing, take-no-prisoners, tent-revival-like speeches to his employees, and so much of this film is Scorsese just turning his cameras on Leo and watching him go — the Mick Jagger of Wall Street jag-offs.

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8

‘Revolutionary Road’ (2008)

DiCaprio and his Titanic partner Kate Winslet were reunited for this adaptation of Richard Yates' classic novel about suburban despair and thwarted dreams, American style. The two movies could not be more different: If the earlier blockbuster was a proudly florid melodrama about two kids pining for a life of adventure, this is a chilly, precise and ultimately heartwreenching drama about two adults slowly discovering that the world they once imagined is nothing like the living hell they have now. And DiCaprio is excellent as a man caught in a downward spiral of disillusionment, slowly coming to terms with the fact that he will never make anything of himself.

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7

‘Django Unchained’ (2012)

As the sneering, charismatic slave-owner Calvin Candie, DiCaprio is the dirty, demented heart of Quentin Tarantino's controversial Western-exploitation-revenge flick. What's most remarkable about this performance is the weird affability the actor brings to this pathetic, delusional monster. This is a man who breeds and forces his slaves to fight each other, who has a weird fascination with France, and who is, at heart, a murderous psychotic. But he's also so charismatic that – spoiler alert — once he's dispatched from the narrative, the air goes out of the film. It's a career highlight; he deserved an Oscar for this one, frankly.

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6

‘The Aviator’ (2004)

In Scorsese's expansive and lavish look at the early years of millionaire businessman/inventor Howard Hughes, DiCaprio has to blend his still-fresh faced charm with an obsessiveness that borders on madness. These are the years when Hughes was working on his delirious dogfight movie Hell's Angels, romancing Katherine Hepburn, trying to build the legendary Spruce Goose, and facing off against hostile politicians. The director connects with the man's ambition and compulsiveness, not to mention his gnawing sense of inadequacy. And DiCaprio's performance proves he's versatile as hell.

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5

‘Gangs of New York’ (2002)

At the time of DiCaprio's first collaboration with Scorsese, many were initially perplexed: Pretty-boy heartthrob Leo making a period picture with the king of fast-talking criminals? But the actor wasn't a bad fit for the role of Amsterdam Vallon, an Irish-American young man biding his time in order to avenge the death of his father (Liam Neeson) at the hands of the Nativist gang leader Bill the Butcher (Daniel Day-Lewis, in what might be his greatest performance). More befuddled than rough, Amsterdam has to grow into the role of gang-leader himself — and Leo plays him as a brooding naïf, an ideal approach against Day-Lewis' boisterous, whip-smart villainy.

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4

‘Catch Me If You Can’ (2002)

In this Steven Spielberg hit, DiCaprio plays Frank Abagnale, a real-life con-man who traveled around the country and lived the high life as he impersonated pilots, lawyers, and doctors. It was an inspired bit of casting, capturing the actor right as he was transforming from fresh-faced romantic into a brooding young man — he could still play an innocent. And in the film's first half, as his character watches his parents' marriage break up, his heartbreak is palpable. By the end of the film, he's become a totally different person — a journey from kid to slightly jaded adult that's charted on Di Caprio's face.

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3

‘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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2

‘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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1

‘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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