Leonardo DiCaprio, Revisited: The Secret to His Modern Acclaim

The 'Once Upon a Time in Hollywood' star's biggest roles this century are all connected.

Once Upon a Time in Hollywood Leonardo DiCaprio Filmography
How did Leonardo DiCaprio become this century’s most enduring star? Kaitlyn Flannagan

Hollywood subsists on melodrama, so excuse this indulgence: in the presence of great acting, audiences are transmogrified into witnesses, keepers of idealized memories. With Quentin Tarantino’s Once Upon a Time… in Hollywood sauntering into theaters this weekend, the idea of era-defining A-listers to whom we saddle with representative meaning is once again at the forefront of the pop culture conversation. Why? Because not even Stephen Hawking loved stars as much as the movie-going public.

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There are many worthy contenders for the title of best living actor—Daniel Day-Lewis, Joaquin Phoenix, Denzel Washington, etc.—a nebulous distinction not quantifiable by Academy Award nominations or box office grosses. But a popular choice for the peak of his generation is Leonardo DiCaprio. Once Upon a Time… in Hollywood marks his 26th major feature role and, ironically, 26 years since his big screen debut. In that time, he’s grown from teen heartthrob to “king of the world” to serious actor, while emerging as arguably the most bulletproof celebrity when it comes to critical acclaim. He is a brand unto himself.

SEE ALSO: What Scares Leonardo DiCaprio About the Streaming Industry

What has passed by prying eyes, relatively unnoticed, is the secret to his modern Olympus-toppling career: DiCaprio is really good at playing guys who absolutely lose their shit. Looking through 10 of his biggest performances of this century, the connective tissue between roles begins to crystallize.

Gangs of New York (2002)

“You know how I stayed alive this long all these years? Fear,” Day-Lewis’ scene-chewing Bill tells DiCaprio’s Amsterdam. While the Butcher was referring to the fear he inspires in others, he might as well have been offering a thesis statement on DiCaprio’s career in the 21st century. The 44-year-old is at his best when he’s portraying men drowning in trepidation, who are more concerned with hiding that fear from those around them via explosive emotional outbursts—Bill also tells Amsterdam he has a “murderous rage” within him—than they are with reaching the nearest life raft.

Gangs of New York marked the first collaboration between DiCaprio and Martin Scorsese, a pairing that has gone on to produce sterling work for nearly two decades. In sports, there are often catalysts for a good player making the leap to become a great player. For DiCaprio, finding his directorial muse in Scorsese is arguably that launching point, and it ironically all began in a movie that squarely belongs to his co-star.

Amsterdam is a man fueled by revenge. Like Edmond Dantès before him, the character enables that pulsating hatred to drive him forward, even as all else in his life recedes to the background. That idea of a sustained mental collapse, whether the result of fear or rage, across the course of a film would be at the core of DiCaprio’s characters for years to come.

Catch Me If You Can (2002)

To DiCaprio’s credit, he has always sought out the best filmmakers. By the time he teamed up with Steven Spielberg for Catch Me If You Can, he had already worked with Baz Luhrmann, James Cameron, Danny Boyle and Scorsese. But Spielberg was able to take full advantage of the actor’s boyish youthfulness in a way that perfectly complimented this breezy and likable caper. The director draws out the character’s downward spiral with an undercurrent of childish fear. Fear of a broken home, fear of being alone, fear of one’s true self—these are the teenaged anxieties that root the film’s characterization of the real life con man, check forger and imposter Frank Abagnale Jr.

DiCaprio builds that frazzled energy into a manic episode in the above scene as the walls close in around him. But Catch Me If You Can is a more gentle wielding of the actor’s tension than the aggressive percussion of Gangs of New York. Abagnale trades identities like a hermit crab rotates shells; his desperation for an anchoring paragon is bleary-eyed and wan—the underside to Amsterdam’s rage and fury. Here, DiCaprio funnels his go-to descent into madness trope into something more palatable and fun. It’s a lighter touch than his normal dramas which often bear the weight of a stone dropped into a pond.

The Aviator (2004)

Scorsese understands something about DiCaprio’s composition as an actor that not every director always taps into.

“A key thing about Leo—and I always tell him this—is he’s a natural screen actor,” the filmmaker recently said. “He could have been in silent films. It’s the look on his face, the look in his eyes. He doesn’t have to say anything. It just reads, and you can connect with him. Not everybody is like that.”

That ghastly look on Howard Hughes’ face as he stares into the mirror in the fleeting closing scene of The Aviator is the actualization of Scorsese’s sentiment. It says everything it needs to without a word. It helps that Hughes’ real life struggles fit with DiCaprio’s preference for instability. The billionaire multi-hyphenate sadly suffered from OCD, chronic pain from a near-fatal plane crash and progressive hearing loss.

The Aviator would score DiCaprio his second Oscar nomination. Though it fell squarely within his wheelhouse of tortured characters, it would help move the perception of Leo as a boyish spirit of rebellion—at 28, he played Abagnale from age 16 to 21 in Catch Me If You Can—to something more mature. This would prove crucial to his next film.

The Departed (2006)

In Breaking Bad, Walter White’s cancer didn’t lead him down a path of villainy, it merely liberated what was always lurking within him. Similarly, The Departed‘s Billy Costigan doesn’t transform into a violent aggressor because of his challenging undercover duty. The job just enables him to slip into pre-existing patterns. The constant fear that springs from his double life manifests itself into unstable behavior that steadily devolves as the tale unwinds until reaching a tragic conclusion. That’s Leo’s sweet spot.

His scenes with Vera Farmiga are particularly revealing, allowing him to color in the different shades of anxiety that plague him throughout. This is a pained and lonely man (“there’s no one else,” he tells her late in the film) enveloped by life-and-death stress; sooner or later, the fuse is going to burn out and the dynamite will explode. His “how I feel” bit in the scene above is the first instance of genuine expression he’s had in months. It’s depressingly cathartic.

Shedding the baby face and innocence of movies past, The Departed is really the first time in DiCaprio’s career that he feels dangerous. He’s fully formed here, not just owning the screen but the whole damn theater.


Blood Diamond (2006)

Another tricky accent—you can’t ever say DiCaprio shies away from a challenge!

Blood Diamond is more of a sharp commentary on exploitation better suited to hard-hitting documentaries than a narrative feature. Predictable story compromises and a familiar skeleton keep the film from reaching its full potential. But DiCaprio puts in a strong effort to humanize his character, Danny Archer, the eager sinner.

Archer is not a good man. He does a good thing at the end of this movie, thus fulfilling Western cinema’s need for top line redemption. But he is not a good man. He’s a former Angolan mercenary who smuggles diamonds in return for weapons that he then passes to a rebel army prone to mass murder, rape and kidnapping.

Ironically, though, DiCaprio may be at his most interesting when he’s deliberately playing with kinetic swagger rather than reluctance. He’s like a star NBA player who enters the zone only when his team is desperately trailing on the scoreboard. The actor paints Archer with just enough soulful regret against the backdrop of his nihilistic fatalism that his sins are rendered thin next to his passion. It’s emotional manipulation, sure, but it mostly works.

It’s hard to understate just how much Blood Diamond belongs to DiCaprio, who contorts his normal losing-his-shit arc into something a bit more commercially external (gun fights and romance!). His leading presence seems effortless in a way that suggests everything around him would collapse in his absence.

Shutter Island (2010)

Yoda famously once said that “fear is the path to the Dark Side.” Well, in Teddy Daniels’ case, willful ignorance is the first step.

Shutter Island takes DiCaprio’s on-screen propensity for mental drain circling to the hallucinogenic next level. This time, however, we’re largely working backwards from the end point. It is revealed at the end of the film that his character ignored his wife’s deteriorating mental state, which ultimately led to the destruction of his family and his complete descent into senility.

Liking or relating to the central character is the single-most integral element in convincing an audience to buy into a story. Here, DiCaprio weaponizes guilt and grief, inseparably pairing the powerful duo in a character study disguised as a mind-bending puzzle. We may not necessarily root for him, but we understand his pain and sympathize with his decision to do away with it via a literal soul-crushing lobotomy. Remorse is universal.

The eccentricities of Shutter Island don’t hide that nucleus, it merely repackages it, like Picasso taking a crack at his own version of the Mona Lisa. Whether or not that’s actually welcomed and enjoyed is up to each individual audience member.

Inception (2010)

In retrospect, it’s difficult to discern where the reality-altering Shutter Island ends and the fantasy-making Inception begins.

In Shutter Island, Daniels’ remorse was justified as he was responsible for the tragedy that plunged him into dire anguish. There, he cocooned himself from the truth by escaping into his delusions. Christopher Nolan’s Inception is the inverse in which reality offers DiCaprio’s Cobb an opportunity for salvation.

“No matter what I do, no matter how hopeless I am, no matter how confused, that guilt is always there reminding me of the truth,” he says while speaking to the dream version of his dead wife summoned by his own subconscious (there was a lot going on in this movie). Inception is all about internal torment made external; the dream’s subconscious projections are a creatively modern execution of Shakespeare’s internal monologues.

Again, it is DiCaprio battling against his own psyche while examining the terrifying and uplifting sides of human nature. It’s also a validation of the prestige actor as an action star in much the same way that The Bourne Identity added another dimension to Matt Damon. Nolan managed to combine DiCaprio’s love of anxiety-riddled mourners struggling to decipher what’s real with the traditional wish fulfillment masculinity of a full-fledged blockbuster. No easy feat.

(Side Note: Directors need to retire the dead wife trope.)

Django Unchained (2012)

By now, the story of DiCaprio’s injury in the above scene has become famous. Rather than cut after accidentally slicing his hand open, he soldiers through, seemingly replenished by the bloody mishap.

Remember what we said about Blood Diamond and DiCaprio’s ability to twirl center stage? Put him in a morally dubious position and let him peacock, and you can see why the man is one of the last remaining movie stars. As the reprehensible, slave-owning Calvin Candie, all DiCaprio does is strut.

While the majority of the actor’s filmography over the last two decades sees him slowly deteriorate over the course of a film, Django Unchained has him start at the bottom and stay there. Candie, a cruel and unforgiving intellectual wannabee insulated by money, is a functionary of the highest order. His anxiety over wanting to be taken seriously against a sneaking sense of inferiority sparks the madness that is present throughout.

Quentin Tarantino is many things but subtle is not one of them, and DiCaprio charges into the role of antagonist with gleeful abandon, relishing the opportunity to fully break bad for the first time in hyper-stylized fashion.


The Wolf of Wall Street (2013)

A splinter of his work in The Aviator, The Wolf of Wall Street sees DiCaprio take on another real-life figure who flew too close to the sun. Stockbroker Jordan Belfort rode a meteoric rise to a devastating crash fueled by drugs, booze and greed.

The Wolf of Wall Street is a story of excess and that also applies to Leo’s fully committed performance. Never before has he been so on board with acting BIG than he is here, going full gonzo in a disheveled tour de force (Hollywood, get this man in a straight comedy pronto). The materialistic extravagance, the full-throated speeches—all of it is only there to remind us that this is not really a man but indulgence incarnate.

Jordan Belfort’s struggles are a bit more realistic than that of DiCaprio’s dream spy, but the framework of his character follows the same basic formula the actor has stuck to over the last 20 years. The undoing of a man from the inside out can be wrought in a variety of ways.

The Revenant (2015)

Grief and fury power Hugh Glass in The Revenant, and it’s not a stretch to assume the same might have been true for DiCaprio in his never-ending quest for Oscars gold. The real-life lengths DiCaprio went to for this one are either impressive or idiotic. He eats raw bison, sleeps in animal carcasses and crawls into sub-freezing rivers all in the name of performance (seriously). Basically, he drew on his on-screen persona to become a real-life crazy person for the role.

If that’s not the culmination of slipping into the most deranged, violent and delusional characters the last 20 years has to offer, what is?

Leonardo DiCaprio, Revisited: The Secret to His Modern Acclaim