Leonardo DiCaprio’s Best Performances Ranked

With five Academy Award nominations and a win for “The Revenant,” Leonardo DiCaprio has established himself as a Hollywood icon who has stayed classy, opting for challenging roles with major auteurs including Quentin Tarantino and Martin Scorsese — all the while chasing humanitarian issues through his prolific environmental activism.

In “Once Upon a Time in Hollywood,” DiCaprio played a washed-up movie star at the end of his tether — which is perhaps the biggest stretch yet for an actor with such an esteemed pedigree and enviable body of work. With nearly $3 billion dollars of global box office to his name, and a list of roles that prove his selective instincts each time out, DiCaprio is one of the few movie stars working today who always delivers something worth seeing.

That includes in his latest film, Adam McKay’s end-times satire “Don’t Look Up,” which finds DiCaprio back in the awards conversation for his turn as a flustered astronomy professor heralding a planet-annihilating comet to deaf ears. DiCaprio gets many a chance to chew the scene — including in a few pivotal, “Network”-inspired, blistering monologues about the idiocy of the modern world — but it’s in the film’s quieter moments as Dr. Randall Mindy that DiCaprio reminds us of his subtle comic gifts and the human touch he brings to his characters. (See the film’s final moments, where DiCaprio delivers a touching line-reading that he ultimately improvised.) And while DiCaprio may have started his career as a marquee heartthrob in films like “Romeo + Juliet” and “Titanic,” he’s now equally adept at playing somewhat schlubby, affable outsiders.

While “Don’t Look Up” may not be DiCaprio’s best-ever turn, there are plenty of great performances from the Oscar-winning actor to look back on. Below, IndieWire picks 11 of his best.

1. “The Wolf Of Wall Street”

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Charting stockbroker Jordan Belfort’s (DiCaprio) rampant, raucous descent into corruption and self-destruction beginning in the late-1980s, “The Wolf of Wall Street” is director Martin Scorsese’s finest collaboration with his 21st-century leading man. As Belfort, DiCaprio delivers both his funniest and most heartbreaking performance as a megalomaniac for whom the road of excess leads to the palace of wisdom — the hard way. However, while Belfort is a contemptible figure who epitomizes the worst tendencies of capitalist greed, DiCaprio takes on the radical task of injecting sympathy into the man all the way through, transforming this scheming moneymaker into the ultimate paradox of our troubled times.
2. “The Aviator”

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DiCaprio stars as billionaire and aviation tycoon Howard Hughes in Scorsese’s Hollywood epic, tracing the Tinseltown magnate’s decline on the way to Shakespearean levels of power-grubbing and greed. The actor tragically portrays Hughes’ unraveling into an obsessive-compulsive disorder that would alienate those closest to him.
3. “The Revenant”

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DiCaprio’s turn in Alejandro G. Iñárritu’s man-versus-nature epic is a barbaric yawp of a performance, plunging the actor into everything from pitiless conditions in Calgary, Argentina and the U.S., to the innards of a bear corpse. The actor may not be known for physically daunting transformations, but “The Revenant” allowed him to go to new extremes as an actor even as he dazzled with the kind of masculine confidence for which he’s always been known. He won his long-overdue Academy Award for Best Actor for his performance as frontiersman struggling against the elements. As a bracing man-versus-nature odyssey, the movie became the ideal vessel for DiCaprio’s ecologically concious activism, which he acknowledged in his Oscar speech.
4. “Django Unchained”

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DiCaprio’s willingness to play the bad guy was a risk, but he’s committed to portraying a kind of irredeemable awfulness as beguiling Candyland plantation owner “Monsieur” Calvin J. Candie in Quentin Tarantino’s revisionist slave story “Django Unchained” — so committed, in fact, that the actor gashed his hand open during a take and still didn’t break character. DiCaprio managed to avoid getting typecast as the villain in subsequent performances.
5. “Shutter Island”

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Scorsese’s closest approximation to a horror a film, “Shutter Island” offers a showcase for DiCaprio as haunted U.S. Marshal Teddy Daniels. Portraying a man chased by a dark past that is ineffably out of reach, DiCaprio keeps us precariously on the razor’s edge between the real and the imaginary, brooding through Scorsese’s hallucinatory set pieces to create a picture of anguished masculinity. The movie’s eerie, Val Lewton-inspired atmosphere gave the actor the chance to channel a degree of psychological turmoil that he had never shown before onscreen.
6. “Once Upon a Time… in Hollywood”

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DiCaprio gives his most physically comic performance to date in his second collaboration with Tarantino, a world apart from his evil turn in “Django.” As perennially sotted Western star Rick Dalton, DiCaprio brings a touch of pathos to his character’s complicated journey as he ambles through the easy, breezy Los Angeles of 1969 — where disaster loomed just around the corner. Struggling to find outlets for his talents in an ever-changing industry, Dalton is a wistful figure who can’t tell if he’s actually in decline, and allows the actor to give his role a touch of melancholy that feels entirely new for him.
7. “The Departed”

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It’s thanks to DiCaprio’s gritty portrayal of Boston police academy rookie Billy Costigan that, when it comes to Martin Scorsese’s remake of the 2002 Hong Kong film “Infernal Affairs,” you just can’t help pronouncing it “The Depaaahted.” DiCaprio’s Billy endures ups and downs on a road to corruption that, quite memorably, ends with an unexpected bang. This gruff, testosterone-fueled performance helps define this Best Picture winner’s tough atmosphere as much as Scorsese’s own investment in it, and marked a key turning point in the maturation of the actor’s screen presence.
8. “Romeo and Juliet”

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DiCaprio is swooningly good in Baz Luhrmann’s 1996 adaptation of the William Shakespeare classic, leveraging his boy-next-door good looks and debonair charm to embody the ill-fated Romeo Montague, opposite Claire Danes as his doomed lover. With “Romeo and Juliet,” he was, at the time, the epitome of the 1990s teen heartthrob, firing on all cylinders in a charismatic, devastating performance that announced DiCaprio’s stardom to the world.
9. “The Basketball Diaries”

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At just 21 years old, DiCaprio tackled the moving role of heroin-addled basketball star Jim Carroll in director Scott Kalvert’s adaptation of Carroll’s autobiography. DiCaprio portrays the damage and frenzied desperation of drug addiction with aplomb, opposite a terrific cast including Lorraine Bracco and Mark Wahlberg. This is uneasy territory for any actor, but DiCaprio’s ability to pull it off without any distracting showboating provided a window into the delicate maneuvering that would continue to evolve over the course of his career.
10. “Revolutionary Road”

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To watch Sam Mendes’ stately Richard Yates adaptation “Revolutionary Road” is to witness the crumbling of a marriage in real time, with Mendes’ then-wife Kate Winslet sparring with DiCaprio amid the dreary ennui of 1950s suburban Connecticut. Imagine if Jack and Rose survived the sinking of “Titanic” and shacked up to pursue the American dream, only to discover the big fat lie at its core, and you might get some sense of this nightmarish experience. As boozing, womanizing, chain-smoking Frank Wheeler, DiCaprio conveys repression and regret with a furtive glance, and the flick of a cigarette.
11. “Catch Me If You Can”

Image Credit: DreamWorks/Courtesy Everett Collection

Steven Spielberg’s snazzy adaptation of the autobiography of master of deception Frank Abagnale features a brilliantly shifty (and quite debonair) Leonardo DiCaprio as a man who worked as a doctor, lawyer, and a pilot — all before he turned 18. With Tom Hanks’ FBI agent Carl Hanratty always one step behind him, DiCaprio compellingly nests several performances in one. With each new identity he puts on, DiCaprio delivers one carefully calibrated impersonation after another, making the many faces he wears as hypnotic to the audience as to the people in Frank’s orbit falling for his smarm and cajolery.