Leonardo DiCaprio's 17 Best Performances

After all these years, there is no denying that Leonardo DiCaprio is one of the best leading actors of his generation—or any other for that matter. As a performer who has been in the industry since he was five-years-old, he has had his ups-and-downs, yet most of those came before he landed his breakthrough role opposite Robert De Niro in This Boy’s Life, a part for which he was handpicked by De Niro amongst 400 other young actors; DiCaprio was 18-years-old. From that point on, it was a meteoric rise that took him from the heights of teenage heartthrob celebrity to slowly, but surely, a self-made dramatic thespian who has rejected that earlier image. Today, he enjoys the reputation of being one of the best (and choosiest) movie stars in Hollywood.

And yet, there is still a strange, quiet backlash against the former heartthrob. Whether it is his matinee idol good looks, which only recently age (and plenty of roles requiring facial hair) could downplay, or simple envy for his unmitigated early success, DiCaprio has developed a reputation for always being the nominee and never the winner when it comes to Hollywood’s golden night. On Sunday, he will enjoy his fourth nomination for a performance at the Academy Awards, but despite the hopefulness of others, will still likely be applauding McConaughey’s inevitable win for Dallas Buyers Club, not least of all because McConaughey is enjoying his much deserved McConaissance. Nonetheless, DiCaprio has not needed a renaissance, because he has remained reliably fantastic for 20 years. Oscar can continue to turn a blind eye like the male population of 1997 to his talent, but we won’t.

For those counting, here are 17 terrific performances from Leonardo DiCaprio.

17. Gangs of New York (2002)

Kicking off our list is the role that first introduced the partnership of DiCaprio and legendary filmmaker Martin Scorsese. When it was announced in 2000, it made sense on a business acumen level: Scorsese could make the movie he wanted provided that he cast a bankable star, and this was only several years past DiCaprio headlining the most successful film of all time. Yet, the financial sense of the decision would soon give way to the artistic one, as DiCaprio proved every bit the quality actor described by De Niro in a recommendation to Marty. For Gangs, it was an ultimately secondary role of adolescence; the angry young man who has come home to avenge the death of his father by cozying up like a surrogate son to the murderer. It is all very operatic, but DiCaprio was forced to surrender the screen as merely another orbiting figure around the bigoted brilliance emanating from Daniel Day-Lewis’ iconic big screen Nativist, Bill the Butcher. Gangs of New York is a movie that works chaotically on many levels about the American dream and the bloody, violent collision of it with tribe mentality in 19^th century New York (though it is still ever present throughout parts of the country). As messy as the city herself, the movie relies on DiCaprio’s vengeful Amsterdam as its through line. He does not necessarily gain the spotlight that he should on paper, but DiCaprio never loses the character or the audience’s attention since he brings palpable rage to the chiseled face of American immigration.

16. The Beach (2000)

DiCaprio’s third film after Titanic, The Beach was his first serious attempt to break free from the celebrity face plastered on every tabloid in the country. By working with English auteur Danny Boyle (Shallow Grave, Trainspotting), DiCaprio sought to earn back some of his indie cred from earlier projects by starring in this genre-defying pitch black dramedy about an American who gets in over his head, quite literally, when he discovers a hidden, cult-like island community secretly thriving on a marijuana plantation in the South Pacific. DiCaprio is the typical bundle of exposed nerves associated with Boyle protagonists, but he also brings a certain desperation and intentional callowness to his collegiate tourist. Simply being an American in a foreign land causes DiCaprio’s Richard to emit more than a whiff of entitlement that is broken down in a tight-knit group of free love and fresh fish…at least until more strangers drift ashore and the landlords discover their beach bliss existing in its own parallel universe.

15. Body of Lies (2008)

Marketed as a meeting of the minds, and incredibly strained screaming volumes, between DiCaprio and co-star Russell Crowe, Ridley Scott’s Body of Lies turned out to be something far more obtuse and disorienting than expected. Based on a screenplay by Kingdom of Heaven and The Departed scribe William Monahan, Lies is a slick, stylish funhouse mirror that attempts to reflect the inanity of American foreign policy in the Middle East through its labyrinthine 128 minutes. However, the performances are uniformly excellent, with DiCaprio eliciting an unpredictable weariness as a CIA operative who has seen it all and only maintains disgust for the stupidity of his bosses. A slick star role that allowed DiCaprio to play a secret agent, it’s a nice part with a showy payoff whenever he and Crowe either share the screen or even mere verbal communication.

14. The Basketball Diaries (1995)

Controversial upon its release for focusing on a simple dreamer…of school shootings—an uncomfortable premise, which has only grown more wearying over time—The Basketball Diaries still features an early strong performance from DiCaprio, who lives and breathes impotent teenage anguish and confusion so well that we can forgive the fact that he does not look like a basketball star. DiCaprio’s Jim Carroll is a piece of work from a bad home that he evades first through basketball and then later street heroin in exchange for different kinds of back alley one-on-ones. Arguably a victim of an ambivalent school system, Carroll falls hard into drug addiction and misanthropy. Still a few years out from his heartthrob days, Basketball Diaries continued DiCaprio’s brief stint as the go-to troubled youth, as there was always something a little caged and menacing behind those piercing blue peepers. Whatever you think of the movie’s subject matter or execution, even at the age of 20, DiCaprio was leaving one hell of an impression.

13. Inception (2010)

As the second biggest hit in DiCaprio’s career, there is still plenty of love for this Christopher Nolan original, and for good reason. Inception is still the most beautifully executed and intelligent big budget effort produced by Hollywood during the last half decade. A mission statement by blockbuster magician Nolan, the film is slyly mischievous in its intent to explain how an artist must insert their wildest cinematic dreams into the heads of happily oblivious moviegoers. Often times as loud as Hans Zimmer’s blaring riff on Piaf, DiCaprio’s muted central performance allows the celluloid Rubik’s cube its vital pulse underneath. With this fairly cool and cerebral film (at least for a blockbuster), DiCaprio is left to ground the entire movie’s premise on his need to overcome the guilt of a dead wife. It is a potentially ludicrous scenario that the star pulls off with genuine empathy and grace, allowing all the exposition and mythological world-building to rest easily on his widower’s grieving shoulders. The movie works because of this surprisingly restrained turn by the frequently vociferous DiCaprio, allowing all the fun and intrigue of a heist movie inside a mind to be executed with the deftest sleight of hands.

12. Romeo + Juliet (1996)

As the real beginning of Leonardo DiCaprio The Movie Star, Romeo + Juliet slowly became a launching pad for the 21-year-old talent. Director Baz Luhrmann wanted to follow up his well-received Strictly Ballroom with an ambitious “modernized” vision of William Shakespeare’s classic ode to young love, or at least the infatuation that spurs it, for the MTV generation. DiCaprio believed in the project so much that he paid his own expenses to appear in its workshop and ultimately became the guiding star that much of the rest of the cast was built around (thus out Natalie Portman and in, the slightly older, Claire Danes at 16). Indeed, DiCaprio and Danes’ chemistry is electrifying enough to light the famed swimming pool they glide through like the cinematic equivalent of a Rodin sculpture. Even today, when the movie’s initial up-to-the-minute pop soundtrack and excessive editing creates a piece of 1990s nostalgia kitsch, Romeo + Juliet still glows from their aggressive euphoria, as well as an underrated turn of brilliance from John Leguizamo as Tybalt. Bawdy, operatic, crass, and romantic, like all of Luhrmann’s best movies, Romeo + Juliet is a kaleidoscope of energies, brought out by a young cast whose hunger more than makes up for their lack of fluidity with iambic pentameter.

11. Revolutionary Road (2008)

After the success of Titanic, Kate and Leo simply had to work together again; they simply had to! Thus, the announcement of a reunion is unsurprising, but the underwhelming quality of this heavy-handed film turned out to be just so. Directed by Sam Mendes at a time when he was still chasing another American Beauty, this cautionary tale of 1950s horrors leaves something to be desired, but it is not from the acting. Both DiCaprio and Winslet turn in memorable work as a couple that dreams of gender equality in Paris during the honeymoon phase, but ultimately settles for complacency in the suburbs. However, their lifestyle is anything but simple with warring words turning into desperate actions executed for sheer escape from their happy homebody hells. As the “artist” who finds his inner-Ward Cleaver at the expense of his marriage, DiCaprio is both empathetic and ultimately repellent in a performance that threads the needle just right. Still, the highlight of the actual movie likely remains Michael Shannon’s brief but stunning moment as the judging eyes on both spouses’ failures.

[related article: The Enigma of Leonardo DiCaprio]

10. Titanic (1997)

There is simply no way of ignoring this movie. The second most successful film of all time nearly 20 years on (and still more successful than Avatar if one factors in inflation), this is a juggernaut of a film that rocketed the careers of its young stars into the stratosphere and remains to this day—despite all the protesting, kicking, and screaming from any number of detractors—one of the most beloved romances in movie history. This is in large part because James Cameron hit the jackpot when he combined the old school Hollywood formula of a big, broad, soapy love story in the context of a “historical” epic tragedy. And nothing was more on the nose of that jackpot than whom he cast as Jack. In one of the few performances where DiCaprio embraced his matinee idol features, his Jack Dawson oozes American “aw shucks,” underdog charm, street rat wit, and iconoclast artistic sensibilities. Cameron was firing his own Cupid’s arrows into every teenage girl’s heart circa 1997 with perfect accuracy. Yet, it didn’t just win 11 Academy Awards and $2 billion of moviegoers’ hard earned money based on shrewd demographic appeal. The truth is this film had a four-quadrant enticement with its stunning visuals of Edwardian Armageddon and genuinely likable leads in DiCaprio and Winslet who brought the right kind of touch to this material, making their scenes as seared into the mind as James Horner’s unapologetically weepy score that you can still hum along to. Admit it.

9. The Great Gatsby (2013)

When adapting one of the great American novels, particularly F. Scott Fitzgerald’s shimmering and succinct The Great Gatsby, there is going to be some blow back about any cinematic infidelity. This is likely the reason that Baz Luhrmann made such a baroque spectacle of the whole affair, calling attention to the fact that this is as much, if not more, his Gatsby as it is the one in every high school across the country. For such an introspective text, a sumptuous piece of literature that lives best on the page and in the deep recesses of Nick Carraway’s acquiescent mind, Luhrmann audaciously makes the most faithful adaptation yet by ignoring the impulse for stilted, museum-ready wax portraits of the 1920s and instead opts for an opulent decadence so grotesque that it captures the banned booze fury of the Jazz Age, if not its actual sound and look. But one figure cuts the image exactly perfect, and that is Leonardo DiCaprio in the finely cast role of Jay Gatsby. At the point where his good looks have aged into All-American swagger, DiCaprio seems born to play Fitzgerald’s tragic dope; a man who could have been truly great if not for Daisy’s dock, or rather a potentially great man who willingly feeds himself to the wolves and other idle beasts of New York high society. Infinitely charismatic and charming, DiCaprio pulls off both the seduction and ridiculousness of the fellow in a cool, pink suit, with the words “old sport” perpetually curled on his lips. A figure of tragedy and foolishness, DiCaprio realizes Jay Gatsby in a way that should please any Fitzgerald scholar, even if the rest of the movie will not.

8. Catch Me If You Can (2002)

In DiCaprio’s final “young man” role, the actor continued his trend of teaming with the biggest names in Hollywood by partnering with Steven Spielberg and Tom Hanks for this light-hearted romp into 1960s confidence. As Frank Abagnale Jr., DiCaprio briefly returns to his earliest roles as a troubled kid who couldn’t come to terms with his mother (Nathalie Bay) divorcing his father (Christopher Walken). However, unlike other misguided protagonists, Frank flourishes, at least for the audience, when he becomes a Blake Edwards-styled conman that talks his way into working as a permanent rookie pilot for Pan Am airlines, playing the role of lawyer in courtrooms, and even trying his hand at being a doctor. This is all supposedly based on a true story, but besides coming from the words of the real Frank Abagnale himself after he made a deal with the FBI, it also has more than a touch of Spielberg’s fantasy by way of Bondmania. There is a very tender moment where after years abroad, Frank returns home on Christmas Eve to find himself replaced by his estranged mother with a new family, happily oblivious when he peaks through their frosted window. The anguish, in the otherwise smiling eyes of DiCaprio, sells this pain better than any Peter Pan adaptation before or since. Deceptively endearing in his manipulation, DiCaprio and Frank won over every person they met, both on the big screen and off it.

7. Blood Diamond (2006)

Usually overlooked due to its proximity with the Scorsese and DiCaprio powerhouse that is The Departed (which opened during the same autumn), Blood Diamond can be ignored by fans, despite strangely being the performance the Academy chose to recognize that year. However, there is still good reason for that, because DiCaprio continues his trend of tackling local dialects far outside of most actors’ comfort zones. And his South African brogue in this Edward Zwick actioner twists around the Serra Leone landscape with perfect ease. Somewhat of a cliché and formulaic drama about the menace of conflict diamonds, complete with selfish bad boy, Danny Archer, earning a last minute redemption by sacrificing himself for noble Solomon’s (Djimon Hounsou) family, the flick is still undeniably effective. And the chemistry shared by DiCarpio and Hounsou elevates the action tropes into a memorable pair of traumatic turns for both actors.

6. Django Unchained (2012)

Before Django Unchained, DiCaprio may have had grindhouse aficionados’ curiosity, but now he has their attention. In a deliciously ham-fisted role as Calvin Candie, the wealthy planter of a Mississippian plantation nicknamed Candie Land, DiCaprio camps it up in classic Tarantino fashion as the nastiest host of Southern hospitality this side of Deliverance. As a slave owner who obliviously quotes Alexander Dumas and feeds his runaways to dogs, DiCaprio more or less plays a comic book villain who has wandered into a Spaghetti Western and then took a wrong turn toward Dixie. The only thing arguably more uneasing than DiCaprio’s literally skull splitting antics is his all too willing sidekick, Stephen, played with sickening deference to Calvin by Samuel L. Jackson. Not to be mistaken as a serious or historical rendering of the institution of slavery that forever leaves its scar on the American psyche, DiCaprio and Jackson’s demented duo are still two of the vilest and most repulsively entertaining baddies in recent memory.

5. What’s Eating Gilbert Grape (1993)

In the role that garnered DiCaprio his earliest mainstream attention as a young force to be reckoned with, he wowed critics and moviegoers alike by playing Arnie Grape, the handicapped brother of Gilbert (Johnny Depp). It is meant to be a touching and tender story about simple yokels in the heartland, which might seem ever more slightly offensive to said yokels in the context of director Lasse Hallstrom’s other tear-jerkers, including Chocolat and Dear John. Yet, there is something genuinely touching in Gilbert Grape’s earnestness, whether through the very low-key but magnetic lead performance by Depp or in the 1990s quirk ingénue Juliette Lewis. Yet, the real memorable turns lie in Darlene Cates’ larger-than-life performance as mama and in DiCaprio’s announcement to the world as being a great actor by playing a mentally challenged kid with real pathos, as opposed to the typical crocodile tears, allowing him to cut through the film’s bountiful fountains of syrup and into something still surprisingly extraordinary. It earned DiCaprio his first of many Oscar nominations and remains a highlight in his career.

[related article: The 9 Stages of Matthew McConaughey's McConaissance]

4. The Wolf of Wall Street (2013)

The movie of the moment has proven to be very close to DiCaprio’s heart, as demonstrated by his increased visibility during this Oscar campaign season. On the one hand, it is probably due to the fact that he’s a producer on the project. However, it is also quite evident that DiCaprio has reason to be proud of this one. It’s the kind of relatively big budgeted, big studio uninhibited passion project that went out of fashion decades ago. Indeed, Scorsese hasn’t been this unconstrained and unapologetic since Goodfellas, while the moral majority’s outrage hasn’t been stroked in almost as long. The Wolf of Wall Street is a lurid tale of excess that’s even excessively long by about half an hour. It is the kind of go-for-the-throat moviemaking that Hollywood bean counting has steered away from in favor of capes and cowls, and it is more than welcome here with a picture that is unafraid to frame Wall Streeters as the masters of a hedonistically dead universe. I’d dare even say that Scorsese chooses to paint this image of disdain a shade darker than he reserves for his usual wiseguys. They may kill you, but at least they’ll smile right up until then! On Wall Street, everyone’s a rat waiting to squeal as the all-mighty dollar isn’t only their God, it is their love, their dreams, and even their sexual fantasy of choice for the most talented of brokers (as relayed in a scene-stealing Matthew McConaughey cameo).

And none are more talented than the exceptionally soulless Jordan Belfort played with a ravenous hunger for cash by DiCaprio that can only be eclipsed by his character’s love for cocaine. Well coke, Quaaludes, crack, and whatever is rolling around on his Lamborghini’s floor as he is tearing up country clubs. It is a fearless performance that is constantly hilarious and terrifying in equal measures, never once asking for audience sympathy or understanding. He is a smiling bastard through and through and if you are still seduced after 180 minutes, you’re just as gullible as the rest of the saps in the final shot. It is the kind of lead role that is meant to entertain but never once pleads for pity, which is likely why the Academy will have none on Sunday.

3. The Aviator (2004)

The passion project that DiCaprio never thought he could equal again, The Aviator is a beautiful love letter to the creator’s spirit, limitless ambition, and the golden age of Hollywood, all subjects of adoration for Marty too. The director’s first collaboration with DiCaprio offered a good vehicle for the capable leading man, but The Aviator is the film that announced a true artistic union between the two and also DiCaprio’s full emergence as one of his generation’s best. Despite being handicapped by playing over 40 at the film’s end, the youthful DiCaprio transforms himself competently from the “kid” who made Hell’s Angels to the middle-aged titan of industry who will spend the second half of his life locked up in dark rooms, peeing into jars. And he pulled off that magic trick in only 170 minutes. Surrounded by great supporting talent to help with the picture’s prestige boanfides, The Aviator still rests squarely on DiCaprio’s shoulders as he impressively realizes the candor and brashness of the aviation enthusiast and engineer who openly mocked the U.S. Senate on camera, as well as imagines what the pits of OCD Hell might have been like for Hughes behind closed doors. This is the story of a man who made the 1920s’ most expensive blockbuster, pushed the buttons of the Breen Office’s good taste in the 1940s (an accomplishment Scorsese undoubtedly admires), and elevated American aviation in historic ways. Plus, that is only the first 30-some years of his life. Flying to such heights came at an Icarus-sized cost—literally, when Hughes crashed the XF-11 into Beverly Hills—that resulted in increased alienation and mentally ill self-destruction. However, DiCaprio’s tour de force posits that it was all worth it. At least for this movie, it might have been.

2. Shutter Island (2010)

Based on mercurial Dennis Lehane’s most sensational novel, Shutter Island’s a locked room mystery that deceptively gives in to thriller tropes with its storm swept setting of a 1950s Asylum for the Criminally Insane. And we are clued into that fact almost immediately thanks DiCaprio’s newly extra-thick townie accent.  However, despite providing a wonderful opportunity for Scorsese to play with his most gleeful Hitchcockian and Kubrickian influences for whenever he lights the dark corners of this post-WWII New England hellscape, it all serves a much more meaningful story that Paramount Pictures clearly missed when they delayed the movie to a barren February release date.

Ultimately, Shutter Island is the most unlikely of proponents for mental health reform, especially underscoring our inhumane treatment of those suffering. And none suffer more than DiCaprio’s remarkably haunting performance as “Teddy Daniels,” the supposed U.S. marshal invited to Shutter Island to investigate the disappearance of a patient. However, the twist is not that Teddy is really a patient himself, but how he has been victimized by a society ready to erase him from existence via lobotomy if this elaborate LARP game fails to end with anything short of a talking cure. In the movie’s final half hour, the thriller elements are completely supplanted by a great character study into a man who has lost all in whole, a tragedy crystallized in the finest scene of DiCaprio’s career: Andrew Laeddis (Teddy’s real name) comes home one afternoon to find that his wife (Michelle Williams), a victim of mental disease herself whose symptoms he ignored, has drowned their three small children in the backyard pond. Other filmmakers would have settled for the shot of floating bodies and tastefully cut or faded away from the horror, but Scorsese allows DiCaprio to be fully enveloped in the dark emotion that is deeper than any lake he could wade through; DiCaprio wallows in a soul-shattering grief as his character is forced to swim from one young corpse to the next, collecting them like daisies drifting in the ripples, and crying impotently at his own failure as a father, a husband, and finally as a human being with the complete waste of life in his arms. It is a harrowing scene that reaches for a crescendo of despair rarely glimpsed at in celluloid, and all but condones the equally horrific murder Andrew/Teddy immediately inflicts on his psychologically disturbed wife. It is the epicenter of sorrow, and a moment that transcends its own film to become truly haunting.

1. The Departed (2006)

Nonetheless, DiCaprio’s best performance to date is fortuitously the best effort his teaming with Scorsese has yet produced: The Departed is a real sucker punch of a movie that even if you have seen Infernal Affairs (its Hong Kong basis), will still take you outback, bust a beer bottle over your head, and have you whimpering in a pool of your own blood before it’s all done. The movie equivalent of a good old-fahsioned Southie donnybrook, The Departed is not so much Scorsese’s ode to the Irish mob, as much as it is his version of classic cops and robbers movies. These neighborhood feuds are more Angels with Dirty Faces than Goodfellas. And at the center is the symbiotic story of two rats who make the mistake that all rats make: they think there is a pot of gold and happiness at the end of this story. Sure, Colin Sullivan (Matt Damon) gets to taste the good life for a little while as Frank Costello’s (Jack Nichoslon) mole in the Massachusetts State Police force—he got bought off during childhood for all of a bag of groceries and a couple of comic books—but like the rest who squeal for a living, he ends up with a bullet or two in his head.

Yet, the real tragedy of this is Billy Costigan Jr., DiCaprio’s guilt-ridden hero who regrets getting out of Southie before it destroyed him as a child. So, he lets a couple of cops trick him into signing his life away to break into Costello’s crew and rat them all out. Luckily, it all works out for him in the end. And if you believe that, maybe you’ll buy the Titanic safely makes port in New York City too. Like the title says, Billy is done before the first chords of “I’m Shipping Up to Boston” are over, and we hate to see him go. Because despite a somewhat exaggerated Boston accent, Billy is another tour de force for DiCaprio. The definition of bundled nerves, Billy’s anxiety casts a jittery shadow over the picture like a bulbous zit that’s ready to pop and spray blood everywhere (and it really does). A good guy who is in way over his head, the whole movie appears to be DiCaprio working himself up to having a heart attack on camera in hopes of going truly method. The desperation with which Billy tries to bring Frank down, but ends up going with him, carries this drama’s genre trappings all the way to a true art. Sadly, it’s one painted in a nice, deep crimson.

So there are the 17 best performances in Leonardo DiCaprio’s career, right? Agree? Disagree? Want to passionately plea why he’ll still win the Oscar? Let us know in the comments section below!

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