Every Leonardo DiCaprio Performance Ranked

These days it’s somewhat difficult to fathom there was a time when Leonardo DiCaprio was not recognized as one of the finest actors of his generation. Born with preternaturally good looks, talent, and an obvious degree of taste, DiCaprio has grown onscreen from precocious child actor to heartthrob, to movie star, and finally to revered leading man. At least onscreen.

With that meteoric career-trajectory beginning at the remarkably early age of 18 in the movie This Boy’s Life, DiCaprio has had the rare opportunity to carefully curate and shape his career from virtually the beginning, and in the process has left behind a body of work that is increasingly choosey—and well chosen. But which are the best performances, and which are the ones that didn’t work out? Read on to find out.

*Editor’s Note: We are focusing only on DiCaprio’s feature film performances where the actor has a leading or major supporting role. So his pre-fame turns on family sitcom Growing Pains or small parts in such auspicious films as Critters III and Poison Ivy will not be included. Also this ranking is based on DiCaprio’s performance, not the films’ overall qualities.

29. Don’s Plum (2001)

It is fair to ask whether Don’s Plum should be included on the list, because if DiCaprio and lifelong pal Tobey Maguire had their way, the film never would have seen the light of day. Barely released on a home media market at the turn of the century, Maguire and DiCaprio alleged the film was only intended to be a short film that they shot around 1995 as a favor to acquaintance R.D. Robb, who directed and co-wrote the film. The two, indeed, were only paid $525 each, which was a bit low, especially DiCaprio who around the same time was having Baz Luhrmann build a gaudy Shakespeare adaptation around him.

Whatever the case, you can see why neither wanted this film to find a wider audience, given each young actor leaves an intensely vain and misogynistic impression in the movie’s scant 89 minutes. Filmed in 16mm black and white and mostly around a single diner location, the pair join Kevin Connolly of future Entourage fame, plus others, in portraying whiny narcissistic youths of ‘90s LA. To be clear, they are playing intentionally callow characters, but reportedly much of the dialogue was improvised, and given the rumors that persist about DiCaprio and Maguire’s alleged “Pussy Posse” of the same decade, the trash these characters talk raises more than a few eyebrows. Ultimately, however, whatever the truth of the film’s origins, it does play like a rough student film with all the performances having a green artificiality to them which does nobody any favors.

28. Total Eclipse (1995)

Released in that awkward era where LGBTQ stories were finally gaining interest in mainstream media, but studios and many audiences still shied away from actually acknowledging the queerness of the material, Total Eclipse plays like a painfully dated arthouse vanity project today, but it’s unlikely anyone found the supposed “erotic drama” much more scintillating then. Based on the passionate, violent, and very romantic relationship between real-life 19th century poets Arthur Rimbaud (DiCaprio) and Paul Verlaine (David Thewlis), Agnieszka Holland’s Total Eclipse fitfully and timidly wants to tell a love story between two men without much in the way of love.

Focusing more on their sexually fluid relations with (and competition over) Paul’s muse (Romane Bothringer), Total Eclipse fails as gripping drama, erotic or otherwise, and this is in large part because of DiCaprio’s most misjudged performance. The film undeniably leans on the actor’s youthful handsomeness, but there’s a self-conscious nervousness to the performance, suggesting the actor either didn’t trust the material or didn’t trust how it might affect his career. Either way, his line-readings are uniformly flat, and when his supposed fiery poet makes a Belle Epoque indecent proposal, the conviction is about as believable as the chemistry between the two male leads.

27. The Man in the Iron Mask (1998)

As a child of the ‘90s, Randall Wallace’s The Man in the Iron Mask still works as a bit of a guilty pleasure. With its bombastic score by Nick Glennie-Smith, and scenery-chewing performances by Jeremy Irons, Gérard Depardieu, and a wildly miscast John Malkvoich as Athos (the Oliver Reed role), this is as grandiose a Hollywood adaptation as we’re ever likely to get of Alexandre Dumas’ final Three Musketeers novel. Still, it’s not good, and unfortunately DiCaprio is one of the movie’s biggest problems.

The first film DiCaprio did after Titanic (which gave this movie a big opening when it released three months after that film began its historic box office voyage), the film provided DiCaprio with dual roles: the eponymous Man in the Iron Mask and the part of his dastardly twin brother, King Louis IV. DiCaprio fairs better as the poor sweet lad who spent a lifetime in his mask, but the actor hadn’t quite figured out how to play a heavy just yet, and his Louis is a one-note caricature in royal mustache-twirling (the shoulder length hair also didn’t help). Still, to give this guilty pleasure its due, Gabriel Byrne conversely provides a stoic gravitas which represents the closest Hollywood ever came to putting Dumas’ D’Artagnan on screen.

26. J. Edgar (2011)

By the end of the 2000s, DiCaprio’s grumbling hunger to win an Oscar was becoming deafening. Nominated for a little gold man for the first time at only the age of 19 after  co-starring in What’s Eating Gilbert Grape, he’d been nominated two more times by 2011 and still had no trophy. In fact, he’d been snubbed at least once. Which would explain his garish, pandering, and altogether desperately baiting performance in J. Edgar.

By portraying one of the most consequential American figures of the 20th century, DiCaprio likely hoped to be leaning on Academy voters’ sweet spot when he signed onto Clint Eastwood’s biopic about the founding director of the FBI. Eastwood was also on a recent hot streak with the Academy too, but those accolades began drying up after critics and industry voters alike got a gander at this stilted and tone-deaf portrayal of J. Edgar Hoover. With a hammy play at reconfiguring the man who spied on Malcolm X and attempted to blackmail Dr. Martin Luther King Jr., among many other sins, as a figure of tragedy and LGBTQ-misunderstanding, J. Edgar is an insufferably leaden movie with DiCaprio at his most emotive and least natural. The accent is pretty good, but the eyes betray a desperation unrelated to the secret anxieties of G-Men.

25. The Quick and the Dead (1995)

There’s an undeniable performative quality to DiCaprio’s turn as “the Kid” in Sam Raimi’s deliciously pulpy Western, The Quick and the Dead. And it’s difficult to determine whether this is by design. Intentional or not, it works because the Kid is himself a greenhorn; a novice performer who still in the bloom of life is trying way too hard to act like the big bad man his father (Gene Hackman) really is. You never fully believe the Kid’s bravado, and I’m not sure you’re meant to. Here is an undeniably beautiful boy with mountains of charisma, and he’s wasting it all to earn the approval of a monster of a man that’ll squander it all.

In that sense, DiCaprio was well chosen as the secondary love interest for Sharon Stone’s Ellen, the hero of the story, and his undeniable greenness brings a real sense to tragedy when this boy is shot dead in the street by his own father out of a misplaced sense of pride and toxic machismo.

24. Marvin’s Room (1996)

Eschewing the burgeoning leading man/heartthrob persona DiCaprio spent much of the mid-1990s building, the actor instead took a secondary role with Marvin’s Room, a dramatic and awards-friendly vehicle for Meryl Streep and Diane Keaton. DiCaprio does solid work in the margins, too, even if he is asked in that way characteristic of ‘90s Miramax features to overact the big dramatic confessional scenes.

In the film, DiCaprio plays Streep’s troubled son, Hank, a young man who has already been institutionalized and suffers from crippling self-doubt. Ultimately a feel-good family dramedy, his afflictions turn out to be narrow, but the warmth of his enjoyment of sharing screen time with Keaton is wide.

23. Gangs of New York (2002)

Here is the film that first introduced the partnership of Leonardo 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 eventually give way to the artistic one, as DiCaprio later proved every bit the quality actor as described by De Niro in a recommendation to Marty.

For Gangs, however, it was an ultimately secondary role of adolescence and not necessarily DiCaprio’s best variation on it. Here he plays the classic 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, and Donald Trump forefather, 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 the tribal mentality in 19th century New York.

As messy as the city herself, the movie relies on DiCaprio’s vengeful Amsterdam as its through-line. He does not necessarily wrestle the spotlight away from Day-Lewis, but DiCaprio never loses the character or the audience’s attention. It would be a start for better things between the actor and director down the road.

22. The Beach (2000)

As 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 that’s 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 this beach bliss, which actually exists in an imaginary parallel universe.

21. Body of Lies (2008)

Marketed as a meeting of the minds (and screaming voices) 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.

20. Celebrity (1998)

Most folks probably forget that DiCaprio once worked with Woody Allen—a fact he probably isn’t about to start broadcasting next week either—but Celebrity was one of the first times DiCaprio attempted to artistically engage with his stardom to successful results. While Celebrity as a whole doesn’t come together, the scenes with DiCaprio do. The actor in fact seems to be very much enjoying the opportunity to subvert his then thriving heartthrob persona by playing pretty boy movie star Brandon Darrow as an oblivious, shallow, drug-addicted parody of himself and the 1990s’ Young Hollywood scene.

Years before Entourage, DiCaprio delights in sending up movie stardom opposite Kenneth Branagh, who less successfully plays the typical Allen surrogate character: he’s a neurotic and self-effacing writer, in this case one named Lee Simon. Allen’s attempt to weave the misadventures of Lee around town opposite the likes of Judy Davis or Winona Ryder is less successful, but the intentionally spartan black-and-white photography which documents Darrow’s abusive relationships and meaningless sexcapades gives Celebrity some genuine laughs.

19. 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 problematic over time—The Basketball Diaries still features an early strong turn 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 heart throb 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.

18. 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.

17. Don’t Look Up (2021)

Adam McKay has recently admitted his Dick Cheney biopic—which featured a towering performance by Christian Bale—was too angry to be funny. Yet we’d argue Don’t Look Up is far more indignant in its self-righteousness, not least of all because itsit’s thinly disguised metaphor for climate change was of course not heeded. In this way, the film was obviously near and dear to DiCaprio’s heart, who in his middle age has become a spokesman for climate action.

He also visibly relishes playing Dr. Randall Mindy, the malleable and weak-willed scientist who realizes (thanks to his graduate student played by Jennifer Lawrence) that all life on Earth is about to be eradicated by a comet. Even so, he still finds himself seduced into complacency by the power and money of D.C. politics and media celebrity. We find the movie too smugly satisfied in its outrage, but DiCaprio’s eager embrace of a lumpy middle-aged dad who vacillates between crippling anxiety and Cate Blanchett temptation is a sight worth beholding. It’s nice to see the actor cut loose and have fun, even if the movie is its own kind of agony.

16. 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. That’s all the more impressive when one knows that behind-the-scenes, the  two did not get along.

Even today, where the movie’s then-up-to-the-minute pop soundtrack and excessive editing now creates a piece of 1990s kitsch nostalgia, 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.

15. This Boy’s Life (1993)

The role that put DiCaprio on the path to superstardom, his cinematic approximation of author Tobias Wolff’s childhood is still an impressive achievement. Consider that DiCaprio was only 17 or 18 when he played the title role in director Michael Caton-Jones’ adaptation of Wolff’s memoir, and the young blood goes toe to toe with Robert De Niro and more than stands his ground. There’s a reason De Niro recommended DiCaprio to Martin Scorsese after this one.

Set in the 1950s American Northwest, This Boy’s Life is dripping with an authenticity and specificity to time and place. It also pivots on two powerhouse performances, the other belonging to De Niro, who initially appears eager to be playing against type. De Niro’s seemingly nebbish stepfather Dwight is a typical ‘50s square, but beneath that soft smile hides simmering resentments. They eventually boil over during the course of Toby’s adolescence, finally erupting in physical abuse. DiCaprio goes through his paces with subtle nuance and empathy. It’s still one of his best performances.

14. Titanic (1997)

There is simply no way of ignoring this movie. The third most successful film of all time nearly 20 years on (and still more successful than Avatar and Star Wars: The Force Awakens 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 for this cataclysmic win than when he cast the role 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. It may not be great art, but it was artfully done.

13. 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 curious recognition, 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 affective. And the chemistry shared by DiCarpio and Hounsou elevates the action tropes into a memorable pair of traumatic turns for both actors.

12. 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 among the most beautifully executed and intelligent big budget efforts produced by Hollywood during the last 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.

With the film 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.

11. 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.

10. The Revenant (2015)

The one DiCaprio finally got his Oscar for, The Revenant is another impressive performance from the actor who went to a frigid hell and back in order to film Alejandro González Iñárritu’s passion film about nature and its deadly charms. Ostensibly a Western set in the 1820s, The Revenant feels almost like a silent film and biblical vision about the dawn of man, when a primordial nature was untouched by our petty greviances and desires for revenge.

For this role, DiCaprio spent months crawling through snow, appearing half-starved, and eating raw fish in the river. And considering how little dialogue he was given, it was a superb turn for the star. Still, so much of the film also belongs to Tom Hardy as the man who left Leonardo DiCaprio’s Hugh Glass to die that this feels likes like the performance of his career… or at least the one that got his whole body of work recognized.

9. 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 con man that talks his way into working as a permanent rookie pilot for Pan Am airlines, playing the role of a 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 onscreen 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.

8. Killers of the Flower Moon (2023)

A decade after The Wolf of Wall Street, and 30 years after This Boy’s Life, DiCaprio reunites with Scorsese and De Niro in Killers of the Flower Moon, a monumental commentary on the deep-seated and systemic nature of American racism. DiCaprio, in fact, plays its most banal form, a white face with a dim mind who is easily led into heinous ideology (personified by De Niro) because it is the path of least resistance—and he thinks it’ll make him rich.

It’s a multilayered performance, with DiCaprio revealing the nuances of delusion, shame, and finally the bitterest of regret. Although, in all honesty, the fact that DiCaprio (who is also a producer on the film) insisted the movie should be about his murderous racist, instead of the Native American wife he betrayed (a luminous Lily Gladstone as Mollie Burkhart) becomes the movie’s one glaring weakness. DiCaprio is tremendous here, but he might’ve been even better if they didn’t make Killers about him.

7. 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 unnerving 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.

6. Once Upon a Time… in Hollywood (2019)

The ninth Quentin Tarantino movie (if you cheat with the Kill Bill countings), the picture came seven years after the director and DiCaprio teamed on Django Unchained and four years after The Revenant. It’s also one of the more refreshing turns in DiCaprio’s oeuvre that has gone strangely overlooked. Perhaps it’s inevitable since the film is really a two-hander between DiCaprio and Brad Pitt, who plays Rick’s stuntman, Cliff Booth. All old school cool movie star machismo, Cliff is the flashier role and Pitt has rightly been showered with awards praise. But given DiCaprio isn’t necessarily trying to win awards this time, he is doing something quite different on his end: he’s having fun.

Unafraid to play a clown, if a pitiful one, DiCaprio embraces a character whose neuroses and self-loathing is instantly empathetic yet humorous. He is, after all, still portraying a coddled actor with a house in the Hollywood Hills. That plus his plight often involves unflattering roles, like in a brief hilarious insert of Rick’s performance on Hullabaloo, showing off both the character and DiCaprio’s limited singing talent.

More acutely, however, the film is a showcase for DiCaprio’s frequently underutilized comic timing, which can be downright killer when he is ranting and raving about hippies while drinking from a blender full of margarita mix. Rick also allows DiCaprio to slowly but sincerely pay tribute to actors who had very different trajectories from himself. Nothing ever really went right for Rick beyond his initial television success, and that sense of despair and wasted potential underwrites the comedy with melancholic pathos. It also brings subtle growth when a little girl’s dedication to his craft triggers the sly evolution in Rick’s acting from hamfisted to authentic.

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. It allows him to cut through the film’s bountiful fountains of syrup and into something still surprisingly tender. It earned DiCaprio his first of many Oscar nominations and remains a highlight in his career.

4. The Wolf of Wall Street (2013)

The Wolf of Wall Street is the kind of relatively big budgeted, big studio, and uninhibited passion project that went out of fashion decades ago. Indeed, Scorsese hasn’t been this unconstrained and unapologetic since Goodfellas, and the moral majority’s outrage amongst the film press hasn’t been stroked in almost as long either. 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. The stars of his mob movies 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, go-for-broke 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 staring at a pen. It is the kind of lead role that is meant to entertain but never once pleads for pity, which is likely why the Academy turned away yet again.

3. The Aviator (2004)

As 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 by 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 successfully 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 20-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 wounded 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 paddle 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)

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 at the end of the rainbow. 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.