Leonardo DiCaprio has been one of the biggest movie stars for two decades, yet despite the fact that he grew up onscreen, before viewers’ eyes, there’s still an unknowable quality to Leo. Like many actors before him, DiCaprio has spent much of his career attempting to upend our expectations of him – from matinee idol to grim poet to tortured soul and back again – before, in the last decade, finally settling into his comfort zone as perhaps the most interesting, ambitious A-lister currently working. He has worked with Martin Scorsese five times, as well as Steven Spielberg, Quentin Tarantino Christopher Nolan, Baz Luhrmann, Clint Eastwood, Danny Boyle and Woody Allen, but they all seem like his movies as much as they theirs.
With DiCaprio the early favorite to win his first Oscar (after five nominations) for The Revenant, we thought it was time to go run his whole filmography through our regular ranking process, judging them based on the quality of the performance. What struck us most: There really aren’t any sleepwalking performances here. Even when DiCaprio’s not great in a movie, he’s never not giving it his all, or picking something for empty financial gain. An actor, above all, is the choices he makes — and few actors make more consistently fascinating choices than Leonardo DiCaprio.
26. Don’s Plum (2001)
The movie so anathema to DiCaprio that it wasn’t seen for six years after he and Tobey Maguire sued to keep it out of theaters. Honestly, it’s not worth all the fuss unless you want to see a painfully young DiCaprio try to act like a “spoiled Hollywood kid” around a bunch of present and future members of his infamous “Pussy Posse.” (Writer-director R.D. Robb was supposedly kicked out of the group because of this film.) This is a mostly improvised mishmash of every ‘90s indie-movie cliché, with a healthy smattering of misogyny that borders at times on MRA territory. All told, it’s more embarrassing to Maguire than DiCaprio, who at least seems to be trying to add something. The biggest hero here? Jenny Lewis, in her final acting role, who somehow survives with her dignity intact.
25. The Man in the Iron Mask (1998)
The more “serious” version of the Three Musketeers story made in the ‘90s isn’t necessarily much better than the Chris O’Donnell version, but it sure takes itself more seriously. Promoted above its station owing to DiCaprio’s post-Titanic popularity, it’s a mostly dull story that features DiCaprio as both King Lewis XIV and his secret twin brother, who inspire the musketeers (Jeremy Irons, Gabriel Byrne, Gerard Depardieu, and John Malkovich!) to come out of retirement to take out the evil despot. DiCaprio doesn’t give much of himself here and, despite playing two roles, is oddly removed from the proceedings, as if he weren’t quite sure whether this was supposed to be his movie or not. The film is too busy and loud to settle down and be much of anything.
24. Total Eclipse (1995)
In retrospect, this romantic drama about the doomed relationship between poets Paul Verlaine (David Thewlis) and Arthur Rimbaud (DiCaprio) handily demonstrates all the different qualities that the budding star would incorporate much better down the line: the commitment to playing a complicated character, the live-wire intensity, the matinee-idol-with-soul appeal. That hindsight appreciation doesn’t do much to make Total Eclipse any more palatable, however. Director Agnieszka Holland and screenwriter Christopher Hampton fashioned an intentionally distancing but stillborn love story between two miserable, self-destructive personalities who can’t live with each other but also can’t live apart. (Audiences didn’t much care, just so long as they didn’t have to spend any more time with either of them.) At this stage of DiCaprio’s career, he could portray the bratty genius of a young Rimbaud, but not the depth.
23. The Beach (2000)
The end of the Leo Is Trying Too Hard After Titanic phase of his career. This Danny Boyle misfire made sense on the surface — well-reviewed book featuring a lead who’s wrestling with sanity while trying to survive on a remote island — but in practice, The Beach is a total mess, with an unfocused DiCaprio performance and fussy, mostly confused direction from Boyle. (It’s not Boyle’s worst movie, but it’s perhaps the one he had the least control of.) This was the last time Leo would try to headline a big-budget movie still looking like the pretty boy of Titanic; after this, his next four films were for either Martin Scorsese or Steven Spielberg. Boyle and DiCaprio, two artists who have done great work separately, just might not have been a match. But, hey: You do get to watch DiCaprio fight a shark. (This would be the last time DiCaprio would fight a shark … so far.)
22. Blood Diamond (2006)
DiCaprio doesn’t do message-movie earnestness well – he’s too shifty – so he’s a strange fit with Edward Zwick in this overly preachy and stilted “don’t buy African diamonds” drama. Zwick is such a conventional filmmaker that DiCaprio chafes trying to break out of the Reluctant Hero straitjacket Zwick puts him in. This is the type of role Humphrey Bogart would have played 80 years ago, and DiCaprio just isn’t that kind of actor: He doesn’t have that sort of unearned but undeniable cockiness, because he’s too twitchy. DiCaprio’s not the worst thing about this movie – which has aged incredibly poorly, even if its message certainly hasn’t – but it’s a role that seems to sit outside his comfort zone, and strengths, as an actor.
21. The Basketball Diaries (1995)
It must have seemed very exciting for DiCaprio to play junkie poet Jim Carroll, to dig into the role of a drug-addicted wretch at the initial core of his addiction. Unfortunately, the movie — for reasons that still don’t make sense 20 years later — plays Carroll’s story weirdly straight: There are times this feels like a movie of the week about what happens to nice, young, white prep-school boys when they mess with heroin, rather than a piercing look into a damaged soul like Carroll’s. DiCaprio does his best, and you wonder if he’d have been a lot better in this five years later, but the movie is a surface look at a story with countless depths. It showed that DiCaprio was willing to tackle ugly material, but not that he necessarily knew how or, more to the point, knew the right director to go down that path with him. Yet.
20. Body of Lies (2008)
A rare commercial misfire for DiCaprio, Body of Lies is second-tier Ridley Scott, which means it’s appreciably slick without much underneath. Leo plays a hot-shot CIA operative trying to track a shadowy terrorist kingpin through Iraq and Jordan. At the same time, he’s burdened with a romantic subplot concerning a Jordanian nurse (Golshifteh Farahani) that’s meant to personalize a region’s conflicts but more accurately serves as a manipulative plot device once she gets captured by the bad guys. A reunion with Leo’s Quick and the Dead co-star Russell Crowe, whose CIA chief lives a comfortable life back home in the States, Body of Lies is a bland yet professional piece of studio entertainment that tries to be thoughtful about U.S.–Middle East relations. Sure, DiCaprio invests sufficient grit and empathy into the role, but be honest: This might be the one major movie on this list that you forgot he was in.
19. J. Edgar (2011)
DiCaprio is an actor who works best with directors who have strong visions of their own, directors he can challenge and do battle with, all in the name of a shared vision. Clint Eastwood, for all his skills, is not this sort of director: He’s a point-the-camera, do-a-couple-of-takes, get-home-for-happy-hour type of guy. This has its benefits, but it does DiCaprio no favors in this remote portrayal of J. Edgar Hoover. The movie feels like a greatest hits of Hoover’s life, which never really lets DiCaprio cut loose in the way that he loves to: His pain is muted, but not smoldering. (Armie Hammer’s got the juicier role anyway, as Hoover’s lover-protégé Clyde Tolson.) You can imagine DiCaprio, struggling to get into Hoover’s head, looking up in surprise when Clint said “cut.” Wait, we’re done? We’re just using that one? So much of DiCaprio’s career revolves around finding the right match as a director. Eastwood wasn’t it.
18. The Quick and the Dead (1995)
What a strange time capsule of a movie this is for several people in front of and behind the camera. It was directed by Sam Raimi during his post–Evil Dead, pre–Spider-Man period, and it starred Sharon Stone right when Hollywood was trying to figure out exactly what to do with her in the wake of Basic Instinct. Not all that surprisingly, The Quick and the Dead never really evolves beyond its gimmicky “It’s a Western, but starring a lady!” premise. The actors and filmmaker all seem thrown together for a high-concept hook that’s not very interesting beyond Raimi’s inventive ways of staging one-on-one gunfights. As for DiCaprio, he’s perfectly fine as “the Kid,” an ultra-cocky, super-charming gunslinger, but thank god he evolved beyond these sorts of genre throwaways.
17. This Boy’s Life (1993)
This is still in DiCaprio’s up-and-comer period, but it’s the other movie from 1993, the one that wasn’t What’s Eating Gilbert Grape. Adapted from author Tobias Wolff’s memoir, This Boy’s Life finds DiCaprio portraying a young Wolff, who is thrown together with an abusive stepfather (a veins-in-neck-popping Robert De Niro) in 1950s Seattle. This is a coming-of-age tale, but it never quite commits to it; the film flirts with the idea that the stepfather might actually be trying to help the boy, before selling De Niro’s character out and turning him into a horror-film villain. DiCaprio still wins big points for more than holding his own with his De Niro scenes: You could see the ferocity that was coming.
16. Gangs of New York (2002)
The first of DiCaprio’s ultimately fruitful collaborations with Martin Scorsese is the weakest of them all, with Leo in the “lead” but oddly irrelevant to the film as a whole. It would have been difficult for anyone not to be blown off the screen by Daniel Day-Lewis’s mammoth Bill the Butcher, but DiCaprio really gets blown off the screen here: By the end, Scorsese almost seems to move on from him entirely. This was the lone Marty-Leo combo that feels like DiCaprio trying to boost some acting bona fides rather than finding the angry, damaged truth at the core of his character. Of course, these two would get it right eventually.
15. Django Unchained (2012)
Legitimate question: Has there ever been a great actor who is appreciably worse in a Quentin Tarantino movie than he usually is other than Leonardo DiCaprio? Leo’s fine, one supposes, as evil plantation owner Calvin Candie, but the role is not a natural fit for him. He’s more of a physical actor than a verbal one, and while he does what he can to exude menace, he’s arguably the fourth most compelling actor in his big scene at the end. (And having him spar with Christoph Waltz, who might have been genetically engineered in a lab specifically to recite Quentin Tarantino dialogue, does him no favors.) It’s a showy role, but maybe a little too showy, particularly when Candie himself is so entitled and controlled by others. It brings us no joy to say this, but DiCaprio doesn’t quite work here. Would this even crack the top-25 best performances in Tarantino films? We think not.
14. Celebrity (1998)
Leo’s first post-Titanic appearance was a cameo in Woody Allen’s caustic comedy about, you guessed it, celebrity. Playing a preening party-boy movie star who goes ballistic, DiCaprio has a blast sending up the inflated image others had of his stardom, bringing sex appeal and genuine danger to a potentially one-dimensional role that would have only required his natural charisma to get a few laughs. “Apart from being good-looking, he’s a tremendous actor,” Allen would later say of DiCaprio, “an actor up there with the best of them — De Niro, Pacino — a great natural. He’s real and full of intensity and a great improviser.”
13. Revolutionary Road (2008)
Advertised as the reunion of Titanic’s doomed couple, Revolutionary Road marks the start of DiCaprio’s brooding bad-love period, in which he played a handful of characters who discover darkness at the heart of married life. (The other two films in this category, Shutter Island and Inception, are higher on the list.) The screen adaptation of Yates’s debut novel is also a crucial film in DiCaprio’s career in that it’s part of a transitional era where he was confidently moving from next-big-thing to legitimate serious actor, figuring out how his still-boyish looks could help convey immaturity and panic in failing adult characters. This quality is on display in his portrayal of Frank, a 1950s husband who can’t figure out why his seemingly storybook life with beautiful wife April (Kate Winslet) has left him so miserable. As good as DiCaprio is, though, Revolutionary Road really belongs to Michael Shannon, who launched his film career on the strength of a scene-stealing turn as a troubled local man.
12. Marvin’s Room (1996)
DiCaprio is thrown in the middle of some true acting giants – Meryl Streep, Diane Keaton, Robert De Niro – and promptly steals the movie out from under them as the trouble-making son of Streep, who is dealing with her dying father and a sister (Keaton) who has bone cancer and needs a donor. The movie is sad and straightforward, but DiCaprio upends it by keeping it unbalanced, which prevents it from feeling as conventional and theatrical as it would have otherwise. You realize by the end of the film that he’s not just holding his own with this cast: They’re in fact reacting, and responding, to him.
11. William Shakespeare’s Romeo + Juliet (1996)
By director Baz Luhrmann’s outlandishly flamboyant standards, this updating of Shakespeare’s tragedy is practically genteel, but it provided DiCaprio with one of his best early heartthrob roles, playing Romeo as just one more beach kid whose head is on fire and whose emotions are jumping off his sleeve. At the beginning of Leo’s career, he was especially adroit at conveying the essence of what young love feels like with its impossible highs, giddy infatuation, and irrepressible sexual urges. In Romeo + Juliet, he and Claire Danes have terrific chemistry, and they’re so poignant together precisely because you know their whirlwind, fragile romance can’t last. DiCaprio would rinse and repeat this movie’s grandly melodramatic approach a year later for a little film about two crazy kids on an ocean liner.
10. Catch Me If You Can (2002)
Considering all the weighted-down-by-demons types that DiCaprio has portrayed, it was a blast to see him playing a flat-out bullshitter in an underrated entry in Spielberg’s filmography. Light on his feet and clearly having the time of his life, DiCaprio charms your pants off as Frank Abagnale, a teenage conman so skilled at his chosen craft that you can’t help but be swept along by him. DiCaprio smartly gives some heft to this rogue – much of this stems from his sad-sack, brokenhearted father, played beautifully by Christopher Walken – and though the performance works best when he’s having a breezy good time, DiCaprio always lets you see the scared kid underneath. (Tom Hanks is his perfect foil in this way: He’s the everyman, the Frank Grimes, who can’t believe this kid keeps getting away with all this.) We’d love to see DiCaprio try something this light again: When he lets himself go in the service of a great director, it fits him surprisingly snugly.
9. The Great Gatsby (2013)
After The Great Gatsby opened in May 2013, Vulture writer Kyle Buchanan paid special tribute to the film’s introduction of Jay Gatsby, saying, “It’s a scene that’s so over-the-top that it might have hit the moon, and when this magical moment happened onscreen, you had no choice but to laugh, cry, or applaud.” For the record, we laughed and applauded: It’s one of the great moments in recent movies in which a director (Baz Luhrmann) and his star (DiCaprio) are sharing one big, knowing chuckle with their audience. The whole film is wrapped up in that moment, and it’s why DiCaprio is so good in this remake, even though the movie itself is exhausting and misguided. As Gatsby, the unattainably impressive man of wealth and status, DiCaprio projects the kind of movie-star wattage we just don’t see much anymore, at the same time hinting at the romantic duress that renders all his achievements ultimately meaningless. As in Celebrity, DiCaprio plays into our flattering, envying notion of who he is — and he has an absolute ball both confirming and sending up our glowing assumptions.
8. The Revenant (2015)
This is DiCaprio’s All Is Lost, his Cast Away. Directed by Birdman Oscar-winner Alejandro G. Iñárritu, The Revenant is a brutal tale of survival, in which an 1820s frontiersman endures in quick succession a Native American ambush, a bear attack, and a betrayal by one of his companions (Tom Hardy) who leaves him for dead. Leo’s character is a man of few words, but in a story this primal, words don’t matter: The Revenant is easily the most physical role of his career, the actor grunting, straining, and fighting his way across unforgiving terrain to make it back to civilization. All everybody wants to talk about is DiCaprio’s Oscar chances, and if he does win it’ll be another example of a well-respected actor getting his Academy Award because he’s “due” rather than for doing the best work of his life. Don’t get us wrong, The Revenant is great stuff, but because the performance has an unrelenting jackhammer intensity, it doesn’t contain the brilliant range of his most indelible roles. Still, this may be the movie where some people finally stop moaning that DiCaprio doesn’t have the heft to play rugged characters.
7. Inception (2010)
DiCaprio’s biggest hit since Titanic, Inception is the first real event movie he’s been a part of since that James Cameron sensation. (Remarkably, Inception is also his first summer blockbuster.) We bring this up because, frankly, part of this thriller’s pleasure is that he’s the one at the center of it all, bringing just the right amount of soulfulness and sophistication to his role as a thief who infiltrates people’s subconscious. It’s to DiCaprio’s eternal credit that he didn’t parlay his early stardom into a string of lame tentpole flicks, and in Inception he found that rare four-quadrant thriller with sufficient smarts, emotion, and nuance. Dom Cobb isn’t a tragic figure because he lost his wife, but rather because he never came to terms with it, and DiCaprio provides the character with endless anguish that supplements the film’s stunning effects and twisty sci-fi concept. Popcorn movies aren’t his style, but he can do them quite well.
6. Titanic (1997)
If you’ve watched Titanic recently, one of the big takeaways might have been, “Good lord, look how young Leo and Kate are.” Because both have blossomed into significant actors, it’s easy to forget that they were really just kids when they made this movie — which, by the way, is still the second-highest-grossing movie of all time. Even in the Terminator movies, writer-director James Cameron had always had a flair for down-to-earth protagonists, and in Jack he came up with a plucky commoner that DiCaprio transformed from an immigrant cliché into a great romantic hero. The trick was that Leo was young when he made this film: Having just turned 23 when Titanic opened, he filled the character with the reckless abandon and cocky, wide-open optimism that would have made him catnip for a prim-and-proper upper-crust beauty like Rose (Kate Winslet). DiCaprio would develop more nuance as an actor as he got older, but in terms of old-fashioned star appeal, this was his peak. When his character dies in Titanic, a world of impressionable filmgoers were his for life.
5. What’s Eating Gilbert Grape (1993)
It’s easy to be cynical about actors playing characters with illnesses or developmental issues in order to get Academy Award nominations, but DiCaprio’s first Oscar nod was no mere stunt. Playing Arnie, the younger brother to Gilbert (Johnny Depp), DiCaprio doesn’t permit his character to be a simple, adorable variation on disablement. What’s great about the performance is that Arnie is powerfully complicated, even infuriating at times, the boy being such a handful that we understand why Gilbert and his family are cracking under the burden of caring for him. That’s critical: Rather than ennobling Arnie (and therefore coming across as patronizing), DiCaprio gives him a messy, lovable dignity that’s actually more humane. Plus, Leo’s chemistry with Depp was an early indication that the young star could hold the screen against formidable talents.
4. The Wolf of Wall Street (2013)
And thus, we enter the final four … all of which are Martin Scorsese films. These are four very different performances, but they’re all terrific in their own way, not to mention the purest expression of DiCaprio’s impressive skill set. We start with the most recent one, the one that we suspect is going to age perhaps as well as any on this list. DiCaprio is playing a truly loathsome character (Jordan Belfort), but he plays him with such zest and go-for-fuckin’-broke gusto that it’s perhaps no surprise young Wall Street types have ignored the subtext all together and just taken this movie as the story of a hero’s journey to the top. DiCaprio’s fantastic, start to finish, but we particularly love how he never winks, never gives in one bit that this guy is a monster, never evinces anything other than absolute certainty that the world was made specifically for him to conquer, strip bare, and eviscerate. And let’s not forget the great discovery of this DiCaprio performance: his total mastery of physical comedy. His drug-infused slow-motion meltdown wouldn’t be out of place in a Marx brothers’ movie.
3. Shutter Island (2010)
Among the most divisive films in DiCaprio’s career, Shutter Island is an elegantly unnerving portrait of a man slowly losing his shit. As U.S. marshal Teddy Daniels, who thinks he’s on the hunt for a missing inmate on an island for the criminally insane, DiCaprio has to play his character’s psychosis straight, all the while hinting at the horrible truth: He’s actually a patient himself, unable to accept the fact that his wife (Michelle Williams) killed their children. Whether or not you like Shutter Island’s twist — we’ve argued before that it’s actually entirely beside the point — the film is really about exploring the depths of misery and denial churning within this man, and DiCaprio is electrifying in that specific function, conveying all the grief that’s eating Teddy alive. Shutter Island is often compared to Hitchcock movies, which is appropriate since Leo gives a performance that’s on par with Jimmy Stewart or Cary Grant, two previous Hollywood stars who bravely went dark while working with a master filmmaker.
2. The Departed (2006)
The dirty secret of this DiCaprio performance is that it’s perhaps his most heroic: Of all the cracking-up leading men DiCaprio has played, this is the one who is the film’s moral center. Everyone else in The Departed is out for themselves, in one way or another, but it’s DiCaprio’s Billy — a devoted cop who thinks he’s making a difference even as he’s collapsing from the stress of living a life undercover among jackals — who truly sacrifices for the greater good. And, you know, a lot of good it does him. (It’s telling how many different adjectives we’ve had to use for cracking up and crumbling and collapsing while describing DiCaprio’s characters on this list.) DiCaprio has the least showy role in a movie practically invented for scenery-chewing — but he’s the reason the movie works.
1. The Aviator (2004)
Several of Leonardo DiCaprio’s best performances subvert or tweak his good looks, encouraging us to see the uglier, messier undercurrents beneath his characters’ appealing surface. Never was that truer than in this Oscar-nominated biopic directed by Martin Scorsese. Leo’s performance as Howard Hughes was hard to fully grasp at the time — he was still shaking off the last vestiges of post-Titanic teen heartthrob — but here was where he really established himself as a major adult actor, bringing to life Hughes’s fiery competitiveness as well as the increasingly erratic behavior that would be his undoing. His Hughes is a towering figure because we know he’s doomed — and, on some level, we sense he does, too — but DiCaprio continually pushes back against the eccentric’s demons, in the process delivering a hypnotic, strangely heroic portrait of ambition in conflict with mental collapse. There’s something quintessentially American about The Aviator, how we keep striving for greatness even as everything is crumbling around us; casting one of our most photogenic young actors to embody all that was a master stroke on Scorsese’s part. DiCaprio rewarded him with an astounding portrayal that’s powered by a central irony: He came into his own by playing a man who was coming apart.