Leonardo DiCaprio's Movies, Ranked Worst to Best - Rolling Stone
Home Movies Movie Lists

Leonardo DiCaprio’s Movies, Ranked Worst to Best

From ‘Titanic’ to ‘Once Upon a Time…in Hollywood,’ we rate the good, bad and WTF ugly of Leo’s big-screen career

Leonardo DiCaprio, Best to Worst

Illustration by Ryan Casey

Over a nearly three decade career, Leonardo DiCaprio has grown to become one of our most dedicated, intense actors. It was apparent from the start that this was a young man of rare talent: He won acclaim for movies like the rough coming-of-age story This Boy’s Life, and had garnered an Oscar nomination as early as 1993, for playing a mentally disabled teenager in What’s Eating Gilbert Grape? A series of romantic roles in the 1990s — in films like Baz Luhrmann’s MTV-style Shakespeare adaptation of Romeo + Juliet and that little movie about a sinking ship and an iceberg that nobody remembers — turned him into an international heartthrob.

DiCaprio could have easily coasted on that matinee-idol success for the rest of his career; instead, he combined his stardom with ambition and talent to became a first-class leading man, working with directors like Steven Spielberg, Quentin Tarantino, Ridley Scott, and, most notably, Martin Scorsese — the latter of whom he’s made five movies with (and a sixth on the way.) And, with his stellar turn in Tarantino’s Once Upon a Time…in Hollywood still fresh in audiences’ memories, now seems like a good time to go over his marvelous career from stem to stern. Here are all of DiCaprio’s movies — not his roles, mind you, but the actual films — ranked worst to best.

Critters 3 - 1991

New Line Cinema/Oh/Kobal/Shutterstock

29

‘Critters 3’ (1991)

The third installment of the low-budget sci-fi horror comedy franchise about cuddly little monsters is now notable mainly for being DiCaprio’s big-screen debut (even if the movie wound up going straight to video). Here, he plays a troubled, floppy-haired skate-punk tween who joins a family trapped in his dirtbag dad’s tenement building as it’s terrorized by these man-eating furballs. Sure, it has a low-rent, get-high-and-watch-it-at-3-AM vibe to it, but the film’s mind-numbing longueurs and its dialogue do away with any Z-movie verve one might be expecting. DiCaprio isn’t too bad as a pissy kid; indeed, he seems to be the only cast member who can actually act. BE

The Man In The Iron Mask - 1998

United Artists/Kobal/Shutterstock

28

‘The Man in the Iron Mask’ (1998)

This was the first DiCaprio film to be released after the success of Titanic, and it became a hit for that very reason. But with all due respect to Monsieur Dumas, it’s dreadful: A dumbed-down, star-studded period piece about the Four Musketeers’ attempts to replace the sneering, playboy King Louis XIV with his long-imprisoned twin (both played by DiCaprio). The young actor seems out of his element here, and not even the veteran actors surrounding him — Gabriel Byrne! John Malkovich! Gerard Depardieu! Jeremy Irons! — can’t do much with the dopey script. BE

The Basketball Diaries - 1995

Island/Kobal/Shutterstock

27

‘The Basketball Diaries’ (1995)

Leo went full Brando in this overbaked adaptation of Jim Carroll’s memoir about his teenage descent from high school basketball star to broken, homeless drug addict. You have to have some respect for a movie willing to go so over the top, but the scenery-chewing acting, the deliriously overdone montages, the addiction-drama cliches … it’s all a bit much. Still, coming on the heels of his Oscar nomination for What’s Eating Gilbert Grape?, this performance made it clear that this was a young actor willing to take huge risks. BE

J Edgar - 2011

Moviestore/Shutterstock

26

‘J. Edgar’ (2011)

Clint Eastwood’s long, lumbering, awkward biopic about the man who changed the face of American surveillance asks a lot of Leo – he has to age decades, he has to make a monster likable, he has to depict forbidden, and barely repressed passions. But the movie itself doesn’t really give him the support he needs, and the script alternates between the obvious and the inert. Although DiCaprio gives it his best, the film mostly leaves him flailing. That said, the chemistry between DiCaprio and co-star Armie Hammer, playing J. Edgar Hoover’s longtime love interest and companion, is occasionally quite compelling. BE

Body of Lies - 2008

Snap Stills/Shutterstock

25

‘Body of Lies’ (2008)

DiCaprio brings the required amount of breathless desperation to his role as a CIA operative who gets in too deep in Ridley Scott’s Middle East-set terrorism-and-espionage thriller. As his portly, affable, but duplicitous boss, Russell Crowe is also quite good. But the generic storyline and the by-the-numbers filmmaking get the better of this adaptation of David Ignatius’s novel. Lacking political nuance, narrative invention, or any real suspense, it’s a mostly forgettable movie — despite the staggering amount of talent booth behind and in front of the camera. BE

Poison Ivy - 1992

Kimberly Wright/New Line/Kobal/Shutterstock

24

‘Poison Ivy’ (1992)

Leo’s literally only in this for a couple of seconds. (A reminder that we are ranking his movies, and not his performances per se.) Although it was very early in his career, the blink-and-you-miss-him brevity of his appearance is a little odd; he’d been a regular on TV for some years at this point, so one suspects his other scenes were cut. And this weird seduction thriller, which helped resurrect former hell-raising child star Drew Barrymore’s career, hasn’t aged as well as anticipated. Still, the actress’ turn as an obsessive, murderous teenage sexpot who takes over Sara Gilbert’s family, is wonderfully nasty, Skinemax-style clichés or not. BE

Total Eclipse - 1995

Fit/Portman/Sfp/Kobal/Shutterstock

23

‘Total Eclipse’ (1995)

Agnieszka Holland’s literary epic about the tempestuous, forbidden affair between 19th century poets Paul Verlaine (David Thewlis) and Arthur Rimbaud (DiCaprio) barely got released back in its day – in part because of its then-scandalous subject matter, including some fairly intense sex between the two leads, but also because, well, it’s not very good. DiCaprio seems purposefully miscast as an all-too-modern young punk version of the legendary live-fast-die-young poet who comes into Verlaine’s life, seduces him, and disrupts his mentor/lover’s marriage. Instead of conveying the brazen genius of these men, however, it mostly conveys their obnoxiousness. BE

MarvinsRoom
22

‘Marvin’s Room’ (1996)

The young actor’s penchant for playing disturbed teens had become almost a joke by the time he appeared in this family melodrama as Meryl Streep’s troubled, pyromaniac son. The film, about two estranged sisters (played by Streep and Diane Keaton) reuniting when one needs a bone marrow transplant, is a fairly predictable, occasionally touching wallow in sentimentality, enlivened by a fine cast (which also includes Robert De Niro). By this point, DiCaprio was already an Oscar-nominated teen idol; that he could hold his own against such heavyweights was just further proof that there was massive talent there. BE

Blood Diamond - 2006

Snap Stills/Shutterstock

21

‘Blood Diamond’ (2006)

Leo and co-star Djimon Hounsou won some acclaim for this well-meaning but turgid political action-drama about an enslaved Mende fisherman who partners with a Rhodesian smuggler (DiCaprio) to return to his family in exchange for a massive diamond. The two actors play well off against one another — with DiCaprio’s likable sleazebag contrasting nicely with Hounsou’s desperate, stone-faced family man. And while the film did shine a light on the corrupt African diamond trade, it managed to do so in a thoroughly ham-handed, Hollywoodized manner. BE

DonsPlum
20

‘Don’s Plum’ (2001)

This no-budget, black-and-white indie (filmed from 1995 to 1996) was notable mainly for co-stars DiCaprio and Tobey Maguire attempting to stop it from being released in the wake of their newfound stardom. They shouldn’t have been so worried: A talky, vignette-based story about a group of teens meeting in a diner called Don’s Plum, R.D. Robb’s film features numerous strong performances and a loose, improvisatory feel. But the film is also often undercut by random, irritating bits of arty, faux-poetic stylization, which mark it as a mid-Nineties curio — and because of its reputation and overall unavailability, a brief cause celebré when it screened at the Berlin Film Festival in 2001. BE

The Quick and The Dead - 1995

Tri Star/Kobal/Shutterstock

19

‘The Quick and the Dead’ (1995)

Sam Raimi’s hyper-stylized, neo-spaghetti Western drops master gunfighter Sharon Stone, arrogant young cowboy DiCaprio, and mysterious outlaw Russell Crowe in a sadistic marksmanship tournament put on by evil frontier strongman Gene Hackman. An admirable, if ultimately unsuccessful, attempt to rejuvenate the baroque horse opera at a time when the genre was on the ropes, Raimi’s film is strangely pointless. But as a brash young kid who gains our sympathy, DiCaprio is really quite good. BE

The Great Gatsby - 2013

Bazmark Films/Warner Bros/Kobal/Shutterstock

18

‘The Great Gatsby’ (2013)

DiCaprio reunited with his Romeo + Juliet director for this version of F. Scott Fitzgerald’s borderline-unfilmable novel, and the results are less dire than might have initially been feared. No, Baz Luhrmann still doesn’t “crack” Gatsby – like other directors before him, he can’t help but try to make it a love story, even though it’s actually the opposite of that – and his all-too-faithful recounting of Fitzgerald’s plot works against the overall revisionist spirit the enterprise. (Cue opulent party set to a Fergie song.) But the star himself is such a charmer, and somehow accessible despite his obsessiveness, that it almost doesn’t matter. This is the first film in many years that allowed him to showcase a real smile; for a brief moment, it was nice to have Leo the Romantic back in our midst. BE

Celebrity - 1998

Sweetland/Kobal/Shutterstock

17

‘Celebrity’ (1998)

Woody Allen’s homage to Fellini’s La Dolce Vita, in which Kenneth Branagh does his best Woody Allen impersonation as a hotshot magazine journalist whose insecurities get the best of him. Once you look beyond Branagh’s too-nebbish-by-half performance, the film is actually a pretty funny, semi-cutting portrait of modern celebrity culture. But even its detractors agree that DiCaprio is the best thing in the film, playing an entitled, bratty movie star who invites the writer-hero to witness, and participate in, his debauched shenanigans.You may draw your own conclusions, folks. BE

The Revenant - 2015

Kimberley French/20th Century Fox/Regency Enterprises/Kobal/Shutterstock

16

‘The Revenant’ (2015)

Or: The One in Which Leo Fights a Bear, Eats Raw Bison Liver and Wins an Oscar. Alejandro González Iñárritu’s grueling frontier-revenge tale pits a grungy DiCaprio against the elements, forcing the actor to portray a fur trapper battling for his life — against extreme weather, ice-cold rivers, hostile predators, and Tom Hardy, not in that order — in the most immersive way imaginable. (“Sometimes it was just ‘[Hugh] Glass walks up a hill,'” he told Variety, “and the bear fur weighs 120 pounds wet, and I’m freezing my ass off, and it became some of the most difficult stuff to do.”) It’s a highly physical performance, compounded by the fact that he has to convey much of his character’s journey from ailing, wounded survivor to avenging angel without the use of his voice. But it’s also a masterclass in the concept of “action is character,” with DiCaprio giving you an incredible sense of who Glass is, what keeps him going and why he needs to see this vengeancequest through. The award was well-deserved. DF

WhatsEatingGilbertGrape
15

‘What’s Eating Gilbert Grape?’ (1993)

In this sharply observed but gently told coming-of-age tale, DiCaprio plays Arnie, the mentally handicapped younger brother of Johnny Depp’s titular small-town slacker. The film, based on Peter Hedges’ novel, is an offbeat mix of typically quirky elements, and it could have easily been hard to stomach. But the author and director Lasse Hallstrom’s affection for these characters shines through. Their greatest asset is the young Leo himself, in his first Oscar-nominated role, bringing great sensitivity and complexity to a part that might have come off as cloying or cynical. BE

Romeo and Juliet - 1996

Merrick Morton/20th Century Fox/Kobal/Shutterstock

14

‘Romeo + Juliet’ (1996)

To a generation that came of age with this Shakespeare adaptation, DiCaprio and Clare Danes were the last word in star-crossed pairings, playing the Bard’s doomed couple in Baz Luhrmann’s histrionic, gang-war-filled modern take on the classic play. The Aussie filmmaker’s over-the-top treatment of the material is often laughable — but the chemistry between the leads is undeniably amazing, and Danes gave one of her best early performances in this. DiCaprio, for his part, sounds great and looks even better; his success here helped lay the groundwork for his epochal turn in Titanic a few years later. BE

The Beach - 1999

Peter Mountain/20th Century Fox/Kobal/Shutterstock

13

‘The Beach’ (2000)

Until it goes off the rails in its final act, Danny Boyle’s adaptation of Alex Garland’s thriller about a small colony of folks who’ve settled a remote Southeast Asian island is a moving portrait of generational angst. These Western travelers and backpacking ex-pats are searching for utopia in a highly technologized world, and DiCaprio’s charming cockiness comes in handy as his adventurous tourist goes from looking for connections to desperately trying to survive. This highly anticipated film, which was the first project DiCaprio signed on to following his Titanic superstardom, didn’t win much love back when it was first released. It’s worth another look. BE

Shutter Island - 2010

Paramount/Kobal/Shutterstock

12

‘Shutter Island’ (2010)

DiCaprio’s work with Martin Scorsese has always centered around obsession, and this noirish mystery is their most haunted film yet — as well as the most vulnerable the actor has ever been. He plays an investigator looking into the disappearance of a cryptic inmate at a creepy island insane asylum. As he delves further into the case, however, his own psyche starts being called into question. So DiCaprio not only has to carry the narrative, but he also has to tear down his character as the film proceeds. To keep us watching while fostering such uncertainty is the mark of a truly great actor. BE

ThisBoysLife
11

‘This Boy’s Life’ (1993)

This adaptation of Tobias Wolff’s memoir gave DiCaprio one of his earliest leading roles: Toby, the loving son of troubled single mom Ellen Barkin. When she shacks up with a seemingly respectable but domineering and abusive Robert De Niro, it’s war between the adolescent offspring and his stepfather-to-be. It’s an evocative, touching little movie, defined by the powerful bond between Barkin and DiCaprio. And as the young actor’s character goes from being a wide-eyed son to a rebellious greaser to an independent, sensitive young man, his performance gains complexity. BE

The Wolf Of Wall Street - 2013

Appian Way/Paramount/Kobal/Shutterstock

10

‘The Wolf of Wall Street’ (2013)

While this is far from Martin Scorsese’s best film, it contains some of DiCaprio’s finest work to date, as real-life penny-stock kingpin and financial huckster Jordan Belfort. The director in recent years has alternated between epic fictions and major musical documentaries — and in some strange way, this is an unlikely combination of both. Belfort was famous for his rousing, take-no-prisoners, tent-revival-like speeches to his employees, and so much of this film is Scorsese just turning his cameras on Leo and watching him go — the Mick Jagger of Wall Street jag-offs. BE

Revolutionary Road - 2008

Snap Stills/Shutterstock

9

‘Revolutionary Road’ (2008)

DiCaprio and his Titanic partner Kate Winslet were reunited for this adaptation of Richard Yates’ classic novel about suburban despair and thwarted dreams, American style. The two movies could not be more different: If the earlier blockbuster was a proudly florid melodrama about two kids pining for a life of adventure, this is a chilly, precise and ultimately heartwreenching drama about two adults slowly discovering that the world they once imagined is nothing like the living hell they have now. And DiCaprio is excellent as a man caught in a downward spiral of disillusionment, slowly coming to terms with the fact that he will never make anything of himself. BE

Django Unchained - 2012

Moviestore/Shutterstock

8

‘Django Unchained’ (2012)

As the sneering, charismatic slave-owner Calvin Candie, DiCaprio is the dirty, demented heart of Quentin Tarantino’s controversial Western-exploitation-revenge flick. What’s most remarkable about this performance is the weird affability the actor brings to this pathetic, delusional monster. This is a man who breeds and forces his slaves to fight each other, who has a weird fascination with France, and who is, at heart, a murderous psychotic. But he’s also so charismatic that — spoiler alert — once he’s dispatched from the narrative, the air goes out of the film. It’s a career highlight; he deserved an Oscar for this one, frankly. BE

The Aviator - 2004

Snap Stills/Shutterstock

7

‘The Aviator’ (2004)

In Scorsese’s expansive and lavish look at the early years of millionaire businessman/inventor Howard Hughes, DiCaprio has to blend his still-fresh faced charm with an obsessiveness that borders on madness. These are the years when Hughes was working on his delirious dogfight movie Hell’s Angels, romancing Katherine Hepburn, trying to build the legendary Spruce Goose, and facing off against hostile politicians. The director connects with the man’s ambition and compulsiveness, not to mention his gnawing sense of inadequacy. And DiCaprio’s performance proves he’s versatile as hell. BE

'THE GANGS OF NEW YORK' FILM - 2002

C Miramax/Shutterstock

6

‘Gangs of New York’ (2002)

At the time of DiCaprio’s first collaboration with Scorsese, many were initially perplexed: Pretty-boy heartthrob Leo making a period picture with the king of fast-talking criminals? But the actor wasn’t a bad fit for the role of Amsterdam Vallon, an Irish-American young man biding his time in order to avenge the death of his father (Liam Neeson) at the hands of the Nativist gang leader Bill the Butcher (Daniel Day-Lewis, in what might be his greatest performance). More befuddled than rough, Amsterdam has to grow into the role of gang-leader himself — and Leo plays him as a brooding naïf, an ideal approach against Day-Lewis’ boisterous, whip-smart villainy. BE

'Once Upon A Time In Hollywood' Film - 2019

A Cooper/Sony/Columbia/Kobal/Shutterstock

5

‘Once Upon a Time…in Hollywood’ (2019)

His name was Rick Dalton, the he-man behind the TV Western Bounty Law and countless cinema du rugged-dude classics. (Who could forget The 14 Fists of McCluskey?) Only now it’s 1969, the counterculture is taking over and Dalton’s star wattage is starting to dim. Quentin Tarantino’s ode to the end of a Tinseltown era is all about the moment when things pass and what we lose in the process, and nobody embodies that better then DiCaprio’s fading lead. The actor allows you to both laugh with Dalton and, in certain moments, laugh at him; he can also make you feel the pain of someone who fears he’s no longer relevant. There’s an undercurrent of pathos that runs under his performance even before we get to the instantly classic on-set freakout scene (apparently improvised), as well as a creeping uncertainty of what comes next. It’s a beautifully vulnerable turn, one that complements the fun of watching DiCaprio recreate vintage movie/TV roles and confirming that he and Brad Pitt make one hell of a good-buddy double act. DF

Catch Me If You Can - 2002

Snap Stills/Shutterstock

4

‘Catch Me If You Can’ (2002)

In this Steven Spielberg hit, DiCaprio plays Frank Abagnale, a real-life con-man who traveled around the country and lived the high life as he impersonated pilots, lawyers, and doctors. It was an inspired bit of casting, capturing the actor right as he was transforming from fresh-faced romantic into a brooding young man — he could still play an innocent. And in the film’s first half, as his character watches his parents’ marriage break up, his heartbreak is palpable. By the end of the film, he’s become a totally different person — a journey from kid to slightly jaded adult that’s charted on Di Caprio’s face. BE

The Departed - 2006

Warner Bros/Kobal/Shutterstock

3

‘The Departed’ (2006)

Scorsese finally won that elusive Oscar with this Boston crime thriller — a remake of the terrific Hong Kong thriller Infernal Affairs (2002) — that had DiCaprio as a cop infiltrating the mob and Matt Damon as a mobster infiltrating the police force. It’s an intricate, fascinating tale of competing cat-and-mouse games, but the director and his screenwriter, William Monahan, infuse it with so much tragedy that it winds up becoming something almost mythic. And DiCaprio is fantastic here, in a totally unglamorous, grubby role as a desperate man who almost loses his identity. It’s one of his all-time greatest performances. BE

Inception - 2010

Warner Bros/Kobal/Shutterstock

2

‘Inception’ (2010)

Christopher Nolan’s sci-fi heist thriller has DiCaprio entering people’s dreams and stealing their thoughts — only this time, for that proverbial one last job, he and his team are hired to implant an idea inside someone’s mind instead of boosting the usual cerebral data. How did a film with a plot so byzantine, and a set-up so offbeat, ever become such a massive hit? Credit Nolan’s dexterity with dialogue and interlocking setpieces, but let’s not also forget DiCaprio’s remarkable, underrated performance as a brilliant, tormented thief trying — and failing — to keep his own demons at bay. This is one of the saddest blockbusters you’ll ever see, and a lot of that is due to to its star, who brings a humanity to what could have easily been a generic brooding hero type. BE

Titanic - 1997

20th Century Fox/Paramount/Kobal/Shutterstock

1

‘Titanic’ (1997)

What’s that you say? You don’t think this movie is all that? Tough. James Cameron’s 1997 box-office record-breaker, Oscar winner, and all-around pop-cultural juggernaut was the most expensive movie of its time — not to mention a years-in-the-making, snidely-dismissed production that sometimes seemed like it would never see the light of day. Then it finally came out … and it was awe-inspiring. As a piece of filmmaking, it does for the vast darkness of the sea what David Lean’s Lawrence of Arabia did for the sensuousness of the desert. It also presents a disaster movie extravaganza without ever losing its sense of tragedy (even as it indulges in state-of-the-art effects to show the devastation of the historic shipwreck).

And then there’s Leo and Kate. Yes, the logline of their relationship – adventurous drifter falls for frustrated, upper class girl – is pure corn. But the two young stars infuse their earnest back-and-forth with so much genuine emotion that it’s hard not to get swept up in their doomed love affair. It’s still the highpoint of DiCaprio’s career, and one of the greatest old-school movies to come out of Hollywood in the last 20 years. BE

Arrow Created with Sketch. Calendar Created with Sketch. Path Created with Sketch. Shape Created with Sketch. Plus Created with Sketch. minus Created with Sketch.