There is a fair argument to be made that Leonardo DiCaprio is one of the last true movie stars left in Hollywood. He hasn't a spandex-clad sojourn, family blockbuster, or sequel to his name – unless of course, we count his feature debut in furry alien DTV fodder Critters III (we don’t). The Titanic star has been making serious bank at the box-office and notching up award-winning roles for three decades now – and it’s not without good reason that he landed a place on our list of the 50 Greatest Actors Of All-TIme.
Earning his first Oscar nod at just 19, DiCaprio went on to become the defining heartthrob of the 1990s, with swooning turns in Baz Luhrmann’s tragic romantic epic Romeo + Juliet and James Cameron’s, well, tragic romantic epic Titanic. But rather than spend his career in an endless run of romances to be adored by the masses, DiCaprio has wielded his star power to chase challenging and subversive roles over the past 20 years, working with filmmakers like Steven Spielberg, Martin Scorsese, Quentin Tarantino, and Alejandro G. Iñárritu – the latter of whom’s The Revenant finally landed Leo his long overdue first Academy Award for Best Actor.
So, as we celebrate the release of Martin Scorsese’s Killers Of The Flower Moon, the legendary filmmaker’s latest team-up with his 21st century muse – whose performance as Ernest Burkhart is already garnering huge awards season buzz – please join us as we count down the 20 best performances of Leonardo DiCaprio’s career. “He’s the king of the woooooorld!” Ahem, sorry – just had to get that out of our system first. On with the ranking!
20) The Beach (2000)
Seeking a departure from his late-’90s commercial streak, The Beach was the first project that DiCaprio chose to star in after Titanic (for context, he was also briefly in the running for Oliver Stone’s ill-fated take on American Psycho). Danny Boyle’s visually ambitious, off-kilter tale saw the actor play thrill-seeking tourist Richard, who joins a problematic community on a Thai island after obtaining a secret map. It was a chance for DiCaprio to channel his heartthrob status into a charismatic traveller, and then turn that on its head as his character unravels, his grip on reality loosening; during a drug-fuelled rampage, Richard runs wide-eyed through the jungle, video game-style, surrounded by 8-bit colour graphics. The film received tepid reviews upon release, but for DiCaprio, it was the perfect showcase of his abilities beyond his poster-boy status. It was the kind of feral role that proved that he had boundless talent.
Read the Empire review here.
19) Don’t Look Up (2021)
DiCaprio’s real-life eco-warrior ethos reaches the big screen in this comedy-drama by Adam McKay, as much a satirical critique on climate crisis inaction as it is a caricature of the disinformation age. DiCaprio is Dr. Randall Mindy, an astronomy professor and “America’s sexiest scientist”; when he and graduate student Kate Dibiasky (Jennifer Lawrence) spot a fast-approaching comet, they inform the White House that the planet has a six-month prognosis at best. Chaos ensues. Not unlike the celestial ball of doom on a collision course with Earth, DiCaprio is an unrelenting rock amidst a whirlwind of wackiness, offering a down-to-earth portrait of heartbreak and desperation, with at least one stock-in-trade DiCaprio frothing-at-the-mouth monologue squeezed in. His “The president of the United States. Is fucking. Lying!” speech is almost worth the price of the apocalypse.
Read the Empire review here.
18) The Great Gatsby (2013)
The jury may still be out on Baz Luhrmann’s The Great Gatsby, a film whose razzle-dazzle is undoubted, but whose fidelity to F. Scott Fitzgerald’s classic Jazz Age romance novella is somewhat less so. DiCaprio, however, is perfectly cast in the titular role as consummate conman Jay Gatsby. There’s a poetic beauty in watching Leo – whose superstardom was sealed years ago as the romantic lead in Luhrmann’s Romeo + Juliet – rolling back the years in Gatsby to play a swooning lover who is himself trying to preserve an image and idea of love and the past lost many years before. With his matinee idol good looks, debonair charm, and wholly unexpected body-popping skills, DiCaprio fits effortlessly into Luhrmann’s anachronism-filled vision of the Roaring Twenties, shining among an ensemble featuring two other great performances by Tobey Maguire and Carey Mulligan. But beyond the meme-able moments and sharp fits, it’s the way DiCaprio hits every note of Gatsby’s isolation and melancholy – in a way the screenplay perhaps doesn’t – that makes his work here so memorable.
Read the Empire review here.
17) Revolutionary Road (2008)
Aka The Film With Kate And Leo That Isn’t Titanic. Any swooning Jack Dawson fans would have been in for a shock had they giddily skipped into Revolutionary Road expecting an encore of James Cameron’s epic romance. At no point in the film’s 119-minute runtime does DiCaprio pronounce that he is the king of the world. And there are zero dolphins. Instead, Sam Mendes’ study of a married couple, Frank and April Wheeler, is a gritty and grim drama which features a) severe marital discord, b) an abortion, and c) DiCaprio acting drunk and saying horrible things to Winslet’s character (“You are an empty, empty, hollow shell of a woman!”). Not an easy watch — and did we mention there are zero dolphins? — but DiCaprio delivers a terrific performance as a deeply unhappy man. And it proved a fine warm-up for the two more unhappy men he’d play next, in Shutter Island and Inception.
Read the Empire review here.
16) Blood Diamond (2006)
This was the first notice DiCaprio had given on film of picking projects which chimed with issues he personally felt strongly about – see also his nature doc narration and climate parable Don’t Look Up – and wanted to bring attention to. He’s Danny Archer, a mercenary fighting in the Sierra Leone civil war, who hears about a huge pink diamond buried somewhere in the countryside. If he found it, it’d be his ticket out of there. He teams up with another smuggler and a journalist to attempt to find it, and it’s not long before the tensions between why each wants to find the diamond begin to bubble to the surface. The gritty modern actioner isn’t a genre DiCaprio returned to, but he certainly left his mark on it.
Read the Empire review here.
15) Gangs Of New York (2002)
There’s an alternate universe in which DiCaprio took the role of Anakin Skywalker in Attack Of The Clones and never teamed up with Scorsese for his bloody tale of sectarian violence in the 1840s. As it happened, the first Scorsese-DiCaprio project came at the right time for both of them. Scorsese found a new, young muse who could refresh him as Bobby De Niro and Joe Pesci hit their sixties, and add box-office muscle to get his films financed; DiCaprio was taken under the wing of a master, and his career shifted gears away from the – apologies, George Lucas – fluff he was being offered. Let’s not pretend this isn’t Daniel Day-Lewis’ movie though. His Bill the Butcher is perhaps the most frightening of Scorsese’s many ultraviolent psychopaths.
Read the Empire review here.
14) Shutter Island (2010)
In Shutter Island, Martin Scorsese’s noodle-twisting psychological thriller-slash-Gothic melodrama, Leo is riveting as U.S. Marshal Teddy Daniels, a man haunted by grief trying to unravel the mystery of a missing woman at a decrepit sanatorium before he himself comes undone. Amidst Scorsese’s hallucinatory horror imagery, Laeta Kalogridis’ mind-mangling pretzel of a screenplay, and eye-catching turns from the likes of Mark Ruffalo, Sir Ben Kingsley, and Max von Sydow, DiCaprio shines as he achieves something incredibly difficult, grounding the film with a performance that’s as emotionally raw as it is psychologically fraught and foggy. Lest we forget, he is – *SPOILER ALERT* – playing a man who believes he is sane and being deliberately driven towards insanity in order to keep him from the truth, who is in fact actually a man who is insane and being deliberately driven towards sanity in order to to help him accept the actual truth. Talk about a twist – we need a lie-down just thinking about it.
Read the Empire review here.
13) The Quick And The Dead (1995)
So certain was Sharon Stone – who both starred and helped to shepherd the film as a co-producer — that Leonardo DiCaprio was right for the role of cocky young gunslinger The Kid (though David Arquette was considered and Matt Damon passed before Leo was up for the film), she paid his salary herself. It was a gamble that paid off — he's a supporting character, but a key one, all braggadocio with a broken heart lurking within, unresolved daddy issues and a tragic fate awaiting him. Sam Raimi directs with typical flair, though critics largely shot it down and audiences didn't show up. And despite his later reputation as a romantic figure, Stone recalls that snogging DiCaprio was not the swoon-worthy experience some have recalled — she described it as "about as sexy as kissing my arm.” You can't win them all, we suppose; especially in a film as lethal as this one.
Read the Empire review here.
12) What's Eating Gilbert Grape (1993)
The film which gave DiCaprio his first Academy Award nomination. What’s Eating Gilbert Grape sees DiCaprio playing Arnie, a Midwestern 17-year-old with a learning disability, cared for by his 25-year-old brother Gilbert Grape (Johnny Depp). Gilbert just wants to be Gilbert, but trouble-seeking Arnie — who has a tendency to climb his town’s water tower — keeps him on emergency standby. This coming-of-age drama showcased DiCaprio’s acting chops early on: a preview of the total character immersion that he would later become known for. The actor leaned into the improv-heavy, loose environment set by director Lasse Hallstrӧm, finding an impish take on rural boyhood which contrasts against the restrained, overburdened soul of Depp’s performance. What’s Eating Gilbert Grape is often understated, and in terms of career breakthroughs it now lies in the iceberg-shaped shadow of Titanic — but at the top of the water-tower in Endora, Iowa, the then-19-year-old DiCaprio must have glimpsed a hint of his future.
Read the Empire review here.
11) The Aviator (2004)
Scorsese’s follow-up to Gangs Of New York turned from one of his obsessions – his home town – to another: the movie business itself. DiCaprio plays Howard Hughes, aviation pioneer and sometime movie producer, as he tries to outpace his rapidly worsening OCD by keeping himself busy inventing dreams. He produces The Jazz Singer, cops off with Katherine Hepburn (Cate Blanchett), sets a new land speed record, and sets about reinventing air travel. The impatience and perfectionism which made him such an innovator start to fray him mentally, though, and paranoia about germs and partner Ava Gardner’s (Kate Beckinsale) loyalty set in. The work DiCaprio did interviewing OCD sufferers made for some of the film’s most poignant imagery, including the scene in which Hughes scrubs and scrubs his hands until they bleed. Moving, sympathetic stuff.
Read the Empire review here.
10) Django Unchained (2012)
When we first heard that Leo would be playing a villainous plantation owner in Quentin Tarantino’s revisionist Western Django Unchained, the news had our curiosity. But from the moment his goateed ghoul “Monsieur” Calvin J. Candie – overlord of the grimly named Candyland – first appears on screen in the film, he has our attention. DiCaprio potently subverts his innate charisma in his first true heel turn, imbuing Candie with an unhinged theatricality that’s constantly underpinned by a palpable air of menace. That DiCaprio gashed his hand during Candie’s dinner-table confrontation with Jamie Foxx’s Django and Christoph Waltz’ Dr. King Schultz has become the stuff of cinematic legend; it's a powerful testament to the star’s complete commitment to his craft – and his character’s utter depravity.
Read the Empire review here.
9) The Revenant (2015)
At last, Leo got his Oscar. He’s Hugh Glass, a fur trapper guiding frontiersmen through the unforgiving landscape of the Dakotas in the early 1800s. On the run from a Native American raiding party, Glass is mauled by a grizzly bear and left for dead by all but one of his party, Tom Hardy’s John Fitzgerald. Unfortunately Fitzgerald turns out to be roughly as sympathetic as the bear. And yet, half-buried alive in the frozen wilderness, Glass survives. And then he sets his sights on revenge. Alejandro G Iñárritu’s story of survival against all the odds – and all the bears – was scarcely less of a trial to film than the actual events would have been to live through, as DiCaprio clambered into dead horses, dunked himself in frozen rivers and nearly gave himself pneumonia. Now that’s commitment.
Read the Empire review here.
8) Romeo + Juliet (1996)
Baz Luhrmann’s pop take on Shakespeare layers 60 years of the movies and TV on top of the Bard’s work – Westerns, music videos, teen dramas, gangster flicks – and DiCaprio’s Romeo is perhaps its most potently 90s element. When we meet him, he’s in an oversized, rumpled tux on a crumbling stage on Venice Beach, smoking a cig and looking luminous in the early morning sun as Radiohead’s ‘Talk Show Host’ echoes across the sand. Romeo is one of the big Shakespearean roles, but it wasn’t one actors have tended to put a stamp on like Lear or Hamlet until DiCaprio’s doe-eyed, excitable, heart-on-sleeve performance here. Forget Titanic for a minute: this is the peak of Heartthrob Leo, and his Romeo is a full-blooded, floppy-fringed, doomed hero for the ages.
Read the Empire review here.
7) The Departed (2006)
A remake of the Hong Kong crime thriller Infernal Affairs, Martin Scorsese’s The Departed translates Andrew Lau and Alan Mak’s tale of corruption, crosses, and double-crosses into a Best Picture-winning Bostonian pulse-pounder. Here, Leo pulls off one of his most understated, internalised performances as Billy Costigan, a rookie cop from a rough background who’s tasked with heading undercover to infiltrate Irish Mob boss Frank Costello’s (Jack Nicholson) crew. Throughout the entirety of the film, DiCaprio – flexing his accent chops with a surprisingly adroit Boston roll – charts Costigan’s arc from hope and righteous fury to hopelessness and sheer desperation, each encounter with Costello playing out as if Costigan’s placing his head in a lion’s maw and trying to convince it he’s not meat. It’s a layered, weighty turn that helps dictate the tone and atmosphere of Scorsese’s film, and it’s a crucial milestone in the actor’s maturation on screen.
Read the Empire review here.
6) Catch Me If You Can (2002)
This might be Spielberg’s most effortless movie: Catch Me if You Can seems to move on oiled castors through its gears, following Frank Abagnale Jr. from small time scammer to the FBI’s most wanted list, via sojourns as a fake pilot, a fake doctor, a fake lawyer and an expert cheque-forger. Soon, Tom Hanks’ Carl Hanratty is on his case, chasing him across the country. DiCaprio plays Frank from the age of 17 to his early 30s with ease, and with a clear streak of a Peter Pan-ish unwillingness to accept that he has to grow up and accept the consequences of his actions. There’s always one more ruse, one more fantasy to fulfill – and though Frank hurts so many people along the way, the naivety DiCaprio draws out beneath Frank’s criminal nous makes him deeply likeable.
Read the Empire review here.
5) Once Upon A Time In Hollywood (2019)
One could theorise that DiCaprio is now in a phase of his career where he alternates between playing a genius and playing a moron. Killers Of The Flower Moon: moron. Don’t Look Up: genius. And before that, he was Rick Dalton in Quentin Tarantino’s daydreamingpaean to late sixties Hollywood. Brad Pitt’s abs got much of the attention, but Dalton is the finest idiot DiCaprio has ever played – a once-hot TV star who can feel himself fading into obscurity, but then hot young things Sharon Tate and Roman Polanski move in next door. Dalton’s search for redemption, and to rewrite the ending he sees coming for himself, gets an explosive coda come the finale. Suffice to say, this is the only DiCaprio movie in which he uses a flamethrower to torch bad guys.
Read the Empire review here.
4) Killers Of The Flower Moon (2023)
Finally, more than two decades after first working with Martin Scorsese on Gangs Of New York, Leo gets to share the screen with the director’s other muse, Robert De Niro, in this bracing, masterful depiction of the murders of the Osage people in 1920s Oklahoma. DiCaprio brings a bumbling, beta energy to the role of Ernest Burkhart – husband of Mollie Burkhart (Lily Gladstone), and an infinitely frustrating pawn in his uncle William’s (De Niro) schemes to manipulate the Osage out of their oil and riches. Even as Ernest slides further and further to the point of no return in his crimes against his wife and her family, DiCaprio manages to imbue him with charm and depth, whilst never shying away from his murky morals. It’s a big performance, in a massive masterpiece of a movie.
Read the Empire review here.
3) Titanic (1997)
The definitive role of DiCaprio’s early career was, when you look at it, one that didn’t really need him to do very much. Jack is a carefree scamp who lives for now, throws his arms open to the world and looks pretty dishy. In another actor’s hands, he could be a fairly rote romantic lead swallowed up by a historical disaster epic. So it’s remarkable that Jack and Rose endure as a movie couple like they do, and a big chunk of the box office-busting success of Titanic has to be down to the electric vibes between DiCaprio and Kate Winslet. James Cameron knows how to make a ship sink in lively fashion, but you only watch it once to see the disaster; you watch it the next seven times to see if Jack and Rose are going to make it this time.
Read the Empire review here.
2) Inception (2010)
In the middle of DiCaprio’s thief era, rubbing shoulders with The Wolf Of Wall Street and Catch Me if You Can, Christopher Nolan’s mind-expanding heist-within-a-heist-within-a-heist-within-a-dream thriller Inception stands as a landmark in properly popular, properly thought-provoking cinema. DiCaprio is professional dream thief Dominic Cobb, who’s tasked with convincing a businessman to dissolve his dad’s mega-corporation and thereby boost his rival. Cobb and his crack team go into the subconscious of their mark to do the job, but Cobb himself has a secret which could shake the whole plan to pieces. It’s an astonishingly imaginative film, and the one which kicked Nolan into the stratosphere. None of it would work, though – and nobody would still be talking about that cliffhanger ending – if DiCaprio hadn’t carried it off with such an inscrutable, contained kind of charisma.
Read the Empire review here.
1) The Wolf Of Wall Street (2013)
Hmm-MMM. Thump-thump. Hmm-MMM. Thump-thump. You could think of DiCaprio’s Jordan Belfort, master of the underhanded deed, as Frank ‘Catch Me if You Can’ Abagnale Jr’s sinister, city-slicker older brother: utterly amoral, ruthless, and with a laser-like focus on extracting cash from anyone foolish enough to trust him. He loses his job on Black Monday in 1987, and builds himself back up by bullishly inflating the prices of stocks before cutting and running with the profits. He becomes a shamanic figure for other young, thirsty, horrible brokers – until, in classic Scorsese style, he goes too far, and the whole thing starts falling apart. In a career full of them, The Wolf Of Wall Street features Scorsese’s finest arrest scenes, as the FBI storm into Belfort’s brokerage office to the strains of the Lemonheads’ cover of ‘Mrs Robinson’. This deliciously, operatically cynical response to the loss of trust after the 2008 financial crash is the high point of one of modern cinema’s greatest collabs.
Read the Empire review here.