Leonardo DiCaprio's best—and worst—films

Released months before What’s Eating Gilbert Grape, Leo’s breakout role came via , the adaptation of Tobias Wolff’s memoir chronicling his teenage war against his mother’s abusive new live-in boyfriend, who has turned their loving and peaceful home into a war zone. This might have veered into cringey after school movie territory, but DiCaprio goes toe-to-toe with acting greats Ellen Barkin and Robert De Niro like he’d been doing it all his life, giving an early glimpse at the versatile greatness to come.

Both DiCaprio and costar Djimon Hounsou earned Oscar nominations for , a well-intentioned but Hollywoodized political drama centering on the corrupt African diamond trade in war-torn Sierra Leone. DiCaprio is a diamond smuggler who teams up with Hounsou’s enslaved local to find a huge pink diamond that’s been buried near a river. What saves this movie from being just another treasure hunt is the likable way the two mismatched buddies play off each other, with DiCaprio bringing the caddish touch of Catch Me If You Can to his smuggling sleazeball. Still, one wonders how this got him the Best Actor nod over The Departed in 2006.

Baz Luhrmann is perhaps an acquired taste; some people never get it, while others get it immediately. Depending on where you fall, his take on Shakespeare’s classic tragedy is either brilliant or laughable as the modern-day Capulets and Montagues—now tattooed and pink-haired rivals crawling around Verona Beach—fire off lines as quickly as they fire off bullets. Is tragic—or tragic comedy? You decide. Campy and exhaustingly weird as Luhrmann’s movie is, DiCaprio as Romeo and Claire Danes as Juliet have an undeniable chemistry that shines through the stylish overkill.

Martin Scorsese is famous for saddling his characters with a nagging, sometimes unconscious guilt they must contend with, and , his first foray into noirish 1950s psychological horror is no different. Leo stars as a U.S. Marshal investigating a woman’s mysterious disappearance from an insane asylum on a creepy remote island, where the sinister doctors and claustrophobic environment gradually grind him down. The plot may be slight compared to other Scorsese movies, but DiCaprio turns in a devastating performance as a man struggling with his inner demons and forced to see things about himself that he never wanted.

At first glance, Leonardo DiCaprio doesn’t stand out as the first choice to play debonair, delusional millionaire and eccentric Howard Hughes. But Martin Scorsese had faith. And lots of makeup. takes place at the time of Hughes’ life when he was directing the movie Hell’s Angels, wooing Katherine Hepburn and Ava Gardner, designing and flying his own planes, and dealing (badly) with crippling paranoia and increasing OCD. DiCaprio lurches from astonishing heights to paralyzing lows (literally—he crashes a plane into a couple of Beverly Hills mansions) as he embodies the aviation magnate. Even if the movie sugarcoats its subject somewhat, in the end you can’t imagine anyone else in the role.

Martin Scorsese’s is set in the hellscape that was Civil War-era New York City before it was a city. It tells the story of the gangs who fought to control poor neighborhoods leading up to the Draft Riots of 1863 between Irish and German immigrants and African Americans. At the time, casting DiCaprio (in his first movie with the director) raised a few eyebrows—wait, that kid from Titanic in an ultraviolent Scorsese period pic where people take each other out with sledgehammers, razors, pickaxes, and meat cleavers? You don’t say! He stars as Amsterdam Vallon, the Irish-Catholic son of Irish immigrants determined to avenge his father’s death at the hands of a rival gang leader (Daniel Day-Lewis, co-starring with Leo for the first and only time) by infiltrating the gang and becoming its leader’s protégé. A magnificently ham-fisted achievement of the histrionic kind, Gangs Of New York belongs to Day-Lewis’ over-the-top dandy, but DiCaprio is convincing as someone struggling not to like the man he’s determined to kill.

There’s method acting, and then there’s what DiCaprio did for . For this grueling tale of a fur trapper dead set on revenge, he covered himself in ants, suffered subzero temps and performed despite a terrible flu, among other things. Was it worth it? Well, he finally won that elusive Best Actor Oscar, which was most definitely deserved—even though Alejandro González Iñárritu’s Old West epic was more character study than dialogue-driven drama. It’s a story told through DiCaprio’s actions rather than words, as he helplessly sees his son murdered and then embarks on a torturous quest for vengeance through the wintry forest, enduring starvation, cold, and indescribable injury. It’s a journey both appalling and impossible to look away from.

You probably don’t often say “Martin Scorsese” and “LMAO” in the same breath, but that’s exactly what delivered as the director’s first straight-up comedy in years. Based on the memoirs of corrupt stockbroker Jordan Belfort, it opens with a live midget toss in his office where orgies were the norm, as was doing a line of coke with your morning coffee. While DiCaprio isn’t famous for being particularly funny, he flexes his comedy chops with the best of them, breaking the fourth wall and regaling employees with hilariously inspirational, hard-R speeches like a revivalist Gordon Gecko. Ultimately you like him—but you don’t look up to him.

It can be very easy to go very wrong playing someone disabled (we’re looking at you, ). But , a sweet coming-of-age drama starring Johnny Depp as a restless kid tasked with caring for his mother, sisters, and mentally disabled brother (DiCaprio), features strong performances that come off as authentic rather than acting for the fences. Director Lasse Hallström gives us a quirkily affectionate and sometimes funny look at this small-town family, while DiCaprio deservedly earned his first (and to date only) Best Supporting Actor Academy Award nomination for his endearing, water-tower obsessed Arnie.

It would be seven years after Django Unchained that DiCaprio starred in another Tarantino movie. And his role in was wildly different, that of washed-up TV Western actor Rick Dalton. Tarantino brings uncharacteristic emotional melancholy to the proceedings, and DiCaprio delivers heartbreaking vulnerability to his fading star—it should be noted that he completely improvised the flip-out scene in his trailer. Tarantino’s indulgent three-hour movie about two aging buddies and their run-ins with the Manson family never feels long; we could hang out with Dalton and his stunt-double buddy Cliff Booth (Brad Pitt) all day. (And it was even better to find out these two are friends offscreen, even making pottery together.)

The spaghetti Western marked the first collab between Quentin Tarantino and Leo. Although DiCaprio’s sadistic plantation owner Calvin Candie isn’t the biggest role in the movie—you don’t meet him until well into the film—it is an unquestionable career high point. Tarantino is a master at crafting the best worst people and as the detestable slaver who forces his men to fight each other in what he calls “Mandingo” style, DiCaprio might be Tarantino’s most detestable villain; a Francophile who can’t speak a word of French comes off weirdly gracious as he offers his phrenological theories on what makes black people submissive and delights in his slaves killing each other with hammers for money. Christoph Waltz won Best Supporting Actor for his role, but one could easily make the case for DiCaprio instead.

Upon its release, everyone was talking about , Christopher Nolan’s brainy sci-fi heist film, for its spectacular special effects and labyrinthine plot, which has DiCaprio playing a mind-crime thief named Dominic Cobb. Cobb’s an “extractor” of information from his targets’ brains, but in his final job, he’s hired to implant an idea into his mark. The movie has all the usual Nolan hallmarks—scientific exploration, creative use of time, mind-bending set pieces and effects – but don’t sleep on DiCaprio’s performance as a brilliant yet tortured criminal unable to fight off his personal demons.

Was one of the best films of DiCaprio’s career? Certainly not, but it’s arguably his most important—James Cameron’s Oscar-winning, groundbreaking, record-shattering love story launched the young actor into the stratosphere, and his career would never be the same. We all know the deal: the scrappy, adventurous drifter and stifled rich girl meet cute and fall in love on the eve of the great ship’s sinking in a sort of fluffy 1940s-style romance that somehow, amazingly, worked on just about every level. That we still talk about it decades later proves just how well.

is director Steven Spielberg’s stylishly buoyant caper that tells the true story of con artist Frank Abagnale Jr., who became a teenage criminal and passed himself off as a pilot, a lawyer, and a pediatrician while cashing $4 million in forged checks by the time he was in his early 20s. As played by DiCaprio, Frank is a disillusioned 16-year-old in the 1960s watching the American Dream collapse before his very eyes, and as his family splinters, is forced to choose which parent he wants to live with. Instead, he does what any self-respecting kid would do—he runs away and begins a life as a con artist. It’s genius casting, as DiCaprio (in his late 20s but still baby-faced) perfectly captures Frank’s transformation from innocent kid to jaded adult felon on the run, surviving only on his audacity and nerves of steel.

, Martin Scorsese and DiCaprio’s third team-up, is a remake of the great 2002 Hong Kong film Infernal Affairs, and it turned out to be the charm for Scorsese, who finally won his elusive Best Director Academy Award for it. While Jack Nicholson and Alec Baldwin were chewing up the scenery in the Boston-set mob crime drama, DiCaprio was quietly over there stealing the show as a thuggish undercover cop who nearly loses his identity in one of his grittiest and greatest roles. You can make the usual Scorsese criticisms about the movie’s length and nonlinear narration, but ultimately the top-notch performances and the film’s sensational ending make it one of the most satisfying crime dramas of the century.

Ewan McGregor may be glad he dodged a bullet by avoiding , an adventure drama directed by Danny Boyle, in which he was supposed to star before (allegedly) Boyle was given more money to cast the hot-off-Titanic DiCaprio instead. Based on a novel by Alex Garland, it’s the story of a backpacker who travels to Thailand in search of a legendary beach untouched by tourists and hooks up with a commune of expats. Still cruising on his post-Titanic fame, DiCaprio as a shirtless alienated young guy angsting around on a beautiful island wasn’t the draw everyone had hoped for. And he earned a Razzie for his bother.

How could a biopic with luminaries like director Clint Eastwood and stars DiCaprio, Naomi Watts, and Judy Dench go so completely, disastrously wrong? The problem with isn’t Leo DiCaprio’s performance, which is predictably masterful; it’s everything else: the long-winded and underwhelming script, clumsy prosthetics, banal direction, and boring narrative. Instead of giving us an illuminating portrait of a fascinating and controversial figure, Eastwood wimps out, handing us a ponderous and colorless mess that wasted DiCaprio’s committed performance and made him look like a waxy Philip Seymour Hoffman to boot.

You get twice the DiCaprio yet half the fun in , Braveheart screenwriter Randall Wallace’s cheesy, clunky directing debut. Based loosely around Alexandre Dumas’ Four Musketeers characters, it stars Leo as both the despotic King Louis XIV and his mysterious twin, who has been imprisoned in an iron mask and hidden away. It was the actor’s first film after Titanic, which can only be the reason for this astonishingly bad film’s success—he comes across young and out of his element (that Yankee accent does him no favors), while not even the veteran all-star cast of Musketeers (Gabriel Byrne, John Malkovich, Gerard Depardieu, and Jeremy Irons) could save this goofy gaffe from itself. As one critic wrote at the time, “There’s so much unintentional mugging in this film I feared for my wallet.”

Handily proving it doesn’t matter how much talent you have in front of and behind the camera, director Ridley Scott’s espionage thriller is a sludgy take on the war on terror. The film features the dream team casting of DiCaprio and Russell Crowe as CIA operatives searching for terrorists in the Middle East. You have lectures about the evils of oil money, Crowe affecting an Arkansas accent to let folks know he’s in the business of “saving civilization, honey,” and a jingoist script at odds with Scott’s straight-ahead action movie intent. It all adds up to a politically muddled and only vaguely compelling film that lacks a much-needed emotional punch, despite the lead actors’ capable performances. Bury this Body in the desert where it belongs.