Every Leonardo DiCaprio Movie, Ranked

After Titanic turned Leo into the biggest box-office star on the planet, one of his former pals saw an irresistibly juicy opportunity to cash in. Back in 1995, two years before DiCaprio would become the King of the World, a wannabe director named R.D. Robb shot this embarrassingly amateurish black-and-white cheapie about a bunch of baby-faced bros (including Tobey Maguire) misogynistically yukking it up in L.A. after dark. Needless to say, the post-Titanic Leo didn’t want it to see the light of day—and not just because he picks his nose and eats his own boogers onscreen. The star sued Robb, claiming he appeared in the film as a favor and never expected it to be released. The suit was eventually settled with a clause prohibiting Don’s Plum from ever being shown in North America. But as someone who’s suffered through its 89 minutes of torture, trust me, you’re not missing anything.

It’s hard to beat boogers, but by God, Total Eclipse nearly does it. Think of it, in our great canon of Leo films here, as the warm-up for Romeo + Juliet. It’s not Shakespeare, per se, but Total Eclipse is an erotic historical drama in which a young DiCaprio plays the poet Arthur Rimbaud. Close enough! Give or take a couple hundred years. Total Eclipse is a tonal mess, made worse by the story itself—which depicts the affair fellow French poet Paul Verlaine has with the 17-year-old Rimbaud. Better off leaving this one in the history books.

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To be fair, Leo was just a floppy-haired teenager when this low-rent schlock-fest landed on the straight-to-video shelves at your local Blockbuster. Also, it’s hardly the worst creature feature to piggyback on the success of Gremlins (especially if you have some edibles handy). Still, the third chapter in the killer-fuzzball “Critters Cinematic Universe” isn’t exactly a highlight on DiCaprio’s CV. And while it would certainly be a hot take to say that if you squinted just a little at DiCaprio’s performance in his movie debut you could see the promising future that lay ahead, it would also be a big, fat lie. Its zero-percent Rotten Tomatoes score feels about right.

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Woody Allen’s caustic tale of Hollywood excess may star Kenneth Branagh as the writer/director’s onscreen proxy, but this 1998 comedy is most notable for DiCaprio’s Brandon Darrow, a spoiled and volatile young actor who’s one of the many outlandish entertainment-industry characters who floats into the orbit of Branagh’s journalist. Whether laying waste to a hotel room or abusing his girlfriend (Gretchen Mol), DiCaprio’s character is the embodiment of narcissistic young stardom, and what makes his performance work is not only his burgeoning—and blistering—charisma but also his own budding party-boy reputation, which sells Darrow as a wholly convincing, autocritical caricature. It’s a small part, but even in a project filled with older A-listers, DiCaprio shines.

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Sure, Leo gets a boost from *checks IMDB* Meryl Streep, Diane Keaton, and Roberto De Niro, but Marvin’s Room, at times, feels written partly as a showcase for DiCaprio’s range. Playing Hank, a troubled teen living in a mental institution, Leo goes from 0 to 100. Then from 100 back to 0. Then back up to 100, as he goes from seeming like a kind kid who loves to tell stories to an arsonist screaming at anyone who crosses him. Of course, we’d see much, much more of this kind of impressive back-and-forth over DiCaprio’s career, but the early days felt especially thrilling.

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He’d been a teen dreamboat on Growing Pains and an Oscar nominee for What’s Eating Gilbert Grape before his 21st birthday, and Leo was determined to keep showing range. So he chose what may be the ultimate ’90s indie project: a film adaptation of punk poet Jim Carroll’s memoir of teenage drug addiction, prostitution, and high school basketball in New York City. Music fans got to see how some of the “People Who Died” died, and everyone else got to see that baby face get hooked on heroin. A smart play for credibility right before he dived into the high-profile matinee-idol parts. We’d rank this higher if he hadn’t been just a little bit upstaged by Mark Wahlberg, who we were just beginning to notice could really act.

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Considering the talent involved, this botched prestige picture about the infamous FBI battle-ax J. Edgar Hoover should have been so much better. Or at least a lot less boring. Director Clint Eastwood’s biggest sin here (apart from his soporific narrative) is turning Leo into a distracting waxwork ghoul buried under so much God-awful old-age makeup that it feels like a biopic of Jiminy Glick instead of Hoover. Despite the bulldog jowls, DiCaprio does the best he can with one arm tied behind his back. But even he’s not a miracle worker.

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When The Man in the Iron Mask debuted in theaters on a March weekend in 1998, it was the second-biggest movie at the box office, landing behind a slightly better-known DiCaprio film: Titanic. A hilariously inaccurate mash-up of The d’Artagnan Romances, The Man in the Iron Mask has the look and feel of a Disney Channel Original Movie with Leo playing dual roles as both the hero and the villain. One could likely attribute most of the film’s financial success to spillover from the dawning of the DiCaprio era. Leo is giving it his all, something he’ll become known for, but the performance just doesn’t stack up against what he’d accomplish in the long career ahead of him.

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There’s a part of me that’ll always feel like the Leo we saw in Body of Lies is prime Leo. You know him well: Action Hero Leo. (Also seen in Inception, Blood Diamond, and The Departed.) Action Hero Leo sits at tables, sipping espresso inquisitively, as he plots his next move. Action Hero Leo speaks many languages and knows many people. Action Hero Leo has recently discovered a large Al-Saleem safe house and training cell here in Amman! Oh shit. No one outsmarts Action Hero Leo.

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Not too far out from his career-making role in What’s Eating Gilbert Grape, DiCaprio starred in the Sharon Stone–led western The Quick and the Dead. None of those words make too much sense together, but that’s half the point. The enigma fits pretty well with the overall gist of the film. Though the movie itself might have been a bomb, it’s become a beloved cult classic and features DiCaprio in a charming, if not a bit campy, depiction of “the Kid,” a gangly would-be gunfighter … if he didn’t meet such a tragic end. Oh, fun fact: Sony wasn’t sure about DiCaprio, so Sharon Stone paid his salary. Thank you for that, Sharon.

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Still hot off the blockbuster success of Titanic, young DiCaprio starred in this Danny Boyle cult classic as Richard, an American backpacker shipping off to Thailand in search of “something more beautiful, something more exciting, and something more dangerous.” With a treasure map from a local lunatic in hand, Richard and his pals set sail for a secret island utopia, but they soon learn that nirvana isn’t all it’s cracked up to be. DiCaprio’s trademark “freak out” skills were first honed in The Beach’s notoriously off-the-wall third act, when Richard, like the locals before him, descends into pure sociopathic madness. It’s all lurid, laughable, and characteristically Boyle, but DiCaprio gave it his all, slicing through the stylized noise to craft a parable about how nothing gold can stay.

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DiCaprio leads the star-studded cast of this Adam McKay comedy as Dr. Randall Mindy, a nebbishy astronomer swept into a whirlwind of deception and disillusionment when a planet-killing comet sets a collision course for Earth. Though the film is ostensibly a comedy, DiCaprio finds tender tones within the story, turning in a tragicomic performance as a good man led astray by doomsday temptation. It’s a more muted performance than what we usually see from the actor, but don’t worry—he still finds time for a classic Leo Freakout when he loses his cool on cable-news anchors played by Cate Blanchett and Tyler Perry.

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Hard to blame a kid for overcrying in a movie about teens who tragically fuck up the scheduling of an otherwise great prank on their parents, which results in both of their deaths—especially when cast opposite the most talented crier of her generation, Claire Danes. But if he’d given us just a little less on “I defy you, stars!” this Baz Luhrman–directed extravaganza could have swapped spots with The Great Gatsby. Don’t watch that without first watching this one. The sweaty, molly-fueled ballroom scene in this flick walked so the one in The Great Gatsby could run.

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In Scorsese’s 2010 gripping psychological thriller, DiCaprio plays Edward “Teddy” Daniels, a U.S. Marshal brought to a creepy, remote psychiatric facility on an island in order to investigate the case of a missing patient with his new partner, Chuck Aule (Mark Ruffalo). Of course, it becomes clear that that isn’t really the case. In a film with one of the greatest twist endings of all time, Leo offers a layered performance in the complex role of a paranoid man whose greatest mystery to solve is his own mind.

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I suppose you could say this about several of DiCaprio’s roles, but Jay Gatsby feels like a character he was tailor-made to play. Despite the paparazzi’s best efforts, it feels as if Leo’s life is full of mystery yet to be surfaced. Dressed to the nines. A slick do. A whole lot of insecurity brewing beneath the surface. It’s no surprise Leo nailed this one.

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Premiering eight months before his Oscar-nominated turn in What’s Eating Gilbert Grape, DiCaprio’s breakout big-screen role came as the real-life Toby Wolff, whose memoir about childhood suffering and domestic strife is the basis for Michael Caton-Jones’s drama. As the young Wolff, DiCaprio goes toe to toe with Robert De Niro’s physically and verbally abusive Dwight, who moves in with Wolff and his mother (Ellen Barkin) and promptly turns their home into a war zone. Exuding a determined fierceness that he wears like a suit of armor, designed to protect him from the slings and arrows (and wallops) of De Niro’s nasty father figure, DiCaprio proved that he was born for the spotlight, exhibiting the intensity, range, and depth of emotion that he’d further develop in later years.

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This is where audiences and critics first really took note of the actor who would in short order become one of his generation’s bona fide greats. It’s DiCaprio’s star-is-born moment—not to mention one that would be recognized by the Academy with Leo’s first Oscar nomination. As Arnie, the sweet, mentally challenged younger brother of Johnny Depp’s going-nowhere-fast Gilbert, DiCaprio is devastating and affecting in equal measure without hitting any of the false notes that so many other young actors would have succumbed to. It’s a magical conjuring act of Method intensity, heart-tugging empathy, and technical precision. Yes, Depp was ostensibly the above-the-title attraction here. But it’s DiCaprio who had your attention when you walked out of the theater.

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Having already thrived under the stewardship of Spielberg, Scorsese, Cameron, Nolan, Luhrmann, Boyle, Eastwood, and Mendes, DiCaprio provided a unique scene-stealing performance for yet another auteur—Quentin Tarantino—in Django Unchained. DiCaprio’s Calvin J. Candie is a 19th-century southern plantation owner of the vilest sort, and his ownership of Kerry Washington’s Broomhilda makes him the prime target of Jamie Foxx’s vengeful freed slave. With slicked-back hair, a devilishly pointed goatee, and a shit-eating smirk that belies his cold, ruthless sociopathy, Candie is an over-the-top upper-cruster with low morals and even lower, darker instincts, and he serves as a captivatingly detestable counterweight to Foxx’s righteous avenger. It’s thrilling confirmation that, leading man though he may be, DiCaprio is expertly suited for villainy.

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It’s a dream in a dream in a dream (in a dream!), and it’s a damn fine outing from DiCaprio. Leading an ensemble cast, DiCaprio navigates Christopher Nolan’s mind-bending thriller as Dom Cobb, a man who performs mental heists by breaking into people’s dreams and stealing information from their subconscious. He and costar Elliot Page share a particularly electric chemistry as the two dive deeper into the mental void together, addressing Dom’s own trauma as his subconscious leaks into the minds of others. It’s the DiCaprio version of an action film, but damn if it isn’t a good one. (Also, the top fully fell down.)

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There is a famous story of two Hollywood directors bumping into each other on a remote sand dune in the Sahara on their separate shoots some 65 years ago. The demand for tales of Africa haven’t lessened in the decades since. (In fact, the year Blood Diamond released, it stood alongside two other noteworthy features shot in Uganda and Morocco, respectively: Last King of Scotland and Babel.) With a lesser lead, Edward Zwick’s epic would have remained just a treasure hunt, lost among the other films from the continent that tried. But with DiCaprio as Danny Archer, a diamond smuggler with neither a country nor a moral compass, it became a (then) career-highlight performance. The film is desperate for a redemption narrative—DiCaprio refuses it. Instead, he plays Archer as the scum he is. This also works, powerfully, against the actor’s own physical form. He refuses to let you like him—which is, of course, why we love him.

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