Leonardo DiCaprio recently starred in Netflix’s Don’t Look Up, but how does this film rank among his worst, and best, movies?

DiCaprio is one of the biggest and highest-paid movie stars of all time; from the “Leo Mania” with the one-two punch of James Cameron’s Titanic and Baz Luhrmann’s Romeo + Juliet, to DiCaprio’s movie collaborations with Martin Scorsese, to his eventual Oscar win for Alejandro G. Iñárritu’s The Revenant, it feels like the actor has been around forever — and he’s still got a long career ahead of him. DiCaprio will next star in an adaptation of Erik Larson’s The Devil in the White City, a TV mini-series for Hulu with Keanu Reeves, as well as the police thriller The Black Hand, and a film adaptation of the book Killers of the Flower Moon.

DiCaprio began acting at the age of 14, transitioning from commercials for Apple Jacks and Mattel to appearances on television shows like Roseanne and Growing Pains. After a breakout role in the film This Boy’s Life with Robert De Niro and What’s Eating Gilbert Grape with Johnny Depp, he evolved seamlessly from a bona fide child star to a teen heartthrob to a dramatic adult actor with a vast and varied filmography, starring in multiple high-profile projects with a vast array of collaborators. Seven Oscar nominations and one win later, DiCaprio has cemented himself as a movie star dedicated to taking on bold, diverse, and challenging roles, leading to some of the best Hollywood has to offer.

DiCaprio has taken on many roles since his arrival in Hollywood, including actor, producer, and adamant environmentalist. His production company, Appian Way Productions, has produced a number of his own films, as well as documentaries, features, and TV projects, including Orphan, Out of the Furnace, Richard Jewell, The 11th Hour, Ice on Fire, and more. DiCaprio has run the gamut in his busy career, collaborating with some of the most prominent filmmakers working today, from Scorsese to Spielberg to Nolan to Tarantino. Indeed, his resume could almost double as a time capsule of the last 30 years of American cinema.

Leonardo DiCaprio has starred in 29 films so far. These vary from his early b-movie entries like Critters to his high-profile, critically acclaimed roles, like Titanic or Shutter Island. Here’s a look back at all of his films, ranked from worst to best.

29. Critters 3

Leo fans could probably debate for a year about his greatest performance and never make one mention of his 1992 film debut in Critters 3. A critically-derided Gremlins wannabe, its bare-bones plot concerns a race of hairy aliens infesting an apartment building. Leo plays the landlord’s son, Josh, and while he survives his encounter with the titular critters, he did not return for the intergalactic-set fourth entry.

28. The Man in the Iron Mask

The remake The Man in the Iron Mask is another weaker Leonardo DiCaprio movie. Riding the success of 1997’s monster hit Titanic, this loose adaptation of Alexandre Dumas’ second sequel to The Three Musketeers actually performed quite well at the box office. Alas, audiences more than a decade removed from “Leo Mania” may wonder what all the fuss was about; this is ultimately a pretty low-grade, cheesy effort, wasting a cast that includes legends like Jeremy Irons, John Malkovich, Gerard Depardieu, and Gabriel Byrne. Leo himself plays the dual role of King Louis XIV and his imprisoned twin brother, making little impact with either. Directed by Braveheart’s Randall Wallace, the expectation was for something more polished, but the film struggles to find that level of quality.

27. Total Eclipse

Based on the real-life love affair between 19th-century poets Paul Verlaine and Arthur Rimbaud, this erotic drama was a box office bomb owing mostly to the controversy of a series of fairly-explicit sex scenes between its two actors, Leonardo DiCaprio and David Thewlis. While that sounds groundbreaking in a pre-Brokeback Mountain and Call Me By Your Name age, the resulting film is made almost unwatchable due to the obnoxiousness of its lead characters, who are rendered here as two of the most snobbish, egotistical, and selfish people to ever fall in love in a movie.

26. The Basketball Diaries

The Basketball Diaries tells the story of Jim Carroll, a gifted high school basketball player who falls prey to drug addiction, and while it’s based on Carroll’s autobiographical novel by the same name, it too often comes across as disingenuous, overwrought, and cliche. Brimming with over-the-top performances and copious montages of basketball and drug use, it’s a miserable descent into the depths of addiction that’s only really worth watching for Leo’s performance, which gives a sense of the big but committed swings he’d continue to make as his career progressed.

25. J. Edgar

The idea of Clint Eastwood tackling a DiCaprio-led biopic about the legendarily controversial director of the FBI may seem ripe with potential. Alas, the resulting film tries too hard to have it both ways, as both a full-blown monster movie about an American villain and as a fair and balanced story about a man whose sexual repression led him to wage war on the marginalized people of his own country. Floating in the midst of this wishy-washy tone is DiCaprio’s performance, which is plenty capable but too often at the mercy of the muddled, ultimately confusing film around him, not to mention the pounds of poorly-executed old-age makeup he’s buried under.

24. Body of Lies

The 2000s were understandably awash with action thrillers confronting terrorism. Casting Leonardo DiCaprio and Russell Crowe certainly goes a long way to separate Body of Lies from the rest of the pack, but unfortunately little else does. Ridley Scott’s direction is tense and polished, but there’s something disappointingly workmanlike about the way it hits its familiar beats and then gets out of dodge. Even with a script by The Departed’s William Monahan, Body of Lies never reaches the heights it could have, given the talent behind it. For all involved, it’s just a fairly forgettable entry.

23. Don’s Plum

The most interesting aspect of this black-and-white curiosity is what happened behind the scenes. Shot in 1995 and 1996 and starring a pre-Titanic Leo and pre-Spider-Man Tobey Maguire, the film snagged some buzz when the two actors sued in 2001 to block the film’s release. Retrospectively, Don’s Plum poses very little threat to their stardom; the two are perfectly fine in this intriguing but meandering slice-of-life talk-fest about a group of young friends who meet at a restaurant every Saturday night. It’s worth a look for completionists who can find it; the film is still banned from release in the U.S. and Canada.

22. Don’t Look Up

Director Adam McKay’s satirical doomsday comedy stars DiCaprio as a scientist who helps discover a rogue comet heading toward Earth with little time to stop it. Joined by an all-star cast that includes Jennifer Lawrence, Meryl Streep, Jonah Hill, Tyler Perry, Cate Blanchett, Timothée Chalamet, Mark Rylance, and Rob Morgan, the Netflix-exclusive film was a controversial release, taking a shot at everything from politics, news, science, greed, etc., attempting to shine a light on the current cycle of division throughout the world, particularly when faced with a global threat. DiCaprio plays a more low-key, demure character here, but still gets his moment to shine when unleashed, even though it’s hardly enough to put the performance in a “best of” category. Ultimately, the heavy-handed satire got people talking, but not about how good the movie was, but rather the divisive issues it brings up.

21. Marvin’s Room

The film version of Scott McPherson’s play, itself now a staple of community theaters around the country, is a solid piece of work from four-time Tony Award winner Jerry Zaks. It of course doesn’t hurt that it stars Meryl Streep, Diane Keaton, and Robert De Niro, but they can only elevate what’s ultimately a fairly standard family drama so much. Leo, playing Meryl’s son who’s been committed to a mental institution for setting her house on fire, holds his own magnificently against these legendary stars, but also seems almost feel him itching to break out of the troubled teen mold for greater pastures.

20. The Quick and the Dead

In 1995, Sam Raimi directed a Sergio Leone-inspired Western wherein Gene Hackman, playing a sadistic mayor, organizes a quick-draw tournament between Leo, Sharon Stone, and Russell Crowe (amongst others). As visually stylish and packed with special effects-driven violence as one might expect from the director of the Evil Dead franchise, The Quick and the Dead doesn’t quite stack up to Raimi’s best. However, Leonardo DiCaprio fits into its pastiche style well, donning a cocksure swagger as a Billy the Kid-esque cowboy with a deeper connection to the mayor.

19. Celebrity

Woody Allen’s 1998 Fellini riff is somewhere between the vivacity of his early work like Annie Hall and Manhattan, and the drudgery of his seemingly endless run of late-career European travelogues. This time, he cedes his usual neuroses to Kenneth Branagh, who does a grating Allen impression while playing a nebbish entertainment journalist hopping from one celebrity encounter to another. The best of those encounters is with DiCaprio himself, in a scene-stealing performance as a recently branded superstar reveling in debauchery. While the rest of the DiCaprio movies moves in fits and starts, it comes wickedly alive whenever he’s onscreen.

18. Blood Diamond

DiCaprio and his co-star, the always-fantastic Djimon Hounsou, both received Oscar nominations for their work in Blood Diamond, an ambitious but formulaic war thriller from director Edward Zwick (Glory, The Last Samurai). The DiCaprio movie is about a black Mende fisherman (Hounsou) who partners with a white South African smuggler (DiCaprio) to recover a rare blood diamond and thus return it to his family. Its aspirations of importance, dealing with the titular diamonds mined in war zones and sold to finance conflicts, aren’t often met; however, it’s still a solidly engaging piece of work with some strong action and engaging characters.

17. The Beach

The first project Leo signed onto post-Titanic, Danny Boyle’s The Beach, based on the novel by Alex Garland, is neither a rubber-stamping of Leo’s heartthrob status or a method-acting, transformational subversion. Instead, the then-25-year-old star basically plays a version of himself, searching for a utopian island away from the technological woes of society. It’s a film that gets a bad rap, but its first hour is a gorgeously shot immersion in this idyllic getaway, anchored by a wonderfully easy DiCaprio. Sure, things go off the rails in a Lord of the Flies-meets-Apocalypse Now third act, but there’s an ambition and risk on display throughout, particularly from the film’s lead actor. Leo could’ve cruised on his Jack Dawson charm forever; with The Beach, he made his first step toward a more interesting career.

16. This Boy’s Life

Leo’s first leading vehicle, This Boy’s Life is an adaptation of author Tobias Wolff’s memoir. Leo plays a young Tobias, whose world is rocked when his loving single mother, played by Ellen Barkin, settles down with the seemingly mild-mannered but abusive Dwight Hansen (Robert De Niro). The film itself is a touching, hidden gem, but it’s most notable for being an early bellwether for the complexity DiCaprio was capable of bringing to a role even at a young age. This film asks a lot of its young actor, and DiCaprio measures up beat for beat, both going toe-to-toe with De Niro and crafting a powerful, heartwarming relationship with Barkin.

15. The Revenant

Otherwise known as the movie where Leo gets mauled by a bear and eats raw bison liver, The Revenant made Alejandro G. Innaritu the first since 1950 to win Best Director two years in a row and director of photography Emmanuel Lubezki a record-setting three-time consecutive winner for Best Cinematography. Whether this Malickian take on a revenge narrative deserves all that history-making acclaim is up for debate. Indeed, it’s gorgeously shot with a dynamite opening sequence, but too often this relentlessly punishing slog through the elements becomes a relentlessly punishing slog for the audience, even with the contrasting story of Tom Hardy’s villainous character onscreen. All that said, Leo puts himself through the wringer in an intensely-committed, physical performance, and he was rewarded with a long-deserved Oscar.

14. Gangs of New York

Leo’s first collaboration with Martin Scorsese is not their best, but it’s a solid prelude to the films to come. DiCaprio himself is fine as the vengeful Amsterdam Vallon, if a bit strained in his first real “adult” role, but he’s nearly swallowed alive at every turn by Daniel Day-Lewis’ gargantuan turn as William “Bill the Butcher” Cutter. Aside from that performance, this film’s treats are mostly visual, featuring painstaking recreations of mid-19th-century New York by production designer Dante Ferretti and sumptuously detailed costumes by Sandy Powell.

13. The Great Gatsby

Before it was made an overused meme, Leo’s entrance as Jay Gatsby was a bit of an inspired reunion between the actor and former Romeo + Juliet director Baz Lurhmann. The Great Gatsby’s famously kinetic director doesn’t butcher the classic source material as some might argue; in truth, many of his revisionist impulses (the hip hop-laced soundtrack, for instance) work solidly enough. The cast is equally kinetic, including DiCaprio, Tobey Maguire, Carey Mulligan, and Joel Edgerton. It’s when Lurhmann has to leave the party and settle in for the plot mechanics of Fitzgerald’s text that things can get a little dull. What’s not dull is DiCaprio’s performance, a welcome return to the romantic charm he so easily oozes but so often seems intent on shoving aside. His movie star smile, the puppy dog anxiety he betrays when the love of his life reenters his life – it all amounts to one of his more underrated turns.

12. Romeo + Juliet

For a certain generation, this Baz Lurhmann film was not only an introduction to the world’s most famous tale of star-crossed lovers, but to the boundless freedom of interpretation William Shakespeare’s work grants. It’s true Lurhmann’s operatic, hyper-kinetic style isn’t for everyone, but there’s such a visceral punch to it all that it’s no wonder teenagers connected more strongly to this material here than they ever did in English class, especially with a cast that includes DiCaprio and Claire Danes. Of course, it helps matters that the titular couple’s chemistry is beyond palpable, with Leo’s passionate performance smoldering from his Radiohead-scored entrance to his tragic final moments.

11. Django Unchained

Quentin Tarantino’s blood-soaked, Spaghetti western take on slavery isn’t likely to convert his haters, and at times his usual glibness seems to waltz giddily into the realm of the irresponsible. Of course, it’s all still pretty wildly entertaining, with a deep bench of scene-stealing supporting performances, from Samuel L. Jackson’s villain to Christoph Waltz’s Academy Award-winning turn as Dr. King Schultz to Jamie Foxx’s heroic turn as the slave-turned-cowboy out for vengeance. The biggest and baddest of them all, though, is Leo’s Calvin Candie, a flamboyantly psychotic plantation owner who has a bizarre obsession with France and forces his slaves to fight each other. It’s a disgusting, demented performance, but it’s also impossible not to notice that the film’s quality dips significantly once he leaves it.

10. The Aviator

Martin Scorsese and DiCaprio’s second movie collaboration earned the actor his first Oscar nomination since 1993’s What’s Eating Gilbert Grape, and justly so. Contrasted with his somewhat-strained Gangs performance, Leo carries this epic but personal Howard Hughes biopic on steady shoulders from beginning to end with a supporting cast that includes Cate Blanchett, Kate Beckinsale, John C. Reilly, Alan Alda, Jude Law, Danny Huston, and more. It’s perhaps unsurprising he can turn on his iconic youthful charisma for the film’s earlier sequences about the aviation whiz-slash-blockbuster filmmaker, but it’s his thoroughly-believable descent into an obsessive, paranoid hellscape that makes this such an important turning point in the legendary actor’s career. With The Aviator, DiCaprio undeniably crossed into the realm of legitimate leading man and hasn’t left since.

9. The Wolf of Wall Street

Martin Scorsese followed up his most family-friendly film, Hugo, with his most profane to date. The Wolf of Wall Street sees the iconic director tackling the real-life character of Jordan Belfort, a superhuman sleazebag who merrily defrauds wealthy investors out of millions of dollars while riding a seemingly never-ending gravy train of sex and drugs. Leo plays this monster of depravity with a ferocious sense of glee, and it’s arguable he should’ve won the Oscar alone for his riotously dorky yet undeniably sexy wedding dance moves or for a scene where he drags himself to his car in a quaaludes-induced semi-coma. It’s an excessive performance in a film about excess, and while its 180-minute running time can feel overstuffed with crass, one-note satire, it’s a bit contagious seeing Marty piling on the nastiness and needle-drops to make his liveliest and most energetic film since 1990’s GoodFellas.

8. Revolutionary Road

A reunion 11 years in the making, Leonardo DiCaprio and Kate Winslet returned to the screen together with striking results in this achingly moving adaptation of the Richard Yates novel from American Beauty director Sam Mendes. Revolutionary Road is far from the waters of Titanic, however, trading in that film’s breathless romance for suburban ennui and dreams deferred. Frank and April’s stark contrast to Jack and Rose would be palpable enough, but the stars’ performances are two of their best, with Winslet’s passion and verve drowning in the prison of this 1950s homemaker and DiCaprio absolutely heartbreaking playing a disillusioned man coming to the realization that his life isn’t getting any better.

7. What’s Eating Gilbert Grape

Lasse Hallstrom’s sentimental tale of a small-town boy shouldered with the responsibility of his mentally-handicapped younger brother seems at first glance a minefield of cliche pile-ups and cloying predictability, yet somehow defies the odds with an underlying tenderness and exceptional performances. Chief among them is DiCaprio, whose Oscar-nominated turn as Arnie Grape is a scene-stealing breakthrough for the ages. This remarkably affectionate, vivid portrayal transforms a potentially cynical awards-bait bid into a gauntlet-laying promise of the complexity and truth to come in the career of this then-19 year old performer.

6. The Departed

For an actor famous for his intensity and commitment, it’s remarkable how one of his best performances is one where he’s asked to keep a lid on things. Playing an undercover cop in The Departed who insinuates himself into the Boston mob underworld, Leo has to constantly keep it cool, lest he blow his cover in front of Jack Nicholson’s Frank Costello. In this way, his often “big for the sake of big” choices are simmered down to a low boil, with his character Billy’s anxiety so captivatingly portrayed it feels like both he and the audience might wind up with a heart attack. DiCaprio goes toe-to-toe with some powerful actors here (outside Nicholson), including Matt Damon, Vera Farmiga, Martin Sheen, and Mark Wahlberg. By the movie’s end, he’s just another corpse in the body count of the film’s ominous title, but his work here shows that this director-actor collaboration is anything but dead.

5. Shutter Island

Unfairly buried with a February release and soon overshadowed by that other 2010 Leo thriller Inception, this underrated Scorsese gem initially seems like a pure genre exercise for the masterful director, with DiCaprio lending his movie star swagger to the lead role of this duly appointed federal marshal, backed up by a cast that includes Mark Ruffalo, Ben Kingsley, Michelle Williams, Max Von Sydow, and Jackie Earle Haley. Eventually, though, the artifice shatters with a late-breaking twist that forces the audience to recontextualize everything they’ve seen, and Leo to deconstruct the character he’s built before their very eyes. This ultimately leads to a flashback climax containing perhaps the actor’s most nakedly vulnerable scene. His portrayal of the crumbling illusions of a broken man makes this haunted film well worth a second look.

4. Catch Me If You Can

Steven Spielberg’s 2002 adaptation of Frank Abagnale Jr.’s autobiography is often framed as a light-hearted romp, one of the director’s frothier offerings. Indeed, this tale of a real-life wunderkind con artist embraces its caper status, supported by one of John Williams’ more playful scores and centered around a DiCaprio performance that caught the actor at the exact moment he was trading in his boyish heartthrob status for something darker and more adult. All that said, there’s an undercurrent of melancholy that might surprise viewers upon rewatch; this is essentially the story of a scared little boy who flies off on adventures to protect himself from the cold hard facts of life. In this way, it’s a more effective take on Peter Pan than Spielberg’s own Hook, with Leo giving both a fresh spin to “the boy who wouldn’t grow up” and a meta-textual comment on his own career; this is an actor who has never stopped reinventing himself.

3. Inception

11 years on, submerged in a culture where box office is dominated by sequels, remakes, and superhero movies, it’s amazing to think that one of the highest-grossing films of the 2010s was a sci-fi heist movie about invading people’s dreams and stealing their thoughts. It’s a credit to Christopher Nolan that the whole thing goes down so easy, melding an intricate labyrinth of rules and surreality with a simple, “one last job” genre frame. DiCaprio’s performance could easily go uncelebrated, but it’s one of the actor’s best, a remarkably subtle and tortured turn that could only be performed by a movie star of his stature. Cast someone else and Nolan’s film could easily lose the underlying sadness that gives this blockbuster its incredible sense of gravity.

2. Titanic

After tying Ben-Hur for most Oscar wins of all time and becoming the highest-grossing film in history at the time, it’s understandable James Cameron’s magnum opus would undergo a bit of a cultural backlash. That said, there is a reason the Titanic is so well regarded in film history. It’s at once a sweeping love story; an exhaustively-detailed period piece; a tale of class and gender, liberation and oppression. It’s an Old Hollywood romance that transitions seamlessly into a nail-biting action thriller, a showcase for groundbreaking special effects that never loses a sense of gut-churning despair and tragedy. Everything about it is iconic, and rightfully so; this is old-fashioned moviemaking that can sit proudly on a shelf beside legendary epics like Gone With the Wind and Lawrence of Arabia. Of course, it must be said, none of it works without the sizzling chemistry of Leo and Kate. The young star who brought life to Jack Dawson may have spent the rest of his career trying to put this film behind him, but there’s nothing to be ashamed of here. 100 years from now, Titanic will be as special as the day it was first released.

1. Once Upon a Time… in Hollywood

His first film after nearly freezing himself to death in The Revenant sees an Oscar-winning Leo with nothing to prove and everything to show. His turn as faded film star Rick Dalton is in its own way a tapestry of what makes this actor so special: the sexy charisma, the wounded vulnerability, the volatility that explodes in a “trashing the trailer” rant for the ages. It helps that the movie surrounding him is so good; despite a polarizing ending that for better or worse sees Tarantino returning to his uber-violent roots, this is one of the writer-director’s most mature and sublime works, a moving portrait of the end of Old Hollywood synchronized with the impending dread of one of America’s nastiest losses of innocence – the Manson murders. The supporting cast is one for the ages as well, with DiCaprio’s relationship to Brad Pitt’s Cliff Booth a classic movie buddy pairing. The threat of bloodshed looms over the film like a silent phantom; meanwhile, Leo just wants to get his lines right. When breakthrough actress Julia Butters approaches him after he finally nails a take and whispers in his ear, “That was the best acting I’ve ever seen,” it’s doubly powerful, the end of Rick Dalton’s struggle through a day at work, and Leonardo DiCaprio’s best performance yet.