Ranking Every Leonardo DiCaprio Film Performance From Best To Worst - US TV INSIDER

Please try not to have a panic attack from all the excitement. 

Not to mention the seven Oscar nominations (one win) and 13 Golden Globe nominations (three wins) he’s got under his belt. 

As with my rankings of Anne Hathaway, Emma Stone, and Margot Robbie, I will be ranking Leo’s film cameos and voice-over roles. However, his appearances in documentaries, shorts, commercials, and TV shows are off limits. (Sorry, Growing Pains!)

Also, this ranking is based solely on Leo’s performances and NOT the movie as a whole.

Most actors’ filmographies are riddled with cameos, bit roles, and small supporting parts. Due to Leo’s previous television career on shows like Parenthood  and Growing Pains, as well as his rapid ascent in film, this is the only bit role on his IMDb page. He’s got no lines here, and simply walks out of a classroom carrying some books. The film, an erotic thriller, is about a woman named Ivy (Drew Barrymore) who is obsessed with her best friend’s dad to the extent that she murders her mother and attempts to take her place. Leo’s character, “Guy,” is blissfully unaware of this drama. He’s just trying to pass Calc. And so, because Leo is asked to do literally nothing here outside of walking, I’m ranking this last. 

Buy the DVD on Amazon. 

Ah, yes, the original demon twink, French poet Arthur Rimbaud. On paper it’s Oscar cat nip: a period drama with high-pedigree stars playing mentally unwell literary figures in the midst of a torrid homosexual affair. In reality, the film and Leo’s performance are just pure chaos. DiCaprio’s Rimbaud is taking his clothes off for no reason, pissing at dinner parties, and howling at the moon. A little restraint would have gone a long way here, but if you’ve been jonesing to watch young Leo top Professor Lupin, this film does scratch that itch. 

Buy the DVD on Amazon. 

Who is really to blame here? Is it Clint Eastwood’s choice of low-saturation, near-gray scale lighting? Is it the botched facial prosthetics that make the elderly J. Edgar Hoover look like he’s wearing old-age makeup from a high school production of Fiddler on the Roof? Is it the fact that, infamously, Eastwood rarely allows more than three takes of a scene, forcing his actors to get it right on the first try? Is it the ham-fisted script that rattles along like a resume more than a story? Or is it Leo, himself, weighed down by a here-one-moment-gone-the-next bizarre accent choice and shouting “Clyde” like a maniac? The film is both incredibly boring and poorly constructed in nearly every aspect (but somehow not in a fun way), and even a talented actor like Leo can’t carry this rotting corpse on his back. So is he doing a bad job here or is the film so terrible it’s not allowing him to perform well? At the end of the day, for our purposes, it doesn’t really matter. This is one of Leo’s few misses, and a big one. 

Watch it on HBO Max. 

Better than J. Edgar is baby Leo’s first-ever film role in which he plays a kid living in a building that is overrun by evil alien woodchuck-like predators. He and his merry band of co-tenants must swat away the slime-filled, spike-shooting vermin as they flee to the roof. Leo plays his GameBoy and runs from monsters, but seems oddly unconcerned when his father is killed. Blame a newbie’s instinct to go for a nuanced, understated performance of grief in a straight-to-VHS third horror sequel about murderous gophers. 

Watch it on HBO Max. 

Remember that period post-9/11 where seemingly every other movie or TV show had a plot line about secret Middle Eastern terrorist organizations? Well, Leo starred as the CIA operative at the center of Ridley Scott’s take on the genre. His performance isn’t so much bad as it is bland. Everything about this film, like its desert backdrop, is a muted, beige, unremarkable haze. I watched this movie a week ago, and it’s already slipping from my mind like a palm full of sand. It’s supposedly a thriller, but the plot is both incoherent and dull, and Leo drowns along with it under the dunes.

Watch it on Netflix. 

If you’ve been looking for a film that is 90% just a young Leo walking around shirtless, well then congratulations, we have you covered! Aside from his tan abs, however, Leo (and this Danny Boyle film) aren’t offering much. Leo plays a wayward American trying to find purpose on a trip to Thailand when he stumbles upon a secret beach cult (run by Tilda Swinton in an early breakout role). In some ways, Leo does take some swings here, especially during some hallucination scenes during the middle of the movie, but ultimately he’s not given a great deal of space to spread his wings. For his first lead role post-Titanic, he’s still playing it too safe (and in a movie that critics reviled no less). 

Rent it on Prime Video. 

Perhaps a controversially low placement for one of DiCaprio’s six acting Oscar nominations, but I’m going to stick to my guns on this one. First, Leo has many strengths but accent work is unfortunately not one of them. (J. Edgar and Body of Lies send their regards). The poor guy limps through already questionable dialogue like, “You know in America it’s bling bling, but out here it’s bling bang” with a lead tongue’d South African accent to no one’s satisfaction. And then there is this scene that I would have pegged as Leo playing Chet Hanks in an SNL sketch had I not cringed through it during the movie. If you (like me) are wondering how he managed to land an Oscar nom for this weird/average performance, let me shed some light. In 2006, DiCaprio also starred in The Departed. After landing Best Actor noms for both films at the Golden Globes, his PR teams decided to bump the Departed role to Supporting in order to prevent him cannibalizing votes in the same category. Unfortunately, Supporting was a MUCH stronger category (and already stacked with Djimon Hounsou and Mark Wahlberg among others), so Leo lovers piled their votes behind the Blood Diamond performance in order to honor both films. Plus 2006’s Best Actor lineup was one of the weakest in recent memory, and so a spot was easily within reach. 

Watch it on HBO Max. 

No, Leo did not star in a rah rah sports drama in his early years. This is actually the tale of a gifted high school basketball player who stumbles into drug addiction. As with his other 1995 film Total Eclipse, what appears to be an Oscar-worthy story is dragged down by an unwieldy screenplay and attempts to say too much. Unlike Total Eclipse, however, where DiCaprio is doing too much, here he’s doing a bit too little. Leo is young and plays this role very by the book in a way that lacks nuance or interest. It’s not a bad performance per se, but it feels uncalibrated and up against his tremendous filmography, it slides toward the rear. 

Buy the DVD on Amazon. 

Ya’ll this is a VEEEEERY odd little film, but I got to say that I enjoyed it and feel like it is RIPE for a remake. The premise: It’s the wild west and all the best quickdraw shooters convene in a town for a Hunger Games-style tournament of champions where they kill each other in duals until only one survives. It’s a grizzly, high-concept premise that doesn’t quite find its footing here, but Leo (in a rare supporting role) plays the hot shot son of Gene Hackman, the town’s evil quick-drawing mayor. Leo’s using every ounce of charisma and youthful charm he’s got here, and his final duel gives him the room to flex his acting chops. A solid early turn for our man, and might I suggest that if there’s a remake, we cast Leo as the evil Mayor? 

Watch it on Prime Video. 

Leonard DiCaprio x Martin Scorsese 1.0. The launch of the 20th century’s premiere actor/director combination started off with more of a whimper than a bang. Perhaps that is simply because in this film about feuding lower-class factions in 1800s New York, Leo has the least interesting role. While he’s off playing the straight man and nursing a romance with Cameron Diaz, Daniel Day-Lewis is unhinging his jaw and swallowing the rest of the film whole. Never fear, the Marty/Leo dynamic duo will quickly bounce back. Also, an interesting bit of trivia is that both this and Scorsese’s The Irishman were nominated for 10 Oscars without winning a single statue. Tough luck there. 

Watch it on HBO Max. 

Bonus points here for Leo pulling a Parent Trap and playing both twins in the same film. In this Three Musketeers property, Leo plays both the spoiled French king as well as the titular man in the iron mask, who turns out to be the king’s docile twin brother. Because The Three Musketeers from 1993 is a Disney property and this stars a young Leo, I assumed this is a children’s movie. IT IS NOT. And even though this adult film fared well at the box office (it came out during Titanic‘s run and definitely benefitted from the Leo hype), it got poor ratings. Leo does a serviceable job in two roles, but the world (and much better roles) were opening before him. 

Watch it on HBO Max. 

Up until this point on the list, we’ve been primarily dealing with Leo’s performances in so-so to average films. I would say that this drama about a dysfunctional, estranged family reuniting to figure out who gets to be Diane Keaton’s bone marrow donor is actually a very good film as a whole. Meryl Streep, who plays DiCaprio’s mother here, is exquisite in a role I haven’t seen her take on elsewhere and Keaton’s Oscar-nominated turn as Streep’s sister is both charming and heartbreaking. Leo does solid work here, but it’s a thin supporting role in a film focused entirely on his elders. 

Watch it on Paramount+. 

It was apparent to everyone who saw Leo’s first film with a lead role that he’d go on to great things. Here he plays Toby, a wayward boy whose mother (Ellen Barkin) runs from her problems straight into the arms of a new abusive husband (Robert De Niro). De Niro and DiCaprio go head to head the entire film as Leo bristles under the increasing restraints that De Niro places upon him until a brutal physical showdown between the two sends everything crashing down. A remarkable early performance.

Rent it on Prime Video. 

Never heard of Don’s Plum? That is probably because the film was never released in the US. And honestly that’s okay because the behind-the-scenes drama swirling around this black-and-white hang out flick is endlessly more interesting than the film itself. In the ’90s, Leo, friend and This Boy’s Life co-star Tobey Maguire, and Kevin Connolly were infamously part of a friend group dubbed the “Pussy Posse.” In their free time, the posse made this completely improvised, low-budget indie about a similar group of friends who spend a Saturday evening shooting the shit and causing a ruckus at an LA diner. According to Maguire and DiCaprio, they thought they were making a short film and never intended on starring in or releasing a feature. The film was therefore locked indefinitely in a post-production purgatory until it was released online in 2014 (a legally dubious move). The entire salacious, juicy saga is detailed in the New York Post‘s documentary and, boy oh boy, is it worth a watch. Ultimately Leo’s performance in the film as one of the worst versions of a human imaginable (he somehow is racist, ableist, classist, sexist, homophobic, and just plain mean all in under two hours) is well done. All he really does is sit in a booth and say terrible things, but he does so with a convincing flair.

This film is currently unavailable to stream or purchase. 

With Don’s Plum buried in litigation (it was shot in 1995), Leo felt comfortable recycling the character in a (also black and white) Woody Allen movie. In the ensemble film about a screenwriter (Kenneth Branagh) trying to get his picture made, Leo pops in for about 15 minutes as a spoiled, party-boy actor. We meet him in a full on brawl with his celebrity girlfriend and follow him and Branagh on a night of drinking, gambling, and group sex. As with Don’s Plum, his magnetism gasses up an otherwise dull affair, and he capitalizes on his post-Titanic stardom to play the worst version of what people believed young, rich movie stars to be. 

Watch it on Hulu. 

Really, from this point on, it’s an embarrassment of riches. On any given day you could ask me about these 15 performances and they’d fall in a completely different order. (I mean he was nominated for Golden Globes for 11 of them). We’re really splitting hairs at this point, but for you I’M GOING TO DO IT. 

This is casting perfection. As an English major, I’ve spent a lot of time with Mr. Jay Gatsby, and I don’t know if there is another human alive who could embody this character as well as DiCaprio does. He’s the charming shyster with a hopeless romantic buried inside, and DiCaprio has an effortless charisma and ability to play earnest characters that is unmatched. His slow unravelling when Daisy says she loves Tom. His throwing shirts around. His raising a champagne glass. All spot on. This is only here at 15 because Gatsby is a surprisingly small part of the film as a whole, and doesn’t require Leo to use his full actor’s tool kit. 

Watch it on HBO Max. 

And now we go from drowning in a pool to falling in a bathtub. Inception is a near perfect film, and I could easily make the argument that it is the best film Leo has ever starred in. The Christopher Nolan psychological thriller got eight Oscar nominations including Best Picture (and won four). The top-spinning scene is instantly iconic cinema. The hallway fight sequence is consistently ranked as one of the greatest action sequences. Yet, this ranking is specifically about Leo’s performance which I would argue is top-notch, but both limited by the film’s ensemble nature and overshadowed by Nolan’s mind-bending story as a whole. Leo’s scenes with Marion Cotillard push him into a more emotional zone, but for most of the film he is just setting up rules and instructions for the others to react to. 

Watch it on HBO Max. 

Unfortunately, we do have the return of Leo doing an accent, but at least in this, his fourth Scorsese collab, he seems to be fully in it rather than wandering in and out. Here he plays a U.S. Marshall sent to investigate the disappearance of a woman on an infamous psychiatric hospital island. DiCaprio is broody and taking no shit from anyone as he tromps around in a trench coat before his mind begins to unravel, leading toward the film’s shocking ending. The role is JUICY and Leo is lapping up every tender morsel he can. It’s surprising that this role didn’t garner more awards attention, but like Inception it’s more of a thriller than your typical Oscar fare. The cop role is also played fairly by the book through the first three quarters of the film, which also hurts it here in the ranking of spectacular Leo performances. 

Watch it on Netflix. 

Romeo, Romeo, where for art thou Romeo? On this list Romeo art at spot number 12. Lost in the Miami heat and Hawaiian shirts of this film is the fact that DiCaprio, Claire Danes, and crew are actually performing Shakespeare, something not to be taken lightly. The degree of difficulty here for Leo is HIGH and the fact that he can march his way through monologues in Elizabethan English is quite impressive. He makes you feel every heartbreaking moment of their young love with lines that are full of “thee”s and “thy”s. If only he’d got a drag queen lip sync, this might have cracked the top 10. 

Rent it on Prime Video. 

Yes, this is the film that Leo finally won his Oscar for after four losses and several snubs. No, I don’t think it cracks the top 10 for this incredible actor. And here’s the reason why: While Leo is giving a VERY believable performance here as a man stranded alone in the wilderness during winter seeking revenge on men who murdered his son and while he did endure all manner of hardship on the set while method acting with the best of them, I still think this is more of a triumph in survival than acting. If you forced me to swim across a frozen river, I’m pretty sure I could give a convincing performance as someone swimming across a frozen river (because I’m not acting). I’m not trying to take anything away from this 12-time Oscar nominee and impressive film. I’m just saying that Leo has done better and more difficult work elsewhere. 

Rent it on Prime Video. 

We’ve arrived at the top 10 and we’ve got four acting Oscar noms, six Best Picture nominees, two Best Picture winners, and one giant jewel necklace still in the mix. Not to mention, Leo was nominated for a Golden Globe for every single one of these 10 roles. 

At number10 we have the third DiCaprio/Scorsese collaboration. DiCaprio plays a cop undercover in the Irish mafia facing off against Matt Damon, the mafia member planted inside the Boston police. Leo’s performance is well calibrated as he begins to lose his resolve and the tension heats up. Unfortunately for Leo, this is another ensemble film filled with mighty performances (Mark Wahlberg, Jack Nicholson, Matt Damon, the CGI rat), and so he’s got to share the screen. I’ll never think of an elevator the same way again though. I have him and Marty to thank for that. 

Rent it on Prime Video. 

I stand corrected. THIS is the best film that Leonardo DiCaprio ever starred in (sorry Inception). And the universe agrees. It’s made over two billion dollars. It was number one at the box office for 15 consecutive weeks. It was nominated for 14 Oscars and won 11 (both records). And right there at the center of the film is the performance that changed Leonardo DiCaprio’s life forever. His joyful, youthful exuberance. His earnest, full-bodied love. His tragic demise. He basically gets to recycle his Romeo + Juliet performance but is now unfettered from the Shakespearean language. The fact that the Oscars couldn’t give him a Best Actor nomination for this is baffling. For goodness sakes, he had a sex scene in an old timey car. What more could you ask for? 

Watch it on Paramount+. 

In the year of our lord 2021, this film is problematic on nearly every front. You’ve got a whole plot about fat shaming Gilbert’s mom. You’ve got the cancelled Johnny Depp in the lead role. You’ve got Leonardo DiCaprio portraying some kind of nondescript mental illness that might be autism but isn’t labeled as such. The film about misfits overcoming adversity has a lack of nuance that would leave it lambasted by today’s critics, but separating DiCaprio’s performance from the film as a whole, it’s hard not to be impressed. While Arnie Grape may not be an accurate representation of autism (and the film goes out of its way to keep the diagnosis vague), DiCaprio certainly has decided on a character and committed 110%. Watching him work is mesmerizing (especially since the actor has never returned to a performance this transformational), and the rare child Oscar nom was well deserved. 

Watch it on Netflix. 

The newest addition to Leo’s filmography is Adam McKay’s end-of-the-world comedy/political satire. In it, Leo plays a Michigan State professor (GO SPARTANS!) who discovers a planet-destroying meteor headed straight to earth but seems incapable of convincing anyone to take the threat seriously. As a Michigander from Lansing (and I instantly clocked that not a single scene was shot there on location), I can vouch for Leo’s Michigan accent as one of his best. I also really enjoyed seeing Leo depart from his usual slick charm to play a dorky professor incapable of communicating. What’s so remarkable about this performance though is the breadth of emotions he gets to play with, beginning as a shy academic and boiling to a Howard Beale-esque rant on a news program. With the film’s tepid ratings and a stacked Best Actor lineup, it’s unclear whether he’ll crack the Oscar five, but his performance is splendid nonetheless. And if you haven’t treated yourself to the Ariana Grande song from the film’s soundtrack, Merry Christmas. 

Watch it on Netflix.

In his lineup of buzzy, big-budget films, this small period drama certainly fades from memory. If it wasn’t for the historic reunion of the Titanic stars here in another doomed romance, the film likely wouldn’t have registered at all. Since its release, however, I’ve loved this quiet little film and DiCaprio’s performance in it. What happens when you’re in your 30s, seemingly have everything you’ve ever dreamed of, and are still profoundly unhappy? That’s what Kate and Leo grapple with here as their marriage and life disintegrates through repeated acts of depressed self-sabotage. Leo is certainly dialed down here in a way that he isn’t in The Departed or The Revenant, but unlike in his earlier work where low energy meant bland, now it means intimate and nuanced. At this point, Leo has the experience to push an interior performance to a place that is just as captivating as an exterior one. 

Watch it on Paramount+. 

Another day, another Marty/Leo super duper team up! This time DiCaprio is playing Howard Hughes, the businessman, film director, airplane pilot, recluse, and bottle pee-er. The biopic which spans the man’s life is an actor’s wet dream. The whole 170-minutes long film is an acting showcase for DiCaprio, allowing him to be suave, forceful, weak, scared, triumphant, and destroyed several times over. DiCaprio came within a hair of the Oscar (losing to Jamie Foxx after winning the Globe), and confirmed for the first time post-Titanic that he deserved to be held alongside the best in the biz. Come in with the milk indeed. 

Watch it on HBO Max. 

As I said, Leo RARELY takes a supporting role in a movie. Prior to Django, if you rule out the ensemble films, he hadn’t played a truly supporting character since Marvin’s Room in 1996. This turn as an evil plantation master in Quentin Tarantino’s slave revenge film, however, makes me question this choice. Clearly the man is capable of playing an out-of-left field character, and supporting roles often allow actors to try new things. DiCaprio certainly brings something new to the table here as a brutal slaveholder with a Cheshire grin. And he was so committed to the role that even when he accidentally broke a glass and sliced his hand in a scene, he stayed in character. Someone hurry up and cast Leo as another villain. 

Watch it on Netflix. 

We’ve seen Leo play up his charm over and over again. In The Quick and the Dead. In Don’s Plum. InTitanic. Well here is the full unadulterated version. In Steven Spielberg’s underrated cat and mouse game about a real life con-man and the FBI agent sent to track him down, Leo busts off the cap and lets his fire hydrant of charisma explode in every direction. He’s not a pilot. He’s not a doctor. He’s not a socialite. But he’ll have you believing he is with that roguish grin. In many of DiCaprio’s film (like The Revenant), he’s tamping down his Hollywood charm. Here, he’s leaning in fully and the result is undeniable. I’d let him fly me across the country without a license. 100%.

Watch it on Paramount+. 

You f*ckin hippies came up here to smoke dope on a dark road, huh? That line delivered in a very short bathroom while holding a blender full of homemade margaritas? Genius. After teaming up in Django, DiCaprio and Tarantino reunited for this ode to old Hollywood and a revisionist take on the Sharon Tate murder. Leo plays a hot shot actor on his rise to and fall from moderate fame, a role that allows him to tap his charismatic side, tap his dark side, and also go a little off into left field as well. His on-screen friendship with Brad Pitt is infectious. His actor pretending to be an actor is a tightrope performed effortlessly. And this scene on set shooting a Western is perhaps the finest of his entire career. I’m getting teary just watching it. 

Rent it on Prime Video. 

We’ve finally arrived! Mr. DiCaprio’s best performance (and the best of his five Scorsese collaborations) is his portrayal of Wall Street stockbroker/party animal/deplorable human being Jordan Belfort. The role is pure drug-fueled, high adrenaline chaos from start to finish, and Leo chews up every scene with a campy, delicious, talk-to-the-camera flair that makes you like this man even as you despise him. He’s doing drugs. He’s having sex. He’s shaving women’s heads. Belfort is a child in an adult candy shop where everything is free, and DiCaprio is an actor in cinematic candy shop where every choice is on the table. He should have won his Best Actor Oscar for this role. It’s his crowning achievement. Long live Leonardo DiCaprio! 

Rent it on Prime Video.