Leonardo DiCaprio has reached that comical level of stardom where even his early roles now feel like sacred artifacts.
He started out in roles that required him to be bright-eyed and sincere (The Boy’s Life, What’s Eating Gilbert Grape), then slid into romantic heartthrob territory (Titanic, Romeo + Juliet), and then spent the next two decades (wow!) proving he could play morally dubious men who really should’ve considered therapy. Fast forward to today, and we’ve arrived at his latest film One Battle After Another, where Leo is still choosing characters who seem like they’re allergic to being stable. But this is what makes his work fun: Leo’s got range, and he doesn’t shy away from showing it.
With that being said, let’s take a stroll through Leo’s emotional multiverse—the tender, the tragic, and the unhinged—because if there’s one thing Leo is good at, it’s giving an unforgettable performance. Here's a ranking of his ten best movies of all time and a complete guide to where you can watch them on streaming services.
10. Romeo + Juliet (1996)
Let it be known that I actually love this movie, but when compared to Leo’s later work, it’s slightly inconsistent in tone and doesn’t really showcase Leo’s strengths. If you’re a fan of modern Shakespeare adaptations, like 10 Things I Hate About You, then Romeo + Juliet is a ‘90s maximalistic treat. The most watchable part of the movie, even through the frenzied energy, has to be Leo’s earnest teenage sincerity, and his chemistry with Clare Danes which feels volatile and pure at the same time. He delivers Shakespeare’s language with clarity (and we know that if it’s not done correctly, it could sound stiff.) Few actors have survived being heartthrob-level famous at 22 and lived to tell the tale, but Leo’s Romeo cemented him as a romantic lead, long before Titanic made that official. Where The Great Gatsby is more of a refined romantic tragedy, Romeo + Juliet is more impulsive, but Leo’s longing in both stays the same.
9. The Revenant (2015)
Ninth place may seem low for Leo’s Oscar-winning performance, but hear me out! The movie is more about endurance, and the elements sometimes overshadow the acting, making The Revenant not a movie you’d casually put on on a Friday night to relax. The gorgeous cinematography does make up for the lack of dialogue, and Leo fully throws himself into the role—it’s two and a half hours of him crawling, freezing, and screaming—but the emotional arc is thinner compared to his work in The Departed. If grueling, man vs nature survival stories like Apocalypto appeal to you, then The Revenant is worth watching. The movie is brutal and intense (to put it lightly), so needless to say, this movie isn’t for kids. Leo absolutely deserved the win, I mean he ate a raw bison liver (for real!); but let’s be honest, the bear deserved a nomination too.
8. The Great Gatsby (2013)
If you’re someone who loves watching movies with style, aesthetic party sequences, and characters who express their feelings through longing glances, then Baz Luhrmann’s The Great Gatsby is tailor-made for you. Though—and I say this with affection—Luhrmann’s maximalist style sometimes overwhelms the emotional core, Leo’s performance of the charming, yet vulnerable Jay Gatsby, along with sheer spectacle of visuals turns the watchability factor up a notch (or ten!) Compared to Romeo + Juliet, which is another “beautiful disaster” creation by Luhrmann, Gatsby is more controlled, but no less dramatic. No one has ever said “old sport” with more conviction, and that definitely counts for something in my book. If lavish tragic romance is your thing, then the similarly beautiful and similarly tragic Anna Karenina should be your next stop.
7. Revolutionary Road (2008)
If you like watching marital dramas that aren’t afraid to peel off romantic illusions, then you’ve found the right movie. Revolutionary Road reunites Leo with his Titanic co-star Kate Winslet to play Frank Wheeler, a man quietly drowning in the expectations of suburban adulthood. But let’s be clear, Revolutionary Road is not a relaxing watch (in fact, his arguments with Kate in the movie feel so real you almost want to hide behind a pillow.) Leo’s chemistry with Kate is electric yet again, but in a completely different way than in Titanic; here it’s painful and heavy, so if you’re looking for a more breezier watch, then Catch Me If You Can might be a better choice. Leo gives his most emotionally mature and nuanced performance, where he drops the charm and swagger, and isn’t afraid to get real. He leans into fear, selfishness, and fragility without trying to make the character likeable. If you want another emotionally devastating marriage story, then Blue Valentine should be your next watch.
6. Titanic (1997)
Here’s another one for the romantics, historians, and Leo-Kate fans! Titanic is the blockbuster film that made Leo into a global household name. What makes the movie watchable even decades later, is how sincerely Leo plays Jack Dawson (and how good he looks in suspenders), even though it might not be his most nuanced performance. He radiates sweetness and warmth in a way that’s almost shocking if you’re used to his later work, where his characters look like they haven’t had a good day in months. Yes, the movie does veer slightly into melodrama territory at times, but Leo grounds it. Jack Dawson is almost like a fantasy; he’s simple, optimistic, and absolutely willing to die for a girl he met 48 hours ago (which, you know, youth). Titanic is the sunlit, nautical counterpart to the doom-filled romance in Romeo + Juliet, but if that’s the vibe you like, then Atonement should be next on your list. If there’s one thing that’ll outlive us all, it’s the door debate (even though we all know buoyancy physics is not what the movie is about.)
5. The Departed (2006)
Titanic showcased a version of Leo we don’t get to see often anymore—he’s youthful and glowing like someone who hasn’t yet discovered that Martin Scorsese will eventually put him through psychological warfare for sport. This brings us to The Departed, which lies smack in the middle of the list. While it’s an excellent film (there were moments in the film, cough the elevator scene cough, which genuinely took me by surprise), Leo’s performance shares the spotlight rather than owning it, due to the ensemble format; however, he still gives an adrenaline fueled performance as Billy Costigan, a role he plays so convincingly that you want to reach through the screen and tell him it’s all going to be okay (especially during his meltdown at the psychiatrist.) If you enjoy crime dramas and undercover stories like Donnie Brasco, then The Departed offers the same flavor. My only (tiny) critique would be that the film’s pacing can feel a bit uneven, especially when compared to the precision of Inception, still Leo’s emotional unraveling makes it gripping.
4. Catch Me If You Can (2002)
Want a movie that’s effortlessly rewatchable? Then, you’ve stumbled upon gold, because Catch Me If You Can is one of Leo's most playful entries in his filmography. This one’s recommended for the viewers who love watching morally slippery characters undertaking stylish capers with emotional undertones. Leo plays Frank Abagnale Jr. with youthful charm and mischief, running circles around adults using nothing but confidence (and cheekbones!), and it’s so refreshing to watch him play a character who isn’t drenched in trauma. Oh also, Leo and Tom Hanks in a weirdly endearing cat-and-mouse dynamic? Sign us up! The movie is a breezy watch, compared to the gloom of Shutter Island or high-anxiety of The Departed, and that fun shows in Leo’s performance, where you end up rooting for him, even though you know you shouldn’t be because technically, it’s a crime story. If movies with the same slick energy, charm, and lovable criminals hits the spot for you, try Ocean’s Eleven, though this one has more ensemble antics, and lesser childhood wounds.
3. Inception (2010)
In third place is Inception because it proves Leo can anchor a brain-twisting blockbuster without melting into the spectacle. Sleek and ambitious (and sometimes confusing, I’ll admit), Leo plays Dom Cobb, a man weighed down by a memory; he’s guilty, determined, and grieving, not in the explosive way he was in The Departed, but in a more controlled, stoic-with-depth way. At times a bit too polished, Inception manages to be a puzzle, a therapy session, and an existential crisis, all disguised as an action movie with the ability to deliver a “wow, I am both moved and mind blown” effect. Though some fans found the planning and explanation scenes a bit unnecessary, I personally thought it was one of the best parts of the movie. Watching the team brainstorm and break things down, gave me the feeling of excitement that one gets when they’ve successfully solved a complex problem. Inception is for anyone who loves sci-fi movies with a blend of spectacle and emotions, similar to Arrival. Also, the ‘spinning top’ discourse is more interesting than half of the modern film breakdowns on social media.
2. The Wolf of Wall Street (2013)
Leo and Scorsese have done it again. The Wolf of Wall Street is simply Leo at his most unleashed, and it’s glorious. Leo commits, and I mean commits, to his role as Jordan Belfort. The quaalude crawl? Wonderful. The Swiss Bank scene where dialogues were delivered without their mouths moving? Chef’s kiss. Tonally, it’s fast-paced, just like Catch Me If You Can, and where Shutter Island is him simmering until he boils over, Leo in Wolf is 200% unhinged. Sure, the movie is loud, excessive, and three hours long, but with Leo refusing to be subtle and disappear into the background for even a second (except for when Matthew McConaughey out-performed him in that one scene), it’s definitely worth the watch. With explicit language and graphic scenes, the movie isn’t suitable for kids, but for anyone who loves high-energy films, and wants something wild but not depressing, like American Hustle, The Wolf of Wall Street is your crown jewel, where it feels like someone poured Red Bull directly onto the script (in a good way!)
1. Shutter Island (2010)
Number one for me, with no hesitation is Shutter Island. The fourth Leo-Scorsese collaboration brings Leo’s incredible ability to turn dread and the quiet horrors people hide from themselves into art, to the forefront. Shutter Island is the kind of movie you’d recommend to a friend who wants to watch something where the tension builds slowly, but isn’t gory, and who loves films that mess with their brains in the best possible way. Leo truly imbibes his character, and plays Teddy Daniels with raw vulnerability and spiraling paranoia, unlike in Inception (which also plays with themes of memory and reality) where his unraveling is more restrained. What makes the movie watchable isn’t just the twist (which itself hits you like a tonne of bricks), but it’s the film’s unique ability to be layered, where a dozen new details reveal themselves only on rewatches. If you enjoy this brand of psychological storytelling, Prisoners delivers a similarly tense, emotional punch. Shutter Island might be Leo’s best, most underrated performance (as evidenced by his last line in the movie, if you know, you know. What a masterpiece!)
