The 17 Best Leonardo DiCaprio Movies of All Time

While it might’ve taken him a while to finally win an Oscar, Leonardo DiCaprio is easily one of the greatest actors of our generation. His diverse catalog of feature films spans countless genres and has launched him into the top sphere of movie stars. He’s a household name whose commitment to his craft has helped him remain at the top of his game for years.

With decades of incredible work behind him, it’s hard to nail down the best of DiCaprio, but we’ve done our best to put together this list of his greatest performances.

1. The Wolf of Wall Street (2013)

Directed by gangster legend Martin Scorsese (Taxi Driver), The Wolf of Wall Street features DiCaprio at his best, or maybe his worst depending on how you look at it. This black comedy biopic is based on a memoir by former New York stockbroker Jordan Belfort (who DiCaprio perfectly encapsulates) and chronicles how his corrupt firm committed fraud on Wall Street and almost got away with it.

Having earned a Guinness World Record for being “the film with the most intense instances of swearing” in movie history, the film is chock full of sex, violence, and naughty words. DiCaprio is incredible, with his transformation into Belfort further enhanced by Margot Robbie (The Suicide Squad) as Belfort’s second wife, Jonah Hill (22 Jump Street) as Belfort’s best friend and business partner, and Kyle Chandler (Super 8) as the FBI Agent on his trail.

The Wolf of Wall Street features a colorful cast of characters and a witty script that will forever go down as one of DiCaprio’s most intense pictures, and most certainly one of his best. The Matthew McConaughy cameo is also neat. 

2. Inception (2010)

When Christopher Nolan (The Dark Knight) decided to make a sci-fi thriller with DiCaprio as its star, people went nuts. This lucid dreaming-inspired masterpiece is a cinematic classic many consider the auteurs’ “greatest film.” DiCaprio’s Dom Cobb brings a sense of intensity and complexity to the film (which is already both complex and intense) that no other actor could.

Cobb’s deteriorating mental state is on full display as he and his team work to infiltrate the mind of wealthy business heir Robert Michael Fischer (Cillian Murphy, Batman Begins). While Hans Zimmer’s immersive score is the true star of the show, the incredible ensemble cast, including Joseph Gordon-Levitt (The Dark Knight Rises), Ellen Page (Juno), Tom Hardy (Warrior), and Marion Cotillard (Allied), work hard to further enhance the world.

Inception is a modern classic, with one of the biggest reasons being DiCaprio’s ability to captivate his audience with his acting. Top class. 

3. The Revenant (2015)

Often known as “the one that finally got Leo his Oscar,” The Revenant is an insane western-revenge tale based on the true story of frontiersman Hugh Glass. After he is attacked by a bear in the Dakotas and left to die, Glass is motivated to survive by revenge when the man that left him there, John Fitzgerald (Tom Hardy, Mad Max: Fury Road), murders his son Hawk (Forrest Goodluck, The Republic of Sarah).

This film is a beautiful masterpiece full of one-takes, exquisite natural lighting, intense thematic material, and a score that will make your heart sing in sorrow. DiCaprio knocks this one out of the park, fully committing to the survival aspect of the picture in a way no other actor would dare (eating an animal heart is no small feat). Director Alejandro González Iñárritu (Birdman) has truly outdone himself here.

4. The Departed (2005)

We’ve mentioned this one before when writing about the best gangster flicks and as one of Jack Nicholson’s best, but Scorsese also pulls a performance out of DiCaprio that none could rival. Here, he plays the Boston PD’s mole within the Irish mob, Billy Costigan, who does everything he can to get on the good side of mob boss Costello (Nicholson) before his emotional and mental state completely deteriorates. He’s a man teetering on the edge.

The film also follows Costello’s mole within the Massachusetts State Police Department, Colin Sullivan (Matt Damon, The Martian), and when both sides realize there’s a mole within each organization, it becomes a witchhunt and a bloodbath all at once. Things get crazy pretty fast, but DiCaprio does here what he does best, and works to convince Costello (and also us), that he’s on his side. There’s a lot to love about this gangster picture.

The Departed is an epic crime thriller that is probably the best that Scorsese has to offer. Combine that with Leonardo DiCaprio and Jack Nicholson, and you’ve got a hit.

5. Titanic (1997)

Formerly the highest-grossing film of all time (now the third), James Cameron (Terminator 2: Judgment Day) really outdid himself with Titanic, an epic love story (and disaster picture) that launched the 22-year-old DiCaprio into the public eye. If you didn’t know his name before, the release of Titanic changed that drastically. Kate Winslet (Eternal Sunshine of the Spotless Mind) starred opposite DiCaprio and provided just as much star power.

The film, which is one of the most expensive ever made at the time, follows the epic romance of Jack (DiCaprio) and Rose (Winslet) that was doomed even before the Titanic hit the iceberg. Cameron’s commitment to technological revolution is expanded here as scale models, CGI, and a re-built Titanic are all used in shooting the sinking of the infamous ship. But the true sinking occurred in our hearts when Jack finally let go.

Titanic is as impressive in its technological achievements as its performances, but what’s more, it’s a young DiCaprio’s swooning charm that caught the hearts of many.

6. Django Unchained (2012)

Quinten Tarantino (Pulp Fiction) is one of those filmmakers who always sparks controversy, but this film is generally loved by all. Django Unchained is a super stylized tribute to the classic Spaghetti westerns of the 60s and 70s that follows Django Freeman (Jamie Foxx, Just Mercy) as he sets out to rescue his wife from a brutal plantation owner in Mississippi.

Of course, the charming-yet-psychotic plantation owner is none other than DiCaprio, who plays Calvin J. Candie masterfully. Not only has his role as Candie had a certain amount of cultural impact (the memes speak for themselves), but DiCaprio also received lots of critical praise for his performance. Foxx’s role as the titular character is just as impressive, while Tarantino’s trademark dialogue between all the characters flows superbly.

Django Unchained may be a lot to handle at times, but the clashing moments between DiCaprio and Foxx make it all worth it.

7. The Basketball Diaries (1995)

A pre-Titanic biographical sports drama, The Basketball Diaries chronicles the life of Jim Carroll (DiCaprio), who went from being a promising basketball player in high school to a heroin-addicted New York writer. One of his first recognizable performances, DiCaprio plays the addict well and shows just how messed up and sad Carroll’s life turned out.

Between sexual assault and drug addiction, incarceration, and the death of his closest friend, we see a lot that can’t be unseen through Carroll’s eyes, with DiCaprio being the perfect interpreter. DiCaprio is also joined by his Departed co-star Mark Wahlberg, who plays Jim’s addict friend Mickey. The desperation of this piece is clearly seen as a strong warning, while also including a glimmer of hope that one might get out one day.

8. Catch Me If You Can (2002)

Before Scorsese and Tarantino, DiCaprio worked with another of Hollywood’s most iconic directors in Steven Spielberg (E.T. – the Extra-Terrestrial), alongside one of the biggest stars in the industry, Tom Hanks (Saving Private Ryan). Catch Me If You Can follows Frank Abagnale (DiCaprio), who allegedly pulled off some of the most impressive cons in American history, and all before his 19th birthday.

In this “true story,” Abagnale is vigorously pursued across the globe by FBI agent Carl Hanratty (Hanks), who himself is based on rea lfe FBI agent Joseph Shea. This film is both exciting and somewhat hilarious as Abagnale continues to illude Hanratty and the FBI before he figures out just what it is he wants out of his life. To sweeten the pot, Abagnale’s father, Frank Sr., is played by Christopher Walken (The Prophecy), who is always a delight.

Catch Me If You Can is an excellent period drama with high stakes and lots of excitement that will keep you on your toes. 

9. Romeo + Juliet (1996)

This uber-stylized and contemporary adaptation of one of William Shakespeare’s most famous plays has been loved by English teachers and literature professors ever since its release in the mid-90s, and for good reason. William Shakespeare’s Romeo + Juliet stars DiCaprio and Claire Danes (Stardust) as the titular characters as they tell a familiar tale in the California setting of Verona Beach.

A lot of fun, director Baz Luhrmann (Moulin Rouge!) is at his best here, with explosive action sequences (trading swords for guns) and exciting parties. There’s so much to love about this odd and stylistic version of Shakespeare’s greatest story. DiCaprio and Danes play beautifully against each other, creating lots of genuinely sensual tension that makes one wonder how these two couldn’t fall in love.

Romeo + Juliet may be an old story, but this fresh take brings a necessary new life into the Shakespearian world of the Montagues and the Capulets.

10. Once Upon a Time In… Hollywood (2019)

Possibly their greatest-ever performances, Leonardo DiCaprio and Brad Pitt (World War Z) shine like the Hollywood superstars they are in Tarantino’s Once Upon a Time In… Hollywood, which follows actor Rick Dalton (DiCaprio) and his stuntman Cliff Booth (Pitt) as they navigate the ever-changing film industry. All the while, the looming threat of Charles Manson follows closely behind.

DiCaprio and Pitt are at the top of their game here as Dalton’s popularity fades and Booth realizes he isn’t getting any younger. The unlikely pair have each other’s backs as they do their best to stay relevant in an industry that wants new blood. This film is so popular that Tarantino even wrote a novelized version and is set to produce a television series starring DiCaprio about the fictional show (Bounty Law) his character Dalton stars in.

Once Upon A Time In Hollywood has been described as “a modern fairy tale tribute to the final moments of Hollywood’s golden age,” something that’s hard to disagree with. 

11. What’s Eating Gilbert Grape? (1993)

Although this one stars Johnny Depp (Edward Scissorhands) in the titular role, What’s Eating Gilbert Grape? features young Leo in a co-starring role as Gilbert’s younger intellectually-disabled brother Arnie, which earned him an Academy Award and Golden Globe Award nomination at just 19 years old. The complex relationship between Gilbert and Arnie is, in a lot of ways, the backbone of the film, giving it the emotional (un)stability it needs.

As Gilbert comes of age in his small-town in middle-of-nowhere Iowa, he learns some really important life lessons, especially when it comes to caring for his younger brother. DiCaprio’s performance as Arnie is at times unsettling, but that’s just because of how spot-on it is. Depp and DiCaprio feed off each other incredibly well, and their brotherly bond is what drives us to hope for a better life for the Grape family.

What’s Eating Gilbert Grape? is a powerful tale about family and prejudice that will challenge your beliefs, all the while making you think back on simpler times.

12. The Aviator (2004)

Did you know that Leonardo DiCaprio did a Howard Hughes biopic? Well, if not, then you need to check out The Aviator. This film, directed by Martin Scorsese, soars as far as biopics go, with Hughes’ (played by DiCaprio) mental state quickly deteriorating as he becomes a slave to his own obsessions. The film chronicles Hughes’ life from 1927 to 1947, during the period where he became both a film producer and an aviation pioneer.

What more can be said of DiCaprio’s work other than he is consistently brilliant and commitment to his craft, as evident by his incredible portrayal of Howard Hughes in this must watch flick. The Aviator also has a stunning supporting cast that includes Cate Blanchett (The Lord of the Rings), Kate Beckinsale (Underworld), John C. Reilly (Step Brothers), and Alex Baldwin (30 Rock), who are all excellent and help elevate Leo’s performance. 

The Aviator is a thrilling look into the life of the great Howard Hughes that doesn’t fail to disappoint at any juncture.

13. Shutter Island (2010)

​​Another Scorsese picture (they just love working together), Shutter Island is one of DiCaprio’s most interesting films, and among Scorsese’s best. A neo-noir psychological thriller, it follows Deputy US Marshal “Teddy” Daniels as he investigates a psychiatric institution on Shutter Island when one of the patients goes missing. This whole thing will make you feel like a rat in a maze.

Mark Ruffalo (Avengers: Age of Ultron), Ben Kingsley (Iron Man 3), Max von Sydow (The Exorcist), and Michelle Williams (The Greatest Showman) are all excellent additions to a film that honestly only needs DiCaprio to shine. His constant questioning and investigation lead him to some particularly interesting and frightening conclusions about the island that can only be further explored by watching the movie, as we don’t want to spoil it for you.

Shutter Island is the most psychologically of Leo’s filmography, with a gripping mystery that will make you question your own sanity when the credits roll.

14. The Great Gatsby (2013)

Another Baz Luhrmann film that English teachers and literature professors can show in their classrooms, The Great Gatsby is based on the F. Scott Fitzgerald novel of the same name. The movie follows Nick (Tobey Maguire, Spider-Man) as he is suddenly thrust into the prohibition-era world of the mysterious Jay Gatsby (DiCaprio), which turns out to be a bit more than he bargained for.

The blend of contemporary music with the Roaring Twenties has been heavily criticized by audiences and critics alike (though it’s nothing new for Luhrmann to combine the past and the contemporary), but DiCaprio’s performance as Gatsby has been praised by most. The cast shines brightly alongside Leo, though he does consistently steal the show, as he should. 

The Great Gatsby is the most committed adaptation of the original novel, which intensifies the drama and glorifies the era in a way other adaptations never have.

15. Blood Diamond (2006)

An Edward Zwick (The Last Samurai) political action thriller, Blood Diamond follows Danny Archer (DiCaprio) and Solomon Vandy (Djimon Hounsou, Gladiator) as they do their best to attain a priceless diamond in the midst of the Sierra Leone Civil War. Jennifer Connelly (Requiem for a Dream) also stars as Maddy Bowen, an American journalist who is trying to expose the illegal diamond trade.

The conflict between Danny and Solomon’s independent motivations for attaining the diamond is pretty intense, just as the majority of this film can be. It doesn’t shy away from showing the ugliness of the war, which is part of why Blood Diamond was so critically acclaimed. DiCaprio and Hounsou were both nominated for various awards for their performances, including the Oscars and Golden Globes.

Blood Diamond is a harsh war story that gets to the beating heart of all political issues and examines those whose lives are forever changed by the conflicts.

16. Revolutionary Road (2008)

One of the most famous romantic dramas in the past 20 years, Revolutionary Road reunites Leonardo DiCaprio and Kate Winslet as Frank and April Wheeler, a 1950s couple trying to deal with their own issues as their marriage slowly falls apart. This heartbreaking tale is an interesting follow-up to DiCaprio and Winslet’s previous outing in Titanic, making it clear that they just can’t catch a break.

This one makes you feel all of the feelings and will have you reaching for the tissues. DiCaprio and Winslet take their performances here to the next level. If Titanic was all about finding love, then Revolutionary Road is about trying to stay in love. Director Sam Mendes (Skyfall) does a phenomenal job with these two in a film that will have you questioning if the life you’ve chosen is the right one. 

17. The Beach (2000)

Another young Leo picture, The Beach finds Richard, a traveler and American adventurer, seeking out an island rumored to be a solitary and undiscovered beach paradise. While this film has been heavily panned by critics, with DiCaprio having even been nominated for a Razzie Award for Worst Actor, it honestly doesn’t deserve the bad rap. If you can’t get around the story, at least the landscapes are amazing!

The whole “backpacking through Thailand” thing may be a bit cliche now, but at the time of the film’s release, it was pretty cool. DiCaprio, who is incredibly unlikeable in this film, is excellent as always. While not the best you could get from Danny Boyle (Slumdog Millionaire), The Beach really isn’t that bad and at least gives us another solid Leo performance.

The Beach may not be the perfect DiCaprio movie (let’s be honest though, nothing could follow Titanic), but it’s certainly not his worst.

Categories: Entertainment
Source: The 17 Best Leonardo DiCaprio Movies of All Time – Tekmonk Bio, The 17 Best Leonardo DiCaprio Movies of All Time – KOLNetworth, The 17 Best Leonardo DiCaprio Movies of All Time – Blogtomoney