All 29 Leonardo DiCaprio Movies Ranked From Worst to Best|Purgatory Film Rankings

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When it comes to male Hollywood superstars, very few names can stand shoulder-to-shoulder with Leonardo DiCaprio. Starting to act from an early age, DiCaprio first worked in commercials, and later in television, before he finally landed a role in the low-budget horror/comedy – Critters 3.

Since then, Leonardo proved himself as a serious talent when he acted alongside Johnny Depp in What’s Eating Gilbert Grape – a role that would bring him his first Academy Award nomination – and he became the superstar we all know and love when he starred in James Cameron’s Titanic.

Throughout the decades, DiCaprio has given us many excellent films and, in this article, we’ll get ourselves thoroughly acquainted with his work on the big screen by going through all of his filmography and ranking every single one of his feature films from worst to best. So, let’s get started!

“Hey! Don’t go down there, kid! There’s all sorts of wild animals and $#it.” Those were the first words little Leo said in his very first feature film – Critters 3. Sometimes great actors start their careers with a bang, getting their name on a timeless classic, but, unfortunately, that wasn’t the case with Leonardo.

Critters is a film series that began in 1986 and spawned several direct-to-video sequels, with each installment dropping in quality compared to its predecessor. Considering the first film wasn’t a masterpiece, to begin with, when the third installment was released in 1991 it got abysmal ratings and a non-surprising 0% “fresh” on rottentomatoes.com. Not a great start for the young actor, but, at least, he could only go up from here.

Leo’s first movie with Quentin Tarantino. It’s the second time DiCaprio has played a villain in his career, 14 years after The Man in the Iron Mask. When Tarantino releases a movie, it’s routinely proclaimed a masterpiece, one of the year’s best films, and it’s usually nominated for tons of Oscars, despite it’s him making the same movie over and over again.

This is Tarantino’s tribute to the “spaghetti westerns” of the 60s he grew up with but with all the awesomeness of the genre stripped away. It’s just 2 hours and 45 minutes of the same old needles over-the-top violence and the boring, never-ending dialogues Tarantino is known for. DiCaprio did a great job as the villain, Calvin Candie, though.

Speaking of overrated Tarantino movies, Leo had the “honor” of working with the director again in 2019, this time doing a tribute to the late 1960s Holywood movies. It’s the first time DiCaprio got to share scenes with greats like Al Pacino and Brad Pitt.

Once again – like with all Tarantino movies – the film received critical acclaim and was nominated for tons of Oscars for absolutely no reason whatsoever. It’s supposed to be a comedy/drama, except there is nothing funny or heart-touching throughout its almost 3-hour running time. But (of course), because it’s a Tarantino film, we must all clap like penguins and pretend like it’s some masterpiece.

The Man in the Iron Mask takes the fictional tales of the four musketeers (Athos, Porthos, Aramis, and D’Artagnan) and combines them with the real story of the Man in the Iron Mask – a man who was imprisoned in France in 1669, held in captivity until he died in 1703, but whose crime and identity remain a mystery because he was forced to wear an iron mask for the entire duration of his imprisonment. It’s the first time DiCaprio has played a villain – King Louis XIV. The film was a financial success but only got mixed-to-negative reviews with many critics noting that it doesn’t do justice to Alexandre Dumas’s books which it’s based on.

Occasionally, director Woody Allen can deliver a timeless masterpiece, but for 90% of his films the rule is – if you’ve seen one, you’ve seen them all. Celebrity is such a movie. This Allen formula almost always involves tons of love triangles and overly emotional characters who cannot shut up about their feelings and cannot help but give their unwanted and uninteresting opinions about anything and everything for two hours straight.

The only good thing about Celebrity is that, at least, it’s not a musical like some of Allen’s previous movies. And if you’re considering watching the movie for DiCaprio alone, you shouldn’t bother, because he doesn’t even appear for the first 50 minutes, and even then, it’s just for about 15 minutes or so.

DiCaprio plays famed French poet Arthur Rimbaud (1854 – 1891) in this historical erotic drama directed by Polish filmmaker Agnieszka Holland. He also has his first scene where he’s kissing a man (Rimbaud was bisexual).

The film does a good job accurately portraying the turbulent relationship between poets Arthur Rimbaud and Paul Verlaine (David Thewlis), as the script was written following the numerous letters and writings the two have exchanged and written about each other.

However, despite the historical accuracy, and strong performances from Dicaprio and David Thewlis, the film falls short of achieving greatness. It’s one of those instances where the whole is not better than the sum of its parts.

J. Edgar is a 2011 biopic about the life of John Edgar Hoover (1985 – 1972), the founder of the F.B.I. The iconic Clint Eastwood directed it and it’s DiCaprio’s first and only collaboration with the famed filmmaker. The film was a financial success (grossing $85 million against a $35 million budget) and DiCaprio’s performance was highlighted for praise, but it only got mixed reviews. Despite being a fairly historically accurate portrayal of Hoover and his troubled life. at times it seems the movie is completely devoid of excitement and suspense. It works much better as a history lesson than entertainment. Also, that makeup is terrible!

By 1996 Leonardo was already a well-established actor in the industry, getting to work with more and more Hollywood heavyweights with each new release. It’s DiCaprio’s second collaboration with Robert De Niro and his first with legendary actresses Diane Keaton and Meryl Streep.

Although not as powerful as Leo’s previous family dramas like This Boy’s Life (1993) and What’s Eating Gilbert Grape (1993), Marvin’s Room got mostly positive reviews from industry professionals, with special praise being given for Streep’s and Keaton’s acting. It’s the last project DiCaprio worked on before teaming up with director James Cameron to film Titanic – the blockbuster that would turn him into an international megastar.

This is a 1996 modern adaptation of the greatest love story of all time, with Leonardo playing Romeo Montague and Claire Danes playing Juliet Capulet. It got a mostly positive reception and was a massive box-office success – grossing $147 million against a $14 million budget – but some critics found the use of Shakespearian English in a modern setting out of place. Also, the film was generally considered inferior to the Academy-nominated 1968 adaptation. Nevertheless, DiCaprio’s performance was well-received and he won the Silver Bear Award for Best Actor at the Berlin International Film Festival.

Actually, do look it up. This apocalyptic black comedy has DiCaprio and Jennifer Lawrence playing astronomers who discover a large comet that heads towards the earth and is sure to end human life everywhere, but they are frustrated that no one takes them seriously. They also don’t get along with Ariana Grande very well.

This is the first time DiCaprio reunites with Maryl Streep 25 years after filming Marvin’s Room in 1996. The film got only mixed reviews, but was a massive success, becoming the second most-watched film on Netflix behind only Red Notice. Not quite a classic, but it definitely has its classic moments. Recommended!

Leonardo plays probably the most iconic character in the history of American literature – Jay Gatsby. This is the sixth film adaptation of the Great American Novel after 2 television movies (1958 and 2000) and 3 big screen productions (1926,1949, and 1974).

Now, is the movie as great as the novel? Well, not exactly, but it’s still the best adaptation so far, considering the bar for Gatsby adaptations is not set that high to begin with. The visuals, the costumes, and the acting received strong praise though. So go ahead and give it a watch old sport!

11 years after Titanic, Leo reunites with actresses Kate Winslet and Kathy Bates in Revolutionary Road. The movie is based on the acclaimed 1961 novel of the same name. DiCaprio and Winslet are excellent here and their acting is superior to their roles in Titanic.

The movie was showered with positive reviews, with many praising DiCaprio, Winslet, and supporting actor Michael Shannon (who received an Academy Award for his performance), as well as the movie’s faithfulness to the novel.

But, if you want a Titanic-like romance, you better look elsewhere, as Revolutionary Road has a lot more in common with movies like American Beauty (1999) and series like Mad Men (2007 – 2015). It’s about the failure of the “American Dream” and examines the flaws of the perfect suburban family who seemingly “has it all.”

Leonardo reunites with his long-term collaborator – Martin Scorsese, this time to make a biographical comedy/crime film based on Jordan Belfort’s 2007 memoir. This is their fifth movie together. Right after its release, The Wolf of Wall Street became a favorite among cold-callers and people who worked in sales in general, but wait! Why only 3-and-a-half stars?! Isn’t this a modern masterpiece worthy of praise and admiration?

Well, not exactly.

The film relies way too heavily on profanity, nudity, and a bunch of grown people acting like they never left puberty, but it doesn’t offer much in terms of complexity and character depth. Still, Leonardo’s performance was widely praised and he got another Academy Award nomination. If you want to read more about the less-than-stellar rating, click here and read this article.

By the end of the 2000s DiCaprio was one of Hollywood’s most well-known and respected film stars, having already worked with three of the greatest film directors of all time – James Cameron, Steven Spielberg, and Martin Scorsese. But, in 2008, it was time to add another legendary name to his list of collaborators – Ridley Scott.

Body of Lies is an adaptation of the 2007 novel of the same name by author David Ignatius, and it sees Leo reuniting with fellow actor Russell Crowe, thirteen years after filming The Quick and the Dead in 1995. It’s a solid spy thriller, getting mixed-to-positive reviews upon release, but, unfortunately, it doesn’t reach the high quality of some of Scott’s previous films. The acting is top-notch though.

Leo’s first Western, The Quick and the Dead, allowed DiCaprio to work with legendary filmmaker Sam Raimi – known for his Evil Dead movies, and later, the Spiderman films series starring Tobey Maguire. But, unfortunately, the film only got mixed reviews upon release and was a box-office failure, despite featuring an impressive ensemble cast of icons like Gene Hackman, Sharon Stone, and Russell Crowe.

In the following years, however, The Quick and the Dead would get a critical revaluation, with many labeling it one of Raimi’s finest and most underrated movies. It doesn’t quite reach the heights of other ’90s Westerns like Unforgiven (1992) and Tombstone (1993), but it does come pretty close.

Leo’s first movie, Critters 3, was a critical disaster and it wasn’t a good starting point for the young actor. But, only two years later, Dicaprio was able to put his name on a masterpiece that would allow him to shine and show his true potential. You could say this is where his legendary career really took off.

Featuring Hollywood legends like Robert De Niro and Ellen Barkin, This Boy’s Life is a true story based on the memoir of the same name by author Tobias Wolf, where DiCaprio portrays the author during his formative years throughout the 1950s and the beginning of the 1960s. A masterfully acted and directed coming-of-age drama, This Boy’s Life received excellent reviews with De Niro and DiCaprio’s performances receiving particular praise.

Like DiCaprio’s two previous movies, The Basketball Diaries is a book adaptation. It’s based on the autobiographical novel of author Jim Carroll (1949 – 2009), following his early teens from 1963 to 1966. It’s easily one of DiCaprio’s best non-Academy Award-nominated performances and, considering the content, “The Heroin Diaries” would be a more appropriate title.

For some reason, The Basketball Diaries received only mixed reviews upon release and would be a subject of much controversy in the years to come, as there is a fantasy scene where DiCaprio shoots up a school. Some people thought that this scene might have been an inspiration for the 1997 Heath and 1999 Columbine High School shootings.

But despite all the negativity surrounding it, The Basketball Diaries is a well-crafted work of cinema and, when it comes to quality, it’s on the same level as DiCaprio’s previous two films – This Boy’s Life and What’s Eating Gilbert Grape.

The Beach is DiCaprio’s first, and, to this day, only collaboration with English director Danny Boyle. It’s an adaptation of the bestselling 1996 novel by author Alex Garland. Despite being a moderate success at the box office, (making $144 million against a 50 million budget), professional critics were especially harsh towards the movie, giving it mixed-to-negative reviews, calling it a watered-down version of the novel, and criticizing the ending.

The film was also no stranger to controversy, as some Thai politicians didn’t like how their country was portrayed. But, despite all the negativity, The Beach has enjoyed a critical revaluation in recent years, with many praising the cinematography and the visuals, and applauding DiCaprio for taking on such a risky project.

The first two collaborations with director Martin Scorsese turned out to be real gems in Leo’s filmography. Both were huge financial successes, critically acclaimed by professionals, and both were nominated for “Best Picture” by the Academy. Still, it’s their third collaboration that finally won the Oscar for “Best Film”. The Departed is a Hollywood remake of the 2002 Hong Kong movie Infernal Affairs.

Many DiCaprio fans consider this their all-time favorite film, worthy of nothing short of 5 stars, but I disagree. It has lots of flaws with some plot elements making sense in Infernal Affairs, but not making sense here. If you’re interested in a more detailed breakdown, I suggest you watch this video here. It’s a solid 3-and-a-half-star movie with the extra half-star added for the strong performances from Mark Wahlberg and Alec Baldwin.

Two years after the release of Gangs of New York, DiCaprio reunites with director Martin Scorcese for another historical epic. This time, Leo plays the legendary American business magnate – Howard Hughes. This is not the first time Hughes’s life has inspired a film, but perhaps nobody did such a good job portraying him as DiCaprio did in 2004.

The movie got similar acclaim as the previous Scorsese – DiCaprio collaboration: it got 11 nominations at the 77 Academy Awards ceremony (including Best Picture) and it also got Leo his second Oscar nomination. Easily one of his best performances.

Wow! Leo is almost unrecognizable with that makeup! This is his sixth film with his long-time collaborator, Martin Scorsese, and it seems these two are incapable of making a bad movie together. Just like most of their previous films, Killers of the Flower Moon is based on the book of the same name, and this time the focus is on the infamous murders committed against the wealthy Native Americans of the Osage Nation that took place during the 1920s.

As always, Scorsese shows us why he’s a master of his craft, DiCaprio, De Niro, and Gladstone deliver stellar performances, and the movie does a good job of treating historical accuracy with respect. The only negative thing that might be said is the massive running time, and with its 3-and-a-half hours, Killers of the Flower Moon is easily the longest film DiCaprio has ever been in.

2002 was an important year for DiCaprio, for that year, he collaborated with two of the greatest film directors for the first time – Steven Spielberg and Martin Scorsese. Now, the Spielberg collaboration turned out to be a one-time thing, but Gangs of New York was the beginning of a long-lasting partnership between DiCaprio and Scorsese, as the two would collaborate on numerous projects in the following decades.

Although not without flaws, Gangs of New York, for the most part, reaches Scorsese’s extremely high standards for excellence, as the film was showered with positive reviews and received 10 Academy Award Nominations (including Best Picture). Leo’s acting was also solid, but this time he got overshadowed by Daniel Day-Lewis’s excellent performance.

Finally, after 5 nominations, Leo got his much-deserved Oscar! The Revenant is his first collaboration with Mexican director Alejandro González Iñárritu, an adaptation of the 2002 novel of the same name by author Michael Punke. The story, however, is based on a real historical event during an 1823 expedition, when a fur trapper named Hugh Glass (DiCaprio) survived against all odds after being attacked by a grizzly bear and left for dead by his fellow explorers. This is the second time Glass’s story inspired a movie, as a film about the same events was made in 1971 (Man in the Wilderness).

Iñárritu’s direction and DiCaprio’s and Tom Hardy’s acting drew considerable praise, with Iñárritu and DiCaprio winning Academy Awards for Best Director and Best Actor respectively, and Hardy receiving a nomination for Best Supporting Actor. The only reason it receives four-and-a-half stars instead of five is its lengthy running time. It’s a 2-and-a-half-hour movie that should have been just a 2-hour one.

Inception is probably DiCaprio’s most ambitious and complex movie he ever made. It’s Leo’s first, and to this day, only collaboration with Director Christopher Nolan. Many fans consider it their favorite DiCaprio film, and it’s currently the highest-rated of all of his movies on imdb.com. But that said, is Inception a perfect film?

Hardly.

There are quite a few times when the script doesn’t make sense (a lot of times, actually), and you’re not alone if you get lost in the dreams, unable to follow the logic of the events. But despite its flaws, Inception is one hell of a ride and is one of Leo’s biggest financial and critical successes.

1993 was an excellent year for DiCaprio. Not only did he make an amazing movie with Robert De Niro (This Boy’s Life), but he really took his acting skills to the next level in What’s Eating Gilbert Grape. The movie was showered with positive reviews, with many calling it one of the best of the year, and Leo’s acting was so good that he became one of the youngest actors in history to receive an Academy Award nomination.

DiCaprio would go on to be nominated for the prestigious award numerous times throughout his career, and he even won it in 2016 for The Revenant, but this is still arguably the best acting he has ever delivered on the big screen.

Finally, DiCaprio got to do a movie with Steven Spielberg, starring as one of the greatest conmen in U.S. history – Frank Abagnale Jr. It is based on Abignale’s 1980 semi-autobiographical book, although much of the events in the book are now disputed.

But, you know what they say – never let the truth get in the way of a good story, and a good story is certainly what you’ll get here (although not a very historically accurate one).

The movie got DiCaprio his third Golden Globe nomination and, in addition to being his first collaboration with Spielberg, it’s also his first collaboration with legendary actors Tom Hanks and Christopher Walken (who received an Academy Award nomination for his acting here).

The doomed voyage. The Celine Dion song. The Romance of the Century. Leo rising his fist in the air and yelling “I’m the king of the world!” When it comes to DiCaprio’s filmography, there is only “before” and “after” Titanic. Until this point, he was improving his talents as a young actor, trying to make his name known to the world, and, with Titanic, he finally became the superstar we all know and love today.

One of the biggest epics of all time, Titanic was nominated for a staggering 14 Academy Awards, winning 11 (including Best Picture), and was the first movie in history to gross over $1 billion at the box office. Only director James Cameron could make such a masterpiece on such a grand scale. It’s DiCaprio’s first, and, to this day, only collaboration with the famed filmmaker.

Leo is about to enter… The Twilight Zone! DiCaprio and Scorsese are excellent partners when it comes to making movies. They’ve already worked on three films before this novel adaptation, even winning the Oscar for Best Picture in 2006 (The Departed), but Shutter Island may be the best damn thing they ever made together!

Featuring DiCaprio alongside Mark Ruffalo and Michelle Williams, as well as legendary actors like Ben Kingsley and Max Von Sydow, Shutter Island combines horror, mystery, and suspense on a level only Hitchcock was capable of delivering in the past, and gives us one of the most mind-blowing twist endings of the 21st Century! A must-watch for psychological horror/thriller fans!

Over the decades, DiCaprio has given us many excellent performances, some of which were Academy-nominated, and one of them (The Revenant) finally won him the almighty Oscar. But when it comes to Leo’s best performance in his career, it’s a tie between What’s Eating Gilbert Grape and Blood Diamond.

DiCaprio, Jennifer Connelly, and Djimon Hounsou (who, like DiCaprio, was also nominated for an Academy Award for his performance) star as three individuals trapped in the Sierra Leonean Civil War (1991 – 2002), and not only give us killer performances and a wonderful adventure, but also bring attention to the illegal trade of “blood diamonds” and the human cost to obtain them.

Leo has worked with some of the greatest filmmakers of all time, giving us many excellent films and breathtaking masterpieces over the years, but Blood Diamond is probably the closest thing to perfection in his filmography.