Leonardo DiCaprio Movies: Ranked from WORST to BEST
#29: “Critters 3” (1991)
The third installment of this creepy, crawly film was considered a low point in a franchise that didn’t set the bar that high to start with. Leo’s performance didn’t exactly stand out as terrible against the backdrop of this strange movie, but he was the star, so he had to take a bit of the heat. This direct-to-video film was the very first performance in his filmography, and although he put in a valiant effort, even he couldn’t save this movie. Filled with weird, fake-looking creatures, a strange plot, and a below-par performance from his co-stars, this sci-fi film that was supposed to be scary definitely came off more as laughable.
#28: “The Beach” (2000)
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Over the years, we’ve seen DiCaprio get nominated for countless awards for his performances, but his role as Richard in “The Beach” scored him his first nomination for a Raspberry Award. Set on Ko Phi Phi Le, Richard is trying to get away from our technologically advanced society, but everyone on the island turns on each other and they pack it in. This movie came out at the turn of the millennium, and Leo had already starred in many big movies, so it was shocking to see him in this one. While he didn’t end up taking home the Worst Actor award, the fact that he was even nominated was a huge indicator of how terrible this movie was.
#27: “Total Eclipse” (1995)
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This mid-90s movie based on a 1960s play about an affair between two 19th-century poets had good source material and a lot of potential, but it never quite lived up to it. The film’s portrayal of same-sex lovers was ahead of the curve, but it didn’t get properly recognized because, despite a well-intentioned plot, the execution was clumsy. While we have seen Leonardo in period pieces before, he didn’t quite seem to fit the mold for his role as Arthur Rimbaud. Unfortunately, he and his co-star instead came off as unlikeable and unpleasant.
#26: “The Man in the Iron Mask” (1998)
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The best part about this film was we got Leo times two, as he played the titular character Philippe Bourbon, as well as his twin King Louis XIV. Even a double casting couldn’t transform this period piece about the four musketeers into something watchable, as audiences remembered it more for being funny and strange. In reality, the man in the iron mask’s identity remains a mystery to this day, but the writers took a strange creative turn in making him the King’s twin. Needless to say, that risk did not pay off. This was DiCaprio’s first film to be released after “Titanic,” so everyone had high hopes, but it did not live up to the hype.
#25: “Don’s Plum” (2001)
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Leonardo DiCaprio and Tobey Maguire have been friends since childhood, and it was fun watching their mostly improvised performance in this film. But, it will not be remembered as one of their best. Although it was amusing to watch at times, “Don’s Plum” was also awkward as it tried too hard to be an edgy work of art. The film was originally supposed to be a short film but was re-edited to be a full-length one, which led to it having no real plot. It was filmed in 1995 and ‘96 before DiCaprio and Maguire became big stars, and they didn’t even want the movie to be released, which should tell you all you need to know about it.
#24: “Celebrity” (1998)
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This movie was written and directed by none other than Woody Allen. While it had DiCaprio and many other big actors at the helm, “Celebrity” was still not a hit. The film took a look at the lives of modern celebrities along with the obsession that seems to follow them around, and Leo stands out in the film as a young, bratty movie star. However, “Celebrity” was a commercial disappointment, and it didn’t even make back half of its budget. For some reason, it was not a well-known film despite its impressive cast and crew. Critics thought it was a bit derivative, so we definitely can’t blame Leo entirely for this movie becoming a flop.
#23: “J. Edgar” (2011)
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This biopic told the story of J. Edgar Hoover, who was the director of the Bureau of Investigation and an allegedly closeted gay man. He worked to increase the Bureau’s power while blackmailing political figures like Franklin D. Roosevelt and Robert Kennedy. To top that off, this film was directed, produced, and scored by Clint Eastwood. So, needless to say, it should have been a home run. Unfortunately, it was critiqued for its poor production quality and the fact that Leonardo didn’t look much like Hoover, especially in his old man makeup. While DiCaprio did end up getting a Golden Globe nomination for his role, this story that had a ton of potential ended up falling flat.
#22: “The Quick and the Dead” (1995)
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While seeing a young Leo as a conceited cowboy in this non-traditional spaghetti western was a treat, it wasn’t enough to carry this film. “The Quick and the Dead” had an all-star cast that included Gene Hackman, Sharon Stone, and Russell Crowe, and this was one of DiCaprio’s first roles before making it big. He gave a strong performance as “The Kid,” but the movie was criticized for not being very convincing, largely because of the other actors in the film. As a result, this movie didn’t perform well at the box office, but on the upside, it garnered more praise in the years after its release.
#21: “Body of Lies” (2008)
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Over a decade after they appeared together in “The Quick and the Dead,” Russell Crowe and Leonardo DiCaprio shared the screen in this drama. They complemented each other well in their roles as members of the CIA in the Middle East who attempt to capture a terrorist. This political movie looked at the tensions between the Arab world and Western societies, and it was released during Leo’s peak “hero” phase in his acting career. While it was not necessarily a bad movie, it was a conventional, run-of-the-mill espionage film that didn’t have anything new to bring to the genre.
#20: “The Basketball Diaries” (1995)
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While this film was not a bad one per se, as it featured an adorable young Leo who showed off his impressive acting chops even though this was still early in his career, it wasn’t one of his best. “The Basketball Diaries” was based on Jim Carroll’s autobiography about a drug-addicted high school basketball player who tried to cope after his best friend died from leukemia. Leo as Jim took center stage in this gripping cautionary tale, but the story got a bit messy. The protagonist came off as unlikeable and we were never truly sure if he ever recovered or redeemed himself.
#19: “The Great Gatsby” (2013)
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Leonardo DiCaprio reunited with some former collaborators in this flashy take on F. Scott Fitzgerald’s novel alongside longtime friend Tobey Maguire as old sport, Nick Carraway. They also performed under Baz Luhrmann’s direction, who had previously directed Leo in “Romeo + Juliet.” He brought his signature splashy, colorful, and fun aesthetic to “The Great Gatsby.” While this movie was undeniably a bit over-the-top, it was fun to see Leonardo in a romance movie again after years of exploring other genres. Leo was the perfect choice to play Gatsby, as he is similarly someone who is idolized, he is lavish yet approachable, yet we know very little about his life.
#18: “This Boy’s Life” (1993)
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The third film in DiCaprio’s repertoire was one of the better ones in his early years. “This Boy’s Life” is about Leo as Toby who copes with his mom’s abusive partner, Dwight, played by Robert DeNiro, and Toby’s friendship with a boy named Arthur. In this role, DiCaprio showed off his acting expertise with a range of emotions which were impressive for an actor of his age. We got to watch Toby go from a young boy, to a rebel, to someone who finds his own way. We were impressed that DiCaprio was able to stand out in this film considering who he was acting alongside, and we’re not surprised this film is known for being his break-out role.
#17: “Don’t Look Up” (2021)
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This Netflix film was Leo’s most recent picture which was made up of an ensemble all-star cast. “Don’t Look Up” is about a comet destroying Earth while the leaders of the world tell the population not to look up to try and keep them in the dark. The film was a satirical look at the world’s indifference towards climate change and preoccupation with irrelevant things. Considering DiCaprio’s environmental activism, we are not surprised he took on the role of a seasoned Ph.D. scientist, which he played convincingly. The movie is oddly funny and depressing at the same time as it rang true to the situation of the world at the time, and there was a true passion in Leo’s performance.
#16: “Marvin’s Room” (1996)
No, we’re not talking about the Drake song. After he starred alongside DeNiro in “This Boy’s Life” and before we saw him in “Don’t Look Up” with Meryl Streep, Leo was in this underrated flick with both of them. Streep played DiCaprio’s mother, and they played Lee and Hank respectively. Lee is estranged from her family until her sister, Bessie, is diagnosed with cancer and needs a bone marrow transplant. DiCaprio as Hank is 17 and in a mental institute after an arson incident, but he eventually stops his rebellious streak and tries to help his family. It may have been hard for Leo to shine amongst an already star-studded cast, but this mysteriously unpopular movie is still worth watching.
#15: “William Shakespeare's Romeo + Juliet” (1996)
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Baz Luhrmann’s interpretation of this Shakespeare classic set in modern day with dialogue that is anything but was brought to life by DiCaprio and his co-lead, Claire Danes. The entire film had a tone that was a bit all over the place, as it was an acid trip-induced party paired with a tragic love story and a grand act of teenage rebellion. But, DiCaprio as Romeo was undeniably dreamy, and we can’t blame Danes as Juliet for falling for him instantly and marrying him just as quickly. Everyone in the film tends to over-act and the film is definitely dramatic, but then again, so is getting married and then dying when you’re in your early teens.
#14: “Shutter Island” (2010)
Leo went through a phase of starring in movies that could put your brain into a pretzel, and this film was definitely one of them. In one of the many great collaborations between DiCaprio and Martin Scorsese, he gave a stunning performance as an investigator and patient in a mental facility, who seemed just as shocked as we were when that twist was revealed. The film was solving an entirely different mystery than we were led to believe, and Leo kept us captivated all throughout. Who could forget that ambiguous ending, where Andrew ponders whether it is better to live as a monster or die a good man? How did it take this guy so long to win an Oscar?
#13: “Revolutionary Road” (2008)
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Kate Winslet and Leonardo DiCaprio together again. This movie received three Academy Award nominations, which tells us a lot about the cinematic chemistry these two bring to the screen. Based on a novel, this film tells the story of a young couple who fell out of love as they fought for their relationship. They went through the ups and downs of trying to have children and extra-marital affairs, without holding back on the hardships that some couples face. The couple disagreed on life decisions while trying to keep up with the Joneses. Both DiCaprio and Winslet give dark, heartbreaking performances as the film takes a tough look at a marriage on the rocks.
#12: “Blood Diamond” (2006)
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While the storyline and writing in this film were questionable at times, DiCaprio was always on his game. Armed with an impressive South African accent, Leo played a mercenary on a hunt for a gem that would change his life, going through rebel territory on a hunt for the diamond. While the film was about the corruption behind the world of African diamond trading, it was clumsily watered down for Western audiences. Nevertheless, DiCaprio’s outstanding performance as Danny Archer was highly praised and he was nominated for Best Actor, but ultimately lost out for the third time.
#11: “What’s Eating Gilbert Grape?” (1993)
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This was the film that got DiCaprio his first Oscar nomination and put him on critics' and viewers’ radars. He played Arnie Grape, whose big brother was the titular character who struggled to care for his family amidst all of their hardships. Gilbert Grape, played by Johnny Depp, was at the center of this film, but it was DiCaprio’s performance that pulled at our heartstrings. While this challenging role may have been hard to watch at times, it was a testament to the young actor's abilities. Even though he was just starting his film career, DiCaprio was able to keep up alongside a cast that included Depp, Juliette Lewis, and Mary Steenburgen, and for that, he deserves all the praise.
#10: “The Aviator” (2004)
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This film, based on real-life business tycoon Howard Hughes, was another successful collaboration between Scorsese and DiCaprio. Hughes’ life was anything but boring, and DiCaprio was the perfect choice to bring this larger-than-life man to the big screen. Howard Hughes set air speeds in the 1940s and helped Las Vegas become the city it is today, all while battling a debilitating disease that would eventually lead to his demise. DiCaprio’s portrayal showed the crumbling life of this highly successful man in an endearing and powerful way. Because of Leo’s strong performance, not to mention a laundry list of A-list actors as co-stars, this film was nominated for eleven Academy Awards and earned Leonardo yet another Oscar nod.
#9: “The Revenant” (2015)
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The movie that will forever be known as the one that finally gave Leonardo DiCaprio his Academy Award after four previous nominations. Or, people may remember it as the film in which he survived a bear attack and briefly lived inside a horse. Either way, “The Revenant” was a true story from the 1800s centered completely around Leo as fur trapper Hugh Glass. There were several scenes where it was just him against the elements, and he was completely captivating in this physically demanding role. This was a big change from his roles as Jay Gatsby and Jordan Belfort just a couple of years earlier, and this film gave him a chance to show his versatility on screen.
#8: “Gangs of New York” (2002)
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At this point in the list, it should be clear that DiCaprio does well in period dramas, and “Gangs of New York” was no exception. This historical drama about a Catholic-Protestant quarrel over control of Manhattan marked the first in a long line of collaborations between Martin Scorsese and Leo. As an Irish immigrant group protested the draft, Leo as Amsterdam battled against Daniel Day-Lewis’ Bill the Butcher. Both of these seasoned actors really showed off their acting chops, and “Gangs of New York” was nominated for 10 Academy Awards. It kicked off DiCaprio's career in serious, gritty movies after being in romantic flicks like “Titanic” and “Romeo + Juliet.”
#7: “Once Upon a Time in Hollywood” (2019)
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Quentin Tarantino’s love letter to the golden age of Hollywood saw DiCaprio as Rick Dalton, a former star of a western TV show who was fighting to stay relevant. Dalton struggled with the reality of aging in the film industry while showing what happened to actors when the cameras weren’t rolling. We were treated to a great, improvised performance when Rick had a breakdown at the turning point of the film in a moment that solidified Leo as a stand-out in a sea of great performances. The only thing better than DiCaprio’s performance was his on-screen chemistry with the equally impressive Brad Pitt as Cliff Booth. We aren’t surprised that they both got Oscar nods for this film.
#6: “Inception” (2010)
Leo is Cobb, a thief who escapes into people’s subconscious to steal their thoughts, but he’s tasked with instead planting information into someone’s mind in order to erase his own past. DiCaprio’s mental heists take a turn as his past leaks into other people’s subconsciouses as viewers try to unravel this dream within a dream in a dream. Sounds confusing? That’s because it is, but it’s also genius and intriguing, and we wouldn’t expect anything less from writer/director Christopher Nolan. Leo brings humanity to this mind-bending film as a loveable criminal who we only hope finds peace in the reality he ends up in, with the spinning top relentlessly turning.
#5: “Catch Me If You Can” (2002)
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In this Steven Spielberg film, Leo played Frank Abagnale Jr., a man who successfully impersonated a pilot, doctor, and lawyer, while he was on the run from the FBI. Just like we really have watched DiCaprio grow up before our eyes over the last few decades, we watched Frank transform from an innocent teenager to a confident swindler. This role captured Leo arguably kicking off the prime of his acting career, and even though this story has garnered some controversy in recent years, the performances are still memorable. DiCaprio is always charming, so he was a logical choice to play this daring con man, as we think we’d believe anything he told us to.
#4: “Django Unchained” (2012)
This Tarantino film depicted the Southern United States during the 1850s, and Leonardo starred as Calvin Candie, the owner of a plantation called Candyland. His acting was superb, and that dinner scene where he smears his blood on Kerry Washington’s face was not only haunting, it was improvised. This was a genius move for DiCaprio as he accidentally cut his hand, and while we’re used to seeing him play the good guy, this performance cemented that his acting range is unmatched. Christoph Waltz as Dr. Schultz and Jamie Foxx as Django were at the heart of this film, but Leonardo DiCaprio as Mr. Candie was the villain we didn’t know we needed.
#3: “The Departed” (2006)
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“The Departed” was Scorsese’s first film to score him an Academy Award, and the film won three other Oscars to boot. This movie is a who’s who of prominent male actors of the 2000s as it starred DiCaprio alongside Matt Damon, Mark Wahlberg, and Jack Nicholson, to name a few. Leo shipped up to Boston to play Billy Costigan Jr., an undercover cop in the mafia, contrasting Matt Damon’s Colin Sullivan, who’s a mobster pretending to be a police officer. We were never entirely sure who was bad and who was good, and we never knew when the next kill might be around the corner. One thing we do know is that DiCaprio’s performance in this exceptional film was one of his best.
#2: “Titanic” (1997)
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James Cameron’s epic story was the most expensive movie ever made at the time, and he clearly invested in the right actors. “Titanic” was nominated for a whopping 14 Oscars, but someone was clearly missing from the ballots. Leo didn’t get an Academy Award nomination despite this film centering around Rose telling the story of Jack Dawson. DiCaprio’s performance encouraged all viewers to make it count as Dawson’s charismatic and carefree character was a dream come true in this period drama. We can’t blame Kate Winslet’s Rose DeWitt Bukater for falling in love with the boy from third-class, and these two were irresistible as one of the most iconic couples in cinematic history.
#1: “The Wolf of Wall Street” (2013)
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We loved Leo as a romantic lead, but seeing him as a chaotic, selfish, no-holds-barred broker who rose and fell as quickly as the economy was a treat. He took all of us on a cocaine-infused, lavish adventure through New York’s high-rolling society, and it was as intoxicating as he was. While “Titanic” may be his most memorable role, “The Wolf of Wall Street” was one of the few DiCaprio movies in which he took the reins of the film without having to depend on any side characters. Even though Jonah Hill and Margot Robbie appeared in supporting roles, this movie will always be remembered for Leo, as he was at the helm of this chaotic ride.
