Leonardo DiCaprio isn’t just the definitive movie star of his generation; he’s approaching the all-time status of greats like Robert De Niro, Al Pacino, Gene Hackman, and Jack Nicholson. DiCaprio may have had a big jump start to his career with Titanic, but he’s earned all the success that he’s earned through years of hard work alongside virtually every great living director.
DiCaprio has very few misses on his resume, and the few that he does have are at least spectacular (looking at you, Critters 3 and Don’s Plum). Here are the greatest Leonardo DiCaprio movies of all-time, ranked.
25 ‘The Beach’ (2000)
The Beach was an interesting new step for director Danny Boyle, who was previously known for his work on small scale crime films like Shallow Grave, Trainspotting, and A Life Less Ordinary. Comparatively, The Beach was an international adventure film about the young man Richard (DiCaprio) as he searches for a mysterious island.
While DiCaprio would generally stay clear of Hollywood blockbusters in his post-Titanic career, it’s interesting to see him in a youthful heartthrob role. While his performance can be a bit grating at times, DiCaprio does his best working with the relatively simplistic nature of the source material.
24 ‘Body of Lies’ (2008)
Ridley Scott may be best known for his work on science fiction films and historical epics, but Body of Lies saw him taking on the espionage genre in a modern context. The film stars DiCaprio as an American military operative that goes to Jordan to thwart an emerging terrorist threat.
Despite the seemingly inflammatory nature of the subject matter, Scott does a great job at not lionizing the CIA or any of the United States’ overseas military activity. It was the rare case where DiCaprio got to play an action star, something he’s long avoided doing.
23 ‘The Great Gatsby’ (2013)
Baz Luhrmann’s adaptation of F. Scott Fitzgerald’s The Great Gatsby is everything that someone would come to expect from the notoriously stylized director; Luhramann decided to capture the excitement of the “roaring 1920s” with hyper-active visuals and a soundtrack populated by hits by recent artists.
DiCaprio is perfectly suited (no pun intended, but he does have some snazzy outfits) to play the embodiment of wealth and class that is Jay Gatsby. Beneath the good looks of someone who seems so “in the moment” is a deeply wounded, lonely soul in desperate search of love.
22 ‘Blood Diamond’ (2006)
DiCaprio had the rare challenge of competing against himself at the 2007 Academy Awards; since the Oscars only allow an actor to be nominated for one film in a single category, DiCaprio’s Blood Diamond performance got in over his (arguably superior) work on Martin Scorsese’s Best Picture winner The Departed.
Blood Diamond stars DiCaprio as the mercenary Danny Archer, who reluctantly agrees to help a South African man (Djimon Hounsou in an Oscar-nominated performance) find his missing son in the midst of a civil conflict. DiCaprio does a great job mastering the notoriously difficult South African accent.
21 ‘J. Edgar’ (2011)
J. Edgar is one of the more underrated films within the late filmography of Clint Eastwood. While not all of the makeup effects are necessarily great, Eastwood does a great job at showing how childhood trauma and being forced to mask his sexuality forced J. Edgar Hoover to create one of the most powerful (and most dangerous) institutions in the history of the United States.
DiCaprio has never shied away from onscreen intimacy, and Eastwood shows both restraint and respect in showing the gradual romance that develops between Hoover and his long-time partner Clyde (Armie Hammer).
20 ‘The Man In The Iron Mask’ (1998)
It takes a truly talented actor to play twins on screen and turn them into two completely distinguishable characters with an opposite set of skills and mannerisms. In this dark action drama centered on Dumas’ musketeers (now a little older and worse for the wear), DiCaprio stars as both the villainous tyrant King Louis XIV and his potential successor, Phillippe.
This is very much the 1990s version of The Three Musketeers, which means there’s a lot of flashy action, onscreen sensuality, and overblown speeches. It may not be the most family-friendly slant on the classic adventure story, but it certainly has all the pomp and circumstance that the novel demands.
19 ‘This Boy’s Life’ (1993)
Before they were on screen together in Scorsese’s 2023 crime epic Killers of the Flower Moon, DiCaprio and Robert De Niro shared the screen together in this underrated family drama. This Boy’s Life follows the young boy Toby Wolff (DiCaprio), whose life is destroyed when his mother Caroline (Ellen Burkin) marries an abusive new partner (De Niro).
Despite being quite young at the time of the production, DiCaprio shows a remarkable vulnerability and ability to lead a film. DiCaprio and De Niro approach the nature of child abuse with a degree of respect and needed vulnerability.
18 ‘Don’t Look Up’ (2021)
DiCaprio rarely gets the chance to flex his comedic muscles, but Don’t Look Up gave him the rare chance to be a bit wacky. He stars as Dr. Ernest Burkhart, a brilliant scientist who must convince the administration of the tyrannical President of the United States (Meryl Streep) to listen to the researchers when it becomes evident that an asteroid is set to collide with Earth.
Similar to Adam McKay’s previous films The Big Short and Vice, Don’t Look Up does a great job at blending in social commentary with a fast paced sense-of-humor.
17 ‘Marvin’s Room’ (1996)
Jerry Zaks’ 1996 family drama was based on the acclaimed stage play of the same name by Scott McPherson. The film follows the inner conflicts within a family unit in the wake of an unexpected reunion. It was DiCaprio’s last “child role” before Titanic skyrocketed him into serious stardom.
The film gave DiCaprio the chance to appear alongside many of the best performers in the history of cinema, including Diane Keaton, Dan Hedeya, Gwen Verdon, and his future co-stars De Niro and Streep. Keaton received an Academy Award nomination for Best Actress.
16 ‘The Quick and the Dead’ (1995)
Sam Raimi needs to make more Westerns, because The Quick and the Dead is about as much fun as the genre can get. While it follows all the archetypes of a classic gunslinger adventure, The Quick and the Dead brings in some of the fun blood splatter and eccentric humor of Raimi’s Evil Dead trilogy.
A relatively youthful DiCaprio has a standout role as a young outlaw known as “The Kid,” who competes in a standoff contest in order to get revenge on his abusive father, the ruthless John Herod (Gene Hackman).
15 ‘The Basketball Diaries’ (1995)
Over a decade before they were hurling insults at each other in The Departed, DiCaprio and Mark Wahlberg played best friends in this riveting adaptation of Jim Carroll’s autobiography of the same name. Carroll was a child basketball star who dealt with serious drug addiction within his teenage years, and subsequently turned his challenges into poetry and literature.
While the film is occasionally guilty of sensationalizing the text, DiCaprio proved that he was for more than just a teenage heartthrob in this beautiful story of recovery. It’s sadly one of his more underseen films.
14 ‘Shutter Island’ (2010)
While Scorsese would occasionally try his hand at horror films like Bringing Out The Dead and Cape Fear, DiCaprio hadn’t returned to the genre since his acting debut in Critters 3. While Shutter Island isn’t necessarily the strongest of their collaborations overall, it gave both artists the chance to tackle the horror genre with a restrained and terrifying story.
DiCaprio stars as the U.S. Marshall Teddy Daniels, who ventures to a mysterious remote island alongside his partner (Mark Ruffalo) for an investigation. The film’s ending pushes DiCaprio to his physical and emotional limits with a shocking plot twist.
13 ‘Gangs of New York’ (2002)
DiCaprio’s first collaboration with Scorsese was in the Irish gangster drama Gangs of New York, which also marked his only collaboration with Daniel Day-Lewis (an actor often regarded as the greatest of all-time). Set in the slums of New York during the mid-19th century, Gangs of New York follows Amsterdam Vallon (DiCaprio) as he attempts to stage a plot of revenge on the ruthless gang leader known as “Bill the Butcher” (Day-Lewis).
It occasionally feels like DiCaprio is getting an acting lesson from Day-Lewis, but for the most part, he’s able to hold his own when acting alongside the living legend.
12 ‘The Aviator’ (2004)
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The Aviator was the most ambitious project of DiCaprio’s career at the time of its release. He had to physically transform and wear extensive makeup in order to capture the essence of Howard Hughes, all while capturing the edge of madness that the famous inventor was known for crossing.
The Aviator is as beautifully designed as any film within Scorsese’s filmography, but DiCaprio’s performance still stands out amidst the beautiful imagery. He has particularly strong chemistry with Cate Blanchett, who won the Academy Award for Best Supporting Actress for her portrayal of the iconic Old Hollywood star Katherine Hepburn.
11 ‘Romeo + Juliet’ (1996)
Baz Luhrmann’s Romeo + Juliet was perhaps the last film of DiCaprio’s “heartthrob era,” but it was hardly the type of stodgy period piece that Shakespeare adaptations often turn into. Luhrmann took the original text of Shakespeare’s most timeless (and perhaps most frequently adapted) romantic play, but set the film within the context of the modern day Verona Beach.
What could have been a complete misreading of the play’s original story turns into a heartbreaking encapsulation of the fervor and chaos that comes with young love. DiCaprio and his co-star Claire Danes have excellent chemistry as the titular duo, making the infamous ending even more tragic.
10 ‘What’s Eating Gilbert Grape’ (1993)
DiCaprio earned his first Academy Award nomination (and his only in the Best Supporting Actor category) for his riveting portrayal of an autistic teen in the 1993 family drama What’s Eating Gilbert Grape. The film follows the restless young man Gilbert (Johnny Depp) as he attempts to care for both his younger brother Arnie (DiCaprio) and his obese mother (Darlene Cates).
It was a remarkable breakthrough role for DiCaprio, who had only recently made his theatrical debut the year prior in the romantic drama Poison Ivy (as Critters 3 was released directly to the home video market).
9 ‘Inception’ (2010)
Critics might complain that Christopher Nolan pays more attention to plot and action than he does to characters, but that’s not the case with Inception at all. Despite the near constant plot revelations and labyrinth of a story, Inception has a deep emotional core thanks to the emotion that DiCaprio brings to the role of Dominic Cobb.
Cobb isn’t dissimilar from any hero from a classic caper movie; the only difference is that he robs people’s minds, not banks. Nolan writes a surprisingly nuanced drama for Cobb as he deals with the ghost of his late wife, Mal (Marion Cotillard).
8 ‘Revolutionary Road’ (2008)
Sorry Titanic, but DiCaprio and Kate Winslet have their best onscreen chemistry in Sam Mendes’ stirring 2008 period drama. Revolutionary Road follows the romance between the ambitious salesman Frank Wheeler and his wife April from the sensual heights of their early interactions to the crushing heartbreak of their marital breakdown.
Revolutionary Road breaks down the clichés behind “small town American life” that are commonly featured in 1950s romantic melodramas. As much as April and Frank try to avoid being “normal people,” they fall into the trappings of a marriage that loses its luster.
7 ‘Django Unchained’ (2012)
DiCaprio comes across as a fairly endearing guy in any of his interviewed appearances, but he’s never been quite as detestable on screen as he is in Quentin Tarantino’s western epic Django Unchained. The film follows the enslaved man Django (Jamie Foxx), who is freed by the quirky bounty hunter Dr. King Schultz (Christoph Waltz) and agrees to join the doctor’s dangerous profession.
DiCaprio’s performance as the slaver Calvin Candie is perhaps the most cruel and purely evil character that Tarantino has ever written; even if Waltz ended up winning the Oscar for Best Supporting Actor, the work by DiCaprio was equally as deserving.
6 ‘Catch Me If You Can’ (2002)
What does a con man’s life look like when he’s completely lost track of his identity? Catch Me If You Can addresses this question in what may be Steven Spielberg’s most profound work of the 21st century. The film deals with all the challenges of a coming-of-age story through the lens of an exciting heist thriller.
Loosely based on a true story, Catch Me If You Can explores the life of the con artist Frank Abagnale Jr., who masqueraded as a pilot, a lawyer, and a doctor all before he reached adulthood. DiCaprio and Spielberg perfectly capture the shift in tone; what begins as a fun caper turns into an emotional drama about the life of crime.
