Now Reading
13 Greatest Leonardo DiCaprio Movies, Ranked

13 Greatest Leonardo DiCaprio Movies, Ranked

Leonardo di caprio best movies

From Inception (2010) to The Revenant (2015), here’s ranking the best Leonardo Dicaprio movies.

Leonardo’s first gig as an actor was in a TV show titled The New Lassie. He was all 15. Born November 11, 1974 in Los Angeles, California, his father was a comic book artist and mother a legal secretary. Though DiCaprio’s parents divorced when he was a kid, they both cultivated and encouraged his interest in the creative side, respectively. Post his first gig, DiCaprio later played small roles in sitcoms including Growing Pains. His feature film debut was the awful direct-to-video horror sequel Critters 3 (1991). But soon he landed a breakthrough performance in This Boy’s Life starring opposite veteran Robert De Niro. This was followed by an Oscar-nominated role in What’s Eating Gilbert Grape. DiCaprio played the mentally challenged younger brother to Johnny Depp’s central character. 

From then on, it was a step-by-step climb to stardom with Titanic (1997) instantly turning him into a heartthrob. But DiCaprio took on challenging roles that didn’t simply typecast him as the handsome young man. The year 2002 was important in the actor’s career. His first of the many collaborations with director Martin Scorsese happened through Gangs of New York. In the same year DiCaprio played the suave anti-hero in Spielberg’s Catch Me If You Can. Later, he played darker and layered characters in films such as Blood Diamond Revolutionary Road, and Django Unchained

Leonardo DiCaprio is also a politically active celebrity who has taken great efforts to shift public attention towards climate change. The 11th Hour, Before the Flood, and Ice on Fire are all eye-opening documentaries he’s produced on the subject. Apart from environmental activism, DiCaprio is also committed to humanitarian causes. 

Very quickly then, here’s a look at some of the best performances of the most respected star actor of our generation: 


13. Gangs of New York (2002)

Image Source:

In his first collaboration with director Martin Scorsese, DiCaprio plays Amsterdam Vallon, an Irish-American seeking vengeance for the murder of his father. Although the film drew a lot of criticism, it’s one of Scorsese’s ambitious projects and the most exquisitely detailed one. It’s set in the mid-1800s New York, where the poor are left to survive amidst the relentless war between gangs of Protestant natives and Catholic Irishmen. 

DiCaprio plays his character with necessary gravitas and vigor. He succeeds in conveying the viewers Vallon’s inner turmoil. Yet this wasn’t one of the most well-written Scorsese movies. Moreover, DiCaprio was clearly overshadowed by Daniel Day-Lewis’ phenomenal performance. The sheer intensity with which he plays Bill the Butcher makes every other character pale in comparison. DiCaprio himself has cherished the chance to work with Daniel Day-Lewis, who also admired the actor’s complete commitment to his roles. 


12. Blood Diamond (2006)

Image Source:

Edward Zwick’s Blood Diamond is a lot different from the usual white men savior narratives of Hollywood. DiCaprio plays Danny Archer, an unscrupulous smuggler and mercenary who gets caught in Sierra Leone’s civil war while involved in search of a rare pink diamond. But Blood Diamond largely tells the story of a fisherman (Djimon Hounsou), who is displaced because of the war. For self-centered reasons, Danny accompanies the fisherman to help reunite him with his family. Nevertheless, the inhumanity he encounters gradually changes Danny.

In order to play Danny Archer, DiCaprio gained some muscles and is said to have trained with former Rhodesian soldiers. The character wasn’t written with much depth. But DiCaprio in his own way brought certain nuances and energy to carry the role. He gets a particularly touching moment towards the end. DiCaprio received an Oscar nomination for the role.


11. Catch Me If You Can (2002)

Image Source:

DiCaprio played highly-skilled con man Frank Abagnale, Jr. in Steven Spielberg’s Catch Me If You Can. It’s based on a real-life cat-and-mouse chase that unfolded between Frank and the FBI. This is a performance that largely relies on DiCaprio’s confidence and charisma. Frank is a simple young man who takes on many false identities, including a doctor, prosecutor, and a flight attendant. In one early scene, he passes himself off as a substitute teacher. Frank is so convincing in the various identities he took over that soon his con games became bigger and dangerous. 

Catch Me If You Can came after DiCaprio’s two underwhelming movies, The Beach and Don’s Plum. However, the charm he exudes in this lead role cemented his reputation and he became a force to be reckoned with. The actor is particularly impressive in the scene where he convinces Tom Hanks’ FBI character that he is really a Secret Serviceman. 


10. Shutter Island (2010)

films like Fight Club
Image Source:

Based on Dennis Lehane’s mystery novel, Scorsese’s Shutter Island is set in a 1950s Asylum for the Criminally Insane. DiCaprio plays Teddy Daniels, a U.S. Marshal invited to the somber island to investigate the disappearance of a patient. Soon, a shocking twist reveals that this isn’t a simple case of disappearance. Released just before Inception, Cobb and Teddy Daniels share a lot of traits, particularly their tenuous and waning grasp on reality. The choices and fate of both these DiCaprio characters also end on an eerily ambivalent note.

Perhaps, DiCaprio’s Teddy Daniels is more complex and his trauma is more severe than Cobb’s. In the later-half, Shutter Island becomes a character-driven story that looks into one traumatized individual’s tragic past and present. DiCaprio gradually and precisely unravels his character’s insecurities and deeply repressed memories. It’s a master class in acting which was sadly ignored by the Academy.


9. Titanic (1997)

titanic movie facts
Image Source:

James Cameron’s record-breaking feature – at both the box-office and Oscars – became a global cultural phenomenon during its time. Cameron’s filmmaking brought back the old-school Hollywood epic feel. It especially reminded us of David Lean movies’ expansive scope. However, the beating heart of this disaster film’s visual extravaganza was the familiar yet robust love relationship between a young drifter and a despairing upper class girl. In fact, it is the enchanting perspectives of Kate Winslet and Leonardo DiCaprio’s characters that bring genuine warmth to the proceedings. 

DiCaprio has had box-office success before Titanic, particularly Baz Luhrmann’s Romeo + Juliet (1996). But Jack was a high point in the actor’s career. Looking back, the King of the World sequence seems to have announced the arrival of this versatile actor to international moviegoers. Decades have passed since the release of Titanic and DiCaprio himself has played many other better and challenging roles. Nevertheless, Leonardo DiCaprio would be remembered by many as Jack


8. The Wolf of Wall Street (2013)

films adapted from books
Image Source:

DiCaprio and Scorsese teamed up once again in probably their funniest collaboration. Based on Jordan Belfort’s memoir of the same name, it’s a drug-fueled, testosterone-infused tale of capitalist excess and the American dream. Gordon Gekko in Oliver Stone’s Wall Street (1987) might have said “Greed is Good”. But it’s Belfort who lived and thrived by those words. 

Scorsese held absolutely nothing back in terms of sexuality, nudity, and profanity. Some could say it was a bucket load of fun. Yet, one criticism directed against the work is that Scorsese came closer to turning guys like Belfort into folk heroes, whose abject crimes were nearly absolved, while the blame is smartly shifted to the American way of life. In fact, it’s not the film’s problem per se, but the memoir was itself written in a way that eventually projects Belfort as a survivor. Of course, DiCaprio in the central role was at his flamboyant best. He mesmerizes us every moment he’s on screen. Deep down, we may know that the guy is a douchebag, drug addict, and a fraudster. Yet DiCaprio’s commanding presence turns The Wolf Of Wall Street into an engrossing roller-coaster ride.


7. Inception (2010)

best movie shots
Image Source:

Christopher Nolan’s Inception is the second biggest blockbuster in Leonardo DiCaprio’s career. It also brought puzzling high-minded ideas into a big-budget production. The actor plays Cobb, a master thief of the dreamscape who is guilt-ridden by the death of his wife. Desperate to reunite with his children, Cobb takes on a high-risk assignment for the wealthy business magnate Saito

Though Inception has a lot of spectacular set-pieces, it is a largely character-driven tale tackling Cobb’s moral quandaries. And DiCaprio gives a powerhouse performance as he confronts his character’s inner demons while caught in the dreamland. Inception starts by showing Cobb as a cool-headed guy who stays on top of the game. As the narrative unfolds, DiCaprio brilliantly delves into Cobb’s anxiety and vulnerability. On paper, the scenario might sound ludicrous and Cobb’s characterization can come across as simple. But the surprisingly restrained performance keeps us engrossed in the character’s mission. 


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

Leonardo dicaprio best movies
Image Source:

In Lasse Hallstrom’s brilliant drama, Leonardo DiCaprio played a mentally-challenged teenager who is looked after by his brother (played by Johnny Depp). Depp plays the titular character, who also has to take care of his housebound 500-pound mother and two sisters. The narrative tracks Gilbert’s efforts to live a life of his own. 

DiCaprio has often attempted to stay true to the roles he played. For Gilbert Grape, the actor visited homes for kids with mental disabilities and studied their mannerisms. Since his role wasn’t written in a very structured manner, DiCaprio is said to have brought his own nuances to the role. A lot of what he did on the set of Gilbert Grape was pure improvisation. In fact, it is a character that lives in his own world. The 19-year old DiCaprio rightly received his first Oscar nomination for this unbelievably vivid performance. 


5. The Departed (2006)

leonardo dicaprio 10 best movies
Image Source:

Leonardo DiCaprio’s exuberant performance in The Wolf of Wall Street is often credited as the actor’s best among his collaborations with Scorsese. But I’d argue that it was DiCaprio’s ill-fated protagonist in The Departed that offers the best among their creative partnership. It’s a remake of Hong Kong crime drama Infernal Affairs (2002). The plot revolves around an undercover cop infiltrating a gang, and a cop who works for the gang. A cat-and-mouse game ensues as both try to unveil the hidden identities of each other.

DiCaprio plays Billy Costigan, an exhausted undercover police officer who is gradually spiraling down because of the criminal activities he witnesses on a day-to-day basis. He spellbindingly showcases his character’s inner turmoil while trying to protect his years of undercover work. The performance could be called mercurial, since Billy constantly keeps on a mask, yet deep down fears that his deceptive tactics would be revealed. 

See Also
korean movies on netflix


4. Django Unchained (2012)

leonardo dicaprio movies
Image Source:

Before Django Unchained, Leonardo DiCaprio had worked with Hollywood’s greatest directors like Martin Scorsese, James Cameron, Ridley Scott, and Steven Spielberg. One director he was really interested in working with was Quentin Tarantino. And when the chance came up, he grabbed it, even though he had to play a despicable antagonist role. DiCaprio has mentioned that it was very uncomfortable playing Calvin Candle. The man is a sadistic slave owner with whom he couldn’t connect on any level. Yet DiCaprio did a brilliant job in convincing us of Calvin’s downright evil nature. 

Django Unchained can’t be mentioned without the crucial glass-smashing scene. He cut his hands while the cameras were rolling. But he ignored it and stayed in character with the bloody hand adding more intensity to the already tense scenario. Irrespective of the glass-smashing incident, DiCaprio truly terrified us with this wicked and ruthless act. 


3. The Aviator (2004)

leonardo dicaprio best movies
Image Source:

The Aviator marks Leonardo DiCaprio’s second collaboration with Martin Scorsese. This time they came together to make a biopic on Howard Hughes, a renowned business magnate, pilot, engineer, and a filmmaker. Aviator depicts young Hughes whose aspirations are close to becoming obsessions. Unlike any other films DiCaprio did before, Scorsese’s movie gave him the chance to showcase his full range of emotions. 

The actor extensively prepared for the role, which includes befriending a man diagnosed with O.C.D. He understood the key character traits and perfectly brought it to screen in the important moments. DiCaprio is particularly astonishing in the memorable closing scene when Hughes gets stuck with a phrase. DiCaprio also spent some time with Jane Russell who has acted in a film made by the real Hughes. The profound performance surprised critics and audiences alike. He received his first lead-role Oscar nomination, but unfortunately lost it to Jamie Foxx. 


2. Once Upon A Time in Hollywood (2019)

leonardo dicaprio movie ranking
Image Source:

Quentin Tarantino in his second collaboration with Leonardo DiCaprio bestowed upon him a lead role that pushes the actor to showcase a wide range of emotions. DiCaprio’s Rick Dalton is an aging TV star, whose heydays are long behind him. Though he stays in Hollywood, the industry people have nearly forgotten him. Rick plays tough guy roles on-screen, but off-screen he is a mess. The only person who listens to his lamentations and quells his insecurities is Cliff Booth, his stunt double as well as best friend. 

Once Upon a Time… unfolds like a tragicomedy and DiCaprio perfectly anchors this tone as his portrayal of Rick is simultaneously poignant and humorous. DiCaprio’s performance is brilliantly layered, especially in the sequences where we see Rick acting a bit part in a Western. This is also his second physically comic performance after The Wolf of Wall Street.


1. The Revenant (2015)

best di Caprio movies
Image Source:

Alejandro González Iñárritu’s survival revenge tale finally got Leonardo DiCaprio his first Oscar after three nominations in the same category. Leo had to go to the extremes of method acting for this one. He plays frontiersman Hugh Glass in 1823, who gets left for dead by a group of trappers upon getting mauled by a bear. The Revenant, however, isn’t a typical Western. It has a more art house approach as every grueling step in Glass’ journey becomes the central focus. The film definitely has a lot of graphic violence yet it’s not stylized in a manner that you’d expect from a Tarantino picture.

It’s impossible to be unmoved by the range of emotions DiCaprio expressively conveys to showcase his character’s suffering. Moreover, the sheer physicality of his performance is daunting. DiCaprio had to endure sub-zero temperatures to achieve the performance he intended. From sleeping inside animal carcasses, going out in a frozen river to eating raw meat, DiCaprio’s efforts are astonishing. 



Leonardo DiCaprio will continue to be Hollywood industry’s most bankable A-list star and his career is far from over. Though he took a break in 2020, he returned with the satirical drama Don’t Look Up which combined his passion for climate change activism and acting. To his credit, DiCaprio is probably the only major Hollywood star to not be part of any franchise cinema. Two more exciting projects with Martin Scorsese are lined-up. One is Killers of the Flower Moon, an adaptation of a true crime story revolving around the murders of Osage tribe members. The other is a biopic on the former US President Theodore Roosevelt.


View Comments (0)

Leave a Comment

Discover more from Flickside

Subscribe now to keep reading and get access to the full archive.

Continue reading