13 Best Leonardo DiCaprio Movies, Ranked – Flickside

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 called 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 (a year after his birth), both nurtured and encouraged his creative side. Post his first gig, DiCaprio played small roles in sitcoms including Growing Pains. His feature film debut was the very awful direct-to-video horror sequel Critters 3 (1991). Soon however, he landed a breakthrough role 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 there, it was a steady rise to stardom, with Titanic (1997) turning him into an instant heartthrob. But DiCaprio picked roles that challenged him beyond the handsome young man stereotype. The year 2002 was pivotal, marking his first collaboration with Martin Scorsese in Gangs of New York. The same year DiCaprio played the suave anti-hero in Spielberg’s Catch Me If You Can. Later, he played darker, layered characters in films such as Blood Diamond Revolutionary Road, and Django Unchained

Impressive acting career aside, Leonardo DiCaprio is politically active and dedicated to raising awareness about climate change. He’s produced eye-opening documentaries such as The 11th Hour, Before the Flood, and Ice on Fire. Quickly then, here are the best performances of one of the most badass actors of our generation:


WATCH: Leonardo DiCaprio’s Greatest Screen Moments


Best Leonardo DiCaprio Movies

13. Gangs of New York (2002)

Source: Looper

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

DiCaprio brings necessary gravitas and vigor to Vallon, brilliantly conveying his inner turmoil. However, the film’s writing was not its strongest aspect, and DiCaprio was overshadowed by Daniel Day-Lewis’ phenomenal performance. Day-Lewis’ sheer intensity as Bill the Butcher makes every other character pale in comparison.

DiCaprio cherished the opportunity to work with Day-Lewis, who in turn admired DiCaprio’s complete commitment to his roles.


12. Blood Diamond (2006)

Source: Warner Bros.

Edward Zwick’s Blood Diamond breaks from the typical Hollywood white savior narrative. DiCaprio plays Danny Archer, a mercenary caught in Sierra Leone’s civil war while searching for a rare pink diamond. But Blood Diamond largely tells the story of a fisherman (Djimon Hounsou), who is displaced by the war. For self-centered reasons, Danny helps the fisherman reunite with his family, but the inhumanity he encounters gradually changes him.

To play Danny Archer, DiCaprio gained muscle and trained with former Rhodesian soldiers. Although the character lacked depth, DiCaprio infused him with nuance and energy. He delivers a particularly touching moment toward the end, earning an Oscar nomination for the role.


11. Catch Me If You Can (2002)

Source: Letterboxd

In Steven Spielberg’s Catch Me If You Can, DiCaprio plays Frank Abagnale Jr., a highly skilled con man in a real-life cat-and-mouse chase with the FBI. This performance hinges on DiCaprio’s confidence and charisma. Frank, a young man who assumes various false identities, including a doctor, prosecutor, and flight attendant, even poses as a substitute teacher in one early scene. His convincing cons grow increasingly bold and dangerous.

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


10. Shutter Island (2010)

Source: Indiewire

Based on Dennis Lehane’s mystery novel, Martin Scorsese’s Shutter Island is set in a 1950s asylum for the criminally insane. DiCaprio plays Teddy Daniels, a U.S. Marshal investigating the disappearance of a patient. A shocking twist soon reveals that this isn’t a simple missing persons case. Released just before Inception, Teddy Daniels shares traits with Cobb, particularly a tenuous grasp on reality. The fates of both characters end on an eerily ambivalent note. Teddy Daniels is perhaps more complex, with deeper trauma than Cobb.

In the latter half of Shutter Island, the film delves into Teddy’s tragic past and present. DiCaprio gradually unravels his character’s insecurities and repressed memories, delivering a masterful performance that was unfortunately overlooked by the Academy.


9. Titanic (1997)

Source: Vox

James Cameron’s record-breaking Titanic became a global cultural phenomenon, dominating both the box office and the Oscars. Cameron’s filmmaking revived the old-school Hollywood epic, reminiscent of David Lean’s expansive scope. The heart of this disaster film, however, lies in the compelling love story between a young drifter and a despairing upper-class girl. Kate Winslet and Leonardo DiCaprio’s charming performances bring genuine warmth to the narrative.

DiCaprio had box-office success before Titanic, notably with Baz Luhrmann’s Romeo + Juliet (1996), but playing Jack was a career milestone. The iconic “King of the World” scene announced his arrival to international audiences. Decades later, despite taking on many other challenging roles, DiCaprio is still fondly remembered by many as Jack.


8. The Wolf of Wall Street (2013)

Source: Prime Video

DiCaprio and Scorsese teamed up again in what is one of their most fun collaborations. Based on Jordan Belfort’s memoir, The Wolf of Wall Street is a drug-fueled, testosterone-infused tale of capitalist excess and the American dream. While Gordon Gekko in Oliver Stone’s Wall Street (1987) famously said, “Greed is good,” Belfort lived and thrived by those words.

Scorsese held nothing back in terms of sexuality, nudity, and profanity. While some found it wildly entertaining, critics argued that Scorsese risked turning Belfort into a folk hero, nearly absolving his crimes while shifting blame to the American way of life. This issue stems from the memoir itself, which projects Belfort as a survivor.

DiCaprio, in the central role, delivers a flamboyant performance, mesmerizing every moment he’s on screen. Despite knowing Belfort is a despicable drug addict and fraudster, DiCaprio’s commanding presence makes The Wolf of Wall Street an engrossing roller-coaster ride.


7. Inception (2010)

Source: Warner Bros.

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

Despite its spectacular set-pieces, Inception is a character-driven tale exploring Cobb’s moral quandaries. DiCaprio delivers a powerhouse performance, confronting his character’s inner demons in the dreamland. Initially, Cobb appears as a cool-headed operator, but as the story unfolds, DiCaprio reveals Cobb’s anxiety and vulnerability. On paper, the scenario might seem ludicrous and Cobb’s characterization simple, but DiCaprio’s restrained performance keeps us engrossed in his mission.


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

leonardo dicaprio best movies
Source: Screenrant

In Lasse Hallstrom’s brilliant drama, Leonardo DiCaprio played a mentally-challenged teenager who is looked after by his brother (Johnny Depp). Depp plays the titular character, who also takes care of their housebound 500-pound mother and two sisters while trying to carve out his own life.

DiCaprio is known for his dedication to his roles, and for Gilbert Grape, he visited homes for mentally disabled children to study their mannerisms. Since his role wasn’t strictly structured, DiCaprio brought his own nuances to the character, with much of his performance being pure improvisation. His portrayal, deeply immersed in its own world, earned the 19-year-old DiCaprio his first Oscar nomination for an unbelievably vivid performance.

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5. The Departed (2006)

Source: ACMI

Leonardo DiCaprio’s exuberant performance in The Wolf of Wall Street is often hailed as his best collaboration with Scorsese. But for me, his role as the ill-fated protagonist in The Departed is their finest work together. This remake of Hong Kong’s Infernal Affairs (2002) centers on an undercover cop infiltrating a gang and a cop working for the gang, engaging in a tense cat-and-mouse game.

DiCaprio plays Billy Costigan, an exhausted undercover officer spiraling downwards due to the criminal activities he witnesses daily. He spellbindingly showcases his character’s inner turmoil while trying to protect his years of undercover work. The performance could be mercurial, as Billy constantly keeps on a mask, yet deep down fears his deception will be exposed.


4. Django Unchained (2012)

Source: IMDb

Before Django Unchained, Leonardo DiCaprio had already worked with top directors like Martin Scorsese, James Cameron, Ridley Scott, and Steven Spielberg. One director he was eager to collaborate with was Quentin Tarantino. When the opportunity came along, he seized it, even though it meant playing the despicable antagonist Calvin Candie. DiCaprio admitted feeling very uncomfortable portraying Candie, a sadistic slave owner with whom he felt no connection. Despite this, DiCaprio delivered a brilliant performance, convincingly portraying Candie’s evil nature.

And you can’t talk about Django Unchained without mentioning the crucial glass-smashing scene! He accidentally cut his hand but continued acting, adding intensity to the already tense moment. Regardless of this incident, DiCaprio truly terrified audiences with his wicked, ruthless performance.


3. The Aviator (2004)

Image Source: Letterboxd

The Aviator marks Leonardo DiCaprio’s second collaboration with Martin Scorsese, this time creating a biopic on Howard Hughes, the business magnate, pilot, engineer, and filmmaker. The film portrays a young Hughes, whose ambitions verge on obsession. Unlike any previous roles, this movie allowed DiCaprio to showcase his full emotional range.

To prepare, DiCaprio befriended a man with O.C.D. to understand the character’s traits and convey them authentically on screen. His portrayal is particularly astonishing in the memorable closing scene, where Hughes gets stuck on a phrase. DiCaprio also spent time with Jane Russell (who acted in a film made by the real Hughes). His profound performance surprised critics and audiences, earning him his first lead-role Oscar nomination, although he ultimately lost to Jamie Foxx.


2. Once Upon A Time in Hollywood (2019)

Source: Columbia Pictures

In his second collaboration with Quentin Tarantino, Leonardo DiCaprio takes on a lead role playing Rick Dalton, an ageing TV star whose glory days are behind him. Though he remains in Hollywood, he is largely forgotten by the industry. On-screen, Rick plays tough guys, but off-screen, he is a mess. His only confidant is Cliff Booth, his stunt double and best friend.

The film unfolds like a tragicomedy, and DiCaprio perfectly anchors this tone with a performance that is both poignant and humorous. His portrayal of Rick is brilliantly layered, especially in the scenes where Rick acts in a Western. This role also marks DiCaprio’s second physically comedic performance after The Wolf of Wall Street.


1. The Revenant (2015)

leonardo dicaprio 10 best movies
Source: Mubi

Alejandro González Iñárritu’s survival revenge tale, The Revenant, finally earned Leonardo DiCaprio his first Oscar after three previous nominations. DiCaprio went to extremes of method acting to portray frontiersman Hugh Glass in 1823, who is left for dead by trappers after being mauled by a bear. Unlike typical Westerns, The Revenant takes an art-house approach, focusing on every grueling step of Glass’ journey. The film features graphic violence but lacks the stylization typical of Tarantino’s work.

DiCaprio’s performance is profoundly moving, remarkably showcasing Glass’ suffering. The physical demands of the role were daunting; DiCaprio endured sub-zero temperatures, slept inside animal carcasses, waded through frozen rivers, and ate raw meat to achieve the authenticity he intended. His efforts were nothing short of astonishing.


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