The 15 Best Leonardo DiCaprio Movies You Need To Watch

Distinguished by his incredibly intense, emotional style and powerhouse acting, Leonardo DiCaprio is one of the best actors of his generation. He has been in more great films than any other actor his age, which is clearly reflected in his filmography that boasts plenty of classic films and iconic roles.

His characterized niche is searching, finding, and achieving exceptionally challenging protagonists (and antagonists). He raises the bar with every single performance, and each time the audience views one of his acts, they witness a performer pushing—even breaking—the limits.

Although he is just 38 years old and still has some time to spare, his twenty plus year journey—from scoring a small role in Critters 3 (1991) to captivating the world’s stage in The Wolf of Wall Street (2013)—is a long, illustrious dream run.

At a young age, he began his career working mostly in television. His “breakout” role, What’s Eating Gilbert Grape (1993), in which he plays the titular character’s (Johnny Depp) mentally challenged younger brother, has helped him achieve recognition in cinema.

His lead role as Jack Dawson in Titanic, however, made him a household name. Titanic, which received eleven Academy Awards and was the highest grossing movie of all time, had created the ultimate romantic hero out of Jack Dawson and generated a DiCaprio a sensation.

In his unbelievable career as an actor, DiCaprio has worked with all the great directors: Woody Allen, Steven Spielberg, Clint Eastwood, Ridley Scott, James Cameron, Sam Raimi, Sam Mendes, Christopher Nolan, Danny Boyle, Lasse Hallström, and Baz Luhrmann. His relationship with auteur Martin Scorsese, however, is certainly one of the best actor-director collaborations of the 21st century, and one of the most productive in the history of Hollywood.

One of the biggest names in Hollywood is also one of the most versatile actors working in the industry. DiCaprio has successfully avoided all the Hollywood clichés, traps, and stereotypes. He is a fearless, big-hearted actor who has played a wide array of awe-inspiring characters. In DiCaprio’s filmography, for every blonde heartthrob Jack Dawson, there is a notorious Calvin Candy; for every epitomic Romeo, there is a lost Billy.

Though DiCaprio has approximately 29 films under his belt, below is a list of fifteen films that will inform and remind cinephiles of the adept acting skills and the extreme talent of Leonardo DiCaprio.


15. Romeo + Juliet (1996), dir. Baz Luhrmann


Romeo + Juliet—one of countless adaptations about the immortal tragedy of two “star-crossed lovers,” written by the greatest playwright of all time—is sincerely entertaining. Baz Luhrmann’s hip version, set in beautiful, contemporary Verona, is a candid re-working of Shakespeare’s legendary play. Even though Luhrmann replaced swords with guns, the characters converse in the verse of 16th century England, as the director maintains the veracity of the original work.

This imaginative and ambitious film is a fresh, bold, and visually inventive version of the classic tragedy. Luhrmann’s rich visual and diegetic aesthetics—vibrant colors, stunning costumes, and beguiling soundtrack—accentuate the rich and innovative storytelling.

What truly makes the movie engrossing, however, is the lead pair, Claire Danes as Juliet Capulet and Leonardo DiCaprio as Romeo Montague. The chemistry between both is searing because they play their parts pretty well and produce a good “on screen” couple. The supporting cast is also exceptional, blending with everything else, to make this movie worth the viewer’s time.


14. Marvin’s Room (1996), dir. Jerry Zaks


Based on the play of same name, written by Scott McPherson—who also adapts the story to screen—Marvin’s Room tells the tale of Bessie (Diane Keaton), who has been her incapacitated father’s caretaker for the past twenty years.

When doctors tell her she has leukemia and needs a bone marrow transplant, she turns to her sister, Lee (Meryl Streep), who left her and their father twenty years ago. Bessie attempts to mend the relationship and end their dispute in hopes to receive the transplant. DiCaprio plays Hank (Lee’s eldest son), who is in a mental institution for burning down the house.

This movie, as the plot line suggests, is a drama about a dysfunctional family, but it also has something more to offer than other films of the same genre: it depicts selfless love and the power that maintains relationships. Another aspect in which it differs is the all-star cast of the film, which includes names like Meryl Streep, Diane Keaton, Leonardo DiCaprio, and Robert De Niro.

This film certainly isn’t the ultimate dysfunctional family drama, but it’s a good film nonetheless. There are some flaws in the story and direction; however, what Marvin’s Room lacks, is rectified in the impeccable acting, which allows for the film’s overall cohesive blend.


13. This Boy’s Life (1993), dir. Michael Caton-Jones

This Boy’s Life (1993)

If What’s Eating Gilbert Grape is the film that launched DiCaprio’s filmic career, This Boy’s Life solidified it. The film was adapted from the memoir of the same name, which was written by Tobias Wolff, and takes place in the 1950s. It articulates the anecdotes of young and rebellious Tobias, and the relationship he has with his abusive stepfather, played by the maestro, Robert De Niro.

This Boy’s Life—which marks the directing debut of Sam Raimi—is a touching, riveting, and emotionally-driven narrative augmented by Leonardo DiCaprio’s stirring performance. The relationships in the film are bitter and realistic. The characters create a certain kind of disruptive environment, which gives the story breathing and nurturing space, and allows one act to plausibly flow into the other.

Ellen Barkin, Tobias’s mother, and De Niro put their best foot forward; the almost unknown DiCaprio’s performance throughout the piece is comparable and compelling to the aforementioned stars, making this brutally upsetting drama a fundamentally important film.


12. Titanic (1997), dir. James Cameron

FILM Howlers/Titanic

In 1997, James Cameron wrote and directed the most expensive movie ever made at that time, the $200 million dollar epic “disaster” movie, Titanic. Titanic is a fictionalized account, which illustrates the gradual sinking of the R.M.S. Titanic. The doomed love story is captured through poor, free-spirited artist Jack Dawson (DiCaprio) and young aristocratic Rose Dewitt Bukater (Kate Winslet), who is expected to marry one of her own kind, the pretentious Cal Hockley (Billy Zane).

Titanic is the type of film one watches and becomes mystified and silent after it ends. The viewer instantly realizes he or she experienced a scenario that alters historical accounts, and he or she will not be able to watch “reel” romance—the “boy meets girl, girl meets boy” narrative—the same again. Titanic, however, is not just a love story; it is a human story— a piece about pain and misery.

It is the tale of people losing their loved ones forever in front of their eyes. It is an account of a sinking nightmare in which more than 1500 people lost their lives. Above all, as the title suggests, it is the journey of the ship herself, the titular—almost anthropomorphic—character, “Titanic.”

As mentioned in the introduction, Titanic launched the versatile acting career of Leonardo DiCaprio. He and Winslet were brilliant; their on screen chemistry and romance was truly outstanding and astonishingly realistic. The result: the pair stole the hearts and souls of millions. While the blonde-haired Jack Dawson was the contemporary romantic hero and cult figure, Leonardo DiCaprio became an overnight sensation, a household name, a teenage heartthrob, and a superstar.


11. Gangs of New York (2002), dir. Martin Scorsese

Gangs of New York (2002)

If ever there was a madly ambitious dream for DiCaprio, Gangs of New York had to be it. This conflicted historical period drama film is the first of many impressive collaborations between Martin Scorsese and Leonardo DiCaprio.

Set in mid-19th century in the five points district of lower Manhattan, Gangs of New York is an epic revenge piece about the young man, Amsterdam Vallon (Leonardo DiCaprio), and his mission to kill the man—Bill “The Butcher” Cutting (Daniel Day Lewis)—who murdered his father (Liam Neeson).

Although it is incoherent in a few places, Gangs of New York (like all Scorsese films) is well-paced and entertaining. It is the kind of film that, for its ambition alone, deserves all the praise and glory. This shambolic saga of brutal retribution is a true accomplishment of pure art.

A passion project and lifelong dream of Scorsese, Gangs of New York is undeniably maundering and overwhelming. It also, however—with Scorsese’s design and drive—explodes on the screen. Ultimately, this is Scorsese’s flawed masterpiece—“masterpiece” being the operative term.