Leonardo DiCaprio is undoubtedly one of the living legends of Hollywood, starting in TV commercials and quickly blossoming into one of the most sought-after and gifted talents in Hollywood. With a three-decade-long career, he has worked with some all-time great directors, from Tarantino and Ridley to Spielberg and Scorsese.
Leonardo earned his first Academy Award nomination at just nineteen, marking the start of an illustrious career that would put the star in the limelight. DiCaprio picks his projects meticulously, works with the best, and spawns a masterpiece every time. Choosing and ranking his best movies was arduous – but we did it, anyway! These are our top picks, ranked from worst to best.
1. The Beach (2000)
Danny Boyle has made a few movies that were not outstanding, and The Beach is an example of one of his projects that went off the rails. Based on a book by Alex Garland, the movie is about a group of western travelers looking for a new paradise in Southeast Asia. Unfortunately, it haphazardly goes from an adventure and tourism stint to a struggle for survival.
A Group of Western Travelers Look for Paradise in Southeast Asia
The movie struggles at several points, especially in the third act. But DiCaprio, coming off his success with the Titanic, brings life to the film and makes it worthwhile.
2. The Man in The Iron Mask (1998)
No matter how great an actor is, there’s only so much they can do without a good script, and The Man in the Iron Mask was lacking in the screenplay and with such a hollow plot. In an almost Disney-esque parody of a movie, DiCaprio plays a twin as both protagonist and antagonist. It follows the story of King Louis XIV and the plot to replace him with his secret twin brother.
Plays a Twin as Both Protagonist and Antagonist
While the movie had mixed feedback and criticism from fans, it garnered substantial success. Perhaps the star-studded cast, which included Jeremy Irons and John Malkovich, was a high contributing factor. But Leonardo, hot off his heels from the Titanic success, was one of the best parts of the project.
3. This Boy’s Life (1993)
One of the earliest displays of DiCaprio’s immense range of potential is in this adaptation of Tobias Wolff’s memoir. It tells the story of Toby (Leonardo DiCaprio) and his mother as they survive the cruel machinations of Dwight (Robert De Niro), Toby’s stepfather. The young DiCaprio met with the seasoned De Niro, Toby matching his stepfather’s rage, intensity, and cruelty.
A Young Man Looking To Protect His Mother
The movie sees DiCaprio grow right on the screen from a naïve boy to a young man looking to protect his mother by all means. DiCaprio became one of Hollywood’s most sought-after talents due to his character’s complexity and ability to shine next to De Niro.
4. Gangs of New York (2002)
This marks the first time Leonardo DiCaprio worked with hit-making director Martin Scorsese. The movie boasts an impressive cast, from Daniel Day-Lewis, who got into the role after working with actual butchers, to Cameron Diaz and Liam Neeson.
A Young Man Looking For Vengeance for His Father
Leo plays Amsterdam, a young man looking for vengeance for his father, who was killed by Bill “The Butcher.” Jenny Everdeane (Cameron Diaz) and Amsterdam Vallon (Leonardo DiCaprio) shine in their roles as their young romance blooms—the bloody epic borders on themes of religious fervor and sociopolitical battles for control over New York.
5. Romeo + Juliet (1996)
Before Jack and Rose, there was Romeo and Juliet. DiCaprio stars in the adaptation of the Shakespearian piece, set in modern times. Working alongside Claire Danes, the movie tells the classic story of young love on a fuse. It’s giddy, ripe with emotion, tension, and parents’ frustrations trying to pull back on the insatiable love of Romeo (Leonardo DiCaprio) and Juliet (Claire Danes).
Aside from the natural chemistry between actors, the film represents a generation that took literature paramount with phenomenal dialogue.
The Classic Story of Young Love on a Fuse
DiCaprio, the soft-spoken heartthrob, expertly runs through his lines, leaving viewers caught in the same infatuation he feels for his lover. The movie’s selling point, and what set the stage for Titanic that would come only a year later, is the unstoppable romance between the star-crossed lovers, Romeo and Juliet.
6. J. Edgar (2011)
J. Edgar had the potential to be a great and memorable movie. The biopic centers on the story of the corrupt FBI director who started the fingerprinting database. He spied on everyone he wanted and used his power to hide his relationship with Clyde Tolson (Armie Hammer). As a typical movie by Clint Eastwood, it took the same winding and downright boring route as most of his projects.
The Corrupt FBI Director
While they are usually historically correct, this movie stifles DiCaprio as an actor, as he’s forced to transform from the cherub-faced pretty boy to an aging J. Edgar Hoover. Although the film is lacking, those who worked with Edgar would say that Leonardo’s performance was so realistic it felt like they were watching the real thing.
7. Once Upon a Time in Hollywood (2019)
DiCaprio yelling at himself in his trailer after messing up some of his lines lives rent-free in our heads as one of the star’s funniest and best bits of acting. The movie follows Rick Dalton (Leonardo DiCaprio) and Cliff Booth (Brad Pitt), as DiCaprio is a Hollywood star past his prime with a struggling career.
A Hollywood Star Past His Prime
From the musical score, background marquees, and radio music to cars and even the 35mm film on which they shot it, the movie captures the Golden Age of Hollywood.
8. Revolutionary Road (2008)
The novel by Richard Yates brings back the titanic pair of DiCaprio and Kate Winslet once again, only that they aren’t swooning madly over each other. Instead, they’re adults who realize that the world isn’t as they expected it to be, and more than anything else, they want more from it. Both characters, Frank and April Wheeler, soon realize that their dream jobs and lifestyle are beyond their grasp.
Shows How Complex Everyday Life Can Be
They struggle with their failing marriage and their jobs, extramarital relationships, and childbirth. It’s a simple movie showing just how complex everyday life can be. The performance by DiCaprio and Kate earns them an Academy nomination for Best Actor and Actress, and there is no question about it, as their acting is absolutely stellar. The movie proves that their Titanic performance was only the tip of the iceberg.
9. Body of Lies (2008)
While striving to be a social commentary on the relations between the US and the Middle East, Body of Lies manages an underlying and thought-provoking message but mainly comes across as bland. The B-list movie follows Roger Ferris (Leonardo DiCaprio) as a CIA operative trying to track down and eliminate a terrorist organization in the middle east. Meanwhile, he gets a little too close to his love interest, Golshifteh Farahani, who plays Aisha.
A CIA Operative Trying To Eliminate a Terrorist Organization
DiCaprio and his boss, Russell Crowe (Ed Hoffman), do their best to make the espionage thriller quite the spectacle, with great action sequences and dialogue. But that it’s just another thriller with no authentic voice of its own makes it a pretty forgettable venture.
10. The Aviator (2004)
Only a couple of talents in Hollywood can step into the psyche of the different characters they play with vastly varying mental states, and DiCaprio is one of them. In The Aviator, he portrays the mental state of Howard Hughes, a man plagued by his own passion for innovation and success. In addition, he mirrors Hughes’ compulsive personality disorder, which pushes him to self-destruction.
Portrays The Mental State of Howard Hughes
While he is a larger-than-life billionaire in his second movie with Martin Scorsese, DiCaprio brings a different swagger to his role in this, which is grossly underrated. The biopic intricately shows the life of Hughes, his various business ventures, and his eventual fall into insanity.
11. Don’t Look Up (2021)
Jennifer Lawrence and Leonardo DiCaprio star as scientists discover a comet heading straight for earth. The satirical social commentary hits hard on several issues and proves incredibly self-aware. It tackles themes like societies’ dependence on technology, politics, climate change, and woke culture.
A Scientist Who Discover a Comet Heading Straight for Earth
While it received mixed reviews, it remains a splendid watch. Everyone does spectacular work in the movie. Leo’s facial expressions and incoherent babble share what it’s like to be a man burdened with knowledge.
12. Shutter Island (2010)
The haunting horror/mystery by Martin Scorsese shows an older, more emotional, and fragile Leonardo DiCaprio. The movie takes a U.S. Marshal and his partner, Chuck Aule (Mark Ruffalo), to a remote facility, where they investigate the disappearance of a missing patient. Things quickly take a turn as Scorsese leads the viewers through the twists and turns of the movie, following the paranoid man until he realizes things are not as they seem.
Investigates The Disappearance of a Missing Patient
From cryptic codes to conspiracy theories, mixed with Leonardo and Ruffalo’s antics, the film is a twistedly creepy and perplexing piece of art. However, while the movie’s convenience gives away the end truth to an eagle-eyed viewer, it does not make it less entertaining.
13. Blood Diamond (2006)
Selling the white savior narrative is quite the task. Still, Leonardo masterfully executed it and, by the end of the movie, could convey the emotions and struggles of Sierra Leone during their civil war. As a smuggler, DiCaprio (Danny Archer) plays the antihero who only cares about money. Archer is the action hero, running through war-torn villages to save the family of Solomon Vardy (Djimon Hounsou).
The Antihero Who Only Cares About Money
The movie showcases the tragedies of war, child soldiers, the illegal diamond trade, and many corrupt practices that plagued the era. DiCaprio’s performance earned him an Academy, Golden Globe, and Screen Actors Guild nominations.
14. What’s Eating Gilbert Grape (1993)
Here, Leonardo DiCaprio plays a mentally challenged sibling, which earned him his first Oscar nod at nineteen. Depp was the name that drew you to the movie. Still, DiCaprio’s authentic, empathic, and heart-splitting method of acting captured viewers’ hearts long after watching.
A Young Man Who Has To Take Care of His Family
The movie follows the story of Gilbert Grape, a young man who has to care for his family in a small town in Iowa. The coming-of-age story takes us through the wringer as Gilbert (Depp) finds love, deals with his family, and struggles with his business. While Depp was the main attraction, Leonardo got his Oscar nomination for Best Supporting Actor for his performance in the movie.
15. Django Unchained (2012)
DiCaprio never fails to shine. Even when surrounded by other high-profile stars like Samuel L. Jackson, Christopher Waltz, and Jamie Foxx, he delivers a stellar performance. DiCaprio embodied the role of a racist plantation owner in a movie directed by Quentin Tarantino, delivering his lines with detestable charm and charisma. He’s so deep into the character that he accidentally cuts himself during filming without noticing. And when he does, he continues acting, paying no mind to it – a scene that adds to a phenomenal work.
A Racist Plantation Owner
Although not based on a true story, true events on black exploitation and slavery inspired American western film. It received a long list of accolades for its originality and screenplay.
16. The Departed (2006)
It’s not the first time Leonardo stars in a movie that shows the intricacies of a cat-and-mouse chase. The Departed sees DiCaprio playing a grumbly, desperate, and repulsive officer looking to infiltrate the mob. Billy Costigan (Leonardo DiCaprio) shows how demanding and stressful the ploy of being an undercover cop could be.
A Desperate and Repulsive Officer Looking To Infiltrate The Mob
Scorsese’s Good Fellas will always stand as one of his best works. Still, the betrayals, scandals, twists, and emotional stakes make The Departed a strong candidate for the same position. The movie has no premise of a happy ever after because there’s no telling what comes next, keeping spectators at the edge of their seats until the end.
17. The Great Gatsby (2013)
Tobey’s narration of the life and exploits of his friend and the myth Jay Gatsby, with his calm, almost sultry voice, allows the scenes their free flow and keeps the pace. Gatsby is a man of lavish parties, expensive suits, and a billionaire lifestyle that seems tailored for none other than Leonardo.
An Insecure Billionaire Looking To Win Love
In this superb tale, DiCaprio plays an insecure billionaire looking to win the love of Daisy while working alongside his friend, Nick Carraway (Tobey Maguire). But not all love stories end in paradise, as with the tragic unfolding of Gatsby’s fate. The Great Gatsby also depicts man’s innate selfishness. Yet, despite his lavish parties and benevolence, his best friend, Nick Carraway, is the only one who sticks by him.
18. The Wolf of Wall Street (2013)
“I’ve been a poor man, and I’ve been a rich man. And I choose rich every f–king time.”
In what is considered Leonardo DiCaprio’s best performance, Martin Scorsese’s Wolf of Wall Street is based on a true story. Following the story of Jordan Belfort, a broker turned millionaire fraudster on his way to the top. Leo sells the character, delivering a hilarious yet emotional performance.
A Broker Turned Millionaire Fraudster
Margot Robbie, Jonah Hill, Matthew McConaughey, and Leonardo put together three hours of sheer intensity that resonated with even the casual moviegoer. It is the classic story of a nobody to rich man, but a phenomenal cast and the spectacular acting of DiCaprio spun it into a masterpiece.
19. Titanic (1997)
Titanic won eleven Academy Awards and was the highest-grossing movie ever made for twelve years straight. It was also the first movie to cross a billion dollars at the box office, paving the way for future films. The twenty-two-year-old DiCaprio’s esoteric smile and youthful exuberance contributed significantly to the film’s success.
One of The Greatest Love Stories Ever Made
The romance epic follows two young people, Jack (Leonardo DiCaprio) and Rose (Kate Winslet), from different classes. They meet on the ill-fated ship, Titanic and fall in love.
Titanic holds true to this day as one of the greatest love stories ever made.
20. Inception (2010)
This twisted heist thriller by Christopher Nolan is a prime example of DiCaprio collaborating with ace directors to bring perfection to the cinema.
A Thief Entering The Minds of His Targets
Inception follows a straightforward yet hard-to-grasp premise in typical Nolan fashion. Cobb (Leonardo DiCaprio) works as a thief, entering the minds of his targets to plant ideas and steal information to aid in his work. After a preposition by a business mogul, Cobb teams up with like-minded individuals to execute the one plan that could bring him back home to his family. Inception puts the deviously stunning visuals of Christopher Nolan together with the genius of DiCaprio’s performances as a haunted man hiding from his past.
21. Catch Me if You Can (2002)
Leonardo DiCaprio and Tom Hanks star in this exciting movie, as Leonardo plays a real-life fraudster in Frank Abagnale Jr., running circles around the detective. Leonardo plays a pilot, lawyer, doctor, and several other roles, flaunting his range of expertise. The Steven Spielberg hit earned the actor his third nomination for a Golden Globe.
Plays a Real-life Fraudster
From the musical score to the aura of impending doom, it’s fun to watch the young DiCaprio talk his way out of the FBI’s grips, outsmarting them repeatedly. Two mice fell into a bucket of cream, and by the end of the movie, you certainly know which one Frank is.
22. The Revenant (2015)
The pretty boy gets his charm stripped from him in the 2015 movie as he takes on the elements head-on. Leonardo faces off against blistering cold, falls off cliffs, and is attacked and mauled by a bear. Leonardo spent time in frozen rivers to prepare for the role and got hypothermia. He also ate raw bison liver to get in character for the gritty part.
Faces The Blistering Cold, a Fall, and a Bear Attack
The Revenant is a visual spectacle packed with emotions that makes you want to be a part of the cast to rip Tom Hardy’s character, Fitzgerald, apart. Finally, after several snubs and a mirage of nominations, Leonardo finally gets an Academy Award for his performance.
This article was produced and syndicated by Wealth of Geeks.
Boloere Seibidor, fondly called B.S. is a Nigerian based writer and poet. Her favorite topics to cover include music, especially Hip-Hop, film, lifestyle, and fashion. She’s been published by Feral Journal, Fantasy Magazine, The Temz Review, and most notably, Wealth of Geeks. She enjoys romantic dinners, movie nights, and touring new sites. When she’s not writing, she’s delving back in time to the underground world of Hip-Hop, watching TikTok, or visiting the cinema.
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