If you’re a movie buff, there’s no one who doesn’t know Leonardo DiCaprio. He was selected by Robert De Niro for the lead role in The Boy’s Life (1993). The actor has appeared in a number since of films since then and continues to attract fans.
Leonardo DiCaprio has enthralled fans with a variety of roles; from a pretty young man to a fallen middle-aged star. The oscar-winning actor never seems to disappoint us with his performances. The actor is like fine wine, he becomes better with age. His recent performance in ‘The Revenant’ even led him to win an Academy award.
If you’re also one his die-hard fans, then you’re at the right place.
In this article, we look back at DiCaprio’s trajectory in films handpicked by the Moodmymood editorial team. Take a lost at all these movie recommendations. You may even find a great DiCaprio movie that you may not have seen in this list.
Let’s get started.
- 20. “The Boy’s Life” (1993)
- 19. “What’s Eating Gilbert Grape” (1993)
- 18. “Romeo + Juliet” (1996)
- 17. “Titanic” (1997)
- 16. “The Man in the Iron Mask” (1998)
- 15. “Gangs of New York” (2002)
- 14. “Catch Me If You Can” (2002)
- 13. “The Aviator” (2004)
- 12. “The Departed” (2006)
- 11. “Blood Diamond” (2006)
- 10. “Body of Lies” (2008)
- 9. “Revolutionary Road” (2008)
- 8. “Shutter Island” (2010)
- 7. “Inception” (2010)
- 6. “J. Edgar” (2011)
- 5. “Django the Unchained” (2012)
- 4. “The Great Gatsby” (2013)
- 3. “The Wolf of Wall Street” (2013)
- 2. “The Revenant” (2015)
- 1. “Once Upon a Time in Hollywood” (2019)
20. “The Boy’s Life” (1993)
The film adaptation is an autobiographical novel by author Tobias Wolfe, set in 1957 America. The story-line follows a mother and her son as they move from one residence to another.
DiCaprio plays the role of the son, Tommy. One day, his mother’s violent boyfriend chases Tom, making him run away. He moves from Salt Lake City to Seattle, where he is conspicuously misbehaving, perhaps because of his family background.
Eventually, her mother remarries Dwight, played by Robert De Niro. Tommy rebels against Dwight, who appears to be a gentleman but is actually violent. Eventually, of his own volition, he takes his mother’s hand and moves out. The highlight of the film is the performance of DiCaprio, who was 19 years old at the time and still in his infancy.
19. “What’s Eating Gilbert Grape” (1993)
Leonardo DiCaprio was 19 years old at the time of this film. He was nominated for both an Academy Award and a Golden Globe for Best Supporting Actor for the film. Although he narrowly missed out on winning the award, he received very high praise for his acting skills.
Trapped in an old house in his hometown, Gilbert Grape (Johnny Depp) spends his days working in a grocery store while caring for the mentally handicapped Ernie (DiCaprio). One day, Gilbert meets and falls in love with Becky, a girl traveling in a camper. Later on, Gilbert starts to get urges to run away from the town with her.
18. “Romeo + Juliet” (1996)
The film Romeo & Juliet is directed by Baz Luhrmann. Leonardo DiCaprio played the role of Romeo. The film continues the setting of “Romeo and Juliet”, but shifts the setting to the present day and depicts a war between the mafia.
DiCaprio won the Silver Bear (Best Actor) at the Berlin International Film Festival for this film. More than any other film, this one is filled with Leo’s princely charm.
17. “Titanic” (1997)
This film is based on the real-life sinking of a luxury cruise ship. It’s a masterpiece that won 11 Academy Awards.
It was the highest-grossing film in the world at the time and remained so for a long time until “Avatar” overtook it. DiCaprio has been nominated for a Golden Globe Award for Best Actor in a Leading Role in a Drama.
Poor young Jack, played by DiCaprio, falls in love with Rose, a rich woman. But their love leads to a tragic end when the Titanic sinks.
By appearing in the film, DiCaprio has stepped up to become a global star. In Japan, he has developed a passionate fan base and is nicknamed “Leo-sama”.
16. “The Man in the Iron Mask” (1998)
This movie is inspired from the third part of the “Tales of D’Artagnan” series, “The Viscount of Brajulonne” by French literary great Alexandre Dumas Père. Based on the legend of Louis XIV’s iron mask, this work depicts the activities of D’Artagnan who became a musketeer captain and the three musketeers on the verge of old age.
Leonardo DiCaprio plays two very different characters, Louis XIV and his twin brother Philip. Philip, imprisoned in an iron mask, is replaced by Louis under the guidance of D’Artagnan and the Three Musketeers in a thrilling double role.
The young and beautiful DiCaprio, who got his big break in Japan with “Titanic” (1997), is a fascinating character.
15. “Gangs of New York” (2002)
Martin Scorsese and Leonardo DiCaprio teamed up for the first time in this memorable film. The two are so well-bonded that DiCaprio gave director Scorsese a nod in his greeting when he won the Academy Award for Best Actor in a Leading Role for The Revenant: The Risen One.
The film is set in mid-19th century New York City, where gangs are fighting over turf, and it’s an epic revenge story about a young man, Amsterdam (Leonardo DiCaprio), whose father was murdered 15 years ago, and his struggle to defeat his father’s avenger, gang boss Bill.
And the love scene with Cameron Diaz is not to be missed!
14. “Catch Me If You Can” (2002)
In this film, DiCaprio played the real-life boy genius con man Frank W. Abagnair, Jr. Tom Hanks plays the veteran FBI agent who is on the hunt for him. In addition to a gorgeous double starring role, the director is virtuoso Steven Spielberg.
DiCaprio’s light-hearted performance is charming, and he uses his underhanded face as a con artist and the occasional real face he shows well.
13. “The Aviator” (2004)
Director Martin Scorsese and Leonardo DiCaprio teamed up for the second time in this film about the eventful half-life of real-life millionaire Howard Hughes.
Hughes aims to be “the world’s best golfer, the world’s best pilot, and the world’s richest man” with the assets he inherited from his parents. Even though he succeeds in his business, he is plagued by obsession. Eventually, he commits eccentricities such as locking himself in his room completely naked without washing his face or shaving his beard.
DiCaprio performed the eccentric Hughes in a literal naked body blowout. The supporting cast is gorgeous, with Alec Baldwin as the competing entrepreneur and Cate Blanchett and Cate Beckinsale as the mistress.
12. “The Departed” (2006)
This is a remake of the Hong Kong film Infernal Affairs. The film won an Academy Award for Best Picture. It was the first time a remake of a non-American film had been selected for the Academy Award for Best Picture.
A man, played by DiCaprio, infiltrates a criminal organization as an agent, and a gangster, played by Matt Damon, infiltrates the police force and bites each other in the face.
Jack Nicholson plays the head of a criminal organization that is targeted by the police. Each member of the gorgeous cast gives a unique performance. The sense of emptiness at the end of the film made a big splash.
11. “Blood Diamond” (2006)
Set against the backdrop of Sierra Leone’s civil war, the film is a socially sliced account of the death struggle over a large diamond. This is a fact-based story about African boy soldiers, persecution, murder, slavery, and brainwashing, which are still prevalent today. It’s a thought-provoking film about the ugly and frightening greed of humans.
Completely out of his beauty-boy image, DiCaprio gives a bonafide performance as a conflict diamond broker.
Director Edward Zwick has repeatedly taken on the darker side of history in “Glory,” “The Last Samurai” and “Defiance”.
10. “Body of Lies” (2008)
It’s an action thriller set in the Middle East with breathtaking battles.
Leonardo DiCaprio plays Ferris, a CIA operative who travels around the world hunting down Al Saleem, the leader of an international terrorist organization, covered in scars.
It co-stars Russell Crowe (Gladiator). The role of the CIA Middle East Chief is typical of a bad elite who gives instructions from a safe place such as CIA headquarters or home in the United States, ignoring the situation in the field far away.
The director is Ridley Scott, known for his work on Blade Runner and Gladiator.
9. “Revolutionary Road” (2008)
Leonardo DiCaprio reunites with Kate Winslet from “Titanic” for the first time in 11 years in this film.
In 1950’s America, Frank (played by DiCaprio) and April (played by Kate Winslet) are blessed with children and live happily ever after.
But my wife morbidly believes that where she is now is not the real place, that she has a more special way of life. Their relationship gradually collapses, while her husband lives a life of arrogant happiness in the real world.
It is a work that takes the negative elements of the family to the extreme. DiCaprio was mentally exhausted after filming a scene of a violent quarrel between the couple. He said he needed two months of rest before his next film.
8. “Shutter Island” (2010)
Director Martin Scorsese and Leonardo DiCaprio teamed up for the fourth time to make this film. DiCaprio plays a U.S. marshal in this mystery film that investigates the mystery of a disappearance that occurs in a mental institution on an isolated island.
The portrayal, reminiscent of 1950s film noir, is dim throughout, and the sense of dread is heightened as the protagonist gets closer to the truth. The storyline is intricately intertwined with the foreshadowing and the twist at the end is a masterpiece.
Watch out for DiCaprio’s performance, which conveys a sense of urgency and tension.
7. “Inception” (2010)
This is a sci-fi action film from director Christopher Nolan, who is known for his philosophical depth of filmmaking about time, memory and identity.
Dom Cobb, played by Leonardo DiCaprio, is a spy on a special mission to infiltrate the dreams of corporate dignitaries and steal their ideas. Ken Watanabe plays a man who offers him a job and together they enter into a dream.
The idea of entering a dream is not only entertaining, but the intricate story structure and stunning visuals are well worth a look.
Director Christopher Nolan, who insists on shooting on film, minimizes the use of CG to create powerful effects.
6. “J. Edgar” (2011)
John Edgar Hoover, who was the first director of the FBI. The film is a biographical portrait of Hoover’s life, which explores his personal life hidden in his brilliant exploits, but also hides his gayness. The megaphone is directed by Clint Eastwood, who is also a renowned actor.
DiCaprio plays the lead role of Hoover in this film, and it was a casting he himself was eagerly awaiting. Clyde Tolson, an agent who had a homosexual relationship with Hoover, is played by Armie Hammer.
5. “Django the Unchained” (2012)
A western film directed by Quentin Tarantino. It is the story of Django, a black slave, who is rescued by a German bounty hunter and tries to save his estranged wife. Leonardo DiCaprio plays a plantation owner who exploits black slaves.
It’s a long film, about 2 hours and 40 minutes long, but the story moves along at a good pace and doesn’t feel long. In addition to the poignant action, the hilarious dialogue scenes are a major attraction.
This is the first time DiCaprio has appeared in a Tarantino film. In addition, he became a big topic of conversation when he played a full-fledged villain who dispelled the seriousness of his previous image.
4. “The Great Gatsby” (2013)
In the 1920s, America was booming before the Great Depression. The film is based on F. Scott Fitzgerald’s novel, which depicts a frenzied time when dirty jazz was in vogue and people ignored Prohibition and floated to big parties.
The shaking and darkness of the human heart hidden behind the glittering exterior. On top of that, DiCaprio’s ugly obsession and lust for wealth is portrayed with a mixture of madness and innocence. It’s a different kind of shady rich guy than Howard Hughes’ role in The Aviator.
The colors and music also accurately express the atmosphere of the times. Incidentally, Prada for women’s dresses, Tiffany & Co. for women’s jewelry, and Brooks Brothers for men’s clothing created a buzz.
3. “The Wolf of Wall Street” (2013)
Scorsese and DiCaprio team up for the fifth time in this comedic biography of Jordan Belfort, a highly skilled stockbroker.
It is a shocking true story that exposes the ugly side of human beings who do whatever they want with money, drugs and women. DiCaprio’s versatile facial expressions and acting skills are fully brought out in this film. The character who keeps on tricking people into making a lot of money has something in common with “Catch Me If You Can”.
2. “The Revenant” (2015)
The film marks the return of Leonardo DiCaprio, who declared a break from acting in 2013. Hugh Glass, a skilled hunter played by Leonardo DiCaprio, is attacked and critically injured by a bear during a hunt. Marooned by the same team members, Hugh recovers and goes on a journey of revenge….
DiCaprio won the Academy Award for Best Actor in a Leading Role for this film, his fifth Academy Award nomination and his first win.
Directed by Alejandro González Iñárritu, who won an Academy Award for Birdman or the Unexpected Miracle of Ignorance. Co-starring in the film is Tom Hardy, who DiCaprio has offered to star in.
1. “Once Upon a Time in Hollywood” (2019)
Directed by Quentin Tarantino and co-starring Leonardo DiCaprio and Brad Pitt, this is a gorgeous film.
The setting is Los Angeles in 1969. This is the story of a disgraced actor and his partner who get caught up in the murder of an actress caused by a cult group. DiCaprio plays Rick Dalton, an actor who once took the Western world by storm but is now a fallen actor.
It’s a film full of Tarantino’s love of turbulent 1960s and 1970s cinema and popular culture. It’s a must-see not only for DiCaprio fans, but for everyone who loves the film.
In this article we have reviewed all the movies that Leonardo DiCaprio has starred in, which always show a new face with each film.
DiCaprio entertains fans by playing a variety of roles and always amazes us with his exceptional talents. Why don’t you take this opportunity to look back on his trajectory?