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10 Best Movies With Young Leonardo DiCaprio

Finding a list of the best movies with young Leonardo Dicaprio was surprisingly hard. There are lists of his best movies, but none that specifically focus on his younger years. So I’ve done something about it by creating this awesome list of movies with young Leo.

#10. Celebrity (1998)

Celebrity (1998)

Celebrity is a 1998 American comedy-drama film that stars an ensemble cast and was written and directed by Woody Allen. The screenplay depicts a couple’s diverging trajectories following their divorce.

Lee (Kenneth Branaghprofessional )’s and personal life are at a standstill, so he divorces his shy wife, Robin (Judy Davis), and starts a new position as an entertainment journalist.

His missions take him to the swankiest parts of Manhattan, but as he bounces from one opulent party to the next and engages in a string of hollow romances, he begins to question the value of his employment.

Meanwhile, Tony (Joe Mantegna), a prominent TV producer, falls in love with Robin and exposes her to the world of celebrity.

The film earned mixed reviews from reviewers and was a box office failure.

#9. The Quick and the Dead (1995)

The Quick and the Dead (1995)

Sharon Stone, Gene Hackman, Russell Crowe, and Leonardo DiCaprio star in the 1995 American Revisionist Western The Quick and the Dead, directed by Sam Raimi and starring Sharon Stone, Gene Hackman, Russell Crowe, and Leonardo DiCaprio.

Ellen (Sharon Stone), a mysterious woman gunslinger, saunters into the town of Redemption in search of vengeance. Herod (Gene Hackman), the town’s sadistic mayor, assassinated her father while organizing a quick-draw tournament.

The lady enters, joining a cast of criminals and miscreants in a vicious competition in which the loser is killed. “The Kid” (Leonardo DiCaprio), an upstart with his own score to settle with Herod, is one of the contenders.

Even though DiCaprio was not the main lead in this movie, but he did a great work on it. Which made us choosing it on this list.

#8. Marvin’s Room (1996)

Marvin's Room (1996)

Directed by Jerry Zaks, Marvin’s Room,  is a 1996 American drama film. The script was created by John Guare and was based on Scott McPherson’s play of the same name, which he died in 1992.

Before his death, McPherson had finished a screenplay for a film adaptation; but, when the picture was finally released years later, Guare was hired to revise it.

Marvin’s Room turned out to be a fantastic film, aided by excellent performances by Meryl Streep, Diane Keaton, Leonardo DiCaprio, and Robert De Niro.

Based on 50 reviews and an average rating of 6.7/10, the film has an 84 percent approval rating on review aggregate Rotten Tomatoes. Based on 20 critical reviews, Metacritic gave the picture a 68 out of 100 rating.

#7. The Beach (2000)

The Beach (2000)

The Beach is a 2000 adventure drama film directed by Danny Boyle and based on Alex Garland’s 1996 novel of the same name, which John Hodge adapted for the screen. Leonardo DiCaprio, Tilda Swinton, Virginie Ledoyen, Guillaume Canet, and Robert Carlyle feature in the film. It was shot on Ko Phi Phi Le, a Thai island.

Critics speculated that DiCaprio’s post-Titanic celebrity may have aided the film’s financial success, as it was released less than three years after the James Cameron blockbuster.

The film was a moderate box office hit, but reviewers gave it mediocre to poor reviews. The Golden Raspberry Award for Worst Actor was nominated for DiCaprio.

#6. Romeo + Juliet (1996)

Romeo + Juliet (1996)


Romeo + Juliet was the true start of Leonardo DiCaprio’s career as a movie star, and it served as a springboard for the 21-year-old actor.

For the MTV age, director Baz Luhrmann sought to follow up his critically acclaimed Strictly Ballroom with an ambitious “modernized” depiction of William Shakespeare’s famous ode to young love, or at least the infatuation that propels it.

DiCaprio was so enthusiastic about the film that he paid his own fees to attend its workshop, and he went on to become the guiding star around whom the rest of the cast was formed (thus out Natalie Portman and in, the slightly older, Claire Danes at 16).

Indeed, the connection between DiCaprio and Danes is so strong that it lights up the famous swimming pool they glide across like a Rodin masterpiece. That’s even more impressive given that the two didn’t get along behind the scenes.

The film was released on November 1, 1996, by 20th Century Fox to commercial success, and was met with generally positive reviews.

#5. The Man in the Iron Mask (1998)

The Man in the Iron Mask (1998)

The Man in the Iron Mask is a 1998 action spy thriller film directed by Randall Wallace and starring Leonardo DiCaprio, Jeremy Irons, John Malkovich and Gérard Depardieu.

The film’s storyline is loosely based on the novel The Vicomte de Bragelonne by Alexandre Dumas with certain plot elements from the sequel novel The Man in the Iron Mask .

Leonardo DiCaprio’s portrayal of the lead character in The Man in the Iron Mask (1998) is the epitome of cinema at its best.

Not only are there brilliant period costumes and make-up, but an intricate plotline, inspiring score, and captivating characters combine to create a movie experience far beyond what one would expect from a Hollywood blockbuster.

#4. The Basketball Diaries (1995)

The Basketball Diaries (1995)

The Basketball Diaries was controversial upon its release because it focused on a simple dreamer… of school shootings—an uncomfortable premise that has only grown more problematic over time—but it still features an early strong performance from DiCaprio, who lives and breathes impotent teenage anguish and confusion so well that we can forgive the fact that he does not look like a basketball star. Jim Carroll, played by Leonardo DiCaprio, is a scumbag from a horrible family who escapes through basketball and eventually street drugs in exchange for various types of back alley one-on-ones.

Carroll, who is arguably a victim of an ambiguous educational system, falls prey to drug addiction and misanthropy. Basketball Diaries continued DiCaprio’s brief tenure as the go-to disturbed adolescent, as there was always something imprisoned and frightening behind those piercing blue peepers, despite the fact that he was still a few years removed from his heart throb days. Whatever you think of the film’s subject matter or execution, DiCaprio was already making an impact at the age of 20.

#3. This Boy’s Life (1993)

This Boy's Life (1993)

Based on the bestselling memoir of the same name, This Boy’s Life is a powerful and tragic film that follows the story of young Tobias Wolff as he struggles to find his identity and survive growing up in a dysfunctional family.

The film stars Leonardo DiCaprio as Tobias Wolff and Robert De Niro as his stepfather Dwight Hansen, with Ellen Barkin, Willem Dafoe, and John Getz in supporting roles.

When I watched This Boy’s Life for the first time, I was entranced. DiCaprio’s performance alone is worth watching the movie 100 times over. He did a bang-up job of acting as a young boy who was neglected and abused by his mother (Laura Dern).

#2. What’s Eating Gilbert Grape (1993)

What's Eating Gilbert Grape (1993)

What’s Eating Gilbert Grape (1993) is a movie that follows a young guy named Gilbert, Gilbert Grape (Johnny Depp), who doesn’t speak or say much. He also lives with his parents and his brother.

His little brother, Arnie (Leonardo DiCaprio), is mentally handicapped, but very sweet and not really in the “real world” so to speak. He spends all of his time taking care of his little brother who can’t move on without his brother to take care of him.

This film stars Johnny Depp who played a namesake character earlier in the same year in Edward Scissorhands (1990).  He plays a similar character here as well, being someone who is unable to communicate through normal means but rather chooses to communicate through actions than conversation.

The film was well-received, with DiCaprio’s performance garnering universal acclaim. The 19-year-old received his first nominations for the Academy Award and Golden Globe Award for Best Actor in a Supporting Role, becoming the seventh-youngest Best Supporting Actor nominee for the former.

In fact, there are very few lines said by anybody when it comes to dialogue throughout the film, but that suits well for a film like this.

#1. Titanic (1997)

Titanic (1997)

Titanic is a movie about Jack and Rose, played by Leonardo DiCaprio and Kate Winslet. It’s about their love for each other during the historical tragedy of Titanic, in 1912.

Even for young heartthrob Leo, coming off a string of outstanding performances, starring in the biggest movie of all time wasn’t easy in 1997.

DiCaprio and co-star Kate Winslet drove this disaster epic towards box office and Oscar history, becoming the highest-grossing film of all time and earning 11 Academy Awards, including best picture. DiCaprio possessed charisma as fictional traveler Jack Dawson, and the film elevated him to permanent global superstardom.

Upon its release on December 19, 1997, Titanic achieved significant critical and commercial success, and later received numerous accolades. 

It’s one of those movies that holds up to multiple viewings because every time I watch it I notice a new hilarious piece of business, or realize a clever use of soundtrack.

If you haven’t seen it in a while, consider watching it on a date. It’s always more fun to be watching with someone you enjoy spending time with. Maybe even someone who doesn’t know how the movie ends.

Do you agree with our list? If you have any suggestions or comments please shoot them down in the comments below. 

A full-time movie/Series critic and editor of with one goal: To help you find great content.


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