#20. Catch Me If You Can
One of the most remembered movies that DiCaprio was part of is Catch If You Can alongside Tom Hanks, Christopher Walken, Martin Sheen and Nathalie Baye. Also, the film was directed by the great Steven Spielberg.
The film included topics that love DiCaprio: a true story and stories that are were in the past. Also, to learn more about his character Leo had the help of Frank Abagnale Jr.! Nowadays, the film is considered a classic in the industry.
#19. The Great Gatsby
The Great Gatsby follows the story-life of the multimillionaire Jay Gatsby portrayed by Leo and Gatsby’s friend Nick Carraway portrayed by Tobey Maguire. Perhaps it was not the favorite film of Leo, but he showed great professionalism.
Directed by Baz Luhrmann, the film became very successful in 2017 and won two Academy Awards for Best Production and Best Costume Design. Leo had the chance to act with his best friend in real life, Maguire. Both of them have been together in the industry since Growing Pains and they always help each other.
#18. Django Unchained
Maybe Leo didn’t have a leading role in Quentin Tarantino’s film Django Unchained but the character Calvin Candie is still remembered for his fans. Also, Leo won more than $1 million dollars for that role and became very close to the director that called him for a role in one of his movies years later.
Django has become one of the most successful movies of Tarantino and it had the participation of many talented actors like Samuel L. Jackson, Jamie Foxx and Christoph Waltz.
#17. J. Edgard
Another biopic that Leo was part of was Clint Eastwood’s J.Edgard in 2011. Alongside Armie Hammer, Naomi Watts, Josh Lucas and Judi Dench, the film was a box office hit becoming in every part of the world.
According to some rumors, the relationship between Leo and Clint was not the best and that why Leo had worked again him with the director. We can’t tell if that is true but Leo has often worked again with directors he had worked before.
#16. Inception
We can’t no mention the film Inception starred Leo, Joseph Gordon-Levitt, Marion Cotillard, Ellen Page and Tom Hardy. The psychological thriller was directed by the great Christopher Nolan and became a huge success after it released.
The film won four Academy Awards and had 10 nominations that year. Nowadays, it’s considered one of the best movies of Leo of all time. Also, Leo had promised to work again with the director and we can’t wait to see them together again!
#15. Blood Diamond
The fans of Leo weren’t used to see their favorite actor acting in bad guys role but he did a great job in 2006 at Blood Diamond, directed by Edward Zwick and starred Jennifer Connelly and Djimon Hounsou. Also, Leo’s character proved at that time that he was able to do any role.
Although the big star of the film was Hounsou, Leo and he made a great couple. For the film, Leo won more than $20 million. Nothing bad for a movie!
#14. The Departed
There was a time in Leo’s life that he worked in every film that Martin Scorsese made like The Departed starred Jack Nicholson, Matt Damon and Mark Wahlberg. For the film, Leo won more than $20 million and Scorsese received his first — and only — Academy Award.
It seems that Leo likes to work with his pals as he had worked with Damon in several films. Also, Leo had to compete with Robert De Niro for the role as at that time De Niro was Scorcese’s top star.
#13. The Aviator
Another film of Martin Scorsese that Leo was part of is The Aviator in 2004. Another biopic, Leo enjoyed so much portraying the life of the aviation pioneer and director of Hell’s Angels. The film received eleven nominations for Academy Awards but won only five of them.
Alongside Cate Blanchet, Kate Beckinsale, Jude Law and Alec Baldwin, Leo showed all his professionalism and talent in the film that was a box office hit in the world.
#12. Gangs Of New York
If you put together actors like Leo, Daniel Day-Lewis and Cameron Diaz, the film will probably become a success. Some critics said the movie was not good but we think it has very good performances and some interesting twist plots.
Day-Lewis is in the main role of the film but Leo’s character is still remembered for his fans. Not to mention that the film was under the direction of Scorcese. Gangs Of New York was nominated for ten Oscars but in the end, it didn’t win any of them.
#11. The Beach
For Leo’s fans, his role in the film The Beach in 200o was his start in an acting career in Hollywood, especially because is the most successful film of Leo after the release of Titanic. Critics believed this was Leo’s Titanic follow-up.
The film was directed by Danny Boyle and received many bad reviews although it was a moderate box office success. Some people found the plot a little boring. Leo received $50 million for the movie, nothing bad for a movie with those reviews.
#10. The Basketball Diaries
Young Leo portrayed Jim Carroll, a promising high school basketball player and writer that became addicted to heroin in The Basketball Diaries. Directed by Scott Kalvert and alongside Bruno Kirby, Lorraine Bracco and Mark Wahlberg, the film grossed $2.4 million around the world.
Believe it or not, Leo and Wahlberg didn’t get along and Kalvert had to interfere as the two actors were supposed to be best friends on screen. Kalvert’s words worked for the two promising actors. Nowadays, both actors have a mutual admiration for each other.
#9. Titanic
Our list would be incomplete without Titanic. Nowadays we can consider James Cameron’s film the most successful film of Leo’s acting career for many reasons. First, Titanic grossed more than $600 million over the world and Leo met actress Kate Winslet that together became the most beautiful couple of Hollywood of all time.
Nowadays, the film is also the most successful and famous movie in Cameron’s career and won eleven Academy Awards in 1998.
#8. The Quick And The Dead
Leo was a very young and promising actor in Hollywood when he was part of the Western The Quick And The Dead alongside Sharon Stone, Gene Hackman, Russel Crowe and Kevin Conway. Believe it or not, there was one actress that saw Leo’s talent before everyone else.
According to the rumors, Stone paid for Leo’s salary because she believed in the young actor. Also, it’s said that Robert De Niro choose Leo for a role in This Boy’s Life. Definitely Leo was going to become a star in Hollywood.
#7. Celebrity
Leo was at the top of his career just after the release of Titanic and everyone wanted to work with him. The director Woody Allen had the chance to work with him in his comedy-drama Celebrity. Many people thought it was going to be a huge success but it received many bad reviews and was a commercial disappointment.
People said that Leo’s appearance in the film —that was only 10 minutes and 20 seconds—should be longer. For the film, Leo received $1 million, which means he earned $100.000 per minute!
#6. Once Upon A Time In Hollywood
Definitely the latest role of Leo in Tarantino’s film Once Upon A Time In Hollywood is one of his most memorable roles. Leo portrayed Rick Dalton, a Western actor that is no longer famous and his career is falling apart. Alongside Brad Pitt and Margot Robbie, the film is an ode to Hollywood.
Also, we see Tarantino and Leo working together again and the results were great as we hoped. It seems that Leo keeps his friends close to him.
#5. Revolutionary Road
Fans were waiting for the reunite of Kate Winslet and Leo since Titanic and they couldn’t be happier when Revolutionary Road was released in 2008. Directed by Sam Mendes, who was Winslet’s husband at that time, the film doesn’t tell a happy story but a story full of passion, sadness and love, in some way.
The performances of Leo and Winsley were great but people wanted a happy ended for the old Rose and Jack. Rumors said that Mendes felt a little insecure about Leo and Kate’s chemistry and decided to watch the scenes from a monitor in another room.
#4. Romeo + Juliet
Leo was the most beautiful and promising young actor from Hollywood in the ‘90s, especially after his nomination for his role in What’s Eating Gilbert Grape. That’s why when he became part of the adaptation of Shakespeare’s novel Romeo And Juliet, everyone loved it!
Rome + Juliet was directed by Baz Luhrmann and with Claire Danes as Juliet. Everyone loved the film and was a complete success that not even the directors could be expected. Danes said that she had a lot of chemistry with Leo and we can tell by watching the scenes between them, their performances were electric!
#3. What’s Eating Gilbert Grape
What’s Eating Gilbert Grape follows the story of Gilbert Grape, portrayed by Johnny Depp, that lives with his obese mother and his mentally-challenged young brother portrayed by Leo. For the film, Leo received his first nomination to an Academy Award for Best Supporting Role.
Leo’s performance caught up all the critics’ attention and the film received many good reviews. Also, the chemistry between Deep and Leo was incredible. Fans are still wondering why these two actors never worked together again.
#2. The Revenant
The Revenant is without a doubt one of the most important films in Leo’s acting career. First, after being in the role of Hugh Glass, Leo received his first Academy Award and fans went crazy because they were waiting for that moment to happen many years ago.
Also, Leo worked again with his friend Tom Hardy although Hardy was in the role of Leo’s enemy. Both of them showed very good chemistry on screen. Directed by Alejandro G. Iñárritu, the film was a hit box-office around the world.
#1. The Wolf Of Wall Street
Leo loves to portrayed people that actually existed in real life, like Jordan Belfort at The Wolf Of Wall Street. Directed by Martin Scorsese, nowadays it’s considered the best movie of Leo in all his career, although he didn’t win an Oscar for Best Actor.
Alongside Jonah Hill, the pair made incredible performances and also Margot Robbie rose to fame after the release of the film. People still remember the bizarre scenes of the film! In addition, Leo won more than $25 million for the movie.