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Six definitive films: The ultimate beginner's guide to Leonardo DiCaprio

Leonardo DiCaprio is a star who needs no introduction, known for his fantastic collaborations with some of the best filmmakers working in the world today. Over the course of his illustrious career, DiCaprio experienced a meteoric rise which saw him win almost every major accolade, except the Best Actor Oscar, which he finally nabbed in 2016.

“Life can get pretty monotonous,” DiCaprio once said. “Acting is like living multiple lives. When you make a movie, you go off to different places, live different cultures, investigate somebody else’s reality, and you try to manifest that to the best of your ability. It is incredibly eye-opening. That’s why I love acting. There’s nothing as transformative as what a film, a documentary, can do to get people to care about something else besides their own lives.”

DiCaprio is also an activist fighting against climate change, using his platform to spread awareness about the dangers of global warming. During his acceptance speech at the Oscars, he reminded everyone watching that there were more important things than onanistic award shows: “Climate change is real, it is happening right now. It is the most urgent threat facing our entire species, and we need to work collectively together and stop procrastinating.”

As a tribute to one of the greatest actors of his generation, here is a collection of some of the definitive works from the celebrated filmography of Leonardo DiCaprio.

Six definitive films starring Leonardo DiCaprio:

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

This memorable coming-of-age drama was one of DiCaprio’s breakthrough performances andannounced his competence as an actor to the world. Starring opposite Robert De Niro who played his abusive stepfather, DiCaprio beautifully captures the emotional turbulences of a young boy in a problematic household.

The actor recalled: “In preparation for This Boy’s Life I gave myself a weird at-home tutorial on cinema history. At 15 years old, I said, OK, I have this one ticket and I know this is my opportunity. And I’m going to lock myself away for months at a time and just watch VHS tapes obsessively.”

Titanic (James Cameron, 1997)

One of DiCaprio’s most popular works, James Cameron’s 1997 romantic epic Titanic is an ambitious commentary about class warfare. It features DiCaprio as a struggling artist who manages to get onto the monumental technological marvel that was the Titanic only to fall in love with a rebellious aristocrat (Kate Winslet).

Cameron reflected, “I had dark hours on Titanic as dire as Piranha II. We missed the iceberg by that much. But I’m at my best when I’m neck-deep in ice water trying to work out how we’re going to keep the lights turned on when the water hits the bulbs.”

Adding, “Titanic was conceived as a love story. If I could have done it without one effect, I would’ve been happy. It was definitely a goal to integrate a very personal, emotional style with spectacle – and try to make that not be chocolate syrup on a cheeseburger, you know. The cathartic experience is what made the film work.”

Catch Me If You Can (Steven Spielberg, 2002)

Partially based on the biography of famous criminal Frank Abagnale, DiCaprio steals the show as the charming con artist who can talk anyone into doing anything. He is chased by an obsessive FBI agent (played by Tom Hanks) who wants to catch Frank by any means necessary.

DiCaprio described Tom Hanks as “the best, a consummate professional. Tom is very much a role model for me because he is able to just refine what he does. He has such a passion and exuberance for the work. I don’t want to get cynical about what I do; I don’t ever want to lose that spirit. So he was a great example about how to retain all that even when you’re at the upper echelons of this business.”

The Wolf of Wall Street (Martin Scorsese, 2013)

This is the role that DiCaprio should have received an Oscar for and the snub that must have hurt him the most. Martin Scorsese’s modern meditation on the obscene financial manipulations of Wall Street is a striking look at the operations of the world’s wealthy and DiCaprio fits right into that world.

The actor commented: “It’s incredibly entertaining. The entire film is insane; it’s hedonism at its finest. I mean, it’s — I really came into this film with the attitude of doing ‘Roman emperor right before the fall of the empire.’ I mean, I looked at these people as people that had no real sensibility for anything around them except their own indulgences.”

The Revenant (Alejandro González Iñárritu, 2015)

DiCaprio finally managed to get a firm grip on the elusive Best Actor accolade at the Academy Awards with this 2015 revisionist western. Iñárritu’s film stars DiCaprio as Hugh Glass, a famous frontiersman who has to confront his own mortality in the heterotopic space that is the wilderness.

“It was physically gruelling for everybody,” DiCaprio recalled while talking about the incredibly demanding production process of The Revenant which ultimately won him the Oscar. “We had to have this massive crew go to far-off locations and move around all over the high altitudes, from Calgary to Vancouver.”

Once Upon a Time in Hollywood (Quentin Tarantino, 2019)

Quentin Tarantino’s latest project was a fantastic opportunity for DiCaprio which let him team up with another one of his illustrious contemporaries – Brad Pitt. DiCaprio plays the role of Rick Dalton, a fading actor who has a strange relationship with his charming stunt double Cliff Booth (Pitt).

DiCaprio revealed: “What was very interesting about working with Brad was this strange inherent comfort and ease that we really both clicked into day one. It didn’t need a lot of prep work. We talked about the script, and we instinctively knew that dynamic and relationship, and who these guys were to one another. We both have been in those situations and have had and have those relationships on set.”