Best Leonardo DiCaprio Movies

Some actors in Hollywood are the official trademark of the industry, and Leonardo DiCaprio is easily one of them. He is arguably one of the finest actors from his generation, due to his versatility and range. The Academy Award winner has maintained a formidable presence in Hollywood with a nearly three-decades-long career.

Leonardo DiCaprio Movies: Every Cinephile’s Must-Watch 

To celebrate the actor, here are the best Leonardo DiCaprio Movies of all time.

Titanic (1997)

• Release Date: December 19, 1997
• Box Office: $2.26 billion (worldwide)
• Directed by: James Cameron
• Role: Jack Dawson

Titanic is the second highest-grossing movie of all time and the second film to win 11 Oscars, including Best Picture. Directed by James Cameron, Titanic was the ultimate breakthrough that turned Leonardo into the global sensation he is today.

If you’ve watched Titanic recently, one of the big takeaways might have been, “Good lord, look how young Leo and Kate are.” Since both have blossomed into significant actors, it’s easy to forget that they were really just kids (Leo was just 23) when they made this movie. His ripe age also allowed him to deliver the performance his role required.

Playing Jack Dawson, a poor yet passionate artist who wins a ticket aboard the ill-fated RMS Titanic, Leo infused charm, cockiness and optimism into his role. His chemistry with Kate Winslet remains legendary even to this day. When his character dies in Titanic, a world of impressionable filmgoers was his for life.

Unfortunately, his charm and obvious good looks didn’t impress the Academy enough to include him in the best actor lineup. Still, he would eventually get his due more than 20 years later.

With an initial worldwide gross of over $1.84 billion, Titanic was the first film to reach the billion-dollar mark. It was the first film to surpass the $1 billion mark and held the record for the highest-grossing film for 12 years.

The Wolf of Wall Street (2013)

• Release Date: December 25, 2013
• Box Office: $407 million (worldwide)
• Directed by: Martin Scorsese
• Role: Jordan Belfort

In Martin Scorsese’s scandalous, cocaine-fueled biopic of stockbroker Jordan Belfort, Leo goes full throttle. DiCaprio has often partnered with filmmaking icon Martin Scorsese, but his comedic take on Jordan Belfort’s time of wealth, corruption and drug use is one of the actor’s most jaw-dropping.

The film is unhinged and unfiltered, just how it should have been. It’s a satirical comedy about a real-life douchebag who ends up in a good place in the end, despite his gross behaviour. And let’s not forget the great discovery of DiCaprio’s performance in this movie: his total mastery of physical comedy.

From crawling on Quaaludes to delivering motivational monologues, Leo doesn’t hold back. This role was a high-wire act of indulgence, chaos, and control. He earned an Oscar nomination despite the film being released under the gun, and proved, once again, that he could carry a three-hour film with swagger without letting his mask of “the world is made for me to conquer” slide.

Inception (2010)

• Release Date: July 16, 2010
• Box Office: $836 million (worldwide)
• Directed by: Christopher Nolan
• Role: Dom Cobb

DiCaprio’s biggest hit since Titanic, Inception, is the first real event movie he’s been a part of since that James Cameron sensation. (Remarkably, Inception is also his first summer blockbuster.)

Christopher Nolan’s thriller gave DiCaprio a layered role as Dom Cobb, a thief tormented by his past. Dom Cobb isn’t a tragic figure because he lost his wife, but rather because he never came to terms with it, and DiCaprio provides the character with endless anguish that supplements the film’s stunning effects and twisty sci-fi concept.

Inception was a box office hit and became a modern sci-fi classic, largely due to DiCaprio’s emotional anchor.

The Revenant (2015)

• Release Date: December 25, 2015
• Box Office: $533 million (worldwide)
• Directed by: Alejandro G. Iñárritu
• Role: Hugh Glass

This is the film that finally won Leo his long-overdue Oscar. Playing frontiersman Hugh Glass, DiCaprio braved freezing temperatures, ate raw bison liver, and delivered a nearly wordless performance that was primal and daring.

Directed by Alejandro G. Iñárritu, The Revenant is a brutal tale of survival, in which an 1820s frontiersman endures in quick succession a Native American ambush, a bear attack, and a betrayal by one of his companions (Tom Hardy) who leaves him for dead. Leo’s commitment to the role was nothing short of legendary.

The Revenant is easily the most physical role of his career, with the actor grunting, straining, and fighting his way across unforgiving terrain to make it back to civilisation. He finally proved to people that he can play rugged characters just as well as he can play the others.

Catch Me If You Can (2002)

• Release Date: December 25, 2002
• Box Office: $352 million (worldwide)
• Directed by: Steven Spielberg
  
• Role: Frank Abagnale

In this breezy Steven Spielberg crime caper, Leo plays Frank Abagnale Jr., a teenage con artist who impersonates doctors, lawyers, and pilots.

His youthful charm, slyness, and emotional vulnerability make you root for him even as he commits fraud after fraud. DiCaprio’s dynamic with Tom Hanks (the FBI agent chasing him) is pure gold. This film marked a turning point. After it, Leo wasn’t just a teen idol anymore; he was a serious actor with incredible range.

Unfortunately, only the Golden Globes nominated him for Best Actor (drama) and not the Oscars.

Shutter Island (2010)

• Release Date: February 19, 2010
• Box Office: $295 million (worldwide)
• Directed by: Martin Scorsese
  
• Role: Edward “Teddy” Daniels / Andrew Laeddis

Among the most divisive films in DiCaprio’s career, Shutter Island is an elegantly unnerving portrait of a man slowly losing his sanity.

In this psychological thriller, Leo plays U.S. Marshal Teddy Daniels, investigating a missing patient on a mysterious island asylum. As Teddy Daniels, who thinks he’s on the hunt for a missing inmate on an island for the criminally insane, DiCaprio has to play his character’s psychosis straight, all the while hinting at the horrible truth: He’s actually a patient himself, unable to accept the fact that his wife (Michelle Williams) killed their children.

As the plot twists and Teddy’s own sanity unravels, DiCaprio walks a tightrope between toughness and psychological torment. The film’s haunting final line (“Which would be worse: to live as a monster or die as a good man?”) is a testament to his performance.

Once Upon a Time in Hollywood (2019)

• Release Date: July 26, 2019
• Box Office: $377 million (worldwide)
• Directed by: Quentin Tarantino
  
• Role: Rick Dalton

Quentin Tarantino’s nostalgic Hollywood fairytale gave DiCaprio one of his most complex characters. Rick Dalton, a fading actor dealing with insecurity, failure and the changing tides of fame. Leo’s performance is both hilarious and heartbreaking.

Call it the perfect marriage of an actor feeling like he’s at the crossroads of his career, or maybe it’s his infectiously funny and charming performance, but his Rick Dalton in Tarantino’s look at classic Los Angeles is possibly his best work (yet).

Leonardo DiCaprio: The Actor We Will Remember

Several of Leonardo DiCaprio’s best performances subvert or tweak his good looks, encouraging us to see the uglier, messier undercurrents beneath his characters’ appealing surface.

He’s not just an actor who picks good scripts; he elevates every story he’s in. In the future, new generations will watch Leonardo DiCaprio’s movies and will envy the actor our generation was privileged to have.