The 10 Best Leonardo DiCaprio Performances That Totally Deserved An Oscar

We all fell for the young and charismatic Leo when we saw him in Titanic, the film that turned him into one of the biggest Hollywood stars of our time. However, this was definitely not his big break since, by then, he had already been nominated for an Oscar when he was only nineteen years old. Today, he’s considered one of the best actors in the industry, and even though it took the Academy a really long time to recognize him as such, he’s still managed to create a solid and successful career.

As an environmental activist and A-list actor, Leonardo DiCaprio landed four Oscar nominations before actually winning one on the fifth try with Alejandro González Iñarritu’s The Revenant (2015), though, let’s be honest, it’s not even his best work. For that reason, and celebrating his new film Once Upon a Time in… Hollywood, here are his best performances that totally deserved more than just an Oscar buzz.

10. The Departed (2006)
Dir. Martin Scorsese

Following the style of his previous classic mobster films like Taxi Driver and Goodfellas (Scorsese’s first win in the Best Picture and Director category), the movie tells the story of Billy Costigan (Dicaprio), a young cop chosen to infiltrate the Irish mob to get information about Frank Costello (Jack Nicholson). Certainly, a memorable performance in an iconic film.

9. Gangs of New York (2002)
Dir. Martin Scorsese

This was Leo’s first of five films with Martin Scorsese, and we must say it was a defining move in his career. Here he plays Amsterdam Vallon, a young man seeking to avenge the murder of his father in a gang battle in nineteenth-century Manhattan. Though the film is historically inaccurate in so many ways, the chemistry between DiCaprio and Daniel Day-Lewis was highly praised by the critics.

8. The Aviator (2004)
Dir. Martin Scorsese

https://www.youtube.com/watch?v=JPGhlevhMFU
Keeping up with the Scorsese dynamic duo, Leo went on to play Howard Hughes, the eccentric businessman, entertainment mogul, and pilot who ended up locking himself away from the world as a consequence of his severe OCD. This performance earned him his second Oscar nomination and a great reputation in the industry.

7. Catch Me If You Can (2002)
Dir. Steven Spielberg

After Titanic, Leo made some not-so-great films he probably wishes he hadn’t. Fortunately, he landed this role in Spielberg’s film as Frank Abagnale Jr., a real historical character who, before his nineteenth birthday, succeeded in millionaire cons, eventually catching the eye of the FBI, in the film an agent played by Tom Hanks. Many actually consider this to be Leo’s best performance.

6. What’s Eating Gilbert Grape (1993)
Dir. Lasse Hallström

This movie tells the story of Gilbert Grape (Johnny Depp), a young man who has to look after his family after his father’s suicide. As a coping mechanism, his mother decides to eat her life away, eventually becoming unable to move from the couch, leaving Gilbert to take care of her and his mentally disabled bother, played by a very young Leonardo. His performance was so good that it earned him his very first Oscar nomination and the admiration of many.

5. Shutter Island (2010)
Dir. Martin Scorsese

For his fourth collaboration with Scorsese, Leonardo played US Marshall Teddy Daniels, a man investigating the disappearance of a patient at The Ashecliffe Hospital for the Criminally Insane, but is he really? The movie, which has a really cool plot twist was a huge change of what both Leo and Scorsese had been doing in the past, making it a very interesting piece.

4. Django Unchained (2012)
Dir. Quentin Tarantino

This scene, do I need to say more? Though the Academy neglected Leo to nominate the also amazing Christoph Waltz, I must say this is one of his best. DiCaprio plays the ignorant but powerful Calvin Candie, one of the biggest plantation owners in the south and the man Django and Shultz have to trick to rescue the former’s wife. Not a very common role for Leonardo, but definitely a very memorable one in the Tarantino Universe.

3. Blood Diamond (2006)
Dir. Edward Zwick

Earning him his third Oscar nomination, his role as Danny Archer, an arms trafficker in Sierra Leone, is one of the most emotional ones of his career. Aside from the fact that it ends up being yet another white savior story, the film does expose some issues that hadn’t been dealt with in the mainstream, like many of the horrors that happened during the civil war in Sierra Leone during the nineties. Not to mention that Leonardo DiCaprio and his co-star Djimon Hounsou carry the entire movie with their performances.

2. Inception (2010)
Dir. Christopher Nolan

Dom Cobb is a professional thief specialized in retrieving information by breaking into his victims’ dreams. His part in Nolan’s sci-fi film as his preferred type of character, the tortured hero, didn’t earn him much critical attention. However, it’s still considered one of the best sci-fi stories of the past years.

1. The Wolf of Wall Street (2013)
Dir. Martin Scorsese

His last collaboration with Scorsese (until now, at least) is probably his best. Based on Jordan Belfort’s autobiography, this black comedy goes through this man’s story that went from a random stockbroker in Wall Street to one of the richest investors. Though the Oscar went to Matthew McConaughey (who also had an appearance in the film), this was probably the one Leonardo deserved the most.

In the new Tarantino film, DiCaprio plays Rick Dalton, an actor who’s struggling to stay relevant after the many changes in the industry. In a way, as he’s explained in interviews, it’s the struggle every actor most face at one point in their career. Though he has been focused on other projects outside the industry and he hasn’t worked on a film since his success in The Revenant, we’re sure he still has a lot more to offer, and the Oscar buzz over this new film is proof of that.

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