Nicholas Donovan

10 Best Leonardo DiCaprio Movies Ranked | Man of Many

He then followed this masterpiece up with a stirring supporting performance in the emotionally harrowing What’s Eating Gilbert Grape before moving on to star in the gritty coming of age film The Basketball Diaries. It was here that Leonardo DiCaprio shot to international stardom, and with gusto.

Leonardo DiCaprio Movies – History & Background

The film that broke Leonardo DiCaprio’s movie career, Scott Kalverts The Basketball Diaries is a coming of age tale wrapped in teen angst and genuine heartache. Whilst the critical reviews are mixed, Leo’s performance was undeniably raw and intense, as was the film’s subject matter which explored themes of sex, drugs, social and familial expectations, in a very realistic fashion.

10. The Basketball Diaries

Leo’s other standout film from 2010, Shutter Island (Directed by Martin Scorsese) is a film built on its crazy twist – which we’ll leave unspoiled today for those who haven’t seen it. What we will say, is that it takes a great poker face to pull of a mystery with so many moving parts, without giving it away or coming across as obvious – luckily, DiCaprio was just the man for the job.

9. Shutter Island

Filmed during the absolute peak DiCaprio studmuffin era, Romeo + Juliet was a modern reimagining of Shakespeare’s iconic ‘Romeo & Juliet’ (they changed the ampersand to a ‘+’ symbol you see, #modern). Whilst the movie is frantically paced, as per Lurhman’s core style, Leo brings a smoothness to the role of Romeo – and although he is an emotional basket case for 99 per cent of the film, there is no denying that his performance as Romeo is still held dear by millennials all over the world. As a cult hit, this is one of our most entertaining Leonardo DiCaprio movies.

8. Romeo + Juliet

In one of DiCaprio’s few supporting roles, there was movie magic to be had. Working with rockstar director Quentin Tarrantino for the first time, Leo found his sinister side as ‘Monsieur Candie’ in Django Unchained, without losing sight of the humour and ridiculousness of his character.

7. Django Unchained

Starring Johnny Depp and a very young Mr. DiCaprio, What’s Eating Gilbert Grape is a film not for the faint of heart. This film made the list because playing a character with a mental disability is on its own, a huge challenge. It’s an even more daunting task to do it when you’re a relative unknown and one that’s extremely young.

6. What’s Eating Gilbert Grape

Directed by Christopher Nolan – the maestro of the art of mind-fuckery – Inception signified Leo’s strong entrance into the smart-thriller category. Having done heartthrob, heady drama and intelligent action films to a T, DiCaprio dipped his toe into this new genre for him and boy did it pay off.

5. Inception

As the film that helped make DiCaprio’s career, we perhaps wouldn’t have many of the films starring Leo we hold dear today were it not for the sappy yet genre-defining Titanic. It’s incredible to think that at the time of filming Titanic in 1996, Leonardo DiCaprio was just 22 years old, and Kate Winslet was only 21 years old. Once the highest-grossing film of all time (and for a bloody long time at that), you’d be hard-pressed to find someone born before 2005 who hasn’t seen James Cameron’s Titanic – and you better believe that Leo’s star power and perfect casting played a major part in putting bums in seats.

4. Titanic

In what is his most debaucherous film to date, The Wolf of Wall Street turned heads upon release, if nothing else. With the film being a box office success as much as it was a critical one, Leo’s performance as the notorious Jordan Belfort and IRL Wolf of Wall Street was all stations go, the whole time.

3. The Wolf of Wall Street

It due to his performance as Hugh Glass – an American frontiersman back in 1823 – that Leo finally grasped his fingers around that coveted, and wildly overdue, Academy Award. In pushing himself to breaking point day-in and day-out to ensure his performance was authentic, and for completely disappearing within the role, DiCaprio took the film to a level that no other actor could.

2. The Revenant

Working with one of the best directors of all time, Martin Scorsese, Leo was on a mission to toughen up his image in the Oscar-winning film The Departed  – and undoubtedly, to put his acting skills to the test. Starring alongside heavyweights Alec Baldwin, Mark Whalberg and Jack Nicholson, DiCaprio’s best performance came as a result of the perfect movie mix: great script, great director and experienced co-talent.

1. The Departed

Join our exclusive community