10 Best Leonardo DiCaprio Movies Of All Time

Bear-wrestler, Titanic passenger, stock broker, and gangster… he’s played them all, in a career spanning thirty years.

Since breaking onto the big screen in the early nineties, Leonardo DiCaprio has wowed audiences with his portrayal of unconventional characters and on-screen charisma.

Turning silver screen hits into box office gold, the world-famous actor has received over 100 awards in this time. 

With 72 films to his name, here are ten of our favourite Leonardo DiCaprio movies in order of release date.

Once Upon a Time in Hollywood (2019)

Firmly in the nook of the ‘Tarantino-verse’, Leo takes on the role of Rick Dalton – an actor who lives next door to Roman Polanski and the late Sharon Tate.

Except this is a parallel universe, where the Manson Family go after Rick, not Tate – as sadly happened in real life. Rick’s portrayal of a spaghetti western actor past his peak, is poignantly reflective.

IMDB Rating: 7.6/10

The Revenant (2015)

The movie that finally gave Leonardo DiCaprio Oscar status, and rightly so.

Leo plays Hugh – an intrepid explorer fighting for survival, following serious injuries from that bear attack. He is fully committed to the role, which was gruelling and physically demanding – all translating beautifully on the big screen, making The Revenant compelling viewing.

IMDB Rating: 8/10

The Great Gatsby (2013)

Some actors are born for certain roles, like Leonardo DiCaprio as the ultra-rich Jay Gatsby.

This captivating story of glitz, glamour, seduction, and wealth gets a sprinkling of Baz Luhrmann magic to create a dazzling masterpiece. Transporting you to the speakeasy streets of New York, it’s just one of many Leonardo DiCaprio films you wish you could step inside.

IMDB Rating: 7.2/10

The Wolf of Wall Street (2013)

Witness the excess, the greed and the free-for-all that was 1980s Wall Street, through the eyes of Jordan Belfort (DiCaprio), in this biopic of a hedonistic time in financial history. Leonardo gives a world-class performance, as the protagonist you hate to love.

IMDB Rating: 8.2/10

Inception (2010)

Inception is not a film you want to watch hungover. 

You’ll need all cylinders firing to keep up with this sci-fi action, that toggles between themes of the subconscious mind and corporate espionage. Without DiCaprio bringing an essential human touch to this movie, it could have all-too easily been another Matrix homage. Instead, it ranks as one of the highest-rated in IMDBs top 10 Leonardo DiCaprio films.

IMDB Rating: 8.8/10

Gangs of New York (2002)

DiCaprio broke his heartthrob mold for this raw and gritty role as Amsterdam; a man seeking to avenge his father’s killer. Holding his own against Hollywood royalty – Liam Neeson, Cameron Diaz and Daniel Day Lewis no less, he proves his worth as a formidable actor that can literally roll with the punches in this Scorsese classic.

IMDB Rating: 7.5/10

Catch Me If You Can (2002)

In this Steven Spielberg blockbuster, we’re treated to one of the most iconic Leonardo DiCaprio films.

Harking back to the glamourous heyday of travel, Leonardo is Frank – a hustler and con-man, who smooth talks his way into being a pilot, amongst other guises. Oozing with charisma and charm, he was born to tell this true-life story.

IMDB Rating: 8.1/10

Titanic (1997)

James Cameron’s big-budget blockbuster firmly cemented DiCaprio’s Hollywood legacy, in this career-defining performance. 

But it’s not the Titanic that takes centre stage. Instead, Leonardo DiCaprio and Kate Winslet’s all-too-short love story as Jack and Rose aboard the doomed ship. So influential is this film, that even today you can’t board a boat without doing that iconic ‘I’m flying’ scene! And even with a raft (no pun intended) of films under his belt, Titanic remains the highest-grossing box office movie by the actor.

IMDB Rating: 7.8/10

Romeo + Juliet (1996)

The rousing soundtrack, the beautiful cinematography, the heart-breaking story unfolding in a way that only Baz Luhrmann can do.

Romeo + Juliet was the Teen Scream of its time, catapulting Leonardo into the mainstream, and onto every teenage girl’s bedroom wall. At the tender age of 21, we see Leonardo at his most achingly handsome and vulnerable – it’s impossible not to fall in love with him.

IMDB Rating: 6.7/10

What’s Eating Gilbert Grape (1993)

Before there was DiCaprio, there was Depp. So, this touching story that brings both actors together is a must-watch for die-hard DiCaprio fans.

Billed as a ‘coming-of-age drama, this is a film with great depth and heart, touching on mental illness, obesity and family. A young (19 year old) Leonardo gives a memorable performance as Arnie Grape – a mentally disabled teen, earning himself several industry awards in the process. Looking back at this early Leonardo DiCaprio movie you can see all the hallmarks of a great actor coming to fruition. 

IMDB Rating: 7.7/10

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