The Very Best Of Leonardo DiCaprio

Above: 15 of Leonardo DiCaprio's most iconic movie roles
Above: 15 of Leonardo DiCaprio's most iconic movie roles

On Tuesday, everyone’s favourite Growing Pains alum Leonardo DiCaprio turned 40.

We wanted to do something special to commemorate Leo hitting “The Big Four-O” and as much as we liked the idea of running back a list of the numerous stunning women that have been on his arm over the years, tracking through his impressive filmography seemed like a safer, more logical decision. (Note: this list is in chronological order from most recent to his first big role, not some kind of ranking.)

The Wolf of Wall Street (2013)

Last year’s black comedy from frequent collaborator Martin Scorsese was a great performance and a fun trip from measured to manic and back again for Leo. Based on Jordan Belfort’s memoirs of the same name, DiCaprio picked up an Academy Award nomination for Best Actor for his portrayal of the scheming stockbroker and the film, which he was a producer on, was nominated for Best Picture as well.

The Great Gatsby (2013)

Reviews were mixed, but there is no denying that Leo was outstanding as mysterious business magnate Jay Gatsby in this Baz Luhrmann adaptation of the classic F. Scott Fitzgerald novel. Like all Lurhmann efforts, Gatsby is a stunning visual presentation and DiCaprio was an obvious choice to throw lavish parties, befriend Nick Carraway and have a relationship with Daisy Buchanan.

Django Unchained (2012)

One of the really great things about DiCaprio as an actor is that he’s willing to be part of a collective or take a supporting role like this. Django was very much a Jamie Foxx vehicle and there are times when actors in DiCaprio’s position would miss the mark by overstepping their bounds, but not Leo – he was note perfect in a supporting role as “Monsieur” Calvin J. Candie in this Tarantino gem.

Inception (2010)

Christopher Nolan’s blurring of the lines between dreams and reality is another great example of DiCaprio’s ability to stand out in a strong group without overshadowing everyone around him. His performance as “Dom Cobb” was obviously the central piece of Inception, but it was also a spot where he was able to help showcase the strong work of his co-stars like Joseph Gordon-Levitt and Tom Hardy.

Revolutionary Road (2008)

Directed by Sam Mendes, Revolutionary Road isn’t one of the first films that jump to mind when considering DiCaprio’s filmography, but it is one of his strongest performances to date. Teamed with his Titanic co-star Kate Winslett, Leo brought real life to Frank Wheeler in this adaptation of the 1961 novel of the same name by Richard Yates.

The Departed (2006)

Another DiCaprio-Scorsese collaboration that was an absolute home run. There are a lot of great performances (and lines) in this flick and Leo more than holds his own alongside the likes of Jack, Matt Damon and Martin Sheen, walking the thin line between cop and criminal as undercover agent Billy Costigan in this mob flick set in Southie.

The Aviator (2005)

DiCaprio’s portrayal of aviation pioneer and eventual obsessive-compulsive shut-in Howard Hughes earned rave reviews and an Academy Award nomination for Best Actor, which he would lose to future co-star Jamie Foxx for his work in Ray. This was Leo right in the middle of an incredible run of great performances and one that – when his career comes to a close – will stand out as one of his very best.

Catch Me If You Can (2002)

Playing real life con man Frank Abagnale Jr. opposite Tom Hank in this Steven Spielberg-directed cat-and-mouse movie, DiCaprio showcased all the skills he brings to the table in this one, bouncing from charming and sweet to scared and alone. Unlike some of the big dramatic films DiCaprio has been a part of over the years, Catch Me If You Can is fun, easy and highly re-watchable.

Gangs of New York (2002)

Listen – we’ve got plenty of complaints about this film too, but looking back, this feels like the point where DiCaprio really started to find himself as an actor and elevate his performances to the next level. Those kinds of things happen when you’re working next to one of the greatest actor of all-time, Daniel Day-Lewis. It was also his first of many pairings with Scorsese, so even if you really dislike Gangs, their creative relationship has more than made up for it since.

The Beach (2000)

In between Trainspotting and Slumdog Millionaire, director Danny Boyle delivered The Beach. Starring DiCaprio as a 20-something looking for paradise in Southeast Asia, it was panned by critics but loved by the legions of fans that flocked to Leo post-Titanic. Better than the critics let on, but not as good as the expected, The Beach is one of those solid Netflix watches that shows DiCaprio’s growth and development over the years.

Titanic (1997)

What more needs to be said that hasn’t been said already? This is the movie that truly launched Leo into the stratosphere and remains the starting point of thousands (millions?) of long-standing crushes on the man that played Jack Dawson to Kate Winslett’s Rose DeWitt.

Romeo + Juliet (1996)

This modern twist on the Montagues and Capulets was the film that established DiCaprio as a teen idol, pairing him with post-My So Called Life Claire Danes as the titular star-crossed lovers. Hollywood has tried to do Shakespeare many different times, in many different forms and this is one of the few times it was done really well, as Baz Luhrmann mixed the classic story with “of the time” elements.

The Basketball Diaries (1995)

If Romeo + Juliet is where girls fell for Leo, this is where guys realized he was an actor they could embrace going forward. Based on Jim Carrol’s juvenile diaries detailing his descent into drug addiction, DiCaprio shows glimpses of the brilliant talent he would go on to become. It’s an uneven movie, but Leo is solid and Mark Wahlberg shines as one of his high school running mates in one of the earliest entries on DiCaprio’s big screen resume.

What’s Eating Gilbert Grape? (1993)

Johnny Depp received top billing and was really good, but DiCaprio stole the show in this one, playing Gilbert’s mentally handicapped brother, Arnie. Depp wasn’t quite “Academy Award Nominee Johnny Depp” yet and Leo wasn’t there either, but his abilities jumped off the screen in this film directed by Lasse Hallstrom.

This Boy’s Life (1993)

Reportedly hand-picked by Robert De Niro for the role, DiCaprio more than holds his own opposite the iconic actor as Tobias Wolf in this adaptation of the writer’s memoirs. While Gilbert Grape is where most people first got a glimpse at the immense talent DiCaprio possesses (aside from Growing Pains, obviously), being able to deliver in some of the tough, tense scenes here really announced that Leo has the potential to be a great actor in the future.

E. Spencer Kyte

E. Spencer Kyte

E. Spencer Kyte is a freelance journalist based in Abbotsford, British Columbia, where he lives with his wife and dog. In addition to his work here, he writes about sports for Complex Canada and covers the UFC for various outlets. His mom also still tells him what to do on a regular basis, even though he’s nearly 40. He tweets from @spencerkyte.

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