Like the rest of the world, we’re still on a bit of a high from Leo’s legendary Oscar win last night. Unlike the rest of the world, we’re taking time out of our busy schedules to fit in a much-needed Leo marathon to join in the celebration. And this weekend, you probably should to. Here are our top picks on getting the best of Leonardo DiCaprio.
1. Romeo & Juliet (1996)
Ease yourself in with this Shakespeare-tween-dream classic, featuring a very yummy 22-year-old Leo. Plus, it’s the film that first catapulted him into mainstream spotlight, so it’s a pretty apt first movie to start the marathon with.
2. What’s Eating Gilbert Grape (1993)
Now that you’re all warmed up, hit up the film that critics have unanimously agreed is the one film Leo truly deserved (and was denied) an Oscar for. His supporting role as Gilbert Grape’s (Johnny Depp) developmentally challenged younger brother was the film industry’s first look into Leo’s solid acting chops. 22 years on and he’s finally got the Oscar, but relish in this stellar Depp-DiCaprio pairing because it’s probably the last you’ll ever see.
3. Catch Me If You Can (2002)
Leo seems to have a thing for piloting (think his more sombre The Aviator); Catch Me If You Can straddles comedy and drama as a biographical crime drama film based on the true story of conman Frank Abagnale – who swindled millions of dollars all before his 19th birthday.
4. Blood Diamond (2006)
Things get really heavy with this political war thriller, which we’ve picked over The Departed and Django Unchained as the representative “serious” movie in this marathon. It’s got just the right mix of touchy race politics, adventure, and raw emotion, to keep you alert and on the edge of your seat – something you’ll be needing seeing as you’re four movies in.
5. The Wolf of Wall Street (2013)
Personally, this film felt a tad too crass for our liking – but that’s what makes it the perfect counter-follow-up to Blood Diamond. Biases aside, this Martin Scorsese collaboration – Leo’s fifth and latest – has become quite the iconic DiCaprio flick, and showcases his incredible range as well. You’ll be rooting for this underdog-turned-billionaire every second of the way, even when he’s making ill-informed choices and dancing with the devil. And can you really picture anyone else as The Wolf?
6. Titanic (1997)
You thought we’d missed this out, didn’t you! No explanations needed here; just grab your tissues and fangirl nostalgia.
7. Inception (2010)
We’ll admit it – this is more a Christopher Nolan inclusion than it is one for Leo. That said, Leo as the perceptive “dream stealer” Cobb is what really makes the film. Fun fact: Christopher Nolan had been trying to work with Leo for years, but was only able to convince him to collab with Inception. Brad Pitt and Will Smith were runner-up considerations for Cobb, but let’s face it – Cobb was made for Leo.
8. The Great Gatsby (2013)
It’s a Baz Luhrmann reunion with this literature classic (again), and if you thought 39-year-old Leo couldn’t possibly exude the same charm and charisma as his teen dreamboat self; you thought wrong. Somehow he just blends seamlessly into the 1920s landscape, and Leo’s Jay Gatsby couldn’t be any more suave. Plus, you have this movie to thank for spawning half the Leo-Oscar memes onlines.
9. The Revenant (2016)
Duh!!! Catch this in theatres while you still can; The Revenant should be wrapping up its rounds here on the island, but then again, now that it’s helped make Academy Award history, it might stick around for just a bit longer. And are you really going to pass up the movie that finally, finally got our Man of the Moment an Oscar?
Three cheers for Leo! And the CGI bear who got left out of his acceptance speech.
