Top 10: Leonardo DiCaprio - Rooftop Film Club

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Top 10: Leonardo DiCaprio

Named after the Leonardo da Vinci painting his mother was looking at when he first kicked (adorbs, right?), Leonardo started his career in TV before switching over to film. Leo kidnapped our hearts in What’s Eating Gilbert Grape, in which he played Johnny Depp’s younger brother with autism, and has held onto them ever since.

Even if you don’t like his films (what’s wrong with you?), you gotta like him – generous, smart, and, above all else, Oscar winner.

In no particular order, here’s our top 10 picks…

The Beach

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Plot:

A boy in search of adventure and the perfect life finds himself on a remote island and basically ruins an entire civilisation’s way of life. And he doesn’t even care.

Leo’s role:

Unable to really connect with anyone or anything Leo plays ridiculously responsibility-free Richard, who follows the map a drug-addict gave him (smart move, Richard) to a remote island where he hopes to find paradise.

He doesn’t.

Fun fact:

The film, which is based off of a book, sometimes plays literally on repeat all day long in bars and restaurants in Thailand.

Behind the scenes:

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Shutter Island

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Plot:

A bunch of stuff happens…. but then maybe it doesn’t happen… maybe a bunch of different stuff happens? Leo and Mark Ruffalo head to Shutter Island (a remote prison island) to investigate the disappearance of a woman (the prison is on an ISLAND and the room was LOCKED. Riddle us that, Batman). They get in way too deep with the investigation and start to discover real twisted things have been happening at the hospital. It messes with your head a whole lot. It’s fab.

Leo’s role:

Potentially mentally deranged murderer, potentially innocent U.S. Marshal.

Fun fact:

‘Shutter Island’ is an anagram of “truths and lies”, and “truths/denials”.

Behind the scenes:

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Romeo + Juliet

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Plot:

Two star-crossed lovers (wait…) meet at a party Leo DEFINITELY wasn’t invited to. Their families are rivals and they’re real dramatic about it. They sneak away to get married, people fight, someone dies, Leo is banished from Verona and Juliet’s really smart plan to fake her own death goes horribly wrong. Surprise, surprise.

Leo’s role:

Leo plays stalker Romeo Montague who will stop at literally nothing (even suicide) to be with the love of his life, Juliet. Nobody’s having it, though, and that creates a lot of teen angst.

Fun fact:

Baz Luhrmann wanted to prove that Shakespeare could be for everyone – not just pretentious snobs. Good on you, Luhrmann.


Behind the scenes:

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The Revenant

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Plot:

A man lost in the wilderness fights for survival after being mauled by a f*cking BEAR. After being betrayed by his very own peeps (who left his son for dead. What the hell, right?!) he does everything he can to hunt their asses down and get the revenge he deserves.

Leo’s role:

Oscar-winner who uses his speech to talk about global warming. You’re doing amazing, sweetie.

Fun fact:

Though based on a true story, there’s no proof of the real Hugh Glass ever having a son nor being married.

Behind the scenes:

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The Great Gatsby

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Plot:

A writer and his friend are sucked into the incredible lifestyle of neighbour, Jay Gatsby. Jay is a real party animal, but a party animal with a sad backstory. He loves her, but she’s with another man. They all do everything they can to get Jay back with Daisy, and it all unwinds into a big, messy, complicated love story. What more could we want?

Leo’s role:

Jay Gatsby, millionaire, besotted, real babe.

Fun fact:

Baz Luhrmann is the waiter that brings Nick to Jordan’s table to meet for tea after his lunch with Gatsby.

Behind the scenes:

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Django Unchained

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Plot:

A slave and bounty hunter team up to hunt the South’s most-wanted criminals. Their travels take them to Leo’s shady plantation where Django’s wife still works as a slave, and all hell breaks loose Tarantino style.

Leo’s role:

Plantation and slave owner, Leo is definitely at least a little bit unhinged. Also, Leo’s accent is pretty ace in this, to be fair.

Fun fact:

The films body count is 69.

Behind the scenes:

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The Wolf of Wall Street

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Plot:

A rich man does illegal things (but we’re pretty sure that’s fake news) and the powers that be are slowly closing in on him. With corruption, crimes, and cops, he’s basically living the life we all wish we could. Kinda.

Leo’s role:

The main slice. The man with the plan. The do bad-er.

Fun fact:

Feel free to count if you wanna doublecheck, but a curse word is spoken 680 times throughout the movie.

Behind the scenes:

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(We don’t really know what’s happening there but we kind of love it)

The Basketball Diaries

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Plot:

It will literally make you sob your entire face off. If you came here for the basketball, you might as well leave now. What starts off as some good, clean basketball court fun leads to the mean streets of New York where Leo spirals out of control, becoming addicted to drugs and getting himself into trouble with the law.

Leo’s role:

Just a poor boy who lost his way or burden beyond all help? Either way, the heart breaks.

Fun fact:

The film is based off of Jim Carroll’s autobiography.

Behind the scenes:

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Titanic

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Plot:

Two star-crossed lovers meet on an unsinkable boat that sinks. Despite their class differences, they have a lot in common and things get heated in the back of a car. Celine Dion sings a lot. People die.

Leo’s role:

A poor boy who won his ticket boards the Titanic, not knowing he was about to have an epic romance. He plays heart-throb Jack who dies for the one he loves. #Goals #DontLetGoJack #WeLoveYouJack #OurHeartsWillGoOn

Fun fact:

Jack never actually says he loves Rose… but he does say he loves some stuff ABOUT her…

Behind the scenes:

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Inception

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Plot:

Well, BASICALLY… what happens is – uh… we don’t really know. Communal napping? We vote that be a thing. (Is anyone REALLY sure?)

Leo’s role:

He jumps, we all jump. Leo seems to love playing heartbreaking characters, and he gets us EVERY time. All he wants is love…

Fun fact:

Christopher Nolan spent 10 years writing the script for Inception. Never feel bad about missing a deadline again.

Behind the scenes:

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