5 Ways Leonardo DiCaprio Can Finally Win An Oscar

Another year, another long trophyless walk home for Leo after the Oscars. Many will be asking exactly what he has to do to win one, well here it is....
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From the yellow title screens and Jonah Hill’s ‘You have my money taped to your boobs. Technically, you do work for me’ to Kanye’s Black Skinhead, everything about Wolf of Wall St works perfectly. All in all, it's arguably the best film of Scorsese and DiCaprio’s 5 movie collaboration (a huge claim, considering their previous work includes the likes of The Departed and Shutter Island).

After collaborations with Tarantino, Baz Lurman, Chris Nolan, James Cameron, Danny Boyle, Ridley Scott, Richard Yates, Woody Allen and Clint Eastwood, it’d be pretty hard to argue Leo isn’t a bona fide Hollywood star. Love him or loath him (and honestly, why the hell wouldn’t you love him?) Leonardo DiCaprio is guaranteed to fill cinema seats. Now 38, he’s also not made a truly bad film since the mid-90s (The Aviator and J. Edgar were a bit dry, but The Beach is fantastic) and the majority of his movies have been hugely successful, both commercially and at the box office. Whereas his A-list contemporaries have become content with vapid blockbuster twaddle (Tom Cruise in Oblivion, Will Smith in After Earth) DiCaprio remains committed to making the best movies possible. Yet, despite 4 Oscar nominations for The Aviator, What’s Eating Gilbert Grape, Wolf of Wall St and Blood Diamond, DiCaprio is yet to bag the Academy’s highest prize.

Clearly, this is an unforgivable oversight on behalf of the Academy. To remedy this, I’ve been making my own Oscars out of old toilet roll tubes and glitter, and posting them off to Leo each time he has a new film out. Obviously, he has these stacked up along his mantelpiece and always shows them off to which ever supermodel he’s got round for a cup of tea. (‘No! You can’t touch!’ he says.) Clearly, all Leo cares about is the love of his fans, and I’m sure he’s happy with my homemade Oscars, however, an ‘official’ award is long over due, so, in order to point Leo in the right direction, I’ve had a bit of a brainstorm about the steps he can take to secure himself an award next year. Leo, I love you, buddy.

Play a Villain

Leo was brilliant as Calvin Candie, but was on screen for less than half the movie. Similarly, the bit at the end of The Beachwhere he goes temporarily insane is fantastic. Remember where he pops out of the ganja field to hiss at that tourist, causing her to get shot? Shivers. If Leo did a whole film playing an out and out wrong un, he’d surely be a shoe-in for an Oscar. There is a bit of a problem here, even Leo DiCaprio couldn’t make Hitler a loveable character, so there’d have to be some do-gooder protagonists to feel sorry for. However, they couldn’t be too loveable, as then they might steal Leo’s award. If recent rumours of Leo playing Rasputin (in a film based on a Jason Hall screenplay) turn out to be true, this could be his winning ticket.

Stop Being Rich

When TWOWS was released a few hilarious internet types quipped ‘At least he can keep his clothes from Gatsby!’ Hohoho. In all fairness though, there are a lot of films where Leo plays well off Americans who love to wear nice suits (Inception, Gatsby, Revolutionary Road, J. Edgar) so it might be nice to see him play someone who can’t afford to shop at the same stores as the real life Leo. For me, a highlight of Leo’s career was The Basketball Diaries, a fantastic yet harrowing movie in which a young DiCaprio plays a teenage heroin addict. It’s some of his best work, and a similar role should get him an Oscar. Like Brad Pitt popping up as a pikey boxer in Snatch, Leo playing against the rich, handsome stereotype would be a nice treat. How about getting himself cast in an adaptation of Henry Miller’s Tropic of Cancer? Admittedly, the role of a highly sexual, struggling writer has more of a Johnny Depp vibe to it, but I’m sure Leo could pull it off. He could even keep one of his suits (it was written in the 1930s after all) although he’d have to rough it up a bit with a few tears and stains.


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Play Gay

Straight actors playing homosexuals are catnip for the Academy. They love it. Look at Sean Penn and James Franco in Milk, or James Franco in Howl, or James Franco in James Dean. All fantastic performances, all lauded with applause. For Leo to get himself some of the action, he should ideally play a terminally ill homosexual (see Philadelphia) or a sympathetic Nazi homosexual (see Valkyrie). The perfect film for DiCaprio to star in would be a new adaptation of Breakfast at Tiffany’s as narrator ‘Fred’ (who actually never reveals his name in Capote’s novella). It’d be classic DiCaprio fayre -middle-class white types in nice suits- so we know he’d be able to pull it off. The twist, of course, would be DiCaprio’s penchant for the company of men, which, depending on the director, may draw a new vulnerability or a greater sense of empowerment from DiCaprio. Actually, I really hope this gets made. Anne Hathaway as Holly Golightly anyone?

Star in a Musical

Les Mis cleaned up, didn’t it? Oscars, Golden Globes, BAFTAs, the lot. It was amazing too. Hugh Jackman and Russell Crowe both managed to sing whilst still looking masculine and Eddie Redmayne was also in it. Leo has enough charisma to carry off a whole musical on his own, playing every single character, and obviously he’s an amazing singer too (so I assume). The problem would be finding the right musical. He’d be good as Harry Osborn in an adaptation of the Spiderman musical, the only problem with this would be that U2 would make more money out of it. There’s The Phantom of the Opera, but Leo already (sort of) spent most of The Man in the Iron Mask with his face covered, so that might effect ticket sales. If he’s really struggling Leo could always don some fake whiskers for Cats.

Stop Being Smug

Obviously, Leonardo DiCaprio is one of the most humble, perfect beings to have ever been created. However, a lot of his characters come across as right smug so-and-sos. TWOWS shows Leo smirking and throwing cash at the Feds. He also smirks a lot in Django, Catch Me If You Can and Gangs of New York. He even smirks in Gatsby, showing that even thought Jay Gatz used to be an insecure little Midwesterner, he’s fallen pray to the trappings of a glitzy life. Leo is at his best when he’s vulnerable. He was phenomenal in What’s Eating Gilbert Grape and Shutter Island. Basically, the more shots a film has of Leo staring into a mirror whilst running his hands through his hair and looking bewildered, the more chance it has of winning an Oscar. A remake of the 2008 Kiefer Sutherland stink-fest Mirrors would be perfect for this. It’s a horror film, so Leo could be as emotionally unstable as possible, and obviously there’s bloody loads of mirrors (or so I assume, obviously I’ve never seen it).

As an extra treat, here’s a video of Leo being a right babe. Good luck Leo.

Follow Tom Ward on Twitter here, or check out his first novel, then send it off to Leo’s agent, here.