Leonardo DiCaprio has been nominated for an Oscar five times and has famously gone on to win exactly zero times. The assumptions people make about how frustrated DiCaprio must be about this – though let’s face it, the acclaim, the money and the supermodels are probably easing the pain a bit – have spiraled into a mass cultural frustration, something that every passionate film lover is supposed to take part in. Heck, there’s even an 8-bit video game where players can pound two keys on their keyboard in an attempt to win Leo an Oscar:

Why is the interweb so obsessed with him? Probably because Leonardo DiCaprio’s an excellent actor with an astonishingly wide range, and because his films are incredibly varied and usually damn good. To get prepped for Oscar season, here’s a rundown of films that we believe Leo should have been given the prize for.

This Boy’s Life (1993)

Director: Michael Caton-Jones

The film is an adaptation of the memoir of the same name by writer Tobias Wolff. It follows Toby (Leonardo DiCaprio) as his mother marries the impeccably-middle class Dwight Hansen (Robert De Niro) to try and create a stable home for him. The plan backfires when Dwight turns out to be an abusive bully who becomes obsessed with trying to mould Toby into a model of mindless obedience.

While the movie is kind of a schmaltzy made-for-TV type number, Leonardo DiCaprio near enough takes flight in it. Bear in mind that he’s eighteen years old in this movie and spends most of it going head to head with one of the all-time greats of modern cinema, Robert De Niro.

This Boy’s Life is particularly fascinating if you’re familiar with Leo’s later, more action-packed movies. In his moments of violence – when matched against De Niro – DiCaprio’s talent for physical drama is already evident.

What’s Eating Gilbert Grape (1993)

Director: Lasse Hallström

Gilbert Grape (Johnny Depp) is a 24-year old grocery clerk living in a sleepy Iowa town, who spends his life outside work caring for his morbidly obese mother and his younger brother, who suffers from developmental disabilities (Leonardo DiCaprio). His life is shook up by the arrival of a young woman, Becky (Juliette Lewis) and her grandmother, who both get stuck in the town when their car breaks down.

DiCaprio, all of nineteen years old, got nominated for a supporting actor Oscar for his role, and he really earned it. It’s not just that it’s profoundly difficult to play a developmentally-disabled character without veering into unintentional comedy or ghoulishness – DiCaprio gives such an intense performance that he steals the limelight from one of the most magnetic actors of the era, Johnny Depp. There’s no playing down of any of the disabilities – if anything DiCaprio plays up Arnie’s wide range of tics and by doing so, disarms the audience.

Which isn’t to say that DiCaprio’s the only reason to check this movie out – it’s a genuinely warm, loving look at a bunch of eccentrics which, while at times is light on plot, is heavy on charm.

Romeo + Juliet (1996)

Director: Baz Luhrmann

The only way – the ONLY way – that the plot of this most famous of love stories can make sense, is if you convince an audience that teenage love is so powerful that it can act as a death drive.

Romeo is a uniquely tricky role for any actor to fill, because of the role’s reliance on a paradox. Romeo has to be soft enough to be appealing to a teenage girl who has had very little contact with men and at the same time, convincingly tough because, at it’s heart, Romeo & Juliet is as much about the cult of masculine violence as it is about star-crossed lovers.

Enter stage right, Leonardo DiCaprio. He was actually 22 when he starred in this movie, but looks years younger. Despite the adorable babyface and the flowery speeches (or because of them?), DiCaprio radiates sex appeal. Even with all the stunts and showy violence and musical numbers and newsreader-stand-ins-for-the-chorus, the most captivating thing in the whole movie is the quietly insistent sexual tension between Clare Danes and Leo.

Besides all that, it’s just a really great movie. Sure, it’s not Franco Zeffirelli’s 1968 Romeo & Juliet and that annoys film critics, but this film isn’t designed for an NYU Film School grad with a vendetta. It’s by Baz Luhrmann, so it’s loud, unapologetically brash and a little bit like a two-hour-long music video – all in the best way possible, obviously. Enjoy!

Titanic (1997)

Director: James Cameron

How do you talk about Leonardo DiCaprio without talking about Titanic? You can’t.

If you’ve been living under a rock for the past nineteen years, a quick recap: Titanic centers on an old lady reminiscing about the love affair she once had on the ill-fated boat. Despite being accompanied by her snobby fiancee, Rose (Kate Winslet) swiftly catches the eye of penniless scamp/artist Jack (Leonardo DiCaprio). Romantic intrigue and “I’m the king of the world!” type speeches ensue.

Leonardo DiCaprio deserves an Oscar for this film for the most old-fashioned reason possible: pure charisma. There’s no Oscar-style physical transformation for the role, he doesn’t lose twenty pounds or gain twenty pounds or have to crawl into a dead animal. It’s just DiCaprio and his curtains of hair falling into his eyes every ten seconds. But Leo’s infectious energy carries this film: the audience gets so swept up by the love affair, the most famous iceberg in history practically comes as a surprise.

Catch Me If You Can (2002)

Director: Steven Spielberg

What role could be better for DiCaprio than that of a conman? For a start, there’s that face: which has always been as blank as it is pretty. For all its appeal, it’s a smooth, forgettable face, which makes it the perfect asset for a trickster.

Then there’s the bucketloads of charm. It’s hard to exactly pinpoint the source of DiCaprio’s charisma – it lies somewhere perhaps between the velvety voice and his physical agility – but it’s perfectly suited to a life of confidence.

As such, arguably the role of Frank W. Abagnale is the perfect role for Leonardo DiCaprio. This real-life conman was a brilliant forger whose passion for faking checks meant he earned millions of stolen dollars and got the FBI on his tail.

The film centers on a duet of sorts between Abagnale and FBI agent Carl Hanratty, when Abagnale is always just one step ahead. Reportedly, the real life Abagnale wasn’t convinced DiCaprio was suave enough to play him until he watched the finished version. The DiCaprio charm conquers again – well, everywhere but the Academy.

The Aviator (2004)


Director: Martin Scorsese

This star-studded biopic centers on the life and times of eccentric aviator/entrepreneur/filmmaker Howard Hughes (Leonardo DiCaprio) as he woos Hollywood glamour pusses (Katharine Hepburn played by Cate Blanchett, Ava Gardner played by Kate Beckinsdale), wrangles with the courts and battles with his OCD.

This was DiCaprio’s first actor Oscar nomination and it’s pure Academy bait in every way his role in Titanic wasn’t. It required him to grow funky facial hair and give a spookily convincing performance of the mental illness Hughes suffered from in later life, when he watched movies over and over again and urinated in bottles.

This convincing performance of an OCD sufferer was no coincidence: he got so deep into the character that DiCaprio actually developed the illness himself.

At the time, DiCaprio said: ‘I remember my makeup artist and assistant walking me to the set and going, “Oh God, we’re going to need ten minutes to get him there because he has to walk back and step on that thing, touch the door and walk in and out again. I let myself do it because I wanted that to come out. I was trying to be that character but it became really bothersome – and it continued way after the filming.”

The Departed (2006)

Director: Martin Scorsese

A remake of the legendary 2002 Hong Kong cop film, Infernal Affairs, this Scorsese masterpiece centers on Billy Costigan (DiCaprio) and Colin Sullivan (Matt Damon), who are both pretending to be something they’re not. Sullivan is a mole planted inside the police force by Irish-American mobster Frank Costello (Jack Nicholson), while Costigan is an undercover cop planted inside Costello’s gang.

DiCaprio is great here because he doesn’t get to be DiCaprio. Actually, Matt Damon gets the stock DiCaprio character: the smooth-talking charmer who everyone can’t help but like. DiCaprio is forced to play the straight man – Billy Costigan is every bit as puritanical and self-sacrificing as Damon’s character, Colin Sullivan, is corrupt and charming. The wonderful surprise of the film is how likable DiCaprio still is in this role and how well he plays it.

Although the film’s a remake, don’t let this put you off – this isn’t a lazy Hollywood attempt to cannibalise an inventive foreign movie but was presumably a carefully considered decision, with Scorsese making this Boston set drama every bit as convincing from an Irish-American-Catholic standpoint.

Inception (2010)

Director: Christopher Nolan

Nolan spent ten years writing and revising the script of this sci-fi heist film, $160 million on making it and $100 million marketing it. With that in mind, the sheer amount of expectation placed on DiCaprio alone as the film’s lead, Dom Cobb, must have been crushingly high.

Not to mention what DiCaprio had to compete with: awe-inspiring 3D effects and an ambitiously labyrinthine storyline. The film required a lead actor capable and watchable enough to make the complex story relatable and give a CGI-heavy movie a human heart, and that’s Leonardo DiCaprio: a supremely safe pair of hands.

Django Unchained (2012)

Director: Quentin Tarantino

What’s more delicious than after many years of watching an actor star in earnest, serious roles, to watch them throw themselves into playing the most repulsively evil character? In an ingenious piece of casting, this star-studded spaghetti western sets DiCaprio against his former Oscar nemesis Jamie Foxx (who took home the 2005 Oscar for his performance in Ray, the same year DiCaprio was nominated for The Aviator) as Django, a newly-freed slave trying to reunite with his wife.

DiCaprio plays Monsieur Calvin L. Candie, a cruel plantation owner with impeccable Southern manners. He makes a truly excellent villain – it appears yet another talent he possesses is making the audience love to hate him – begging the question why he wasn’t given a role like this sooner.

The Wolf Of Wall Street (2013)

Director: Martin Scorcese

Perhaps DiCaprio’s powerhouse performance in Django Unchained was what inspired Martin Scorsese to cast him as the similarly vile Jordan Belfort, a real life stockbroker with a talent for excess and dodging the long arm of the law. In real life, Belfort’s company Stratton Oakmont engaged in the sort of high-level fraud that gets you tailed by federal agents.

DiCaprio’s got a lot to compete with in this movie: Matthew McConaughey is good in this. Really damn good. McConaughey plays a coke-snorting, hyper-macho businessman who’s got the sort of personal magnetism normally possessed by cult leaders.

But DiCaprio holds his own. This is partly to do with the script – Belfort was a famously charismatic sorta guy himself – and partly to do with DiCaprio, who seems to have more fun than he’s ever had onscreen in this movie. He’s more or less licking his lips in glee during the famous motivational speech Belfort gives to inspire his colleagues to even more dizzying feats of greed.

If at this point, you’re asking, where’s Blood Diamond? Well – while Leo may have scored an Oscar nomination for his role in it and the movie’s intentions are noble, it hasn’t aged terribly well. While the topic of slavery in diamond mining is important, the film’s treatment of it is singularly preachy and a little charmless.

Another notable exception here is Gangs of New York – while DiCaprio has done a lot of great work with Scorsese, this is not one example of such. Next to Daniel Day-Lewis’ electrifying performance as Bill the Butcher, DiCaprio’s performance feels a little bland and forgettable.

But hey – let’s argue this out in the comments. Which Leonardo DiCaprio films should have made it onto this list?

  • Author: Sophie Atkinson
Words by Contributor