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12 times Leonardo DiCaprio should have won an Oscar


Is Leonardo DiCaprio the unluckiest actor alive or what? The versatile star is in contention for an Oscar with his gruelling role in gritty wilderness thriller The Revenant – but it's not the first time he's been in this position.

Amazingly, despite his consistently brilliant output DiCaprio has yet to land that elusive gong, and we think that's outrageous – so much so that we've compiled the 12 occasions where the Oscar should have been his.


What's Eating Gilbert Grape

The year: 1993

The lowdown: This quirky drama centres on Johnny Depp's amiable Gilbert as he attempts to care for his dysfunctional family. However, the show is stolen by a very young DiCaprio in an Oscar-nommed role as Gilbert's disabled younger brother Arnie: the actor is so convincing in the role that many people believed the disability was genuine. Following a host of TV work, this was the moment where Leo properly exploded onto the movie scene.

This Boy's Life

The year: 1993

The lowdown: The other DiCaprio 1993 offering is a very different kettle of fish: a biographical account of author Tobias Wolff's memoirs, chronicling his troubled upbringing with a violent stepfather. As Wolff himself, DiCaprio shows genuine, raw star power and his confrontation scenes with Robert De Niro as the abusive Dwight are genuinely electrifying.

The Basketball Diaries

The year: 1995

The lowdown: Not just a pretty face, DiCaprio has often shown affinity with gritty material. Case in point: this dark adaptation of Jim Carroll's novel exploring the author's freefall into drug addiction. DiCaprio's gusty, uncompromising performance clearly demonstrates that even at this stage of his career, he was brave and bold in his choice of projects. 

Catch Me if You Can

The year: 2003

The lowdown: Steven Spielberg's delightfully breezy identity theft caper demonstrates a lighter side to DiCaprio that we don't see too often. He plays Frank Abagnale, the teenager who lives several lives by adopting the identities of airline pilots, doctors and much more besides. Tom Hanks is the dedicated FBI agent who comes after him. Accompanied by John Williams' finger-popping score, this is Leo at his most charming, effusive and engaging.

The Aviator

The year: 2004

The lowdown: DiCaprio's second collaboration with the esteemed Martin Scorsese (after 2002's Gangs of New York) gifts the actor a formidably complex and showy role. He plays legendary mogul and aviation enthusiast Howard Hughes, the multi-millionaire tycoon who has everything but is ultimately done in by his own demons. DiCaprio's stunning performance invites both sympathy and repulsion, a wholeheartedly convincing depiction of a very troubled mind.

The Departed

The year: 2006

The lowdown: Scorsese's terrifically violent and foul-mouthed return to classic gangster territory marked the moment where Leo went from boy to man, performance-wise. DiCaprio is street-smart, tough and utterly brilliant as the young cop who must go undercover to infiltrate gangster Jack Nicholson's operation; problem is, the gangsters also have a mole (played by Matt Damon) inside the police who's playing the same game. Amidst a richly enjoyable tapestry of lowlife characters DiCaprio stands out, no mean feat given the heavy-duty players involved.

Blood Diamond

The year: 2006

The lowdown: Slightly wobbly South African accent aside, DiCaprio's not-entirely-sympathetic diamond smuggler is the heart of this politically-charged adventure. It's Hollywood taking on the weighty subject of conflict diamonds so as you might expect, it all feels a bit worthy. Nevertheless, the actor's Oscar-nominated role as Danny Archer is further proof that DiCaprio doesn't need to have an audience on his side in order to deliver a great performance.

Revolutionary Road

The year: 2008

The lowdown: DiCaprio reunites with his Titanic co-star Kate Winslet for a claustrophobic and searing look at stagnating suburban life in 1950s America. Exploring the mundane lives of Frank and April Wheeler, the story (adapted by Sam Mendes from Richard Yates' novel) is one of the most unblinking portrayals of a marriage in crisis in recent memory. As you might expect, Winslet's emotional honesty shines through but DiCaprio more than holds his own as the increasingly anguished Frank.

Shutter Island

The year: 2010

The lowdown: DiCaprio's fruitful collaboration with Martin Scorsese continues in this luridly OTT asylum shocker. Based on Dennis Lehane's bestseller, it's the mind-bending story of two FBI agents investigating the escape of a patient from an isolated psychiatric facility – but is there more to the mystery than meets the eye? As DiCaprio's character Teddy Daniels increasingly unravels, coming face-to-face with his own demons, the combination of the actor's performance and Scorsese's vibrant direction make for enjoyably ripe melodrama.


The year: 2010

The lowdown: Christopher Nolan's gravity-defying, dream-collapsing extravaganza is held together by DiCaprio's gripping performance as mind 'extractor' Dominic Cobb. Amidst all the extraordinary effects and resonant psychological implications, it's Cobb's desire to get back to his kids that lingers longest in the mind, not to mention the haunting moments involving his late wife Mal (Marion Cotillard). It's a deliberately trippy movie but Leo keeps it all grounded.

Django Unchained

The year: 2012

The lowdown: DiCaprio's most repugnant character to date also makes for one of his most uproariously entertaining turns. Director Quentin Tarantino's sprawling slave-revenge tale is anchored by Jamie Foxx's vengeance-seeking title character and the Oscar-winning Christoph Waltz as bounty hunter King Schultz. Nevertheless, it's DiCaprio's repellent slave owner Calvin Candie who steals the show, a revolting figure so assured of his own racist views that his comeuppance can't come soon enough.

The Wolf of Wall Street

The year: 2014

The lowdown: Talking of repugnant characters, this fact-based black comedy offers another showcase for DiCaprio to play a jaw-droppingly unpleasant figure. Once again working with Martin Scorsese, DiCaprio brings to life notorious Wall Street banker Jordan Belfort, a man with so much wealth, drugs and women at his disposal that it would be utterly sickening were it not played for dark laughs. It's yet more proof that DiCaprio is one of the bravest actors in Hollywood – so where's that Oscars?

So, do you think Leo will finally clinch that Oscar for The Revenant? Tweet your thoughts @Cineworld and be sure to watch the movie when it's out from this Friday.