Should DiCaprio have already won a Leading Actor Oscar?

‘Tis the seminal question of our time. The Academy Awards may change each year, but discussion of DiCaprio’s Oscar misfortune is always a constant. He may have entertained millions over two decades in film, but it seems only now will he be recognised with the shiniest award in cinema.

Social media erupted in 2013, following the release of Martin Scorsese’s The Wolf of Wall Street, outlandishly praising only Leonardo’s performance and also his character’s playboy lifestyle. Now, his Wolf of Wall Street character, Jordan Belfort, is certainly not someone to be considered a ‘role-model’, but the career of DiCaprio should most certainly be admired. The Golden Globe and Wilson Award winner has done it all, working with some of the best in the business. Hell, he’s one of the best of the business.

So, how is it that he is without an Oscar? Has the industry got a grudge against him? Is he not as good as percieved? Or has the man just been unlucky? It certainly seems that an actor of his undeniable quality is more than able of deserving cinema’s top prize, and in this article I shall hope to shed some light on why he has been without the top individual award until, potentially, now.

Leonardo DiCaprio has been nominated for three Best Actor Oscars pre-2016, as well as a Supporting Actor nomination at just the age of 19. It happens that younger actors, such as Quvenzhané Wallis and Jacob Tremblay, fail to win many awards, so I will be focussing on Leo’s performances that aim for The Academy’s highest praise. Let’s begin:

His First Best Actor Nomination: The Aviator

Nominated for Best Performance by an Actor in a Leading Role in 2005 – Beaten by Jamie Foxx in Ray.


Leo first struck gold under the helm of Martin Scorsese. The two paired up for The Aviator, a biopic based on the life of the fastest man on the planet, Howard Hughes. Hughes’ story is one of success, ambition, excess and eventually a dramatic decline. DiCaprio is now rightly regarded as a master of this arc, but his Aviator performance affirmed his place as one of the defining actors of a generation. His utter commitment to the role was reflected in his comfortable discomfort in Hughes’ shoes, displaying delusions of invulnerability alongside Hughes’ mental instability with striking ease. DiCaprio’s Othelloian performance is regimented in its form, holding charisma, bravado and weakness all in one hand. In Leo’s grasp, Hughes’ pain, distress and frustration feel as real as the air he breathed.

DiCaprio’s seemingly bottomless search to play radically interesting characters peaked with The Aviator, acting as the precursor to his Wolf/Gatsby trademark, and a defining highlight in a glittering career. It was certainly his finest performance to date, and arguably, his most rounded, best performance ever.


Yet, he came up against another astounding biopic performance in Ray. Another period story of success to excess, Foxx’s Ray reflects Leo’s Howard. Charming, talented, resilient, charismatic, witty and most importantly flawed, both characters share this enticing blend of characteristics. Foxx’s performance is wonderfully tempered. Ray is not only a blind man in a a bright world, but also a black man in a white dominated country. Ray, like Hughes, is a man who breaks. Though their plight differs, the similarities are obvious.

It is also obvious that Foxx’s portrayal is the best part of Ray. In what could have been an average film, Foxx’s impeccable performance raises the story to new heights. His degeneration is powerful, his morals jarring and the pain of his unique situation is truly affecting. Foxx’s performance is one of deep humanity.

It is hard to dispute that Foxx deserved his Oscar. His role feels a harder beast to perfect and whilst DiCaprio’s performance may be more whole, it is hard to be sour. Foxx is Ray Charles, and whilst my personal preference may not align with the result, his performance was deserving of such acclaimed recognition.


His Second Best Actor NominationBlood Diamond

Nominated for Best Performance by an Actor in a Leading Role in 2007 – Beaten by Forest Whitaker in The Last King of Scotland.

Image courtesy of

Leo’s performance in Blood Diamond is another excellent showing. His character, a South African conflict diamond smuggler, is in a most hopeless spot. Stuck in Sierra Leone, he has little chance of prospering. DiCaprio is characteristically charismatic, but he is also deeply conflicted. DiCaprio captures his character’s internal struggle between selfishness, selflessness and cynicism acutely, and transforms his role from villain to hero with expert subtlety.

However, it is hard to win the top prize when you’re performance isn’t the even the best in the picture. Djimon Hounsou is a revelation as a desperate, powerless father, broken by the separation of his family, and willing to give his life to put to back together. Hounsou shows strength, strain, anger and anguish all in equal measure in a remarkable performance. It feels somewhat egregious to me that Hounsou did not pick up the top prize for his performance. This weighed heavy on DiCaprio’s chances of winning his first Oscar, but surely not as heavily as his competition.


DiCaprio was rightly defeated. Forest Whitaker’s performance in The Last King of Scotland is a very special one indeed. Whitaker, playing Ugandan President and dictator Idi Amin, is so alive with happiness and passion, and is utterly terrifying in these moments. Underlying the dictator’s most charismatic moments is the unmistakable air of his unwavering power. With just the frown of his face, Whitaker conveys Amin’s emotional fragility and duality, as the most harmful of scenes turn to deadly situations in the space of a few sentences. Whitaker is astounding in his portrayal of Amin’s emotional collapse as paranoia overwhelms him.

Whitaker’s calibre of performance is simply much higher than that of DiCaprio’s. It is no insult to DiCaprio to say that Whitaker’s Oscar victory was wholly deserved.


His Third Best Actor NominationThe Wolf of Wall Street

Nominated for Best Performance by an Actor in a Leading Role in 2014 – Beaten by Matthew McConaughey in Dallas Buyers’ Club.


DiCaprio’s performance in The Wolf of Wall Street is arguably his most charismatic and physical performance, pre-Revenant. He plays Jordan Belfort, an uber-confident, morally-dubious, dark-souled stock-broker with a less-than-inspirational rags-to-riches story. (Phew, that was a lot of hyphens). Leo sells Belfort’s revolting conduct with such charm and energy, so much so that he managed to dupe a slice of the audience into sympathising with his exploitative actions. Scorsese is obvious in his moral delivery, whilst simultaneously showing that not all evil is duly punished. Leo canters around the screen, manipulating, energising and ultimately implicating all those at Stratton Oakmont, including his sidekick Johan Hill.

DiCaprio’s performance is remarkably human, folding McConaughey’s caricatured advice into his early, naive, ambitious self, creating a personal cyclone. Leo creates a man lost in his own ambition, greed and consumption, a man who is remarkably alive despite his lack of humanity. He epitomises the term ‘leading man’, enveloping every scene he fills.


Yet, DiCaprio’s magic couldn’t overcome that of the McConaissance. McConaughey’s outing in Dallas Buyers’ Club is much more than alright, alright, alright. His character, Ron Woodroof, is a reverse Belfort. Woodroof opens as an offensive, ignorant con-man, sneaking and cheating his way through life. Drugs and prostitutes are par for the course, and whilst Belfort grows into this role, Woodroof is forced to alter his ways after the contraction of HIV. This is a story of redemption as much as it is one of unwavering strength in the face of a death sentence. McConaughey’s performance is pure, raw and unadulterated, hitting with true pain and demanding unyielding sympathy.

His physical transformation is a feat comparable to Christian Bale in The Machinist, and is a big plus for awards voters. His showing is intensified by playing opposite a true equal in Jared Leto’s Rayon. The pair’s chemistry is strained and vital, eclipsing that of DiCaprio and Hill and elevating their individual parts into something much greater. There is no doubt that McConaughey deserved his Oscar; it was just, once again, unfortunate for DiCaprio that he met such dominating opposition.


And that seems to be the theme of Leo’s luck. He has been bested by some truly marvelous performances and there can be little argument against Foxx, Whitaker or McConaughey’s victories. DiCaprio came closest in The Aviator and it may be this year that he reaps the accumulated rewards of his past performances. His legacy may squeak him past his opposition this year, and finally gain the award he deserves.

It is not awards that define a career. DiCaprio will not be defined by his win, or defeat, at this year’s Oscars. He is an exemplary talent that should be highly revered.

Still, it’d be nice for him to get this monkey off his back.

Images courtesy of fanpop, brianjhadsell, overabillion, fromthemovie, virginmedia, 8weekly, highdefdiscnews, forumcinemas, sky, loganbushey and forbes respectively.


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