DiCaprio and the Oscars

In 1993 a young actor named Leonardo DiCaprio was nominated for an Academy Award for Best Supporting Actor for his role as the developmentally disabled younger brother of the title character in What’s Eating Gilbert Grape.  Twenty three years and a further five Oscar nominations later, four for Best Actor and one for Best Picture (as producer), the actor is still waiting to add the gold-plated britannium statuette to his mantel place.  Despite winning multiple awards elsewhere, including three Golden Globes for Best Actor, the Academy Award has continued to elude DiCaprio.

The fact that DiCaprio has failed to grab an Oscar despite multiple nominations and critically-acclaimed performances has become a part of popular culture.  Simply type the words ‘DiCaprio’ and ‘Oscar’ into an internet image search and you will find a host of memes such as these:

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Should Leo have won an Academy Award by now?  Join us as we examine his previous nominations and the eventual winners.



What’s Eating Gilbert Grape stars Johnny Depp as the title character, a grocerty clerk caring for his obese mother and younger brother (DiCaprio), a younger brother who suffers from a severe developmental disability.  A poor reception at the box office was a stark contrast to the critical reviews which emerged with much of the praise on DiCaprio’s intense, realistic and startling performance, leading to several award nominations, among them his first Oscar nod.  The same year saw stiff competition in the Best Supporting Actor category including Ralph Fiennes for Schindler’s List, however the Oscar went home with Tommy Lee Jones for his role in The Fugitive.

Tommy Lee Jones is a fantastic actor and was deservedly nominated for Oscars for JFK (1991), In the Valley of Elah (2007) and Lincoln (2012), yet his role as Deputy U.S. Marshal Gerard is his only Academy win and in retrospect both DiCaprio and Fiennes gave stronger, more deserving performances in 1993.



Despite critical and commercial success including James Cameron’s Titanic (1997) and Martin Scorsese’s Gangs of New York (2002), it would be 12 years before DiCaprio was nominated for another Oscar, this time Best Actor for biographical drama The Aviator.  Directed once again by Scorsese (currently 5 collaborations to date) Leo plays Howard Hughes, an aviation pioneer and successful movie producer who also suffers from a severe case of obsessive-compulsive disorder.  The film depicts his struggle to succeed in the aviation field, pioneering new craft and battling a Senate investigation while his mental health deteriorates due to his OCD and the constant stress he places on himself by his actions.

Support is provided by a multitude of familiar, talented faces including Alan Alda, Cate Blanchett, Kate Beckinsale, John C. Reilly, Ian Holm and Jude Law.  Despite the sea of talent surrounding him, DiCaprio manages to make the film his own in a powerhouse performance full of small moments of madness and outlandish scenes of eccentricity.  Receiving an impressive 11 nominations from the Academy, the film went on to win five but the star missed out again, this time losing to Jamie Foxx for his own wonderful performance in Ray (as Ray Charles).  Johnny Depp (Finding Neverland), Clint Eastwood (Million Dollar Baby) and Don Cheadle (Hotel Rwanda) were also nominated in an exceptionally strong year in which all nominees could have deservedly won.



This time DiCaprio only had to wait two years before his next near miss with an Oscar Statuette for his performance in Blood Diamond, a political thriller where he played a gunrunner trying to smuggle a precious pink diamond out of Sierra Leone, a country torn apart by political unrest.  The film depicts the struggle between the government and insurgent forces and includes many scenes featuring the atrocities of the war, including the amputation of hands to discourage voting.

DiCaprio once again received high praise for his role, particularly for his convincing accent and the subject material helped to finally shed the boyish image he had carried for years.  The winner of the Best Actor Oscar this time was Forest Whitaker who won widespread acclaim for his role in The Last King of Scotland.  Whitaker was undoubtedly the right choice here, giving a career-best performance in which he dominated all the awards ceremonies that year, winning not only the Academy Award but also the Golden Globe, BAFTA and Screen Actors Guild Award plus many more.  If Leo had to lose to somebody, Whitaker was the right person.



DiCaprio teamed up with director Scorsese, both also acting as producers, for The Wolf of Wall Street.  Leo plays Jordan Belfort in this biographical black comedy that recounts the story of Belfort and his time as a corrupt stockbroker which led to his downfall.  The film was a major success and became Scorsese’s highest grossing film yet while co-star Jonah Hill also enjoyed critical success as Donnie Azoff, business partner and friend to Belfort.

The film was nominated for Best Picture and DiCaprio once again got a nod for Best Actor in a year filled with fantastic performances from all the nominees; Christian Bale for American Hustle, Bruce Dern for Nebraska and Chiwetel Ejiofor for 12 Years a Slave all lost out.  The winner was Matthew McConaughey for an outstanding display of acting in Dallas Buyers Club, where he played an AIDS patient during the 1980s.  McConaughey’s performance and physical transformation also won at the Golden Globes and Screen Actors Guild Awards while rejuvenating a career that had become synonymous with romantic comedies.  The Wolf of Wall Street lost out to 12 Years a Slave for Best Picture, meaning Leo was left empty-handed once again, albeit against worthy winners.



This year could belong to Leo.  His role in The Revenant as a man left to die in the wild after being mauled by a bear who seeks revenge on those who abandoned him.  That summary, which sounds like a 1980’s action movie plot, fails to capture what is a harrowing film with another star turn by DiCaprio.  Although he has starred in better movies we once again see Leo giving a stunning performance that captures your interest from the start and takes you along for a sublime ride before a tense finale, with slight echoes of Gladiator, allows you to breathe once again.

On paper the competition looks stiff; Matt Damon, Bryan Cranston, Michael Fassbender and current title holder Eddie Redmayne.  All four are big star names common to awards and nominations for acting supremacy and all have put their best foot forward yet the performance from DiCaprio has become the favourite to win.  His intensity and commitment to the role holds The Revenant together and while the film shouldn’t win Best Picture (Spotlight and The Big Short are better movies as a whole), DiCaprio should be rewarded for the best movie performance of 2015.  He should have won for his performance in 1993.  He should win for his 2015 role.  I can’t wait to find out.  Pretty sure he would like to know as well.

Good luck Leo!

The Academy Awards will take place on February 28th.

N.B. Years used as headings correspond to the year being judged and awarded by the Academy and not the year the Oscar Night took place e.g. The 2016 Oscars are under the heading 2015 as that is the year being awarded.




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