The Many Oscar Failures of Leonoardo DiCaprio


Even if you have never seen any of his movies, you probably heard of Leonardo DiCaprio. He is a prominent figure in the media with a career stretching back two decades. From his relatively humble beginnings as a supporting cast member for Growing Pains (1985) and low-budget horror flicks like Critters 3 (1991), to the teenage heartthrob of the 1990s with movies like Romeo + Juliet (1996) and Titanic (1997). DiCaprio has now become a major Hollywood icon starring in films made by internationally recognized directors such as Christopher Nolan and Martin Scorsese. DiCaprio’s acting portfolio is as diverse as the opening ceremony at the Olympics.

With a rich acting career playing many diversified and esoteric roles, the objectively biased men and women at the Academy of Motion Picture Arts and Sciences still deem him unsuitable for his talent. DiCaprio’s quest for Oscar gold has been a 22 year journey in the making. However, 2016 might be the year in which our friend might finally be able to hoist the statue above his head and list the litany of supporters that made it possible.

From snubs to near misses, this rollercoaster of an odyssey details the times in which DiCaprio should, and rightfully should not, have won.

DiCaprio’s journey begins with the midwestern drama What’s Eating Gilbert Grape (1993). His performance as the title character’s developmentally disabled younger brother garnered widespread critical acclaim and a supporting actor nomination at the Academy Awards. At the age of 19, this was the film that jumpstarted DiCaprio’s career and made him one of the most sought after young actors in the 1990s. His portrayal as a mentally disabled teen was so realistic that many audiences’ and critics’ reviews on IMDB thought he was not an actor playing a role but rather an actor with a mental disorder. When the film first premiered in 1993, Roger Ebert, renowned Hollywood film critic, stated on his website that DiCaprio deserved to win the category he was nominated for. Unfortunately, DiCaprio did not go home with gold that night. Instead the award was giving to Tommy Lee Jones for his role as U.S. Marshal Samuel Gerard in the film The Fugitive (1993).

Fast forward 11 years, DiCaprio is nominated again for an Academy Award, this time for Best Actor. Depicting the legendary filmmaker Howard Hughes in the film The Aviator (2004), Dicaprio succeeded in capturing the decline of the once great pioneer as he slowly drifted into reclusive madness. However, some people believed that without direction from Martin Scorsese, the mastermind behind Goodfellas (1990) and Gangs of New York (2002), DiCaprio’s name would not have even been on the list. Nevertheless, he ended up losing to another biopic starring Jamie Foxx as “The High Priest of Soul” Ray Charles.

Only two short years later DiCaprio’s name finds itself back on the list for Best Actor. His role as Danny Archer, a white Rhodesian gun smuggler, from Blood Diamond (2006) accumulated praise even though some found the narrative to fall a little flat. It was during this time that DiCaprio grew up significantly in terms of his acting career. He went from a name only talked about on the schoolyard to a major player within the industry, knocking at the door that separated himself from film greats. Unfortunately, not even this dramatic transformation could sway the voters into handing him that little golden man. DiCaprio ended up losing the 79th Academy Awards to Forest Whitaker for his portrayal as the third president of Uganda and the “uncrowned King of Scotland” Idi Amin.

DiCaprio’s last and most recent defeat comes from the Hollywood smash-hit The Wolf of Wall Street (2013). DiCaprio plays the character of Jordan Belfort in this overindulgent film about an intuitive and charismatic stockbroker with a laundry list of vices. His performance was praised by many critics and the film was featured in Rolling Stone’s and The Atlantic’s top tens list for films in 2013. It became the highest-grossing film by Martin Scorsese and the magnum opus for DiCaprio, which all his roles will be compared to. Sadly, DiCaprio not only lost the Best Actor award, to Matthew McConaughey in Dallas Buyers Club (2013), but also a Best Picture nomination for which he was a producer.

Regrettably, the Academy has even gone so far as ignoring some of DiCaprio’s best work from the oscar ballot. The two most apparent snubs were for the films Catch Me If You Can (2002) and The Departed (2006). The Spielberg directed film, Catch Me If You Can, recreates the life of check forger Frank Abagnale Jr. who notoriously conned millions of dollars while impersonating a Pan-American pilot, a Georgia doctor, and a Louisiana parish prosecutor. While The Departed sheds light on the corruption in a Massachusetts State Police department and the powers of deception embedded within an Irish crime gang. Though these films are different in almost every way, the two blatantly obvious similarities are DiCaprio’s prowess as an actor and the non recognition for his attempts.

Things might be very different for DiCaprio this year. His role in the American frontier revenge film, The Revenant (2015), might just be the one to end this lengthy endeavour. Plagued with unforgiving weather, frostbite and strenuous working conditions, DiCaprio soldiered on to create one of the best films of the year. DiCaprio even went against his strict vegetarian practices and devoured a raw bison liver for the sake of the film. If not for his outstanding performance as real-life mountaineer Hugh Glass, DiCaprio should win for his sheer dedication.

Hopefully, this will be the year in which DiCaprio’s turbulent pilgrimage will come to an end. Finally, awarded for his efforts. 

Christain Haitz can be reached at

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