The Curious Case of Leonardo DiCaprio

True Story.
True Story.

Leonardo DiCaprio is arguably one of the most talented and bankable actors working today. Having made the difficult and often impossible transition from child star – to teenage heartthrob – to serious actor, Leo has established himself as a Hollywood heavyweight. He’s notoriously selective when it comes to scripts, directors, and personal projects. He’s a serious man, on a serious mission: “Win that Oscar”. Despite starring in Oscar-bait movies and giving critically acclaimed performances, Leo DiCaprio still hasn’t won an Oscar. He’s been nominated a handful of times (three to be precise), while starring in seven best picture nominees. While he has had his string of critical and commercial failures (Man In the Iron Mask?!), it almost seems as if he’s being snubbed on purpose, which begs the question, is Leo Oscar-cursed? I’ve come up with three theories to investigate the Curious Case of Leo Dicaprio.

He’s definitely offended someone on the Academy.

Leo DiCaprio in Django Unchained (2012)
Leo DiCaprio in Django Unchained (2012)

Whether on purpose, or by accident, Leo must have offended someone on the Academy in some way. The films he stars in are usually safe choices (with the exception of Django Unchained), and his political motivations are aligned with the very liberal and left-wing Hollywood elite. If he’s offended anyone, in any way, its most likely for fooling around with someone’s girl. It sounds very “highschool”, but these types of situations usually linger in Hollywood (case in point, Angelina Jolie and Jennifer Aniston). Leo’s known to be a playboy. He usually gravitates to tall, thin and blonde Victoria’s Secret Model-types. Chances are that he messed around with an Academy member’s daughter, or girlfriend, or wife! He seems the type. Could this be the reason that Leo hasn’t won his Oscar?

The transfer of the “Scorsese Oscar-Curse”

Match made in movie heaven
Match made in movie heaven

Leo DiCaprio has been touted as Martin Scorsese’s new Robert DeNiro. They’ve collaborated on brilliant, intense, and highly praised films. Robert DeNiro has starred in eight Scorsese films, and was nominated for his work on Taxi Driver, Raging Bull and Cape Fear. Leo and Scorsese’s relationship started with Gangs of New York, at a time when the director was thought to be “Oscar-cursed”. Scorsese’s Oscar-curse is different from Leo’s, in that Scorsese actually gets nominated for his work. Scorsese has been nominated for seven Oscars for directing (ten overall), with one win for The Departed, a film which ironically starred Leo and garnered a nomination for Mark Wahlberg (Marky Mark!). It’s possible that Scorsese transferred a variation of his own Oscar-curse to Leo. While Scorsese always went home a “loser”, Leo often showed up to the Oscars as a glorified “plus-one” – showing his support for a best picture nomination. Since directing Gangs of New York, Scorsese has earned four Oscar nominations (three for Leo collaborations) and Leo has only received two (for Blood Diamond and The Aviator – another Scorsese project). Could the Scorsese Oscar-Curse have transferred to him? Leo has always said that Scorsese has had a great influence on his career; maybe he’s also influenced Leo’s Oscar chances.

He’s just too good

Better than you.
Better than you.

Most actors go above and beyond their own comfort zones, or exceed expectations in order to get an Oscar nomination. Some actors go to physical extremes to draw public and critical attention to their performance, like Charlize Theron dramatically changing her appearance for her nomination and win for Monster, Robert DeNiro gaining a substantial 60 pounds for his nomination and win for Raging Bull, Robert Downey Jr. donning “black-face” for his nomination in Tropic Thunder. Some actors, like Will Smith (Ali), Hugh Jackman (Les Misérables), and Bradley Cooper (Silver Linings Playbook) step outside of their usual “popcorn action movies” to turn in different and unexpected performances and earn Oscar nominations. Others, like Heath Ledger in Brokeback Mountain, take on social issues with interesting and unforgettable performances. Leo is consistently good. Almost too good. The bar might be set too high. While he’s consistently good, some actors seem to exceed expectations to gain an Oscar nomination. Whether he’s playing a mentally challenged kid (What’s Eating Gilbert Grape?) or a sweet-talking slave owner (Django Unchained), Leo delivers. It’s expected that he will turn in an amazing performance, subtle, complex and completely believable. But could the expectation of a great performance be hurting Leo’s Oscar chances?

Leo DiCaprio’s struggle for an Oscar continues in May with the release of The Great Gatsby. Needless to say, expectations are high. Hopefully, this time, Oscar doesn’t play hard to get.

Leo DiCaprio in The Great Gatsby (2013)
Leo DiCaprio in The Great Gatsby (2013)

I’m personally BEYOND excited for Gatsby.


8 thoughts on “The Curious Case of Leonardo DiCaprio

  1. Brilliant post Ruby! Now I am stoked to see The Great Gatsby!
    One tiny addition is that that Leo was also nominated for Best Supporting Actor in 1994 for “What’s Eating Gilbert Grape” – Kirk Lazarus had the best explanation for why he didn’t win the Oscar:P

    Keep on typing!

  2. Love it!

    I would throw in the venn diagram theory that he is too safe/the context of the other nominees/and the mistakes the academy makes, and that the truth is the intersection of those three.

    I mean he is always good, in everything he does, but do you really ever feel like anything he does anything truly boundary pushing? He maintains a balanced line of talent and powerful roles that are to no real end. Basketball Diaries and Gilbert Grape remain his most “dangerous,” because they were real roles, they were depicting a certain semblance of reality, and he was driving them. His roles since the late 90s always seem to be what you’d expect of a traditional leading man in a Golden Age Hollywood sense, they’re good, and he is good in them, but what difference do these stern alphas ever make? Where is their vulnerability? Reality? And where is his challenge?

    Context of the other Nominees:
    This year is the perfect example, because really, speaking of safe, alpha roles, Matthew McConaughey. Like Leo, most people would never doubt that McConaughey was at least somewhat talented (though he has done a terrible job of reminding us in the past 15 years or so… at least until last year). Yet his roles have always been the “same old alpha dude.” Until last year, his best movie was probably still Dazed and Confused, because his character in it was almost almost a preemptive satire of the roles that we would end up relaxing into. Yet, here comes this year, showing everyone something completely different. Leo was not surprising, nor was his role groundbreaking, which were two ticks in his competition’s column, which happens often to Leo.

    Mistakes the Academy Makes:
    Shakespeare in Love. It happens.

    1. Thanks Ryan!

      The memes are getting out of control since Leo’s loss on Sunday… #PoorLeo was trending within minutes of the Lead Actor announcement. I didn’t think he deserved the win for Wolf of Wall Street…as I secretly think he lived that “wall street” lifestyle for a long long time.

      Leo’s time will come. I know it… and hopefully before the “honorary Oscar” phase of his life.

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