The Curious Case of Leo’s Missing Oscar

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The other night I was surfing the net to check out views and previews of Leonardo DiCaprio’s upcoming movie The Revenant and something caught my eye. I was surprised at the abundance of memes that re-emphasise the fact that Leonardo, despite being an excellent actor with an impressive body of work, is yet to win an Oscar.

The one meme that stood out is a pic of a solemn looking Leo with a caption above his head that read, “what if in like 30 years they make a film about Leonardo DiCaprio and how he never won an Oscar…And the actor who played him won an Oscar”. It stood out for two reasons; why has he never won? And why is he the poster child for good actors who have never won despite there being so many of them? I am more interested in the first thought because he’s one of the best actors of his generation. Plus I’ve traced his career quite well. I said quite!

Leo is picky about his roles and all for good reason. He arguably hasn’t put out a bad screen performance, except for The Beach which is understandable considering the possible Titanic stardom hangover that haunted the 25 year old at the time lol. So why is it that an actor that has given us memorable silver screen moments in The Gangs of New York, Catch Me If Your Can, The Departed, Basketball Diaries, Titanic, The Great Gatsby and Blood Diamond among others has not been given films most coveted accolade?

Well, there are many theories that try to explain Leo’s missing Oscar but as is the case in most situations with multiple possibilities, the simplest explanation is probably on point. And in this case the simple truth is that: he just been unlucky. I mean four Oscar nominations is quite decent (except being snubbed for Titanic). He has been unlucky in that, in the years he has been nominated, he’s come up against actors who have put out career defining performances.


In what is arguably his most sincere screen performance, playing a mentally handicapped teen in 1993’s What’s Eating Gilbert Grape alongside Johnny Depp, Leo played a risky character, avoided being typecast coz of his looks and in the process earned himself his first Oscar nomination at the aged of 19 and only in his second major film role. That year he lost the Best Supporting Actor Award to Tommy Lee Jones who starred as the unrelenting U.S. Marshall you loved to hate in The Fugitive. For his stellar portrayal of eccentric businessman Howard Hughes, DiCaprio was in 2005 nominated for a Best Actor Award but lost to Jamie Foxx who himself entered film’s big leagues with convincing, tear jerking depiction of Ray Charles.

For his rough, rugged and raw performance in the highly publicised Blood Diamonds, possibly also the setting of his most dignified screen death (he dies quite a lot), Leonardo got another Oscar nod for Best Actor but was this time his efforts were towered by Forrest Whitaker’s an awe inspiring if not loveable characterisation of infamous Ugandan dictator Idi Amin. He was most recently nominated for the 2014 Best Actor Award for his gutsy depiction of money laundering stock broker Jordan Belfort in The Wolf of Wall Street. Once more, he was the bridesmaid, losing out to Matthew McConaughey who ditched his cool guy persona to play determined AIDS patient and activist Ron Woodruff in Dallas Buyers Club. On all four occasions, DiCaprio was magnetic and wonderful as usual but you have to admit that on each of those occasions Jones, Foxx, Whitaker and McConaughey produced soaring and deserving performances.

Regardless of Leo’s luck or lack thereof, you have to admire the artistic development he has achieved over the years. Right on screen, he has made the transition from an ill fated, dark , disturbed boy in This Boys Life (1993), What’s Eating Gilbert Grape (1993), The Quick And the Dead (1995), Total Eclipse (1995), Basketball Diaries (1995), Romeo And Juliet (1996) and Titanic (1997) to an action thriller leading man (thanks partly to Martin Scorsese) in The Gangs of New York (2002), The Departed (2006), Blood Diamond (2006), Body of Lies (2008), Inception (2010) and Shutter Island (2010) to rich, bad guys in J. Edgar (2011), Django Unchained (2012), The Great Gatsby (2013) and The Wolf of Wall Street (2013). But even this 180 degrees on screen turnaround from timid boy to entitled adult has not worked for him (certainly worked for Denzel).

But Leo shouldn’t worry, he’s gonna get his. Screen legends Marlon Brando and Jack Nicholson got theirs in their fifties and he’s only gonna be 41 by the time the next Oscar’s come around. His new movie The Revenant is creating a buzz and has a scene where he fights a bear. The guy is really trying here, hope the Academy will notice. The movie will initially be released on Christmas Day then on a wider scale in January but already the actor’s fans and sympathizers are starting to cross their fingers for the 2016 Oscars. Should he not win on that night or anytime soon, he’s in a really cool class of Oscar ‘losers’ that includes Will Smith, Bruce Willis, Johnny Depp, Sigourney Weaver, Brad Pitt, Samuel L. Jackson, Julianne Moore and Tom Cruise. It might be lonely at the top but it’s certainly kicking down here.


2 thoughts on “The Curious Case of Leo’s Missing Oscar

    Josiah-David said:
    May 6, 2016 at 5:55 am

    Must see!
    “Male Celebrities who are SO MUCH Hotter and Talented than Leonardo DiCaprio” ! 🙂
    Thank me later. 😉


      Chief_want responded:
      May 6, 2016 at 8:58 am

      Cool list indeed,just like u said. Thanks 😉


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