ByMark Newton, writer at
Movie Pilot Associate Editor. Email: [email protected]
Mark Newton

It’s the same thing every year. Poor old Leonardo DiCaprio.

For some reason, we just love to lament Leo’s annual disappointment at the Oscars. The Wolf of Wall Street star has racked up three nominations for the Best Actor Award, a single nomination for Best Supporting Actor and a nomination as an executive producer during his career. However, despite this constant recognition he has never got his hands on the coveted golden statuette of some bald dude.

Why do you think this is? Well, let’s try to get to the bottom of it all. Firstly, we need some perspective. DiCaprio has been nominated three times for Best Actor and although this is a quite a lot, he certainly isn’t alone. Robin Williams, Johnny Depp and George Clooney have all been nominated three times without a win, as has the great Morgan Freeman - a man who you automatically assume has won an Oscar at some point in his career. Furthermore, Charles Boyer, Warren Beatty and Albert Finney have all been nominated four times, but also never won. In fact, the legendary Richard Burton holds the record with six nominations and no wins (Peter O' Toole had eight nominations and no wins, although he did receive an honorary Oscar in 2003). In this respect, things could be worse for Di Caprio, statistically speaking.

It is not unusual for actors to be nominated 6, 7, 8 or even 9 times in their careers. Lawrence Olivier and Spencer Tracey both grabbed a record nine nominations, but it does have to be noted that everyone - Burton is the exception - with more than four nominations has won at least once. With this in mind, DiCaprio is right on the border of joining the likes of Boyer and Beatty in the Highest-Best-Actor-Nominations-to-Zero-Wins gang. That’s not a very fun gang.

Indeed, the dreaded four nominations group is a tough place to be, especially for actors reaching the ends of their careers. Luckily, I still think Leonardo has the youth and the ability to grab a few more nominations and potentially bag an Oscar before he retires. In fact, I’m sure of it.

So, why hasn't DiCapro won an Oscar yet? Well, let’s have a look at the films he was nominated for. His first Best Actor nomination came with Martin Scorsese’s The Aviator, a film also nominated for Best Film. Indeed, The Aviator was a biopic which just screamed Oscar bait, while DiCaprio’s own performance was certainly noteworthy. However, 2004 was a rather weak year for Best Actor and Best Film in general, with few actors providing a great traditional - i.e. Daniel Day-Lewis type - performance which the Academy salivates over. Along with DiCaprio, Johnny Depp earned a nomination for Finding Neverland, while he was joined by Don Cheadle (Hotel Rwanda) and Clint Eastwood (Million Dollar Baby) - all strong performances in impressive movies, but none of them particularly stood out or broke the mold. Given this vacuum, it was relative newcomer Jamie Foxx who was able to snatch the award by playing blind piano player Ray Charles. Foxx’s additional requirement to sing and play piano probably helped him stand out in what was a relatively ‘dry’ year for Best Actor, although the fact Ray Charles died a few months before the ceremony could have also had an impact.

In 2006, came Blood Diamond, a conscientious movie which was sure to appeal to the Oscar crowd. However, 2006 also saw Forest Whitaker’s career best performance as Ugandan President Idi Amin in The Last King of Scotland, a movie both geographically and thematically similar to Blood Diamond. Although DiCaprio’s performance in Blood Diamond was certainly commendable (I’m still not sure of that accent though), the gravity and sinister nature of Whitaker’s performance unfortunately meant the result was a foregone conclusion that few could dispute. Leo was good, but he wasn't Whitaker good. Interestingly, 2006 was also the year Martin Scorsese’s The Departed won Best Film. The Academy forbids actors from appearing in the same category twice for different movies, meaning DiCaprio’s performance as Danny Archer in Blood Diamond was selected for his nomination. Personally, I felt his job portraying the troubled and paranoid undercover cop, Billy Costigan, in The Departed was a much stronger performance. I’m not saying it would have won him the gong, but distancing his performance from the clear favorite could have helped.

And then came 2014. The 86th Academy Awards presented perhaps the toughest competition for Leonardo DiCaprio. His prime rivals were Matthew McConaughey - who was flying high on the crest of the so-called McConnaisance - and Chiwetel Ejiofor, an actor who was many bookies’ favorite following success at the BAFTAs. I have to admit, I didn't think DiCaprio had a chance this year. Once again, the serious nature of both 12 Years A Slave and Dallas Buyers Club meant a comedic drama such as The Wolf of Wall Street was unlikely to get much of a look in - in both the Best Film and Best Actor categories. The failure of American Hustle to similarly walk away with any awards is also indicative of this. It might sound insensitive, but films about slavery and AIDS are always going to rule the Oscars.

To put it bluntly, I just don’t think Leonardo DiCaprio has appeared in enough Oscar bait movies, while the Oscar bait he has appeared in just hasn't surpassed the quality of its rivals. Take for example, J. Edgar. Any movie about an American icon should be a surefire Oscar nomination, unfortunately, the movie flopped with both audiences and critics. Its failure meant that, despite a powerhouse performance from DiCaprio himself, the movie was unlikely to generate a Best Actor nomination. On the flipside, movies such as Inception, Django Unchained and Gangs of New York, despite being nominated for Best Film, lacked the Oscar bait necessary - as well as being too dependent on violence and action - to bolster DiCaprio’s chances of nomination and success. But don’t take my word for it. Listen to Kate Winslet explain the Oscar winning potential of Oscar bait below:

So, what does the future hold? Can Leo eventually get his hands on Hollywood’s most prestigious mantelpiece decoration? Well, statistics are on his side. With the exceptions mentioned above, every actor who has received four or more nominations has won an award... eventually. Furthermore, although the Academy officially bestows awards based on individual performances in one movie, it would be naive to suggest an actor’s reputation and entire body of work doesn't come into the mix. Take for example, Paul Newman. The iconic actor was nominated six times from 1958 until he finally won an award in 1986 for his reprisal of Fast Eddie Felson in The Color Of Money. Now, although his performance was impressive, it was by no means a career best, which suggests Newman received the award based less on his actual performance, and more on his entire filmography and legacy. Leonardo is only 39 years old, so he still potentially has a lengthy acting career in front of him. If he stays the course and remains meticulous about the flicks he appears in, he is almost certain to get more nominations and another shot at getting his hands on an Academy Award. The longer he persists, the higher his chances will be.

So what does he have coming up in the future? Well, a quick perusal at his upcoming films does hint at possible Oscar bait. Movies such as The Road Home - which sees DiCaprio playing a war-scarred rancher in Depression-era America - could potentially generate a nomination if not more, especially when you consider Crazy Heart director, Scott Cooper, is helming. Then there’s more historical biopics such as Rasputin and King Harald which traditionally do well, although the current lack of a director means an outcome is hard to predict. However, I personally see a trifecta of potential Academy gold for DiCaprio in Sinatra, The Ballad of Richard Jewell and Wilson.

In Sinatra, DiCaprio is expected - but not yet confirmed - to team up with Martin Scorsese to tell the tale of Ol’ Blue Eyes. A musical performance, combined with a Walk The Line biopic-vibe, is likely to generate some Oscar buzz. Meanwhile, the recently announced The Ballad of Richard Jewell sees DiCaprio teaming up with Jonah Hill for another real-life story, this time about a security guard who is wrongly vilified by the media following the 1996 Atlanta Bombing. The film is based on a Vanity Fair article written by Marie Brenner, the same journalist who also provided the source material for the multi-Oscar nominated The Insider. With this in mind, it could end in Oscar nods, although DiCaprio will only be playing a supporting role in this movie so will not be eligible for Best Actor. His best possible chance could stand with Wilson, another biopic about a great American President. There is still no director, but the wartime setting combined with Wilson’s idealistic visions and his ultimate fall, isolation and depression doesn't get more Oscar baity. Although, having said that, we also thought the same about J. Edgar.

What do you think? Does Leonardo DiCaprio deserve to finally win an Oscar, or is he simply not as good an actor as some of his peers? Give us your opinion below.


Does Leonardo DiCaprio actually deserve an Oscar?


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