It seems like every year in recent memory, when the Academy Awards roll round, there are a legion of fanboys who say ‘This is Leo’s year! He deserves it for being Leo!’. The truth is that this simply isn’t the case, partly because the only Oscar that works that way is the Lifetime Achievement award, and partly because, despite his many exquisite performances over the last two decades (and more), he’s yet to deserve the big prize.

Before I go any further I want to say that I am a huge Leonardo DiCaprio fan, and I would love to see him win an Oscar one day, because he’s one of the best actors of this generation, and he’s pretty reliable in terms of the quality of the films he makes. In truth, I have no doubt that he will end his career with at least one of the gold statues on his mantelpiece, and when that day comes I’ll be cheering, but here’s why I believe he hasn’t been ‘robbed’ of one so far.


To date, DiCaprio has four acting Oscar nominations (and one for being a producer). The first was for one of his earliest roles in 1993’s What’s Eating Gilbert Grape?. This was a great indication of the way his career was going to go, and saw him nominated before he’d even turned twenty. While this is no doubt a great performance, he lost out to Tommy Lee Jones in The Fugitive, who was deserving, but in my opinion even he didn’t deserve the award, as that year also saw Ralph Fiennes get nominated for Schindler’s List, who would have been a more deserving winner, but once again that’s my opinion. The argument could be made that he was around third in line that year, or at the very best second, both of which mean he shouldn’t have won in 1994.

That escalated quickly

His second nomination came around ten years later in 2004’s The Aviator, which was really the true beginning of people saying he deserved the award every year. The film itself won five Oscars, so it was definitely the right kind of film to clean up at the Academy Awards, but once again poor Leo ran into an unstoppable opponent in Jamie Foxx’s performance in the Ray Charles biopic, Ray. This was a pretty sure bet that year, and even without taking into account the other performances (Clint Eastwood in Million Dollar Baby is a case that could easily be argued), It’s hard to say Leonardo Dicaprio would have been a deserving winner.

Now I’m confused

Now we go to what is in my opinion his best chance at winning to date, 2006’s Blood Diamond. Even though the film is only decent, he is a clear stand out, and he took on a very difficult accent that a lot of actors have struggled with, and succeeded so much that there were people who thought it was too fake sounding… which in a strange way was a good thing? This was also the year The Departed was released, making it an all round stellar year for DiCaprio, one of the best for any actor ever really, but much like Jamie Foxx a few years earlier, nobody was going to beat Forest Whitaker’s portrayal of Idi Amin in The Last King of Scotland. With rumours of Whitaker completely transforming into the role, both on and off-screen, nobody else really stood a chance.

Full convert

His most recent nomination (until he no doubt gets nominated for The Revenant) was for The Wolf of Wall Street. Some people said that he didn’t win because this film was too controversial for the old-fashioned Academy, but the truth is (am I starting to sound repetitive?) he was never going to beat Mathew McConaughey’s unbelievable transformation in Dallas Buyers Club. Even if McConaughey hadn’t won, second in line was Chiwitel Ejiofor in 12 Years a Slave. 

Now looking forward to this year, I can once again confidently say that he won’t win, and shouldn’t win. His performance in The Revenant is excellent, and there aren’t many actors that could have pulled off what he did, but looking at what will most likely be the nominees this year, it would be hard for anybody to argue his worthiness.

What do you think about Leonardo DiCaprio’s lack of Oscars? Do you agree with me, or do you think he should have won any of these years? Share any thoughts in the comments.