Best Actor Watch: The Curious Case of Leonardo DiCaprio and Oscar

I’ve spent twenty years online. I was on the internet before there was really a working web. There are things about it I understand and things I don’t. I will never snapchat and it took me a while to figure what memes were and how they figured into daily life. One thing I really never got or ever became immersed in was the internet’s obsession with Leonardo DiCaprio winning an Oscar. My teenage daughter doesn’t know much about who deserves to win Oscars but she knows “everyone” thinks Leonardo DiCaprio should have by now.

The obsession ranges from “Leo wants an Oscar bad” to “Leo should WIN AN OSCAR NOW.” There is a parasite twin meme about Leo dying in movies. Why this sprang up, how it was birthed, how it became a “thing” is something I cannot explain. I will not pretend to understand it but I do see that it’s there. Each time Leo comes up for Oscar consideration the whole thing is whipped up again and with the Revenant the movement is going to reach a fever pitch.

Why hasn’t Leo ever won an Oscar?  Gold Derby’s Tom O’Neil would say he suffers from “pretty boy syndrome.” The middle-aged men in the Academy do not respect pretty boys. Whether there is resentment or jealousy or whether they think they are just getting by on their looks, what benefits good looking women in the Oscar race often does not benefit men.

DiCaprio did not start out his career as a pretty boy. He started out as a respected character actor earning his first nomination in the supporting category for What’s Eating Gilbert Grape in 1993.  In typical inexplicable Academy fashion, they gave Tommy Lee Jones an Oscar for phoning it in because they liked him and his character so much.

Still, DiCaprio was an instant sensation but not yet beloved as a matinee idol. That ship would sail and then crash into the iceberg with Titanic in 1997, although one could argue the seeds were most certainly planted with Romeo + Juliet (le sigh). Once he starred in Titanic that was it. He was redubbed as an icon.

That Titanic was a worldwide sensation and DiCaprio suddenly the object of every woman’s eye didn’t stop him from continuing to stretch as an actor and would, in fact, deliver sensational performances. His Oscar zone would begin in earnest  starting in 2002 when he worked with Martin Scorsese for the first time in Gangs of New York. DiCaprio was noticed for his work but he was yet to fully transform as he had done with Gilbert Grape. The Titanic bombshell put him in a different category where transformation was mostly discarded in lieu of leading man status. That would change with The Aviator, for which he received his second Oscar nomination and his first leading actor nod.

It was too early for DiCaprio to take it that year. The Aviator had entered the race (I remember because I was around and advocating for it hard back then) as the favorite before Clint Eastwood’s Million Dollar Baby strolled in at the last minute and took the Oscar. It was nominated in a staggering 11 categories and won five Oscars. Jamie Foxx won for a physically transformative performance with Ray. He was working the publicity circuit, and virtually became Ray Charles. At the end of the day, Charles was a more likable character than Howard Hughes. It was clear at that time the Academy wanted to reward Scorsese when The Aviator did so well with the Academy. They’d already given Gangs of New York ten nominations but it was ultimately poorly received.  They needed the right movie. They would get it the next time DiCaprio worked with Scorsese with The Departed.

DiCaprio is quietly the best performance in The Departed and that’s saying a lot. The reason he was not nominated for The Departed was because he WAS nominated for Blood Diamond. In both films he did two different accents. He could not have received two nominations and it’s always struck me as strange that he was nominated for Blood Diamond over The Departed. His competition was:

Forest Whitaker for Last King of Scotland – winner
Ryan Gosling for Half Nelson
Will Smith for The Pursuit of Happiness
Peter O’Toole for Venus

Nobody could have beaten Whitaker that year.  It was just one of those undeniable, too big ignore works. DiCaprio, I don’t think, was any competition for him, especially not in Blood Diamond.

And then DiCaprio would give a string of jaw-droppingly great performances, each one different from the next. He went deeper with each one. He was ignored for all of them:

Revolutionary Road – as an emptied out husband his grief was palpable. Insane wife.
Shutter Island – losing his grip on reality, seeing ghosts. Insane wife.
Inception – the scenes with Marion Cotillard were exceptional. Insane wife.
J. Edgar – he gained weight and used a lot of makeup to completely transform.
Django Unchained – a funny supporting turn unfortunately upstaged by the should-have-been-lead Christoph Waltz
The Great Gatsby – maybe the movie was a mess but DiCaprio was, as usual, beyond great.

By the time he works with Martin Scorsese again it’s for the sublime Wolf of Wall Street. After J. Edgar was ignored, DiCaprio seemed to relax as an actor and once again evolved with his masterful, iconic performance as Jordan Belfort. Finally, the Academy did recognize this work as it really was too big to ignore. Alas, he would not win for this because it was the year Matthew McConaughey lost 40 pounds to play a man dying from AIDS.

There was a bit of noise online that DiCaprio might finally pull a win for Wolf of Wall Street but the Academy was never going to turn down a hero who saved hundreds of lives for a guy who put a candlestick in his ass.

Well now we come to The Revenant. The film won’t come out until the end of the year. By then, we should have a good idea of the kind of competition we’re talking about in that category. DiCaprio, I can tell you, will be at the top of the lists — not to mention the kind of transformative work he’ll have to do for a movie about a man who barely survives in the wilderness and is attacked by bears and native Americans. It should be a showcase work, a performance for the ages – much like almost every other performance he’s ever given.

What’s it going to take? It’s going to take a year where there isn’t one they “like” better. Winning an Oscar has to be a perfect storm of events all swirling around a right here, right now moment. Popularity, publicity, likability — all of those things come into play. The mostly shy DiCaprio who is richer than fuck and busy saving the planet might not want to kiss babies, which is what you need to do to win.

We here at Awards Daily do hereby proclaim that yes, internet, you are right about one thing: Leonardo DiCaprio should have won an Oscar by now. I think you’re wrong that he gives a shit. His concerns are so much bigger than a little gold statue to put on the mantle.