Leo’s Quest for an Oscar

For the past 10 years or so, 3-time Oscar nominee Leonardo DiCaprio has been trying to win an Oscar. That is indisputable. Look at the movies he has attached himself to. He has been the lead in four true stories during the span. He has taken on several actors’ acting roles. The one thing that I believe is holding him back from finally winning his Oscar that he deserves is his perception. There are still a large portion of filmgoers that believe that he cannot act, going all the way back to his love or hate work in Titanic. He is also very opinionated about the environment and other social issues. Some people just do not like him, but it is almost impossible to say that he has not deserved to win an Oscar based solely on performance. It is also ignorant to think that quality of acting is the only variable in Academy voting. When will Leo finally win his Oscar? Will it be this year? I will try to figure that out.

Starting back in 1993, DiCaprio had his showiest role of his career, playing the mentally-challenged kid in What’s Eating Gilbert Grape. Four years later, he was cast as the lead in Titanic, which turned everyone off to DiCaprio for some reason, thinking that he was too soft and could not hold a dramatic role in the biggest movie ever. Who else that age could have done that, by the way? I am part of the minority that thinks that he was actually quite good in that movie. It was totally a role that should have gotten Oscar love, but apparently being the lead in the most beloved movie of the year and being a past nominee wasn’t enough.

After that, flops came his way until he got the chance to work with Scorsese and Spielberg in the same year. Gangs of New York and Catch Me If You Can marked the beginning of modern day Leo. He was tremendous and critically-acclaimed in the latter and mired in mediocre reviews in the former. But it was obvious that he was maturing as an actor. Those critical of him still had the complaint that he cannot hold a movie on his own.

Then came The Aviator, his best performance to date and the one that should have won the Oscar. Why did the Academy not eat it up? Well, who knows? They went with the gimmicky Jaime Foxx role in Ray. But, he had to have won everyone over by this point, right? Not exactly. It was not until 2006, when The Departed came out that everyone sort of warmed up to him, or most people did. It was like when Paul Rudd watches Bourne in The 40 Year Old Virgin and goes, “I always thought that he was sort of a Streisand, but I think he’s rockin the shit in this one…” It was like Leo’s coming out party. Everyone loved him in that tough, gritty role that should have won him another Oscar. But, unfortunately, he was nominated for his more Academy-friendly role in the surprise hit Blood Diamond.

Following that, he had a Ridley Scott role in Body of Lies, an actor’s wet dream in Revolutionary Road, a couple showy roles in Shutter Island and Inception. You would have thought that Winslet and DiCaprio, both looking for Oscars, could have won together in 2008. That would have been a great story, but no. They give Leo the finger by nominating Winslet for another role, and shafting Leo’s movie completely.

Now, this year, it appears to be Leo’s year. But, I do not think so. He has the great physical transformation and makeup work, he plays a character whose role spans a long time, he probably dies in the movie, and it is Clint Eastwood. But, the backlash has already started it seems. I almost want Leo to not win. He is so talented that I want him to win for a really great role, not one begging to win. I think he will obviously be nominated this year, but a win will have to wait.

Next year, Leo will be busy. He has three movies that could get him that Oscar. He plays a slave runner in Tarantino’s Django Unchained. This would be awesome to see him win the Oscar for. You know his character is going to be vicious and brutal, and for him to get recognized for something like this, his reputation may change forever. He also has a Todd Field movie and a reunion with Baz Luhrmann playing the title role in The Great Gatsby. Any of those he could totally shine in. But, I have the feeling that his OScar will have to wait for him to get one more important role in a Scorsese picture. They are the perfect team, and whenever that Teddy Roosevelt film finally gets made, it could be nearing the end of Scorsese’s career, and Leo’s Oscar snubbing could be nearing a mythical status. How awesome would it be if Leo gets his due and Marty gets a parting gift at the same time? That would be so cool to see.

So, we will see what critics and audiences think of Leo in J. Edgar. It very well could sweep everything, but the trailer was a little weak, and I already know exactly what to expect from DiCaprio. If he wins the Oscar this year, good for him. I will be happy that he is no longer called Oscar-less. But to really become the kind of actor that he can be and be viewed as one of the best actors of his generation (which he is), he needs to stop with the shameless Oscar-hunting and do something crazy. A villain role (the Tarantino film might be that), some supporting work, some independent dramas, or an unlikable character. Those are the kinds that win Oscars and the kinds that make critics, Academy voters, and mass audiences most connect with them. He has made some pretty great decisions recently, working with some of the best living directors and being part of some really big hits, but he needs to take a couple risks.

So, that turned out to be more of a rant than an informative article, which I did not intend to happen. But, do you agree? What kinds of roles do you want to see DiCaprio take on in the coming years? Will he win the Oscar this year? Next year? Let me know in the comments.