PG Cooper: Does Leonardo DiCaprio Really Deserve An Oscar?

Posted: February 28, 2013 by Daniel Simpson (PG Cooper) in Commentary
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Leonardo DiCaprio is one of the great actors to have never won an Academy Award. Now this has been known for a long time, but it seems like the topic has been discussed a lot more recently, likely as a result of Leo not receiving an Oscar nomination for his work in Django Unchained. Now I’m definitely a DiCaprio fan and I’ve loved a lot of his performances, but I started to wonder if DiCaprio ever really should have won. Sure he’s a great actor with a lot of great performances under his belt, but one also has to consider the competition too. So that’s exactly what I’ve decided to do. I’m going to look at a handful of DiCaprio’s more prominent roles and films as well as the competition from each year in order to find out if DiCaprio really should have won by now. An asterisk indicates a nomination.

1993: What’s Eating Gilbert Grape?*


In all honesty I haven’t seen this film in a long time, but Leo’s performance as stuck with me pretty well. DiCaprio has the role of a mentally disabled young boy and he handles it extraordinarily well. When playing mentally disabled people, it’s easy to fall into offensive territory, especially for a young actor. Thankfully DiCaprio never falls into that hole and portrays his character respectfully and accurately. It’s a great performance, though if I had to point out a weakness it would be that even though DiCaprio does a good job handling the mental disability, there isn’t much of a character out side of that. Granted, this is in part because DiCaprio is in a supporting role, but it’s worth considering all the same. That year, Tommy Lee Jones won the Oscar for a good, albeit not really Oscar worthy performance in The Fugitive. Also nominated however was Ralph Fiennes for a stunning turn in Schindler’s List. Another fine supporting performance came from Sean Penn in the underrated Carlito’s Way. In all honesty, out of the four actors mentioned I think I’d give the Oscar to Sean Penn first, and if not in him than Fiennes. So while DiCaprio made a great case for himself, there were better performances that year.

1996: Romeo and Juliet


Geoffrey Rush won Best Actor for Shine (a movie I haven’t seen), but when I consider the great performances from Steve Buscemi in Fargo, Ewan McGregor in Trainspotting, Kenneth Branagh in Hamlet, and Billy Bob Thorton in Sling Blade, it’s clear Leo had a fair share of competition. More importantly his performance in Romeo and Juliet is actually pretty weak (the man isn’t a Shakespearean actor) and I only included the film because it is notable.

1997: Titanic

Leonardo DiCaprio titanic (1)

The role that turned Leonardo DiCaprio into a household name and still one of his most beloved. In fact I don’t doubt a lot of people posting DiCaprio/Oscar memes think this is the film he should have won for. To his credit, DiCaprio is very good in Titanic. He’s charismatic, charming, and extremely likable. His performance is also one of the most memorable traits in the film. But with that said the character of Jack Dawson is pretty one-dimensional and uninteresting. He feels more like a woman’s fantasy than a real character. This is more of a flaw with the writing but it does limit how effective DiCaprio’s performance can be. Jack Nicholson won the category for his performance in As Good As It Gets, a film I haven’t seen, but given that it’s Jack Nicholson I’m sure it was a good performance. However also nominated was Matt Damon for Good Will Hunting in a performance just as charismatic as DiCaprio’s but with a lot more depth. The same can be said for Mark Wahlberg in Boogie Nights. Guy Pearce and Russell Crowe both gave great performances in L.A. Confidential but may have been seen as Supporting do to the ensemble nature of the cast. Hell I even think Ben Affleck gave a great performance in Chasing Amy, though I realize a nomination for a Kevin Smith film would never happen. Bottom line, while I could maybe see DiCaprio getting an Oscar nomination, he definitely did not deserve to win.

2002: Catch Me If You Can and Gangs of New York


l_217505_603a98ceAfter Titanic, Leo had a few years of irrelevant films before coming out big working with Steven Spielberg and Martin Scorsese. His work in both films is very good. In Catch Me If You Can, DiCaprio takes the same charm and charisma he had in Titanic and applies it to a character with a lot more layers. He’s also pretty good in Gangs of New York, though the character isn’t very deep. Still it’s a good performance and the beginning of DiCaprio moving away from his stance as a teen idol. So let’s look at the competition. Adrien Brody won Best Actor for a very moving performance in The Pianist. Also nominated was Gangs of New York co-star Daniel-Day Lewis gave a phenomenal performance and Nicolas Cage for an unforgettable dual role in Adaptation. That year also gave us Tom Hanks playing against type in Road to Perdition, Ed Norton in 25th Hour, Tom Cruise in Minority Report, George Clooney in Solaris, and even Adam Sandler (yes, Adam Sandler) in Punch-Drunk Love. There were a ton of great performances in 2002. Of all of them, I’d probably have given the Oscar to Nicolas Cage who is amazing in Adaptation. If not him, than probably Daniel-Day Lewis for Gangs of New York or Ed Norton for 25th Hour. So no, I don’t think DiCaprio should have won in 2002. In fact, looking at all the great leading performances, I may not have even nominated either of DiCaprio’s performances.

2004: The Aviator*

aviator leo 1

After over ten years, Leonardo DiCaprio finally was nominated for his second Oscar and I can say it was well deserved. DiCaprio is fantastic in The Aviator. He fully embodies Hughes and gives the man a lot of character and depth. Quite frankly he’s mesmerizing to watch and The Aviator might just be his best performance. But did he deserve to win the Oscar? Well, Jamie Foxx for Ray. Haven’t seen it, no comment. In fact other than DiCaprio, the only nominee I’ve seen is Clint Eastwood in Million Dollar Baby in one of his best dramatic roles. However, there are some great performances from non-nominees. Jim Carrey was incredible in Eternal Sunshine of the Spotless Mind, a film which fully showed off is comedic skill but also downplayed it in favour of some very powerful dramatic beats. Tom Cruise went against type as a chilling badass in Collateral and Paul Giamatti was great in Sideways. There were some fine choices to choose from, and I honestly think it’s a very tough call between DiCaprio and Carrey.

2006: The Departed and Blood Diamond*


leo_narrowweb__300x46401In 2006, DiCaprio only starred in two films but both of which made an impact at the Oscars, earning a total of ten nominations between the two (five each). His performances in both films are quite good, bringing a lot of energy to the roles as well as a certain level of depth. Overall, I’d say his performance in The Departed is the superior role, but like I said he’s good in both films. But what about the competition? Well, Forest Whitaker won Best Actor for The Last King of Scotland, a film I haven’t seen. I have however seen nominee Ryan Gosling who gives one of his best performances as a drug addicted teacher in Half Nelson. That year also gave us strong work from Ken Watanabe in Letters from Iwo Jima, Clive Owen in Children of Men, Daniel Craig in Casino Royale, Hugo Weaving in V for Vendetta, Sacha Baron Cohen in Borat, Ulrich Mühe in The Lives of Others, and Hugh Jackman and Christian Bale were both great in The Prestige. A lot of great performances, but ones DiCaprio is just as good in The Departed as all of these actors are in their films. In fact he’s better than most of them and definitely deserved to be nominated. However, I believe the victory that year should have gone to Ken Watanabe for his moving performance in Letters from Iwo Jima. Though a much more subtle performance than either of DiCaprio’s 2006 efforts, Watanabe brings a fascinating character to life and brings such an air of dignity to the role. He shows a lot of complex sides while delivering a very emotional performance.

2008: Revolutionary Road


Revolutionary Road was a definite step down for DiCaprio after the streak of The AviatorThe Departed, and Blood Diamond. Not that he’s really bad, but the performance consists of a lot more yelling and less character. Now I do think DiCaprio is perfectly cast playing opposite Titanic co-star Kate Winslet. Their couple in Titanic are often seen as the “perfect couple” so seeing the two as a couple slowly failing is very uncomfortable and effective. But like I said, the performance is nothing special. DiCaprio has his moments mind you, but it doesn’t even compare to what was done by so many other actors that year, including: Sean Penn in Milk, Frank Langella in Frost/Nixon, Brad Pitt in The Curious Case of Benjamin Button, Michael Fassbender in Hunger, Benicio del Toro in Che, Josh Brolin in W., Clint Eastwood in Gran Torino, and especially Mickey Rourke in The Wrestler.

2010: Shutter Island and Inception


Inception_Leonardo DiCaprio

In 2010, DiCaprio got to play two very similar characters in Shutter Island and Inception. The movies themselves were very different, but both characters were going through very similar feelings and experiences. I probably lean towards his role in Inception because it allows DiCaprio to handle grief and sorrow but also lets him be a cool infiltrator. At any rate, both performances were very good and a big step up for Leo after Revolutionary Road, but how do they stack up to the other top performances of 2010? Well, Colin Firth won the Oscar for The King’s Speech and for all my complaints about that film he isn’t among them. Other nominees include Jesse Eisenberg in The Social Network, Jeff Bridges in True Grit, and James Franco in 127 Hours. Great work was also done by Ryan Reynolds in Buried, Kevin Spacey in Casino Jack, and Casey Affleck in The Killer Inside Me. Still, DiCaprio’s work is certainly on the level with all those actors, right? Well, most of them. Great as DiCaprio was in Inception (and Shutter Island) the top performance of 2010 has to go to James Franco in 127 Hours. He showed a tremendous amount of range, had a great arc, and carried the film for the most part.

2011: J.Edgar


I liked J. Edgar and I liked DiCaprio’s performance in it quite a bit at the time. But here we are a year and a half later and I barely remember the film or the performance. I still think Leo did a good job, but Best Actor over the likes of Jean Dujardin in The Artist, George Clooney in The Descendants, Ryan Gosling in Drive and The Ides of March, Michael Fassbender in Shame, and Joseph-Gordon Levitt in 50/50? Hardly. Michael Fassbender’s work in Shame was the best performance by a lead actor in 2012.

2012: Django Unchained


I won’t spend too much time on this one given how recent this is so I’ll go through quickly. Samuel L. Jackson gave the strongest performance in Django Unchained and Christoph Waltz was better as well. Also consider the great supporting turns from the likes of Tommy Lee Jones in Lincoln, Javier Bardem in Skyfall, Robert De Niro in Silver Linings Playbook, and of course Philip Seymour Hoffman’s PGCMA winning role in The Master. So Leo really didn’t deserve it in 2012.

So to circle back to the point of this post; does Leonardo DiCaprio really deserve an Oscar? The answer is yes he does… for The Aviator. Sorry for the misdirection earlier, but I couldn’t reveal my answer so early in the post. Anyway, The Aviator is definitely DiCaprio’s finest hour. It’s the film which solidified DiCaprio as a lot more than a teen heart throb and also showcased the most of his talent. No Leonardo DiCaprio film relies on his performance as much as The Aviator and he completely delivers. It ‘s also important to note that he is better than his competition (that I’ve seen). I love Eternal Sunshine and I love Carrey’s performance in it, but I can’t deny how good Leonardo DiCaprio was and is in The Aviator.

So while I don’t claim DiCaprio has been snubbed time and time again, I do claim that he has one performance which was worthy. Keep on mind I haven’t seen Ray, so my opinion may change, but in all honesty I doubt it will. 


  1. Mark Walker says:

    DiCaprio was outstanding in the Aviator bit I would probably have given him it for Gilbert Grape. I thought he was phenomenal in that film. TommyLee Jones did not deserve it that year, that’s for sure. Fiennes was a strong contender but I would still have gave it Leo.

    • pgcooper1939 says:

      I admittedly need to watch What’s Eating Gilbert Grape?, but for me the best supporting performance that year was Sean Penn in Carlito’s Way.

      • Mark Walker says:

        I loved Sean Penn in Carlito’s Way. He was superb in that but I still think DiCaprio had a more difficult role. However, I think the academy were sick of giving out awards to roles of that consisted of learning disabilities. Normally, it’s a shoe-in but sadly not for DiCaprio.

      • pgcooper1939 says:

        That was also the same year Anna Paquin won for The Piano. They probably didn’t want to award two young actors in one year.

    • GaryLee828 says:

      I’m with Mark. DiCaprio was amazing in Gilbert Grape; definitely his best performance I have seen. Tommy Lee Jones for “The Fugitive” beat him? lol. DiCaprio gave what I think is one of the best performances I have seen along with Billy Bob in Sling Blade; Sean Penn I Am Sam. I made a “Best Performances” page on my blog if anyone cares to look. Leo is one of the first ones on the list (although they’re not ranked in any order).

  2. rochpikey says:

    I agree 100% with everything you have said. He has had some nomination worthy performances but if he were to have won one by now, the only one that I really feel he could have was for The Aviator. But should he have won? That’s a tough call since Jamie Fox did an amazing job in Ray. Once you see Ray I think you will see why it was such a close race between the two.

  3. CMrok93 says:

    Yes, he should have won by now, but he will win very, very soon. Hopefully, at least.

  4. Hunter says:

    Jamie Foxx is pretty fantastic in Ray, too. I probably would have also gone with Leo, however, maybe just because I like him more? I’m not sure. I agree that if there was one (though I haven’t seen all of these) he should have won for out of what he has done so far, it’s for playing Howard Hughes. He handles the role really well and makes Howard a sympathetic character, but still brings out he unfavorable qualities. Unfortunately, Jamie Foxx kind of does the same thing in Ray… makes you sympathize with a character when you’re not really sure if you should.
    I was also very impressed with him in The Departed, but I haven’t seen Letters from Iwo Jima yet or really any of those other films you listed so I can’t really comment.
    Have to disagree with you (somewhat) about Django though. Jackson probably was the best out of all those supporting actors, but I think Leo had a more challenging role than Waltz and carried it out just as well. So maybe he shouldn’t have won this year, but he should have at least been nominated.
    There’s still 2013 though! I hope The Wolf of Wall Street is good enough to get him one this year.

  5. ckckred says:

    I would have given him an Oscar for Django Unchained. Him getting snubbed was one of the biggest mistakes the Academy has made this year.

  6. GaryLee828 says:

    You really, REALLY have to watch certain films to help validate your point before writing articles such as these. Since you have not watched “Ray” you have no opinion on who should have won. You can’t write an article like this and just say “Well, I don’t think I would like Jamie Foxx more than Leo”. You’ve got to watch it and THEN assess an opinion. Same goes for your 2006 pick when you said Wantabe deserved the Academy Award, but yet you had not watched Whitaker’s performance.

    I like to see bloggers go into depth and analysis films, and actors, etc., and so I liked reading – but at the moment until you watch “Ray” you really don’t have a voice to say Leo “deserved” the Oscar.

    Now for me, I did watch “The Aviator” and I did think it was one of Leo’s better performances – but I cannot say if it was better than Jamie Fox in “Ray” b/c I never watched “Ray” b/c I don’t like Jamie Fox. Therefore since I have not watched it I don’t have an opinion…

    I think Billy Bob Thornton deserved the Oscar for “Sling Blade” but I have not actually watched “Shine” so I cannot say for absolute certainty that he was robbed. I would not write an article about it expressing my sentiments b/c I can’t state why – b/c I haven’t seen it.

    If you think an actor should have beat out an actor who won then watch the roles and THEN make an assessment and explain why you feel as you do…

    For example:

    I think Sean Penn was robbed for “I Am Sam” in 2001. No way did Denzel Washington deserve it for “Training Day”…and I can say that b/c I watched both films. Denzel was hardly extraordinary. Nigga this, nigga that, smoke it! smoke it! HA HA, my man! is all he did for the course of the film in which pretty much any actor could have emulated just as easily. And Denzel is my favorite actor – so for me to say my favorite actor robbed Sean Penn (and Russell Crowe) holds weight. I thought Denzel should have been nominated in the 2004 Oscars for “Man on Fire” where he puts on his true acting ability. You think Leo was better in The Aviator than Denzel was in “Man on Fire”? I can’t say if Denzel deserves the Oscar over Jamie Fox b/c I can’t bring myself to watch “Ray”. You have seen “Man on Fire” haven’t you? You have to have seen it to answer that question; I don’t care what your guess is! lol.

    I totally agree The Departed was a better performance than Blood Diamond. Nominated for Blood Diamond? What? Like you said, a good performance, but not an Oscar performance.

    I like reading articles like this, but before completing an article like this you just need to back your statements by seeing the actual films you’re talking about. That means if you want to preach Leo was robbed you have to sit through “Ray”. Obviously, like me, you don’t want to, or you would have done it by now. lol.

    I also agree that Samuel L. Jackson was better in DU. If anyone was robbed of a nomination it was him who turned in his best performance since Pulp Fiction and Black Snake Moan. I want to say he should have gotten the nomination over Arkin, but I have not seen “Argo” so I can’t say.

    • pgcooper1939 says:

      I fully acknowledged that I need to see films like Ray in my post, but just because I haven’t seen it doesn’t mean I can’t write a post like this. So don’t tell me I have no opinion on the topic, especially when I never said Leo was better in The Aviator than Jamie Foxx was in Ray. All I said was, based on what I’ve seen, Leo should have won an Oscar for The Aviator. Also, if I had waited to see every notable performance from every year I discussed in this post than it would take me a year or so before I could write something like this. Writing it now was important to me because the discussion of whether or not Leo deserves an Oscar has been extremely prominent recently and I wanted to capitalize on that before someone else did.

      • GaryLee828 says:

        You didn’t need to watch every movie from every actor b/c it would have been moot points since you didn’t feel DiCaprio was the best of that year – but “Ray” was the one film you did need to see in order to drive your point to determine if it was in your opinion better than Leo’s performance from “The Aviator” – but since you didn’t see “Ray” you have no opinion on the matter – and that’s why I read the article to get your opinion. If I am going to write an article about a topic like this then I simply watch the film(s) pertaining to the topic-at-hand so I can provide an actual valid opinion. And I think anyone offering up an opinion on a matter should do the same.

      • pgcooper1939 says:

        I admit, seeing Ray would help my point I admit, but I haven’t and I wasn’t going to not write the article because of that.

        Given how intense you are about this, I wish I’d just lied and said I’ve seen Ray :P

  7. Paula says:

    Interesting post, I’d forgotten about a couple of these. I thought DiCaprio was a pretty good Romeo but maybe that’s just me. I need to watch THE AVIATOR again!

  8. BrikHaus says:

    The Aviator and Leo’s performance in it both blew me away. Fantastic movie, and fantastic acting. I can’t believe he didn’t win for this. Actually, I can, since the Academy sucks giant cock. But, yeah, he ruled in that movie. I can’t imagine him topping that performance, but hopefully someday he’ll be recognized for how good he is.

  9. themovievampire says:

    I don’t think you fully understand just how much of a splash Jamie Foxx made in 2004. This was one of the first biopic performances that tried to replicate the mannerisms of a famous person with that degree of fidelity. I don’t know that we would have seen performances like Phillip Seymore Hoffman in Capote or Helen Mirran in The Queen if Foxx hadn’t started the trend.

    I get why you you’re not all that excited to see Ray. It’s a super straightforward biopic with some terrible dialogue and really weird ending, but I don’t think anyone can really talk about the best performances of 2004 without having seen it.

    • pgcooper1939 says:

      I actually would like to see it and I also know that I won’t know for sure if Leo deserved Best Actor or not until I see it, but I also really wanted to write this post and didn’t want to wait until I’d seen Ray to do so.

  10. I think Leo will eventually win an Oscar at some point in his career, it’s just a matter of time.

  11. maryann kish says:

    Leo has been needing to get his Oscar for years. The beginning for me was Titanic. He puts his All into every movie he takes part in. A movie that the person who wrote the lengthy well exhibited post left out Body of Lies.

  12. maryann kish says:

    I think you ought to consider deleting all the 2013 entry’s.

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