Question of the Week: Which film(s) do you think Leonardo DiCaprio deserved to win an Oscar for?

Today is Leonardo DiCaprio’s 39th birthday. He’s still got that boyish look despite being a year short of 40! It’s been sixteen years since Titanic catapulted him to a matinee idol, but he’s since gained a movie star status and practically shed the *curse* that plagued a lot of child actors who’ve hit it big before they even hit 25.

A toast to Leo – he’ll be seen next in The Wolf of Wall Street

I’ve made a tribute to Leo three years ago as part of my Inception countdown post where I listed why I think he’s got what it takes to be called one of Hollywood’s greatest actors working today, on top of being one of the world’s biggest movie stars.

I haven’t made up my list of Top 5 Leonardo DiCaprio movies yet, but I might do that next year. For now, I’m just going to leave it open to discussion amongst moviegoers, particularly on the topic about why DiCaprio still hasn’t won an Oscar to this day despite having been nominated three times.

2007 Nominated
Best Performance by an Actor in a Leading Role
Blood Diamond (2006)
2005 Nominated
Best Performance by an Actor in a Leading Role
The Aviator (2004)
1994 Nominated
Best Actor in a Supporting Role
What’s Eating Gilbert Grape (1993)

My friend Kristin from All Eyes On Screen blog who was in town this weekend and we had a discussion about this (with her fiancee and my husband) as to why Leo’s still empty-handed. Even when his co-star gets nominated or even won, he often got overlooked.

TotalEclipsePosterIt’s almost become a parody how elusive Oscar seems to be for Leo, there are countless articles/tweets/blog posts etc. ruminating why he continually gets snubbed year after year. It’s a shame really as he’s definitely a talented and brave actor. Even in his early work Total Eclipse back in 1995 where he played 19th century French poet Arthur Rimbaud, it was apparent he wasn’t afraid to play daring, unhinged characters. I was quite shocked that he was willing to do full frontal nudity and gay sex with David Thewlis (who played his mentor/lover Paul Verlaine) early in his career. He seems to have a penchant for playing obsessive/neurotic characters, i.e. Howard Hughes (The Aviator), and roles in Shutter Island, J. Edgar, Django Unchained, and last but not least, The Great Gatsby.

As you can see in Nostra’s ‘The Many Faces Of…’ series on Leo, he’s got quite a stellar resume with about 30 feature films under his belt. He may not be the most chameleon-ic actor and he doesn’t bother with adopting a certain accent even when playing non English-speaking characters, perhaps it’s a good idea though given his unconvincing South African accent in Blood Diamond. That said, I still think he’s due for a major award one of these days. Let’s hope he won’t be the Susan Lucci of the Motion Picture industry. Who knows, perhaps Scorsese’s The Wolf of Wall Street will finally be his ticket to Oscar glory!

So my question to you is, which of DiCaprio film(s) have you seen you that warrant him an Oscar nom and/or win?

[Feel free to speculate as to why you think he hasn’t won… that always makes for an interesting discussion ;)]

86 thoughts on “Question of the Week: Which film(s) do you think Leonardo DiCaprio deserved to win an Oscar for?

  1. Victor De Leon

    Gotta go with The Aviator with this one, Ruth. Loved his work in that film. Hard choice, though. All 3 are great performances. Great post!

      1. Victor De Leon

        Of a non-nominated role I think he should have been nominated and won for “The Departed.” My apologies, I should have chosen that one, lol. 😉

        1. Believe it or not I actually haven’t seen The Departed but I’ve read that Mark Wahlberg shouldn’t have been the one nominated from that film.

  2. Leo’s been great in a lot of things, but I think he outdid even himself in last year’s Django Unchained. How he somehow didn’t even get a nomination for that performance still baffles me.

    1. I REALLY thought he’d be nominated for that as I figure it might be more feasible considering it was a Supporting category. I haven’t seen the film yet but even from the trailer he looked practically unhinged!

  3. Django Unchained. It was the first time he’s given a performance that could have warranted an Oscar, in my opinion. Good as most of his performances are, I’ve never one before Django special enough for that prestigious award.

    Trouble for him was that Christoph Waltz was even better than Leo in that flick. 😉

  4. Ted S.

    I think Leo got what I called “Tom Cruise” curse, he’s been labeled an A-list since Titantic and even if he gives the best performance of his career in a film, he still won’t win the golden statue. Look at his career, it’s very similar to Cruise’s, they both tend to work only with well respected or well known directors and starred in mostly high budgeted films. I think if he does something out of his comfort zone, then he might get a shot.

    As far as his performance that I thought deserves an Oscar, I’d go with The Departed, The Aviator and The Basketball Diaries.

    1. That’s right, Cruise has never won either has he? I suppose neither of them hadn’t really done a small indie lately or even a medium-sized film that isn’t a high profile. I think Leo was more daring earlier in his career pre Titanic. Btw, I heard a rumor that he was gonna pull the dvd sales of Total Eclipse, or maybe his agent, I mean they’re probably afraid he’s gonna turn away his younger fans.

      1. Ted S.

        Yeah, both of them didn’t want to labeled “teen heart throub”, in case of Cruise he didn’t want to belong in that “Brat Pack” of the 80s, he only starred more “daring” movies at the time.

        Same with Di Caprio. I’ve never seen Total Eclipse, but I think I heard that rumor too. He also tried to buy another one of his earlier movies so it couldn’t be shown to the public since he hated it.

  5. I really think he was robbed of not being nominated for Inception and Django Unchained. The latter especially as he was just on fire in that scene where he really got to outshine everyone including Waltz.

    1. Hi Steven! Without having seen Django yet, I can’t say about neither performances but if he were THAT good that he outshone even Waltz, then it’s even more of a bummer that he got snubbed!

  6. davecrewe

    “perhaps it’s a good idea though given his unconvincing South African accent in Blood Diamond.”

    I’ve always found this criticism a little unfair, as he was going for a Zimbabwean (or Rhodesian) accent, not South African. Having known people with that accent, I found it quite convincing!

      1. davecrewe

        Yeah, the film itself wasn’t great (it was clearly constructed as anti-diamonds film, at the expense of the narrative) but I did like Leo in it!

    1. Ah, I guess I didn’t know what accent it was supposed to be. It’s still interesting that he opts to do an accent in this film but not others. He played a Frenchman in Total Eclipse and The Man in the Iron Mask without attempting a French accent.

      1. davecrewe

        Yeah, I hadn’t really considered that! I think it’s a smart move for an actor to avoid an accent if they can’t quite nail it, otherwise you get an otherwise good performance weakened by that one element (see: Pacino in Carlito’s Way).

        1. Ahah, I think Pacino is one of those great actors who just can’t do accents. I think only a select few of actors can do different accents convincingly, a lot of Brits tend to be very good. I suppose you’re right that actors should just forgo the accent if it’s gonna be a stumbling block that’d actually bring down the entire film.

          1. davecrewe

            For some reason us Aussies tend to do pretty well (for the most part) with accents – perhaps because our accent is so lazy that it’s easier to snap out of it? Similar thing with a lot of British accents (the less hoity-toity ones anywa) I suppose!

            1. That’s right Dave! Aussie actors are have a knack for accents as well, just like the Brits. I don’t know about your accent being lazy, ahah, I think it’s just a matter that Brits and Aussies probably just have to work harder to get roles in Hollywood, which means they have to be more versatile in portraying different ethnicity.

  7. I’d have to go with Gilbert Grape although I haven’t seen Django yet. Yeah, like Ted said he does have that pretty boy,Cruise/Depp curse, doesn’t he? Robert Redford had it in his day too His only acting nomination came for The Sting
    while actually winning as a director for Ordinary People. Good news is that at the ripe old age of 77 he’s getting through the roof reviews for his one man movie, All Is Lost. Oddly enough he has only two lines of dialogue in the entire movie..

    I remember seeing DiCaprio go toe-to-toe with De Niro as a youngster in the autobiographical This Boy’s Life.
    While the movie is about as fun as sitting through The Great Santini, seriously, DiCaprio boldly made his case as someone to watch.

    I couldn’t find a good trailer so here’s a scene from it. It’s kind of a pivotal scene so be forewarned if you plan on checking it out. Ellen Barkin was really great in this too. I know she’s in a new TV comedy but really where has she been? Ever since she divorced Gabriel Byrne in ’99 she’s been relatively MIA.

    1. I did see This Boy’s Life and it was quite harrowing to watch. Leo was one of the best teen actors in his day too, and the fact that he’s still prolific and relevant today is a testament to his talent and star power.

    2. Ted S.

      Wow good point about Redford, he’s basically the Cruise/Di Caprio in his prime. Seems like he starred in major films throughout the 70s but never won any awards. I thought he’s great in Jeremiah Johnson, a very underrated western from the early 70s. I’m looking forward to see him All is Lost and as the villain in Capt. America 2.

  8. Ruth I think Johnny Depp is at present the Susan Lucci of the film industry. No? I like that he takes chances whereas Leo tends to play it a bit more safe.

    To think Peter O’Toole never won an Oscar after 8 nominations and Al Pacino basically received a “lifetime achievement award” for not so deserving The Scent of a Woman. I just can’t put Leo in their category but who knows what the future holds for him…

    1. Really? How many nominations have he got? I always think that Johnny is more comfortable acting behind somekind of *mask*, that is all the makeup/costume, etc. to play certain roles.

      Poor Mr. O’Toole! I was certain he’d win for Lawrence of Arabia, but then again Gregory Peck was superb as Atticus Finch!

  9. I really, truly cannot explain why Leo hasn’t won yet. He’s an incredible talent and definitely among the finest actors working today, not to mention one of my favorites. If it were up to me, he would’ve won for Revolutionary Road and/or Django.

  10. The only one where I feel he had a performance worthy of an Oscar was in What’s Eating Gilbert Grape. I thought he perfectly played the mentally retarded character. I knew nothing about the actor and even wondered if he actually had that condition. He had the misfortune of being young (hence voters figure he’s got plenty of time to win later) and being up against some stiff competition. I wouldn’t even have given it to him that year, although I wouldn’t have given it to Tommy Lee Jones in the Fugitive, either. Ralph Fiennes was on the outside looking in despite his chilling performance in Schindler’s List. I have no idea how he didn’t win. Maybe he and DiCaprio split the vote and that left the more comfortable-for-the-audience performance of Jones.

    Being nominated for The Aviator is fitting, but I wouldn’t have had him winning for it with the competition he had from the other nominees that year. I don’t agree with the nomination for Blood Diamond. That was just the industry liking the topic of the film and wanting to reward the people involved with it. I think a nomination for The Departed would have been fitting, but again not a win. And while I loved Django Unchained I feel that Samuel L. Jackson was far more compelling in his supporting role than DiCaprio was in his. That’s not DiCaprio’s fault; he was just given a two dimensional caricature to play, while Jackson had a three-dimensional character.

    One film not mentioned yet (I think) is Romeo and Juliet. Even though the characters are teenagers Romeo is often played by a much older actor because of the difficulty of the part. At 21 he handled not only the Shakespearean dialogue, but also the change of setting to modern times. While not one I feel was Oscar worthy is was a much praised at the time performance that seems to be relatively forgotten now.

    1. Chip, as fine a performance as Ralph Fiennes gave in Schindler’s List Hollywood probably won’t be giving it to a serious Nazi portrayal anytime soon. Sure Christoph Waltz won it for Inglourious Basterds but that was a send up of a Nazi. Also Kate Winslet won for her illiterate, banal portrayal of a guard in The Reader. On the other hand Fiennes’ Amon Goeth was a stone-cold psychopath based in reality. For what it’s worth his portrayal ranked 15th, one of only two non-fiction villains, on American Film Institute’s list of the top 50 film villains of all time. so Hollywood did notice. Of course Hollywood had no problem giving the Oscar to Anthony Hopkins’ fictional psychopathic Hannibal Lector. Even Forest Whitaker won as the brutal Ugandan dictator Idi Amin but Bruno Ganz as Hitler… never had a chance. Reviewer James Berdinelli of ReelViews said at the time “Downfall and Bruno Ganz are deserving of Oscars they will not get.” Ralph Fiennes problem is that his performance.was maybe too good.

    2. Hi Chip! His performance in What’s Eating Gilbert Grape was astounding indeed, glad he’s at least nominated for that. But yeah, it’s really about the competition you’re in as much as the performance itself, no matter how deserving we think it is. I guess that year I’d probably give the Oscar to Fiennes as like you said, it was a bone chilling performance as Goeth.

      I actually thought he was good but not great as Howard Hughes, but yeah, definitely NO for Blood Diamond. I still think it’s nuts that Wahlberg is the only one nominated in the Supporting category for The Departed, ahah.

      I agree that Leo was excellent as Romeo, perhaps the better performance of the two directed by Baz Luhrmann. Tackling the Shakespearean language is quite a feat in itself, whilst his accent as Gatsby is well, indiscernible!

    1. Thanks for participating Michael! I’m however more impressed by Cate Blanchett in that film as Katharine Hepburn, glad she won an Oscar for it.

  11. Dicaprio has an impressive resume. He’s consistently good in just about every role. Perhaps an underrated performance is in Revolutionary Road. I think he should have gotten nominated for Titanic. Of the roles he got nominated for I’d award him for The Aviator.

    1. I haven’t seen Revolutionary Road yet but yeah, it’s odd that he wasn’t nominated for Titanic whilst the two actresses playing Rose got one each!

  12. DiCaprio is interesting. It took me a while to really appreciate him. His early leading actor roles never convinced me because he always looked like a boy playing men (as you mentioned). But with a snap of a finger he suddenly looked like a man and in my eyes became more convincing (weird logic I know, ha). Now in a fan for sure.

    Several of his performances have really blown me away: The Departed, Inception, Gangs of New York, Blood Diamond. But my favorite is from Shutter Island. I know the movie was a bit polarizing in some circles, but I absolutely loved it. I also though Leo deserved Oscar consideration for the performance. Alas he was left out again.

    1. Hi Keith! Y’know for me, it’s actually even weirder. I like him in Growing Pains, then I REALLY like him after Titanic, but then when he got super famous it sort of fizzles out for me. I just didn’t think he’s all that interesting anymore. But now I respect him for some of the roles I’ve seen him in, I still need to see The Departed, Shutter Island and Gangs of New York though.

      1. Naa, not weird at all. Sometimes actors and actresses just don’t strike an interest with us. I think we all have certain names that fall into that category. Of the three you haven’t seen, I highly recommend Shutter Island. I really like that film and it’s a pretty challenging role for Leo.

        1. I value your opinion Keith, I know you won’t watch a lot of stuff I won’t either, so yeah I’ll give that one a shot at some point. Thanks man!

          1. I really appreciate that Ruth. In that same vein let me say that The Departed is really good but I have the TNT television version on DVR. The profanity in the theatrical release is just ridiculous.

            1. Yeah that’s my trepidation about that too. I know my hubby did see it and he said it was rather violent as well, I’m not as keen in checking that one out.

  13. Personally I think “What’s Eating Gilbert Grape” is his finest moment. I didn’t know who he was then and actually questioned whether this young actor was indeed disabled. He was that good. In all honesty, I predicted way back then (alongside The Basketball Diaries) that he was going to be an exceptional actor.

    He also had a shout with The Departed and I really enjoyed him in Shutter Island too.

    Who knows for sure why he hasn’t won yet but it could be to do with the fact that he was quite outspoken about not being nominated for Titanic when everyone else seemed to get one. Or it could be that he will go on to be one of those actors like Pacino or Newman who seemed to take forever to get their hands on one, yet they are two of the finest to ever grave the screen.

    1. Hi Mark! Yeah, that’s the advantage of being unknown at the time, he was so believable as a disabled kid, and his relationship w/ Johnny Depp’s character is very intriguing and sweet. I didn’t realize about his tantrum about not being nominated for Titanic, I do remember he didn’t even go to the ceremony. I suppose he didn’t have the maturity to just shrug off things like that. A lot of other actors took as long if not longer to finally got the golden bald-headed statue!

  14. jackdeth72

    Hi, Ruth:

    Leonardo DiCaprio is a very likeable actor. He’s handsome. Very comfortable in front of a camera. Delivers more than asked or required in many diverse roles. Though, there’s something lacking when it comes to winning in an Oscar caliber role. More of a matinee idol than anything else. Would love to see him exercise his comedic chops in a lead slapstick role!

    Still think his best work has been equally divided between ‘What’s Eating Gilbert Grape’ and his very believable take on Howard Hughes in ‘The Aviator’.

    1. Hi Jack! I don’t know about Leo being the most likable actors, he doesn’t always come across very sympathetic to me, but I think that’s because he’s fond of playing anti-heroes. I think he was quite funny in Catch Me if You Can but yeah, I’d love to see him play more comedic roles, too.

  15. Gilbert Grape deserved a win in my opinion. Also, Django Unchained deserved a nomination for sure, but I’d rate his performance more deserving of a win than Waltz (and I love Waltz so that’s saying something). Hopefully Leo can get his due praise sometime before they have to give him one of those honorary awards for never winning anything.

    1. Hi Jess! Without having seen Django yet, even from the clips and trailers, I was convinced he’d garner a nom. He’s still too young to get an honorary Oscar, let’s hope he’d get one for one of his performances in a given film.

  16. I love DiCaprio, even if it isn’t always popular to do so. That said, I enjoy his early career more so than his current one. That said, he should have been nominated for Shutter Island.

    I give him the win in 96 for Romeo + Juliet. He was BRILLIANT and captured everything that character needed to be. It’s, in my eyes, an iconic performance.

    1. When was it unpopular not to like him? It’s not like he’s a controversial character or anything. Another punt for Shutter Island, I’m very curious now.

      I need to rewatch Romeo + Juliet again, I remember being more impressed w/ him there than in Gatsby.

    1. Catch Me If You Can was a fun film that boast two great performances, Leo’s and Hanks’. I like that he’s able to balance the humor and vulnerability of his character.

  17. I can’t remember if he is my win or not, but my favorite performance of his is Revolutionary Road – he was like young Brando in that. I nominate him for that, Aviator, The Departed, Gilbert Grape and Django. I think he will miss out this year because of Chiwetel, but I’m sure him and Brad Pitt (great actor who is overlooked by Academy too, just not this famously) will have their Oscars one day.

    1. A young Brando? Hmmm, I’m curious about Revolutionary Road now. I somehow never got around to seeing it though I wanted to see his reunion w/ Winslet and also Michael Shannon’s performance.

      I thought Pitt was great in Babel but was he even nominated there?

    1. Hmmm, these comments made me want to rewatch The Aviator. I feel that his performance was good but short of being this great, iconic performance y’know. I was more impressed w/ Cate Blanchett who was superb as Katharine Hepburn. But maybe I should give it another look.

  18. I’d go with his performance in What’s Eating Gilbert Grape. That’s primarily because it’s one of my favorite movies that he’s starred in. Can’t believe he’s 39 years old.

    1. It’s amazing how youthful he still looks doesn’t he? I think he’s one of those actors like Johnny Depp and Keanu Reeves who’ll look young forever!

  19. Popcorn Nights

    There are many he could have been nominated for, definitely. I’d agree with people above regarding Catch Me If You Can, The Departed, The Aviator, What’s Eating Gilbert Grape? and Shutter Island – all very good performances, and a win is now overdue. Also I’d probably add Revolutionary Road to that list. Kate Winslet and Michael Shannon got a lot more praise when it was released, but he is superb in it.

  20. It’s hard to add to this list of great comments because I pretty much second all of the suggestions!! Dare I add Titanic. I love Kate Winslet but a great proportion of her performance is her chemistry with Leo. And, if you watch other actors audition t for Jack Dawson no one can compare to his performance.

    1. Hi Katy! Oh I think he’s very good indeed in Titanic, I mean clearly he’s one of the main reasons the film was such a huge box office hit! I haven’t seen the audition tapes w/ other actors, I have to look that up now!

  21. filmplicity

    Great question Ruth! I was just thinking recently that Leo should have won an Oscar by now. I’ll go with… Titanic? Maybe not. It’s a hard one to call, I haven’t seen Django yet so will withhold judgement until then.

    1. He should’ve at least been nominated for Titanic I agree. Haven’t seen Django either, but he looked poised for a nom on there too. Thanks Ronan!

  22. I think as Dom in Inception. I also LOVED him in Catch Me If You Can as Frank Abagnale Jr. Clavin Candie in Django also got me good. That was such an outstanding role.

    1. I like him in Catch Me if You Can more than in Inception though he was good in it. I just thought there are actors who are more memorable in it, like Tom Hardy and Cillian Murphy. But yeah, he’s done some good work!

  23. Nice post! For sure he should have been nominated for Django. I think he should have already won for Gilbert Grape. Or The Aviator. Nomination for Revolutionary Road, The Departed and This Boy’s Life. I also thought he should have had the nom for Titanic too. I’ve seen most of his work and he usually is that good that he’s worth the nomination almost always, it depends how good work the others are doing in said year.

    1. Hi Satua, welcome to FC! Yeah that’s what I thought, even without having seen the film yet. Like you said though, there are seem to be tough competitions that might’ve prevented him from getting nominated. Hopefully the *stars* would align for him before too long though.

  24. Great question Ruth. I think he should’ve been nominated (and won) for The Departed, but a win for The Aviator makes the most sense. He was the best of the nominees, even though Jamie Foxx won most of the awards that year.

    I still need to see Total Eclipse. I’ll try to watch it before I do my 1995 ballot in a few weeks.

    1. Hi Josh, were you surprised that Mark Wahlberg was the one nominated for The Departed? I thought it was really odd. Jamie Foxx won for RAY right? It was a terrific performance so I guess I understand why he won. Total Eclipse is a nutty one, not exactly an enjoyable film but quite intriguing.

      1. I was surprised that Wahlberg got nominated, but he had been nominated by a few other awards groups. I was more shocked that Leo got in for Blood Diamond. Yeah, Foxx won for Ray. He was good, but I preferred DiCaprio in The Aviator.

        1. Yeah, I didn’t think Leo deserved the nom for Blood Diamond. I do like Foxx for Ray though, I suppose it’s a flashier role than even Howard Hughes.

  25. Now that was a great, well made trailer. DiCaprio seems to be in top form and I would love for this film to finally be the film that gets DiCaprio his long deserved Oscar. I mean how cool would it be to see DiCaprio win for Best Actor, Scorsese (again) for Best Director and the movie win Best Film.

  26. I’m in line with the Academy on this one. I think he was deserving of each nomination he received, or perhaps one or two more, but in every single instance, there were one or two actors who delivered stronger, if not one-in-a-lifetime performances.
    I think of Leonardo Di Caprio as a very very solid actor who still has not delivered that ONE spectacular performance that merits, without question, the Oscar. I’m talking about a Daniel-Day Lewis type of work, or Forrest Whitaker in Last King of Scotland, or Michael Fassbender in Shame (which amazingly got snubbed). The closest one for me was The Aviator, and Django in close second. I still wish him the best of luck with Oscar in the future, and you’re right, The Wolf of Wall Street may be it.

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