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How soon do you think Leonardo DiCaprio will win the second Oscar?

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    Diamond Tier
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    #1204192694

    He’s a big enough star to win in lead again.

    Big stars win in Supporting too (i.e. Clooney & Pitt)

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    Kaloyan Papazov
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    #1204193259

    Ahh, don’t think he’s gonna win again. I really can’t see how there is going to have a narrative when he does have one Oscar already.
    And, let’s make it clear, I think his acting prime was like a decade ago. He is an actor who always plays the same character and I can’t see how he is going to surprise me. Sorry, Leo’s stans

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    Stank83
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    #1204193894

    Ahh, don’t think he’s gonna win again. I really can’t see how there is going to have a narrative when he does have one Oscar already.
    And, let’s make it clear, I think his acting prime was like a decade ago. He is an actor who always plays the same character and I can’t see how he is going to surprise me. Sorry, Leo’s stans

    Oh yeah
    Arnie Grape in What’s Eating Gilbert Grape?
    Jim Carroll in The Basketball Diaries
    Romeo in Romeo + Juliet
    Jack Dawson in Titanic
    Amsterdam Vallon in Gangs of New York
    Frank Abagnale in Catch Me If You Can
    Howard Hughes in The Aviator
    Billy Costigan in The Departed
    Danny Archer in Blood Diamond
    Frank Wheeler in Revolutionary Road
    Teddy Daniels in Shutter Island
    Dom Cobb in Inception
    J. Edgar Hoover in J. Edgar
    Calvin Candie in Django Unchained
    Jay Gatsby in The Great Gatsby
    Jordan Belfort in The Wolf of Wall Street
    Hugh Glass in The Revenant
    Rick Dalton in Once Upon A Time In Hollywood

    They are all the same character…

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    Woody
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    #1204194119

    That hasn’t been enough for Pacino so far, he should’ve won at least two Oscars, just like DeNiro

    DeNiro had a Supporting win not a Lead so that likely helped him, he also was doing great work in the 70’s which he could’ve won for before so him winning another was inevitable.
    Leo seemingly already had this same situation but without already having a supporting win.

     

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    Sir Pierce
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    #1204194240

    It could very possibly happen, but it’s hard to tell. The thing is that I don’t reckon he’d win in Supporting, frankly. It’s rare that an actor who wins in lead, then wins in Supporting in the male categories, at least. The only two times it has happened in the last 50 years is with Jack Nicholson and Gene Hackman… both of  whom are enormously respected in the industry and who won at least one of them Oscars for films that were Best Picture winners. Leo has been in two Best Picture winners – The Departed and Titanic – but wasn’t even nominated for either… Even if there is a thin chance he could have won if he was nominated in Lead for The Departed. But his snub for that film is a whole other conundrum to do with bad campaigning more than anything else…

    If he wins again, I reckon it’ll A) be in lead and: B) be in a film that wins Best Picture or is close to it… Or, at the very least, a performance which gets career-best reviews. This is how Day-Lewis and Sean Penn got multiple Oscars in the lead category. And it’s how Hopkins almost won this year. I think it, also, helps if you are playing a real person (Lincoln, Milk) or working with a renowned auteur director (There Will Be Blood). I reckon DiCaprio could pull it off. But there is no way of knowing for certain. If the Roosevelt flick is a big Oscars player, he could win there. Honestly, not entirely convinced he’ll win for Killers Of The Flower Moon, but, given how good the source material is and how great of a director Scorsese is, then I reckon he could get yet another nomination. Alas, we’ll have to see how his career plays out.

    He certainly has the ability. But I think he needs to be in the right film at the right time, as well.

    A very annoying young man, who loves cinema. 🙂

    Twitter: https://twitter.com/pierce_sir
    Letterboxd: https://letterboxd.com/11higuys/

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    Oleageoun
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    #1204194323

    I don’t think the Roosevelt biopic will happen though. It was announced a long time ago similar to Devil in the White City and that ended up as a television series without either of them.

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    iWantTheGold
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    #1204194678

    Unless he gives another Wolf of Wall Street-caliber performance in a weak year, I think he’s done.

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    Novic
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    #1204196400

    I wish Leo would take more risks. There’s a lot of new filmmakers who are doing exciting things. He needs to breakout from just working with prestige directors and consider more up-in-coming talent.

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    Anything
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    #1204196588

    He could win one as soon as 2023, for Killers of the Flower Moon. Much is made of DiCaprio winning in 2016 because of his overdue narrative, but he would have won regardless.

    Let’s engage in a thought experiment. If DiCaprio had already won his 1st Oscar for, say, The Aviator, who would he have lost to in 2016? Michael Fassbender in a box-office flop that didn’t get a Best Picture nomination? Bryan Cranston in a movie nobody cared about? Or Matt Damon in a science fiction comedy?

    DiCaprio would have won in 2016 even if he didn’t have an overdue narrative, because his performance was always going to generate more industry acclaim than any other performance in that category. And he can win a 2nd Oscar anytime the stars align again, because he is easily more respected than most 2-time Oscar winners.

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