My Oscar Predictions: Who Will Win vs. Who Should Win

By February 24, 2017

It’s almost here! The night where Hollywood subjectively gives out a bunch of arbitrary statues to Tinseltown’s prettiest movie stars is just around the corner. The night that will decide which film that you didn’t see will join the prestigious list of films you’ve never heard of.

So I took it upon myself to predict who will take home the gold in every narrative feature film category, and as a counterpoint which of the nominees I think actually deserves to take home the small statue of a naked bald man covered in gold and holding … a sword, it looks like? Is that what that is?

Meryl Streep, please confirm.

Anyway, on to it.

Will Win: La La Land
Although Moonlight is not to be counted out – especially in such a political atmosphere following two years of #OscarsSoWhite – it’s hard not to predict a La La Land sweep. The only thing Hollywood loves more than awards is awarding Hollywood, and this expertly crafted cinematic comfort food meets that criteria.

Should Win: Arrival
Even without the stellar cinematography and complicated science-fiction elements, the message and emotional punch of the film round out quite the powerful experience.

Will Win: Damien Chazelle (La La Land)
Again, Barry Jenkins could easily pull an upset and become the first black winner in this category, but Chazelle’s flashier and perhaps more meticulous technical direction will probably secure him the gold.

Should Win: Damien Chazelle (La La Land)
Honestly, this was a little tough. I loved what Mel Gibson did with Hacksaw Ridge (despite any personal issues), and I obviously loved what my boy Denny V. did with Arrival. But Chazelle’s exuberant throwback to cinema of old with a modern flair was really special.

Will Win: Casey Affleck (Manchester By the Sea)
Affleck has been the frontrunner for what feels like years after the film first premiered. And that support  probably will take him all the way to gold. Denzel’s win at the SAG awards threw people for a loop, and he might pull an upset. But expect to hear a win for Sad Affleck: The Movie come Oscar night.

Should Win: Viggo Mortensen (Captain Fantastic)
Although he didn’t make my Oscar picks from a few weeks back (a choice I have come to deeply regret) his performance has stuck with me ever since I saw the film. And the more I think about it, the more I have come to appreciate and even love the layers and heart Viggo brought to that movie.

Will Win: Emma Stone (La La Land)
What felt like a three-way race between Natalie Portman, Isabelle Huppert and Emma Stone has quickly whittled down to a frontrunner in Stone for her impressive, moving, heartfelt performance.

Should Win: Amy Adams (Arrival)
Wait, what? She’s not nominated? What is this tomfoolery? OK, I guess Natalie Portman (Jackie) then for her poignant and even haunting performance as Jackie Kennedy.

Will Win: Mahershala Ali (Moonlight)
Truly a supporting performance, Ali only appears in one of the three segments that make up Moonlight, but he absolutely drives those scenes and offers some of the most important insight for the rest of the film.

Should Win: Michael Shannon (Nocturnal Animals)
Look, deep in my heart I do want Mahershala Ali to win. But if I were to rank all the nominees, he would pull in second just behind Shannon for his surprising scene-stealing performance in one of the most under-represented films this Oscar season.

Will Win: Viola Davis (Fences)
Have you been paying attention? This award is Davis’ to lose. The fact that it’s a lead performance fraudulently forced into the supporting category doesn’t hurt her chances either.

Should Win: Naomie Harris (Moonlight)
Had Janelle Monáe been the one who scored the nomination for Hidden Figures, I’d be all over that. But with her out of the picture, I’ve got to give the nod to Naomie Harris for her unrecognizable turn in Moonlight.

Will Win: La La Land
With major competitor Moonlight competing in adapted screenplay, this opens up the category for season favorite La La Land to continue its sweep.

Should Win: 20th Century Women
If this award was for “most” original screenplay, then The Lobster would have this in the bag. But that’s not the category. I’d then give my vote to Mike Mills for his funny, moving, deeply relatable story.

Will Win: Moonlight
Same same. With major favorite La La Land competing in original screenplay, this category opens up for one of the only sure wins for Moonlight.

Should Win: Moonlight
Despite my love for Arrival and the fact that I don’t think Moonlight is quite a perfect movie, the story and the characters are incredibly moving. I haven’t been able to get it out of my head.

Will Win: Zootopia. Many Oscar voters have copped to not caring as much about this category or even watching the nominees, instead voting for what they feel like is supposed to win. With Zootopia sweeping this category at other award shows and its important political message, it’s hard to see anything else winning.

Should Win: Kubo and the Two Strings damn it.
Kubo is the best film of the year of any kind, and you all messed up by not seeing it. It’s beautiful and exciting and masterfully animated and attacks my emotions every time I watch it. I will be deeply saddened when it loses.

Will Win: La La Land
Colors! Long shots! Steadicam! Oh my! It has everything that captures peoples’ eyes and also is admittedly impressive.

Should Win: Arrival
OK, I promise I won’t give everything to Arrival, but honestly this is such a beautiful film. Although the cinematography for Silence was a hell of a thing, and I wouldn’t mind a win for that.

Will Win: La La Land
Boy, look at all those montages!

Should Win: La La Land
But they were good montages.

Will Win: La La Land
I’m less certain about this one since they mostly just shot around Los Angeles. But once that sweep starts going, it’s hard to stop.

Should Win: Fantastic Beasts and Where to Find Them
Not just because no Harry Potter movie ever won an Oscar, but also because the ongoing world building of J.K. Rowling’s universe continues to not only be pretty to look at, but also entirely functional.

Will Win: Jackie
This one I actually see La La Land losing. I mean, they were just kind of wearing suits and stuff. But the attention to detail in recreating not just Jackie’s eclectic collection of outfits – including the infamous pick number – but also the other clothes of the era is something the Academy gravitates toward.

Should Win: Allied
Did you see that green dress Marion Cotillard wore? Swoon.

Will Win: Star Trek Beyond
Although this reboot franchise already won this award for the 2009 film, it’s hard to see the Academy voting for a foreign film no one saw or the critically panned Suicide Squad despite its admittedly great makeup effects.

Should Win: Suicide Squad
Honestly I’d be happy with a win for either Beyond or Suicide Squad for their incredible prosthetic work and character creations, but how great would it be if the phrase “Academy Award-winner Suicide Squad” became a reality?

Will Win: La La Land
Honestly, you can probably take a bathroom break at this point in the ceremony, because if there is any certainty in this world, it’s that La La Land will win the music categories …

Should Win: La La Land
… and for good reason: It’s wonderful. However wins for Jackie, Moonlight, and even Lion would be welcome for their more haunting, stripped down, and at times, moving scores.

Will Win: City of Stars (La La Land)
Although I think “Audition” is the better of the two nominated La La Land songs, “City of Stars” is the one that plays throughout the film and is more closely associated with it, and I think that’s a large contributing factor.

Should Win: How Far I’ll Go (Moana)
La La Land is filled with great songs, but inexplicably most of them are not the ones nominated. And as much as I love “Audition,” I think “How Far I’ll Go” is not only reminiscent of Disney past, but also a great song in its own right.

Will Win: La La Land
This award typically goes to an action or sci-fi movie or something with a lot of sound effects, but Slumdog Millionaire inexplicably won this award, so never underestimate the power of the sweep.

Should Win: Rogue One
The familiar yet still captivating sound of Star Wars was a key factor in transporting us to that galaxy far, far away.

Will Win: Hacksaw Ridge
War moves tend to do well in sound categories (American Sniper, Zero Dark Thirty), and the immersive sound of the battle sequences may be too overwhelming to ignore.

Should Win: Deepwater Horizon
The same could be said for this intense film in which the ceaseless cacophony of sound creates a sense that something else will break or go wrong at any moment.

Will Win: The Jungle Book
This may be one of the most cut and dry categories of the night. Use this for another bathroom break.

Should Win: The Jungle Book
Literally every nominee had incredible, convincing effects with Deepwater Horizon and Rogue One employing more practical effects than you might imagine, Doctor Strange’s kaleidoscope city sequence, and Kubo’s masterful stop motion animation. But only one of these films had an actual talking tiger.

So those are my thoughts. If you feel like countering my thoughts, leave a comment and let me know. If you think I’m right on the money, leave a comment and let me know how smart I am.

Just be nice either way. And see you on Oscar night!

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Matt Brown

Matt Brown

Contributing Writer at GeekNation
Matt is a writer of all sorts and a film addict who's still waiting for his Hogwarts acceptance letter. If you find him at a party, he's probably talking about Xena or doing a Nicolas Cage impression.