93rd Oscars: What Will Win, What Should Win

Every year I make a list of predictions for the Oscars as well as a list of what I personally want to see. This year I thought I’d lay out my thought process a little bit for each category. I didn’t do the mathematical estimates this year, so all of this is coming from the gut.

We’ll start with the above-the-fold awards, then move on to the genre awards and then the technical awards. Sound good? Let’s go.

I already wrote plenty about the Best Picture nominees earlier this week, so I’ll only add that virtually every predictive precursor award, including the highly correlative Producers Guild Award, has gone to Nomadland. If anything else wins, it will be a stunning, and heartbreaking, upset.

Will Win: Nomadland
Should Win: Nomadland

Historically, Best Picture and Best Director frequently go to the same film. In recent years that’s diverged quite often when the Best Picture race is close. The Best Picture race is not close.
But predictable does not mean uninteresting. This is the first year ever there has been more than one woman nominated for Best Director. That makes a grand total of… seven. And for only the second time, one of them will win it. I think that’s worth tuning in for.

Will Win: Chloé Zhao, Nomadland
Should Win: Chloé Zhao, Nomadland

Posthumous nominations aren’t particularly uncommon; there have been seven in the last decade. In acting categories, however, well… the most recent was Heath Ledger. Given the Academy’s tendency to reward an actor for their career rather than their nominated work, expect them to take this final opportunity to honor someone who left a huge mark on Hollywood in such a tragically short amount of time.

Will Win: Chadwick Boseman, Ma Rainey’s Black Bottom
Should Win: Chadwick Boseman, Ma Rainey’s Black Bottom

This is an odd category this year. Five way race. Well, four. Sorry, Vanessa.
Should Frannie McD have three Oscars? Sure, at least. Maybe more! But Viola Davis should definitely have more than one, and at least one that isn’t for Fences. Like I said in my Top 10 of 2020 of 2020, if that transformation she made was in the running for Best Actor, there wouldn’t be a conversation.

Will Win: Frances McDormand, Nomadland
Should Win: Viola Davis, Ma Rainey’s Black Bottom

Two of the five nominees are the titular characters of Judas and the Black Messiah. It’s one of those “What does ‘supporting’ even mean?” years. Putting that aside, this is a very solid list of nominees. We have three stellar performances from black actors and one performance delivered half in sign language. And a fifth one.
Luckily, all signs are pointing to Kaluuya overcoming the potential for vote splitting, by miles. This might be the easiest acting award to predict, although I can't shake the feeling that fifth one is compelling for the voters…

Will Win: Daniel Kaluuya, Judas and the Black Messiah
Should Win: Daniel Kaluuya, Judas and the Black Messiah

I had a whole bunch written here earlier about how the Oscars don’t respect Asian grandmothers as much as I do (#AnOscarForNaiNai) but then Youn Yuh-jung went and won the SAG award! The acting branch of the Academy is the largest, and SAG is willing to do that, it’s hard not to see her as a frontrunner.

Will Win: Youn Yuh-jung, Minari
Should Win: Youn Yuh-jung, Minari

I was a little surprised to notice this is Aaron Sorkin’s first nomination in this category — The Social Network, Moneyball, and Molly’s Game were all adapted. This is a two-way race between The Trial of the Chicago 7 and Promising Young Woman. Between those, Woman has beaten Trial at all the precursor awards they were both nominated for, and the screenplay categories have been where the Oscars are eager to get unconventional recently. If it does go to Trial, I expect that will be an omen of how the rest of the night will go.

Will Win: Promising Young Woman
Should Win: Minari

The Father got the BAFTA, but the BAFTAs are unabashedly biased towards British productions, for obvious reasons. All other signs point to Nomadland. And honestly, what else?

Will Win: Nomadland
Should Win: Nomadland

It’s Soul. As much as I hoped and dreamed and prayed that Wolfwalkers would mount a Spider-Verse-esque comeback victory… time has run out. Whatever. Soul can have it. I’ll cry into my Wolfwalkers steelbook. Wolfwalkers is getting a physical release, right? Right? Apple? …Criterion? Please?

Will Win: Soul
Should Win: Wolfwalkers

Ooh ooh ooh, this one’s easy. If you’re the only Best International Feature nominee also nominated for Best Director, you’re gonna win. That seems straightforward enough. I’d love to see the Academy to prove me wrong.
No, seriously, I’d love to see that. That would be so wacky. We could use a little more chaos this year.

Will Win: Another Round
Should Win: Another Round

I’ll wager the Academy will go with the most capital-I Important film of the bunch, the one about a decades-long fight against racial injustice. How could you oppose that?
So at the risk of being a huge jerk, I’ll be secretly rooting for the one that tugged at my heartstrings the most: My Octopus Teacher, about a lifetime friendship between a diver and an octopus. It’s fluff, but it almost made me cry over a fish, so I can’t help it.

Will Win: Time
Should Win:
🐙

I’ll wager the Academy will go with the most capital-I Important film of the bunch, the one about a decades-long fight against racial injustice.
Huh. Déjà vu.

Will Win: A Love Song for Latasha
Should Win: A Love Song for Latasha

This is the hardest category to predict because there are really no corresponding categories at other major awards. I’ve simply never been able to find a correlation in what ends up winning. It certainly isn’t quality.
I’m gonna go with The Letter Room, because it’s the only one with Hollywood actors in it. That is the extent of my analysis. Do not blame me when this ruins your Oscar pool.

Will Win: The Letter Room
Should Win: Anything besides Two Distant Strangers

Can you believe there was a time when Disney was completely shut out of this category? For decades! And then Paperman won in 2013. Now, Disney is the default frontrunner unless there’s a timely opponent. School shooting drama If Anything Happens I Love You wants to be that this year, but I think it’s too shallow to overcome Burrow’s pure animated joy.

Will Win: Burrow
Should Win: Burrow

Soul seems to have the right ingredients for a win here:
1. Be a movie somewhat about music, and
2. have Trent Reznor.
Mank can only claim one of those.

Will Win: Soul
Should Win: Soul?

This may be my least favorite category, because almost all the nominated songs just play over the credits and are a transparent attempt by a musician to work on their EGOT. If I were in charge, this category would only be for songs actually incorporated in the film. It’s refreshing whenever there’s a “Shallow.”
“Husavik” is this year’s “Shallow.” Yes. 100% sincere.

Will Win: “Io Si,” The Life Ahead
Should Win: “Husavik,” Eurovision Song Contest: The Story of Fire Saga

After decades of being separate awards, Best Sound Mixing and Best Sound Editing have been merged into Best Sound once again. That change will make it hard to predict, as we don’t know what other sound awards are most predictive of this new category.
Is it cliché to bet on the one nominee that directly utilizes the sound mixing narratively? You know, the one that has the name of the category in the title? This might be a case where less technically minded voters confuse “Best” with “Most Noticeable,” but at least they’ll get it right in the end if so.

Will Win: Sound of Metal
Should Win: Sound of Metal

Sometimes, as an Academy voter, you are stuck with a difficult question: Should Best Production Design go to the period film in black and white or the period film set in the Old West? Just pick the one that looks cooler. You don’t really know what production design means, anyway.

Will Win: Mank
Should Win: News of the World

This can go two ways:
• Black and white cinematography is beautiful.
• The American West is beautiful.

The former won the ASC award, but that only correlates about half the time. I’m thinking the latter still has the stronger chance.

Will Win: Nomadland
Should Win: Nomadland

Ma Rainey won the Makeup Artists/Hair Stylists guild award, usually a good indicator. They also honored Birds of Prey, which really makes me wonder why that isn’t nominated. Suicide Squad won this award! Surely Birds of Prey is at least as good as that?!

Will Win: Ma Rainey’s Black Bottom
Should Win: Ma Rainey’s Black Bottom

Let’s look at the corresponding guild award again for this one. Ma Rainey won the period film award, and Mulan won the fantasy film award. Both are nominated. It’s usually safe to assume the period film will get more love, and I can’t imagine an underwhelming Disney remake will be the one to break that rule.

Will Win: Ma Rainey’s Black Bottom
Should Win: Ma Rainey’s Black Bottom

Most of the people who vote for the Oscars have no idea what good editing actually is or does or looks like. [Source] So I’m going to take the pessimistic approach and say the movie that opens with a snappy montage will most likely win.
I mean, it is a really effective montage. I’m not saying Trial is a poorly edited movie, not in the slightest. But can you blame me for thinking the editing in something like Nomadland will go underappreciated?

Will Win: The Trial of the Chicago 7
Should Win: Promising Young Woman

Tenet is literally the only nominee on this list that stands out at all. At all.

At all.

Will Win: Tenet
Should Win: Tenet

My Will Wins and Should Wins line up a lot more than normal this year. That may be a side effect of the weird pandemic year. It's definitely giving me second thoughts about my predictions. It's not the Oscars’ job to be that correct!

Join me for disappointment Sunday night at @pinguinoEO on Twitter!

Half-ghost. Knows a lot about movies. Wishes you could get paid for that.

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