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What Will Win, Might Win and Should Win at the Oscars

What Will Win, Might Win and Should Win at the Oscars

There are no certainties in this year’s Oscars. That’s true even under the best of circumstances, but it’s extra true in 2020 when it increasingly seems like everyone — even Academy voters — are just sort of ticking boxes at random. The way a few anonymous voters have talked this year, it seems like just about anyone would do a better job of choosing which movies are worthy of extra acclaim but you and I aren’t in the Academy. We can only use an admittedly daring combo of guesswork, process of elimination, logical problem-solving and maybe a bit of personal bias to hazard our best estimates for what’s gonna happen at Sunday night’s awards. Here’s our attempt. Good luck with yours.


George MacKay in 1917 (2019)

Will Win: 1917

Might Win: Parasite

Should Win: Parasite

No non-English movie has ever won Best Picture before, so it would take a small miracle for the Academy to overcome its entire history and hand Best Picture over to Parasite. That said, if any movie could do it, it would be Bong Joon-Ho’s class warfare satire/thriller—which was a critical and commercial sensation. But 1917 is handsomely directed by a known Oscar entity in a genre the Academy loves. It’s the safest choice in a year full of relatively safe choices.


Sam Mendes, George MacKay, and Dean-Charles Chapman in 1917 (2019)

Will Win: Sam Mendes (1917)

Might Win: Quentin Tarantino (Once Upon a Time …in Hollywood)

Should Win: Bong Joon-Ho

Bong dissed the Academy as “local,” and Academy members aren’t ones to forgive easily, so he’s fighting an uphill battle for his deserved award. Really, the Academy loves to award ostentatious craftsmanship with this one, and no movie was more ostentatiously crafted than 1917. Expect Mendes to pick up his second Oscar here.


Renée Zellweger in Judy (2019)

Will Win: Renée Zellweger (Judy)

Might Win: Scarlett Johansson (Marriage Story)

Should Win: Saoirse Ronan (Little Women)

Zellweger’s performance as Judy Garland is the sort of stuff the Oscars love, and she’s collected a bunch of smaller awards over the last few weeks to build momentum toward a very likely win. This is one of the evening’s surer bets and there’s no doubt Zellweger’s performance was admirable, but Ronan remains one of the finest talents working in Hollywood who managed an incredibly difficult balancing act in Little Women. We’d favor her victory.


Joaquin Phoenix in Joker (2019)

Will Win: Joaquin Phoenix (Joker)

Might Win: Jonathan Pryce (Two Popes)

Should Win: Adam Driver (Marriage Story)

Phoenix has this one pretty well sewn up and will likely become the second person to win an Oscar for playing Batman’s arch bad guy. Doubtless, his performance was the best thing about the movie, but Driver’s performance in Marriage Story was smaller, nimbler or more balanced; it was far and away the best thing Driver did this year, and he did a lot.


Laura Dern and Scarlett Johansson in Marriage Story (2019)

Will Win: Laura Dern (Marriage Story)

Might Win: Scarlett Johansson (Jojo Rabbit)

Should Win: Florence Pugh (Little Women)

Just imagine if Johansson won both Best Actress and Best Supporting Actress. She won’t, but can you imagine? Anyway, Dern will probably pick up her first Oscar at long last here (though it’s hardly the first time she’s deserved a win). But Pugh’s Amy might just be the most fully realized character in Little Women. Pugh shouldn’t be too worried if she doesn’t win this one—she’s got a long career ahead of her.


Brad Pitt in Once Upon a Time Hollywood (2019)

Will Win: Brad Pitt (Once Upon a Time …in Hollywood)

Might Win: Tom Hanks (It’s a Beautiful Day in the Neighborhood)

Should Win: Joe Pesci (The Irishman)

Brad Pitt’s probably already got a spot cleared out on his shelf for this one, since he’s got it in the bag entirely. And you know what, his OUATIH performance was a lot of fun. But of all the excellent Irishman performances (two are nominated in this category), Pesci’s was the most complicated, nuanced and ultimately moving.


Woo-sik Choi and Ji-so Jung in Gisaengchung (2019)

Will Win: Bong Joon-Ho, Jin Won Han (Parasite)

Might Win: Quentin Tarantino (Once Upon a Time …in Hollywood)

Should Win: Noah Baumbach (Marriage Story)

It’s gonna be cloooose between Tarantino and Bong, two excellent writers at the peak of their respective crafts. Tarantino’s win would tie him with Woody Allen for the most Original Screenplay Oscars (3) but Bong is coming into the Oscars with a lot of momentum. Coin flip.


Taika Waititi in Jojo Rabbit (2019)

Will Win: Taika Waititi (Jojo Rabbit)

Might Win: Greta Gerwig (Little Women)

Should Win: Greta Gerwig (Little Women)

Waititi won a WGA and a Bafta for his Jojo Rabbit script, which makes him the odds-on favorite for this award. It’s hard to begrudge him that—as divisive as his movie ended up being, there’s no denying its nimble power. Still, Gerwig’s shot of energy into Louisa May Alcott’s classic story was nothing less than amazing—and the most remarkable adapted screenplay effort of the year.


Tom Hanks, Keanu Reeves, and Annie Potts in Toy Story 4 (2019)

Will Win: Toy Story 4

Might Win: Missing Link

Should Win: Klaus

Honestly, it’s a stacked year in this category and any of the nominees have a shot at a win. Toy Story has a lot of brand recognition but Missing Link and Klaus both won devoted followings—and rightly so. Go with your gut on this one. There’s no real frontrunner.


American Factory (2019)

Will Win: American Factory

Might Win: Honeyland

Should Win: American Factory

Having the Obamas attached to your documentary never hurt a profile in Hollywood, but American Factory is especially notable for the ways it highlights some of the nation’s ongoing struggles with issues that began in the Obama era. It’s about as gripping and honest a look at the state of American jobs as you could expect.


So-dam Park in Gisaengchung (2019)

Will Win: Parasite

Might Win: Parasite

Should Win: Parasite

It’s gonna be Parasite.


Margot Robbie in Once Upon a Time Hollywood (2019)

Will Win: Once Upon a Time …in Hollywood

Might Win: 1917

Should Win: Once Upon a Time …in Hollywood

If 1917 picks this one up early in the night, it’ll be a good sign that 1917 is in for a huge evening. But the production design on OUATIH was one of the most bedeviling things about it—uncannily transporting viewers to a version of LA that almost existed. An incredible blend of fairy tale and period piece.


George MacKay and Jamie Parker in 1917 (2019)

Will Win: 1917

Might Win: Once Upon a Time …in Hollywood

Should Win: The Lighthouse

1917 definitely has the showiest cinematography of the year, and legendary cinematographer Roger Deakins is well and truly poised to add another Oscar to his collection for a remarkable achievement. Still, it’s hard not to root for the black and white marvel of The Lighthouse, which took such a daring risk that paid off with beautiful terror.


Joaquin Phoenix in Joker (2019)

Will Win: Joker

Might Win: 1917

Should Win: Joker

Joker ended up being one of the year’s most divisive movies, splitting just about everyone’s opinion on whether it was good. But almost had anything bad to say about its thundering strings.


Taron Egerton in Rocketman (2019)

Will Win: Elton John, “(I’m Gonna) Love Me Again”) Rocketman

Might Win: Idina Menzel, “Into the Unknown” Frozen 2

Should Win: Into the Unknown”

Kind of a weird year for this category, since none of the songs really captured the national imagination the way “Shallow” did last year or the previous Frozen entry “Let It Go.” Still, the Academy has a lot of love for Sir Elton and name recognition alone will probably push him to victory here.


Sun-kyun Lee and Yeo-jeong Jo in Gisaengchung (2019)

Will Win: Parasite

Might Win: Ford v Ferrari

Should Win: Parasite

1917 wasn’t even nominated here, for reasons that elude this outlet. With it out of the way, Parasite and Ford v Ferrari are going to have one of the closer races of the evening, and either one could walk away with a victory here. This one is going to throw off a lot of ballots (possibly including this one) but we’re going to call it for Parasite.


Don Cheadle, Robert Downey Jr., Bradley Cooper, Chris Evans, Mark Ruffalo, Chris Hemsworth, and Chadwick Boseman in Avengers: Endgame (2019)

Will Win: Avengers: Endgame

Might Win: 1917

Should Win: 1917

Another extremely close race. Oscar voters may end up going for Lion King, but while those effects were realistic they weren’t particularly special. Avengers: Endgame had some spectacular visuals (How do they make it look like everyone is really talking to Thanos?) and has the benefit of probably being seen by just about everyone, so this seems like the safest place to award the biggest movie of all time. But some Oscar voters love turning their nose up at superhero cinema and might choose the much more subtle, but just as special, effects in 1917? Another very close call.


Timothée Chalamet and Florence Pugh in Little Women (2019)

Will Win: Little Women

Might Win: Once Upon a Time …in Hollywood

Should Win: Once Upon a Time …in Hollywood

Academy voters love fancy dresses and there was no shortage of them in Greta Gerwig’s period piece, so Little Women is the odds-on favorite here. But a lot of fun was had in OUATIH too, which matched its production design’s meticulously crafted 1960s fever dream.


Nicole Kidman, Charlize Theron, and Margot Robbie in Bombshell (2019)

Will Win: Bombshell

Might Win: Joker

Should Win: Bombshell

Bombshell got a lot wrong in its chronicle of the Fox News sex scandal, but the way it transformed Charlize Theron into the spitting image of Megyn Kelly was not one of them. Especially compared to its closest competition, where the white face paint was memorable but not particularly incredible, Bombshell deserves the award.


George MacKay and Dean-Charles Chapman in 1917 (2019)

Will Win: 1917

Might Win: Ford v Ferrari

Should Win: 1917

There’s been a lot of talk of combining these two categories in recent years, given that they tend to go to the same movie anyway and lots of people aren’t clear on the difference (short answer: Sound Editing is what you hear—lightsabers, helicopter blades, a suitcase snapping shut; Sound Mixing is how you hear it—the general mix of noise throughout). 1917 has a flashy sound palette, with lots of bombs, gunfire and mud splats that might snag the Academy’s attention and give this well-loved movie a few more Oscars to take home.

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