Why This Year’s Oscar Winners Are a Crapshoot

But here are my best guesses.

I used to be really good at predicting the Oscars. I had a tidy formula: The picture had to be both accessible and grand in scale or intent; it had to flatter the voters or make them feel virtuous for voting for it. In 2014, a lot of my colleagues were predicting that Richard Linklater’s masterful Boyhood would win Best Picture. After all, it had swept most of the critic’s awards. But I had a strong hunch it wouldn’t. The film was too long, too personal, not quite accessible enough (I’d heard more than one person call it the dreaded B word—boring). I suspected that the far showier Birdman or (The Unexpected Virtue of Ignorance), a film that should’ve been disqualified for the title alone, would win, and I was right.

But all that changed in recent years, as the #OscarsSoWhite hashtag shook the Academy to its core and they were finally compelled to do the right thing and expand their membership to include more young people and people or color. Suddenly, the Oscars were less monolithic (a great thing!) and therefore less predictable.

I predicted that La La Land would win Best Picture in 2017 (and I was right for 30 confusing seconds, too!), but the artsy, meditative, beautiful Moonlight did. An indie coming of age film about a black queer youth? This was unprecedented, wonderful, and, yes, game changing.

All of this is my way of saying, well, I have no idea what’s going to happen this year. A few years ago, I would’ve assumed that my favorite film of the year—Roma—had no shot. Again, too long, too artsy, too personal. It has subtitles! And from friends I’d once again heard the “B” word. I also might’ve considered the fact that a Mexican director—Guillermo del Toro—had won Best Picture the previous year. Would the Oscars really award Mexican directors its highest honor two years in a row? But that’s old-school thinking. My suspicion is that this new class of Oscar voters doesn’t care about trends or legacies. They have good, varied taste and are simply looking for the best picture and performances (how they overlooked Ethan Hawke for First Reformed still remains a mystery).

Okay, let’s take a look at how the race is shaping up with picks for some of the main categories. Again, I know nothing.


A Star is Born


Green Book


Black Panther

Bohemian Rhapsody

The Favourite


Who will win: Roma

Who might win: God help me, Green Book

Who should win: Roma

Analysis: Honestly, this is a pretty mediocre lineup, with one truly great film (Roma), four genuinely good ones (A Star is Born, BlackKklansman, Black Panther, The Favourite), and three duds (Green Book, Vice, Bohemian Rhapsody). There were so many better films this year that should’ve been nominated (Can You Ever Forgive Me?, Eighth Grade, If Beale Street Could Talk, just off the top of my head). If any of my top five wins, I’ll be okay with it. Watch out if one of the bottom three takes the gold. Somebody at the Academy will be receiving a STERNLY WORDED LETTER.


Alfonso Cuarón, Roma

Spike Lee, BlackKklansman

Adam McKay, Vice

Yorgos Lanthimos, The Favourite

Pawel Pawlikowski, Cold War

Who will win: Alfonso Cuarón

Who might win: Spike Lee

Who should win: Alfonso Cuarón

Analysis: Can you believe that this is Spike Lee’s first nomination for Best Director? That is literally criminal. I’d be happy to see him take home a long overdue gold guy, but much as I admired BlackKklansman, I don’t think it’s his best work. It would be tantamount to Scorsese finally winning for The Departed.


Christian Bale, Vice

Rami Malek, Bohemian Rhapsody

Bradley Cooper, A Star is Born

Viggo Mortensen, Green Book

Willem Dafoe, At Eternity’s Gate

Who will win: Christian Bale

Who might win: Rami Malek

Who should win: Bradley Cooper

Analysis: This is my no guts, no glory pick. Most prognosticators are picking Malek to win for his entertaining portrayal of Freddie Mercury. But it would be rare for a television actor, in his first major film role, to take home such a big award. Then again, that’s old school Oscar prognosticator thinking. Aaaah! I just can’t help myself!

(P.S. Both Ethan Hawke, in First Reformed, and Joaquin Phoenix, in You Were Never Really Here, gave better performances than either of the two frontrunners. #SorryNotSorry)


Glenn Close, The Wife

Lady Gaga, A Star is Born

Olivia Colman, The Favourite

Melissa McCarthy, Can You Ever Forgive Me?

Yalitza Aparacio, Roma

Who will win: Glenn Close

Who might win: Olivia Colman

Who should win: Melissa McCarthy

Analysis: What a stellar lineup! Five great performances and any one of these women deserve to win. I’m partial to Melissa McCarthy and Olivia Colman. That being said, her royal Glenn-ness is long overdue and The Wife really allows her to shine.


Mahershala Ali, Green Book

Adam Driver, BlackKklansman

Richard E. Grant, Can You Ever Forgive Me?

Sam Elliott, A Star is Born

Sam Rockwell, Vice

Who will win: Mahershala Ali

Who might win: Richard E. Grant

Who should win: Richard E. Grant

Analysis: Ali is a great actor, but I wasn’t a fan of this film—the script was too facile. But Ali has cleaned up all the pre-Oscar awards so this one is a bit of a no-brainer. That being said, Grant—who gives a career best performance in Can You Ever Forgive Me?—is killing the Oscar campaign season, charming interviewers and fanboying over Barbra Streisand. Could he sneak in for the upset? Fingers crossed!


Regina King, If Beale Street Could Talk

Amy Adams, Vice

Emma Stone, The Favourite

Marina de Tavira, Roma

Rachel Weisz, The Favourite

Who will win: Regina King

Who might win: Rachel Weisz

Who should win: Rachel Weisz

Analysis: The pleasant surprise here is de Tavira, who was so wonderful in Roma and didn’t get a lot of pre-Oscar award-season love. But Rachel Weisz is everything in The Favourite, one of the most smart, perfectly calibrated, and memorable performances of the year (although arguably she and Stone are actually co-leads along with Colman). I’d also love to see Amy Adams to get off the schneid, as they say in sports, and finally win her first Oscar but not for Vice. Never for Vice. That being said, King’s work in If Beale Street Could Talk is the essence of a supporting part. She absolutely shines in a few key scenes. Who could argue with this brilliant actress snatching the gold?


The Favourite

First Reformed

Green Book



Who will win: The Favourite

Who might win: Ugh, Green Book

Who should win: Can You Forgive Me? (But since it’s not nominated, First Reformed.)

Analysis: I’d really love to see Paul Schrader win for his searching, deeply felt First Reformed script, but I’m not holding my breath. But I really dug The Favourite, so I can hardly complain here.


The Ballad of Buster Scruggs


Can You Ever Forgive Me?

If Beale Street Could Talk

A Star Is Born

Who will win: BlackKlansman

Who might win: If Beale Street Could Talk

Who should win: Can You Ever Forgive Me?

Analysis: My guess? Spike won’t win Best Director and this will be his (not too shabby) consolation prize. An aside: Isn’t it wild that A Star is Born—once heralded as Best Picture frontrunner—might walk away with nothing more than a “Best Song” win?


Cold War




Never Look Away

Who will win: Roma

Who might win: Cold War

Who should win: Roma

Analysis: I confess I’ve only seen three of these contenders (Roma, Cold War, and Shoplifters). All are varying degrees of good and great (I was disappointed that Lee Chang-dong’s Burning didn’t make the cut), but Roma is the film of the year. My only concern: Will voters who picked it in the Best Foreign Language Film category feel they’ve been-there-done-that when it comes times to vote for Best Picture?


Free Solo

Hale County This Morning; This Evening

Minding the Gap

Of Fathers and Sons


Who will win: Free Solo

Who could win: RBG

Who should win: Minding the Gap

Analysis: How on earth is Won’t You Be My Neighbor not on this list? That’s it. That’s the analysis.


Incredibles 2

Isle of Dogs


Ralph Breaks the Internet

Spider Man: Into the Spiderverse

Who will win: Spider Man: Into the Spiderverse

Who might win: Incredibles 2

Who should win: Spider Man: Into the Spiderverse

Analysis: Talk about a come-from-behind win (probably). Barely a month ago, Spiderverse wasn’t even in the conversation. Then it came out, blew everyone’s collective minds, and is now poised for the win against some formidable competition.