Who’s Going To Win The 2019 Academy Awards (And Who We Hope Actually Wins)

Decimate your office Oscar pool like a snap-happy Thanos.

Alright, we all know why you're here, so I'll keep this preamble short. I don’t claim to be omniscient on all things Oscar, but I’ve run an Oscar pool or two in my day and I pay attention, and I think I've got a pretty good handle on who's taking home the prize on Sunday night. So buckle up and maybe you too can beat out your coworkers for that gift card to Buffalo Wild Wings and that lavender-scented candle that I’ve already told you I’m allergic to, Cheryl!

Oh, and because I can’t resist throwing in commentary, I’m going to let you know which film I think deserves the prize. Your mileage may vary, but I know who I’m rooting for.

Best Picture

Will Win: Green Book

Should Win: Black Panther

Bohemian Rhapsody
The Favourite
A Star Is Born

I really hope I’m wrong about this one. Realistically, the winner is probably either Green Book or Roma, though it also wouldn’t surprise me too much if BlacKkKlansman squeezed by to give an overdue victory to Spike Lee, but I get the nagging feeling that the old guard in the Academy has solidified around Green Book while the newer and younger members are a bit more split on their top pick. The real upset would be to see Black Panther pull out the victory, and with the ranked ballot it’s at least within the realm of possibility that the superhero film could come out on top as a mutually agreed upon "good enough"; I would be happy to lose a bet for that to actually happen.

Best Actor In A Leading Role

Will Win: Rami Malek, Bohemian Rhapsody

Should Win: Christian Bale, Vice

Bradley Cooper, A Star Is Born
Willem Dafoe, At Eternity’s Gate
Viggo Mortensen, Green Book

Alright, so this is probably the most frustrating category of the year, because none of these guys really feel like they deserve to win, at least in my book. Malek seems like the favorite just so the Academy can feel like they’re justified in recognizing Bohemian Rhapsody without acknowledging the big Bryan Singer-shaped elephant in the room, but Cooper also seems to stand a fighting chance here too. The performance I enjoyed the most of these was Bale’s, but not so much so that I’ll be disappointed when he doesn’t get called to the stage.

Best Actress In A Leading Role

Will Win: Glenn Close, The Wife

Should Win: Olivia Colman, The Favourite

Yalitza Aparicio, Roma
Lady Gaga, A Star Is Born
Melissa McCarthy, Can You Ever Forgive Me?

I’m much happier with the nominees in this category than its male counterpart, so it’s a bit disappointing to realize that the award is probably going to go to Glenn Close not as a testament to the quality of the performance – which was quite good, don’t get me wrong – but because she’s overdue for a win. If this were a meritocracy, I’d prefer Colman or McCarthy, and while Aparicio or Lady Gaga could pull off an upset, as popular as they appear to be, I think Close as this in the bag.

Best Actor In A Supporting Role

Will Win: Mahershala Ali, Green Book

Should Win: Richard E. Grant, Can You Ever Forgive Me?

Adam Driver, BlacKkKlansman
Sam Elliott, A Star Is Born
Sam Rockwell, Vice

Real talk, it’s super weird that Driver and Rockwell are even here, and I have a hard time seeing either one of them pulling out a victory. Elliott is a dark horse I wouldn’t mind seeing win here, but Grant is such a magnetic presence in Can You Ever Forgive Me? that it’ll be a real shame if he doesn’t win. However, my gut tells me Ali’s going to take it for the same reasons I see Green Book taking Best Picture, as irksome as that may be.

Best Actress In A Supporting Role

Will and Should Win: Regina King, If Beale Street Could Talk

Amy Adams, Vice
Marina de Tavira, Roma
Emma Stone, The Favourite
Rachel Weisz, The Favourite

Adams may be a contender, but I don’t think this is the role the Academy wants to finally recognize Adams for. It’s amazing that de Tavira was nominated, but I don’t see the same push behind her that I do behind Aparicio. Stone and Weisz are going to steal votes from each other by virtue of being in the same movie. That’s why I think Regina King is going to take it for her much-deserved turn in If Beale Street Could Talk, a film that merited way more nominations and will probably take this win as a consolation prize.

Best Director

Will Win: Spike Lee, BlacKkKlansman

Should Win: Yorgos Lanthimos, The Favourite

Pawel Pawlikowski, Cold War
Alfonso Cuarón, Roma
Adam McKay, Vice

McKay and Pawlikowki probably don’t have a chance here, and while I personally like Lanthimos’ film best, I think this probably boils down to two very solid choices in Cuarón and Lee. Particularly if the Academy leans more heavily toward Green Book than Roma in Best Picture, I can see them splitting the baby and giving Best Director to Cuarón, but this is also the prime category to finally recognize Spike Lee without necessarily giving him Best Picture, and I think he’s the safest bet here.

Best Original Screenplay

Will Win and Should Win: The Favourite

First Reformed
Green Book

I think this is where the Academy will carve out space to recognize The Favourite, which despite being nominated in many categories isn’t really a solid frontrunner in any of them, which is especially sad considering how much better it is than much of its competition. But if I’m wrong here, you can look to my points about Best Picture and Director for how I guess this will go, with Roma or Green Book nabbing this award either in conjunction with or in consolation to a Best Picture win.

Best Adapted Screenplay

Will Win: BlacKkKlansman

Should Win: Can You Ever Forgive Me?

The Ballad of Buster Scruggs
A Star Is Born
If Beale Street Could Talk

Realistically, I think this comes down to BlacKkKlansman or Can You Ever Forgive Me? with Beale Street acting as a dark horse should they split the vote, but see above why BlacKkKlansman probably has a leg up here. If any of those three win, though, I’ll be more than happy.

Best Cinematography

Will and Should Win: Roma

Cold War
The Favourite
Never Look Away
A Star Is Born

With a lot of love for foreign films this year, the only real shot I see of any film taking this from Roma is with Cold War, but even with how much love the Academy has given Cold War this year – some might say a shocking amount – their love for Roma is clearly stronger.

Best Editing

Will Win: BlacKkKlansman

Should Win: The Favourite

Bohemian Rhapsody
Green Book

I’m of the firm belief that some of the best editing is the editing you don’t even notice because it feels so natural. BlacKkKlansman will probably win for being showy, but The Favourite demonstrates killer comic timing that I personally hope wins the day. If Bohemian Rhapsody wins, your God, whichever God that might be, is dead.

Best Animated Feature

Will and Should Win: Spider-Man: Into the Spider-Verse

Incredibles 2
Isle of Dogs
Ralph Breaks the Internet

The upsets here are either Incredibles 2 or Isle of Dogs, but Spider-Man: Into the Spider-Verse has received a mountain of acclaim right in the middle of awards season and there’s nothing else out there that looks remotely like it. This one feels like a much deserved sure thing.

Best Documentary Feature

Will and Should Win: RBG

Free Solo
Minding the Gap
Hale County This Morning, This Evening
Of Fathers and Sons

Free Solo and Minding the Gap are very strong contenders and fantastic films in their own right, but for my money I think the Academy goes with the political option and awards RBG. This allows them to say they gave an award to female filmmakers Betsy West and Julie Cohen, and I genuinely found the film to be one of the most powerful documentary experiences I had all year, so that’s the way I think the wind is blowing, particularly given the absence of Won’t You Be My Neighbor?

Best Foreign Language Feature

Will Win: Roma

Should Win: Shoplifters

Cold War
Never Look Away

Look, I really like both Roma and Cold War, and the safe bet is to count on Roma winning this one with Cold War potentially acting as the upset should Roma take Best Picture. But I really loved Shoplifters more than either of the potential winners, so why don’t you just let me dream a little, okay?

Best Animated Short

Will and Should Win: Bao

Animal Behaviour
Late Afternoon
One Small Step

Best Documentary Short

Will Win: Black Sheep

Should Win:  Period. End of Sentence.

End Game
A Night at the Garden

Best Live Action Short

Will and Should Win: Marguerite


Best Original Song

Will Win: “Shallow”, A Star Is Born

Should Win: “All The Stars”, Black Panther

“The Place Where Lost Things Go”, Mary Poppins Returns
“I’ll Fight”, RBG
“When A Cowboy Trades His Spurs For Wings”, The Ballad of Buster Scruggs

I'm done making sweeping statements about most of these categories' destined winners, because as the below-the-line categories get further out of the actor-heavy Academy's wheelhouse in the general vote, the more arbitrary their selections can be. I continue to do my best to guess the winners below, but it's honestly just about anyone's game in most of these. However, this category, Best Original Song, is the biggest lock in the whole damn show. Not even a contest. "Shallow" is going to win and you’re crazy to think it will be anything else.

Best Original Score

Will Win: BlacKkKlansman

Should Win: If Beale Street Could Talk

Black Panther
Isle of Dogs
Mary Poppins Returns

Best Sound Editing

Will and Should Win: Roma

Black Panther
A Quiet Place
First Man
Bohemian Rhapsody

Best Sound Mixing

Will and Should Win: Roma

Black Panther
Bohemian Rhapsody
First Man
A Star Is Born

Best Costume Design

Will Win: The Favourite

Should Win: Black Panther

The Ballad of Buster Scruggs
Mary Poppins Returns
Mary Queen of Scots

Best Makeup and Hair

Will and Should Win: Vice

Mary Queen of Scots

Best Production Design

Will Win: First Man

Should Win: Black Panther

The Favourite
Mary Poppins Returns

Best Visual Effects

Will and Should Win: First Man

Avengers: Infinity War
Christopher Robin
Ready Player One
Solo: A Star Wars Story

So do you think I’m way off base, either in my predictions or my own preferences? Sound off in the comments section and we’ll see who takes home the grand prize this year, Cheryl!