For the record, it’s the Oscars that are the 89th Annual, not my picks. I’m only 31, and have only been making picks since 1999. Will Win is my official pick. Should Win is what I would vote for were I a voting member.
Best Picture
Should Win: Arrival
Will Win: La La Land
I have seen all 9 nominees. This is a bite-the-bullet vote for La La Land. It’s not a bad film. It’s not as good as award season has made it out to be (the script is problematic, and that kind of spreads out to everything else). But it has the momentum, the same momentum that propelled The Artist five years ago. Hollywood loves movies about Hollywood. And they don’t particularly care for genre films
Also Nominated: Fences; Hacksaw Ridge; Hell or High Water; Hidden Figures; Lion; Manchester by the Sea; Moonlight
Best Director
Should Win: Damien Chazelle – La La Land
Will Win: Damien Chazelle – La La Land
I have seen all 5 nominees. To be honest, Denis Villeneuve’s work on Arrival could and should be talked about with as much fervor as Damien Chazelle’s on La La Land. Despite all of La La Land’s problems, which can pinned on Chazelle, it still actually is a beautifully executed film, and a lot of what works about La La Land can just as readily be pinned on Chazelle. It’s not worth nearly as much love as it’s getting, but Chazelle’s conducting of the cinematic orchestra that is La La Land is noteworthy. It’s a film that worked in spite of itself.
Also Nominated: Mel Gibson – Hacksaw Ridge; Barry Jenkins – Moonlight; Kenneth Lonergan – Manchester by the Sea; Denis Villeneuve – Arrival
Best Actor
Should Win: Viggo Mortensen – Captain Fantastic
Will Win: Ryan Gosling – La La Land
I have seen all 5 nominees. I think Casey Affleck was great, but there has been some negative personal life press around him that could have hurt him in voting. Denzel was great in Fences, but there’s the specter of the stage play hanging over it, and he plays it as stage work being filmed. Viggo was fantastic in an interesting role which gets him the Should Win slot. But the hype train behind La La Land is strong, and knowing Oscar history… I think Ryan Gosling could walk home with this.
Also Nominated: Casey Affleck – Manchester by the Sea; Andrew Garfield – Hacksaw Ridge; Denzel Washington – Fences
Best Actress
Should Win: Viola Davis – Fences (not nominated in this category)
Will Win: Emma Stone – La La Land
I have seen 4 of the 5 nominees. Really, Viola Davis should be nominated for, and win, Best Actress, but some politicking on the studios part got her into the less competitive Supporting Actress category. The Best Actress category is a mess this year. No Taraji P. Henson, no Amy Adams. While I haven’t seen Meryl Streep’s Florence Foster Jenkins, there’s a large part of me that just assumes she got it on the strength of being Meryl Streep, and not on the strength of the actual performance. But ultimately the La La Land hype train will carry Emma Stone to the win. And for the record, she was good. Better than Adams? Henson? Portman? Davis? Nope.
Also Nominated: Isabelle Huppert – Elle; Ruth Negga – Loving; Natalie Portman – Jackie; Meryl Streep – Florence Foster Jenkins
Best Supporting Actor
Should Win: Mahershala Ali – Moonlight
Will Win:Mahershala Ali – Moonlight
I have seen all 5 nominees. The same studio politicking that kept Viola Davis out of the Lead Actress category also kept Dev Patel out of Lead Actor for Lion. He wouldn’t have won in either category, but at least this got him the nomination, which I understand is an honour in and of itself. But this one’s a no-brainer. Mahershala Ali deserves it. He deserves it for Moonlight. He deserves it for his great TV work over on Netflix’s House of Cards and Netflix’s Luke Cage. He deserves it for his entire 2016. Walter Lucas Hedges in Manchester by the Sea could be a spoiler if the Academy plays it safe. I should point out that Michael Shannon and his Golden Globe winning co-star Aaron Taylor-Johnson were both great in Nocturnal Animals.
Also Nominated: Jeff Bridges – Hell or High Water; Lucas Hedges – Manchester by the Sea; Dev Patel – Lion; Michael Shannon – Nocturnal Animals
Best Supporting Actress
Should Win: Naomie Harris – Moonlight
Will Win: Viola Davis – Fences
I have seen all 5 nominees. Again… Viola Davis is in the wrong category, and in a just world, she wouldn’t be here and Naomie Harris would be the easy pick. But Viola Davis was able to transition her stage portrayal to film better than Denzel was. Nicole Kidman and Octavia Spencer are good seat filler, but it’s a two person race between Harris & Davis, with Davis having the advantage. I don’t even know what Michelle Williams is doing here.
Also Nominated: Nicole Kidman – Lion; Octavia Spencer – Hidden Figures; Michelle Williams – Manchester by the Sea
Best Original Screenplay
Should Win: Yorgos Lanthimos & Efthimis Filippou – The Lobster
Will Win: Kenneth Lonergan – Manchester by the Sea
I have seen all 5 nominees. For all the great work Damien Chazelle did as a director, for all the other awards La La Land will most likely win tonight… the one it is least qualified for is Screenplay, as that is the biggest problem with the film. 20th Century Women was interesting and engaging, Hell or High Water was easily the most thrilling and entertaining. But for a truly original, bizarre, unique screenplay that just draws you in, that’s The Lobster (which overall is largely missing from the awards season chatter). And despite how morose it is, the script for Manchester by the Sea is quite good, and actually quite deserving of the love it has received.
Also Nominated: Hell or High Water; La La Land; 20th Century Women
Best Adapted Screenplay
Should Win: Eric Heisserer – Arrival
Will Win: Barry Jenkins & Tarell Alvin McCraney – Moonlight
I have seen all 5 nominees. Arrival was one of the most interesting films of the year, and I’d hate for it to be shut out, but we all know the Academy’s recent track record with genre films. That said… It was a very fine line that got Arrival into the Should Win category, as Moonlight is an amazing character piece. The supporting players are given little time to do get in and do their work, but they’re given so much and said short amount of time. Jenkins and McCraney paint a glorious backdrop for the stunning primary arc. Allison Schroeder and Theodore Melfi could be a spoiler, if the Academy wants to recognize the great work on Hidden Figures.
Also Nominated: Fences; Hiden Figures; Lion
Best Animated Feature
Should Win: Kubo and the Two Strings
Will Win: Moana
I have seen 3 of the 5 nominees. I have little faith in the Oscars to not go Disney. Of the 15 Animated features to win the award since its creation, only 4 have NOT gone to Disney/Pixar. And now Disney has two nominees. Kubo & The Two Strings should win, but I think the win will go to Moana.
Also Nominated: My Life as a Zucchini; The Red Turtle; Zootopia
Best Documentary Feature
Will Win: 13th
I haven’t seen any of these. But 13th is trending positively. OJ: Made In America could be a spoiler, as it appeared on several Year End lists. It’s a toss up, sure.
Also Nominated: Fire at Sea; I Am Not Your Negro; Life, Animated; O.J.: Made in America
Best Cinematography
Should Win: Linus Sandgren – La La Land
Will Win: Linus Sandgren – La La Land
Also Nominated: Greg Fraser – Lion; James Laxton – Moonlight; Rodrigo Prieto – Silence; Bradford Young – Arrival
Best Film Editing
Should Win: Arrival
Will Win: La La Land
Also Nominated: Hell or High Water; Hacksaw Ridge; Moonlight
Best Visual Effects
Should Win: The Jungle Book
Will Win: The Jungle Book
Also Nominated: Deepwater Horizon; Doctor Strange; Kubo and the Two Strings; Rogue One: A Star Wars Story
Best Production Design
Should Win: La La Land
Will Win: La La Land
Will Win: La La Land
Also Nominated: Arrival; Fantastic Beasts and Where to Find Them; Hail, Caesar!; La La Land; Passengers
Best Original Score
Should Win: La La Land
Will Win: La La Land
Will Win: La La Land
Also Nominated: Jackie; Lion; Moonlight; Passengers
Best Foreign Language Film
Will Win: The Salesman (Iran)
Also Nominated: Land of Mine (Denmark); A Man Called Ove (Sweden); Tanna (Australia);
Toni Erdmann (Germany)
Best Costume Design
Should Win: Jackie
Will Win: Jackie
Also Nominated: Allied; Fantastic Beasts and Where to Find Them; Florence Foster Jenkins; La La Land
Best Makeup/Hairstyling
Will Win: Star Trek Beyond
Also Nominated: A Man Called Ove; Suicide Squad
Best Original Song
Should Win: “Drive It Like You Stole It” – Sing Street (not nominated)
Will Win: “City of Stars” – La La Land (though I would love to see Moana get it so Lin-Manuel Miranda can go full EGOT)
Also Nominated: “Audition (The Fools Who Dream)” – La La Land; “Can’t Stop This Feeling!” – Trolls; “The Empty Chair” – Jim: The James Foley Story; “How Far I’ll Go” – Moana
Best Sound Editing
Will Win: La La Land
Also Nominated: Arrival; Deepwater Horizon; Hacksaw Ridge; Sully
Best Sound Mixing
Will Win: La La Land
Also Nominated: Arrival; Hacksaw Ridge; Rogue One: A Star Wars Story; 13 Hours: The Secret Soldiers of Benghazi
Best Documentary Short
Will Win: Joe’s Violin
Also Nominated: Extremis; 4.1 Miles; Watani: My Homeland; The White Helmets
Best Live-Action Short
Will Win: Ennemis Interieurs
Also Nominated: La Femme et le TGV; Silent Nights; Sing; Timecode
Best Animated Short
Will Win: Pearl
Also Nominated: Blind Vaysha; Borrowed Time; Pear Cider and Cigarettes; Piper
The Empty Theatre 
I like how you formatted this post. Biggest upset of the night in your opinion?
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