(Note: I will make by guesses for who will win for every category, but I will only give my opinions on who should win for categories where I've seen at least half the nominees.)
BEST PICTURE
Will Win: What once looked like a competition between Belfast and The Power of the Dog has shockingly turned into a neck in neck race between Dog, which has 12 nominations, and CODA, which has 3. This is likely because people didn't discover the very likable CODA until after it received its Best Picture nomination. The buzz is currently in CODA's favor after wins at the actors and producer's guild awards. That said, I still think Power has the edge. The Oscars tend to be a touch more highbrow with its more limited membership than those more mainstream organizations. I wouldn't be surprised by either film winning, but I still think the odds are in The Power of the Dog's favor at this point in time.
Likelihood of winning
1. The Power of the Dog
2. CODA
3. Belfast
4. West Side Story
5. King Richard
6. Dune
7. Drive My Car
8. Licorice Pizza
9. Nightmare Alley
10. Don't Look Up
Should Win: I absolutely loved Drive My Car and The Power of the Dog, and I wouldn't be upset with victories by CODA or West Side Story. That said, Dune is my favorite film of the last several years, and would easily get my vote.
Personal ranking of the nominees
1. Dune
2. Drive My Car
3. The Power of the Dog
4. CODA
5. West Side Story
6. Licorice Pizza
7. King Richard
8. Belfast
9. Nightmare Alley
10. Don't Look Up
BEST DIRECTOR
Will Win: Jane Campion has seemed like a lock for several months now for her work on Power of the Dog, even after a particularly tone deaf Critic's Choice Awards speech. When Picture and Director split, Picture tends to go to the more "loved" film while director goes to the more "respected" option. Because of that, Campion should still cruise to an easy victory here, even if the film doesn't take home Best Picture. Also, the main Best Picture competition is not nominated here.
Should Win: Due to the inexplicable snub of Denis Villeneuve for Dune, I'd definitely give Campion my vote.
BEST LEAD ACTOR
Will Win: It seemed like Will Smith's main competition was going to be Benedict Cumberbatch if Power managed to pull a full sweep. However, with Power's buzz fading and Cumberbatch losing the British Academy Award to Smith (where Cumberbatch had a home-field advantage) it looks like there's nothing standing in the way of Will Smith winning an Oscar for King Richard.
Should Win: This is mostly a very good lineup. I'd personally pick Benedict Cumberbatch for his multi-layered performance in Power of the Dog, though I wouldn't be at all upset about a Denzel Washington victory in the fantastic Tragedy of Macbeth
BEST LEAD ACTRESS
Will Win: This is the only acting category that still feels wide open. Jessica Chastain seems like the frontrunner, but it's a soft lead. Nicole Kidman seems good on paper, but her film wasn't able to get nominations outside of acting, Kristen Stewart was the frontrunner for most of the season, but her film lost buzz. The most likely spoiler to Chastain's frontrunner status is Olivia Colman, who is very well respected and who's film was clearly well loved, though it's a more subtle performance than Oscar usually goes for. It'll likely wind up going to Jessica Chastain, but I wouldn’t be surprised by any of the nominees winning.
BEST SUPPORTING ACTOR
Will Win: A two horse race has recently become a foregone conclusion. Kodi Smit-McPhee's subtle and excellent turn in The Power of the Dog got a lot of buzz, but has recently been fully overshadowed by Troy Kotsur. While I'm not sure CODA will be able to ultimately win Best Picture, its increasing buzz has made me more confident in Kotsur's eventual win here, as his performance is the most lauded aspect of the film.
Should Win: Interestingly, the two performances most likely to win are also the two I believe are most deserving. There's really not a wrong choice between Kotsur and Smit-McPhee, and both would make worthy winners. I'd probably ultimately vote for Kodi Smit-McPhee, but it would be a difficult choice.
BEST SUPPORTING ACTRESS
Will Win: Honestly, this has seemed like the easiest race to guess for a while now, and there's no reason to doubt the results. Ariana DeBose will become the second person to win an Oscar for playing the role of Anita in West Side Story, especially since her main competition, Caitriona Balfe, wound up not being nominated.
Should Win: DeBose is great, but my personal vote would wind up going to Kirsten Dunst, who brings so much to her performance in Power of the Dog as one of the two POV characters that find themselves in conflict with Cumberbatch's Phil Burbank.
BEST ORIGINAL SCREENPLAY
Will Win: This category is a pretty difficult one to guess, and a case could be made for nearly any of the five nominees to win, and to lose. Belfast is a well liked film that's unlikely to win elsewhere, but the script is not the most lauded aspect of the film. Don't Look Up is probably the most divisive nominee, but those who like it REALLY like it. King Richard will appeal to the more traditional members of the Academy, but many will feel like Smith is enough of a reward. Licorice Pizza is a great opportunity to finally give the overdue PTA an Oscar on his 11th nomination, but the film has attracted some controversy for a poorly handled racial caricature. The Worst Person in the World is very well loved by those who have seen it, but it's probably the least watched of the five, being a foreign language film not nominated for Best Picture. I'd place my bets on Belfast at this point in time, but it's very tight with Licorice Pizza and Don't Look Up.
Should Win: For me, I would easily give it to The Worst Person in the World, which is the best film nominated here, and the only one where I'd say the screenplay was the best part of the film.
BEST ADAPTED SCREENPLAY
Will Win: It seems, on paper, like The Power of the Dog should cruise to an easy victory here. However, the recent surge in popularity could bring CODA to a victory, plus this is the best place to honor the acclaimed foreign drama Drive My Car. Much like in Best Picture, I still think the ball is in Power of the Dog's court.
Should Win: The Power of the Dog is a fantastic screenplay that forces the audience to participate and pay attention, and would make for a worthy winner. However, Drive My Car is arguably a greater achievement. It's so subtle real and lived in that it manages to fully engross despite being a three hour long drama spoken in four languages that is mostly made up of very long conversations.
BEST ORIGINAL SCORE
Will Win: I'm sure The Power of the Dog and Encanto will get a lot of votes here, but I just don't see them ultimately beating Dune, who's score is so unique, powerful and instantly iconic.
Should Win: Dune, full stop.
BEST ORIGINAL SONG
Will Win: On paper, this seems like an easy get for No Time to Die. Billie Eilish is a big star, and the last two Bond Songs won Oscars. However, I just have a gut feeling it won't pull a repeat here. Encanto would surely win if it's nominated song were "We Don't Talk About Bruno," but I don't see Dos Uruguitas being as popular. I actually have a sneaking suspicion that Beyonce will sneak her way to a victory with the powerful Be Alive from King Richard, which may not have buzz now, but in a category with frequent left field winners, wouldn't be the oddest thing ever.
Should Win: Honestly, my own vote would go to Be Alive. I do really like No Time to Die, but it feels very derivative of Skyfall and Writing's on the Wall to me, rather than feeling like it's own thing.
BEST FILM EDITING
Will Win: This is another category where it seems like any of the five can win. Don't Look Up is the showiest, though just as much in bad ways as in good. Dune is a big action epic, King Richard has those showy sports sequences, and Tick Tick Boom has musical numbers. Weirdly, the only film I don't see winning this is The Power of the Dog, which is a little too subtle. At this point I'd lean towards Dune, but I'm far from convinced.
Should Win: This is very much not the lineup I'd personally have picked. Dune is my favorite of the nominees, but I think Drive My Car, In the Heights and The Last Duel would have made better nominees than those that made the cut.
BEST CINEMATOGRAPHY
Will Win: This is likely a three horse race. Dune is the most visually dynamic overall, The Power of the Dog is an opportunity to award the first female cinematographer, and the Tragedy of Macbeth has a showy, black and white style. I've been going back and forth between the first two, and at the moment am leaning towards The Power of the Dog.
Should Win: My personal pick would be Dune, but honestly all five in this lineup are pretty great picks.
BEST PRODUCTION DESIGN
Will Win: This is down to Dune versus Nightmare Alley. I think Dune has a lot more support than the latter at the moment.
Should Win: Honestly, for me it's a coin flip between the new worlds of Dune and the old school expressionistic minimalism of The Tragedy of Macbeth. The coin landed on The Tragedy of Macbeth.
BEST COSTUME DESIGN
Will Win: This one mostly comes down to Dune versus Cruella. Cruella is all about costumes, which could give it an advantage here. That said, I have a gut feeling that Dune being a more overall well-liked film will lead it to a victory here, a la Mad Max: Fury Road.
Should Win: Dune deserves this one for sure. The costumes are gorgeous, and do so much world building.
BEST MAKEUP AND HAIRSTYLING
Will Win: I think Dune will be competitive, but lately they've really liked makeup that recreates the appearance of historical figures. As such, I think The Eyes of Tammy Faye will wind up victorious here.
BEST SOUND
Will Win: It is tempting to go with a musical here, which would benefit West Side Story. However, lately they haven't been automatic victories, and Dune's soundscape is so impressive in every way that I think it has the advantage.
Should Win: Dune. It's some of the best sound work of all time.
BEST VISUAL EFFECTS
Will Win: Dune, no contest.
Should Win: Dune, no contest.
BEST INTERNATIONAL FEATURE FILM
Will Win: They occasionally go left field in this category, but if a foreign film is nominated for Best Picture, that tends to be a pretty undeniable sign it will win here. Hence, Drive My Car should prove victorious.
Should Win: All three of the ones I've seen (Drive My Car, The Worst Person in the World, Flee) are great, but Drive My Car is the one that most grabbed and enraptured me, as well as sticking in my head until the end.
BEST ANIMATED FEATURE
Will Win: The Mitchells vs. the Machines and Flee are very well liked, but it's not usually wise to bet against Disney in this category, so I think Encanto will walk away with it here.
BEST DOCUMENTARY FEATURE
Will Win: Of the three categories it's nominated in, this one is the best chance to honor Flee. However, Summer of Soul seems to be the more likely victor.
BEST LIVE ACTION SHORT FILM
Will Win: The Long Goodbye has more star power, but Ala Kachuu: Take and Run has the more emotionally fulfilling narrative. I'm leaning towards Ala Kachuu at the moment.
Should Win: Ala Kachuu is my pick, but Please Hold is very excellent as well, and one of the more clever shorts in recent memory.
BEST ANIMATED SHORT FILM
Will Win: Since it's the only family friendly offering nominated in this traditionally family friendly category I believe Robin Robin will emerge victorious.
Should Win: The Windshield Wiper may not have any kind of traditional narrative, but it is a beautiful and fascinating series of vignettes that is the best example of what can be accomplished in short form and animation.
BEST DOCUMENTARY SHORT
Will Win: I don't know. Maybe The Queen of Basketball? It really could be any of the five.
