Note: I don't include the Shorts below because A) I usually see most of them right before I pick so I'm not thinking about them right now and B) no one can say with confidence that they know who will win the shorts. Anyone who does is a fool-the Academy goes crazy when it comes to those categories, and is wildly inconsistent.
Where My Head's At: Casey Affleck has won the BAFTA and the Globe, Denzel Washington has taken the SAG. That's usually an indication that this is a close race, but you should probably go with the man who has never won before and that is, more importantly, in the stronger Best Picture nominee. That's Casey Affleck, who also has the added bonus of his generation of movie stars wanting to crown him "one of the greats." Plus, and this doesn't factor that much but it never hurts-he's genuinely quite excellent in Manchester by the Sea.
...But Then Again: Affleck has been getting pretty bad press thanks to revelations that he was accused of sexual harassment by multiple women. While he settled out of court, in the year of Donald Trump this gets extra scrutiny, and it's hard to compare Affleck in this regard with loyal, popular Hollywood family man Denzel, whose marriage to wife Paulette has lasted over thirty years. That SAG seems very telling that there's an appetite to go in a different direction.
Where I'm Leaning: Part of me thinks, quite frankly, that this could be an Adrien Brody situation (where Gosling sneaks in at the last minute somehow against two complicated frontrunners-Denzel being so because this would be a third Oscar, a rarity for most people). But that seems a gadfly bet. I'm probably going to stick with Washington-I'm getting that rare "third Oscar" vibe right now, and some people have taken home their third in tough competitions (Streep, Hepburn, Bergman).
Where's My Head At: While the Globes threw me for a loop with Aaron Taylor-Johnson, Mahershala Ali's classy speech at the SAG Awards, coupled with him being a smart way to reward the second place Best Picture nominee (a thing that happens quite often-look at Patricia Arquette a couple of years ago), makes him something of the frontrunner.
...But Then Again: I'm not totally sold on the idea that an actor whose principle fame prior to this year was on Crossing Jordan isn't vulnerable. After all, Dev Patel is more famous, is having a bit of a moment this year, and also is in a Best Picture nominee that I suspect plays well on screeners. Plus, he took the BAFTA and is something of a category fraud compared to the minimal amount of screen-time enjoyed by Ali. Add this to Supporting Actor occasionally having room for an upset (just look at last year with Mark Rylance besting Sly Stallone) and you could have a surprise on your hands
Where I'm Leaning: As a general rule you win your Oscar bracket if you pick all of the frontrunners, you just don't get bragging rights or ever get all 24 categories as it's never all the frontrunners. As a result, I'll probably go with Ali unless this is my one random "what the heck?" choice of the night.
Where's My Head At: Here's the thing with some of the remaining categories-the question is just how big the La La Land sweep (I already have the film at eight trophies coming into this) will be. I'm not sold that it takes Actor or Screenplay (thus depriving it of the record outright), but it could tie if it takes the three tech categories listed here, and I think it's going to take at least one. The color palette for the picture is really bold and distinctive-Emma Stone has never looked better.
...But Then Again?: It's a modern film, and the last time the Academy went for a contemporary movie was 1994-that was 22 years ago, and it's not like there's particularly slouch-y nominees against La La Land, what with AMPAS favorite Colleen Atwood an option, and perhaps most importantly, the impeccable design work of Jackie. Recreating the looks of an iconic First Lady could make for an upset.
Where I'm Leaning: Probably to La La Land, given that the branches generally tend to just say the same film everywhere, and it clearly has a massive amount of strength. But I'm not totally sold on that-Jackie is more up-their-alley and (cough) it's better and more impressive work.
Where's My Head At: OJ: Made in America is decidedly the frontrunner, and a critically-acclaimed one at that. In a year where OJ seemed to be everywhere, this would be a way for the Academy to endorse comprehensive storytelling-the nomination is telling after all, and there were rumors it could even make it in for Editing, which would have been a huge moment as well.
...But Then Again?: There has to be a contingent of the Academy who sees that they're cheating their way to an Oscar here. This is TELEVISION, not a MOVIE. It might be excellent, riveting television, but then give it a boatload of Emmys and you'll hear no peep out of me. I wonder if enough of the Academy, pissed that feature documentaries now have to compete against miniseries (this will be repeated in the future considering its success already) will go for a different film. And lo-and-behold, they have another critically acclaimed (film!) in 13th, which is from an iconic and of-the-moment director: Ava DuVernay
Where I'm Leaning: OJ is clearly the frontrunner, and like I said-I almost always pick the frontrunner because generally that's who wins. But I would so easily vote for 13th in this situation that part of me wonders if I wouldn't be the only one. DuVernay would make a great speech, and certain branches have been reluctant to get behind television too heartily in the past (see animation with something like The Simpsons Movie).
Where's My Head At: Who the hell knows. Easily the most frustrating category at the Oscars each year, I figured this was Roy Helland getting a second trophy this year, but then somehow Florence Foster Jenkins missed, as did the overrated Deadpool, and we were left with two underwhelming blockbusters and a foreign language film that few people have seen. My head is mostly at-"all of the frontrunners are gone but there's still no winner."
...But Then Again?: Perhaps Star Trek Beyond? Honestly, it's the film that seems the least embarrassing-it has lots of makeup, is a franchise they've noticed here before, and no one's really going to say two words against it winning even if it's a snooze for the win (considering they won for this same set of actors in 2008 already). That being said, I don't think Suicide Squad, despite its reputation, is in last place thanks to the Harley Quinn iconography. So be afraid...
Where I'm Leaning: Probably Star Trek Beyond, even though it only makes sense when you look at the other two nominees. I've literally seen none of these movies yet so the OVP could be interesting.
Where's My Head At: Generally when a film gets multiple nominations, it's pretty well known which song the studio "wants" you to vote for. See how Alan Menken continually cleaned up here in the 1990's despite competing against himself repeatedly (and Slumdog Millionaire did the same a decade later). It's assumed that "City of Stars" will be the La La Land entry that makes it, and it's hard to imagine an original musical winning Best Picture for the first time since Gigi and not taking this prize.
...But Then Again?: It could happen. Dreamgirls and Enchanted both watched a bushel full of nominations lead to nothing in this category a few years back, and there is a third option here in Disney. After all, the Mouse House has a princess ballad (which is great for picking this up), and it's written by everyone's favorite future human being Lin-Manuel Miranda. It's hardly going to look embarrassing to see him win his EGOT-could this year be the year?
Where I'm Leaning: Probably La La Land, but this is the category I'm thinking I'm mostly likely to go for broke. Miranda is impossible not to like, and it's easy to see both La La Land songs having their own distinct fans.
Where's My Head At: I've already come to terms with the truly apocalyptically bad sound work in La La Land taking the Best Sound Mixing Oscar (heaven help it when we get to that category for the OVP). But Sound Editing's different, and the Academy's generally smart enough to realize that. While I was shocked it made it in here (seriously-what sound editing is even happening in this movie-the car horns in the opening scene?!?), and the Academy has a penchant for going for this a dual pair, I can't help but think this is a very, very weak frontrunner.
...But Then Again?: There's not really a great, awesome, obvious contender here to take down La La Land. Arrival is attractive and sleek, but its lack of nomination for Amy Adams makes me think it's just a "nominate only" sort of movie. Deepwater Horizon did very well this year all things considered, but it's not winning here either. The only movie that probably has a shot is Hacksaw Ridge. It was nominated for a solid six trophies this year (nothing to sneeze at), and this frequently will go to Best Picture action adventures that don't have a legit shot at taking Best Picture (Letters from Iwo Jima, American Sniper, Inception, Gravity). The question is-will enough voters get over the Mel factor to actually give his film a win?
Where I'm Leaning: I'm looking more and more at Hacksaw Ridge, though I'm wondering if I'm being tainted by the fact that (in this field specifically) Hacksaw is far, far more deserving of the trophy, as personal feelings should be tossed aside when it comes to the Oscars. That being said, I can't kick the thought that Gibson's comeback bid won't score somewhere, and if it has to, at least it can be in the category it earned its nomination.
Those are the seven categories I'm most confused by-now you share yours. Who do you think are winning these seven, and what other of Sunday's races do you think are a showdown?