In order of likelihood:
The Curious Case of Benjamin Button
The Dark Knight
I think Slumdog and Button are locks – they both have a shitload of critical acclaim, a lot of awards and award nominations, and most importantly they’re getting award nominations at the right time (the Golden Globe and Screen Actors’ Guild award noms were very favorable for both films). Milk isn’t quite as strong because it got mostly shut out at the Golden Globes, but it’s critically as popular as Slumdog or Button is and Sean Penn carries a lot of Academy weight. The Dark Knight is The Dark Knight, but it’s not as strong a contender as the first three films, mostly because at this point it’s only getting nominated for Heath Ledger’s performance and Christopher Nolan’s direction (which isn’t entirely fair to the film, but whatever). My fifth pick is Wall-E, mostly because I like to pick one longshot every year and this year Wall-E is a longshot despite being an astounding popular critical and popular favorite, mostly because, hey, cartoon. Sure, it’ll win Best Animated Picture in a heartbeat, but winning the ghetto category isn’t hard, you know?
If there’s any deviation from my picks, it’ll probably be either Wall-E or Dark Knight getting replaced with either Frost/Nixon (which really isn’t strong enough to merit a win in most categories and hasn’t done well in critical awards or major award nominations, but it’s a Ron Howard movie and I think Ron Howard could film his cock for ninety minutes and then Ron Howard’s Dick On Film would get a Best Picture nomination with a little luck) or The Wrestler (which is getting a serious push late in the game as it capitalizes on surprise crowd heat, to put it in wrestling parlance).
Danny Boyle, Slumdog Millionaire
David Fincher, The Curious Case of Benjamin Button
Gus Van Sant, Milk
Christopher Nolan, The Dark Knight
Darren Aronofsky, The Wrestler
Best Director picks usually mirror Best Picture picks with one exception so everybody can talk about how “X can be Best Picture but its director isn’t Best Director, what’s up with that?” Boyle and Fincher are locks just as their respective movies are, I think, and I think Christopher Nolan gets a nomination for Best Director even if Dark Knight doesn’t get a Best Picture nod because most of the acclaim for that film that wasn’t given to Heath Ledger was given to him (and rightfully so). Van Sant is a pure if-his-movie-gets-a-BP-nod pick; if Milk gets knocked out, I think he does as well. Aronofsky gets my longshot pick in this category for The Wrestler on the “everybody likes his work and thinks he’s due for an Academy nod of some kind” tip.
Other potential nominees are Ron “my milkshake brings the Academy voters to the yard” Howard for Frost/Nixon or Sam “suburbia sucks, guys, did I mention that” Mendes for Revolutionary Road. Bear in mind that the DGA announces their award nominees on the 9th and that has the potential to introduce an underdog in the mix (maybe Andrew Stanton for Wall-E, say, or Jonathan Demme for Rachel Getting Married), but my list is probably pretty close to what Oscar ends up recognizing.
Sean Penn, Milk
Mickey Rourke, The Wrestler
Frank Langella, Frost/Nixon
Richard Jenkins, The Visitor
Brad Pitt, The Curious Case of Benjamin Button
Penn, Rourke, and Langella all have a 99 percent chance of getting nominated; all three performances are brilliant, Langella’s never won an Academy Award despite being an acting force practically his entire life, Rourke has the magical comeback story and Penn is the recipient of “hey, this guy is the best actor of our lifetimes, maybe we should give him more awards” buzz (and rightly so). Jenkins’ work in The Visitor is a career best from a veteran character actor; I was worried it would get overlooked but then he got a SAG nod, and SAG nods tend to translate to Oscar noms. The final slot probably boils down to either Pitt or Leonardo DiCaprio for Revolutionary Road – both are popular actors, both are relatively underrecognized by the Academy despite strong bodies of work, and both would look really good accepting an Oscar. I’m going with Pitt, who had a better year than DiCaprio thanks to a critically popular role in Burn After Reading in addition to Button, and who got the SAG nod.
(Yes, I am aware that my list is a straight copy of the SAG best actor nomination list. Fuck off.)
Other than DiCaprio maybe swapping in for Pitt or Jenkins, I don’t see this list differing too much. Maybe, if Dustin Hoffman (Last Chance Harvey) or Brendan Gleeson (In Bruges), both nominated for a Golden Globe, get lucky… but it would take an awful lot of luck.
Anne Hathaway, Rachel Getting Married
Meryl Streep, Doubt
Angelina Jolie, Changeling
Kate Winslet, Revolutionary Road
Sally Hawkins, Happy-Go-Lucky
Hathaway, at this point, is a lock not only to get nominated but also probably has very good odds to win the award: she’s a critically acclaimed young ingenue, and Oscar loves critically acclaimed young ingenues. This would bother me more if Hathaway weren’t so inherently fantastic. Meryl Streep is Meryl Streep and she will get a nomination because she is Meryl Streep and there is nothing at all wrong with that. Jolie has the critical heft behind her, but here’s the thing: the Academy actually doesn’t like her that much, mostly because – and this is stupid – she’s “tabloidy” in that she acts out and cusses and and has a vial of Billy Bob Thornton’s blood somewhere and she does action movies and she steals Brad Pitt from people. I think she’ll get the nom anyway, though.
Kate Winslet isn’t going to win this year, not in Best Actress, and I’ll be the first to say that the fact that Kate Winslet does not have seventy billion Academy Awards right now is a bigger crime against humanity than Darfur. Well, no, not really, but it’s pretty bad. But she has a good chance at getting nominated. Hawkins didn’t get a SAG nomination, but her performance has gotten a lot of critical attention, and it’s a really cheerful movie that people like watching, and that helps a lot.
If there’s any differing from my list, it’ll be a swapout of Winslet or Hawkins for Melissa Leo in Frozen River (because she got a SAG nomination, despite nobody actually seeing her movie) or Michelle Williams in Wendy and Lucy (which is actually probably the best female performance of the year overall, but it was released really late and thus missed the opportunity to build up steam). Note that Williams also gets a little “grieving widow” cred (morbid as it might be to say that, but the Academy does pay attention to that sort of shit).
BEST SUPPORTING ACTOR:
Heath Ledger, The Dark Knight
Philip Seymour Hoffman, Doubt
Robert Downey Jr., Tropic Thunder
Josh Brolin, Milk
Dev Patel, Slumdog Millionaire
Ledger is a lock and 99 percent sure to win it as well, and something like that means the rest of the nominations get taken more on a “performances we want to honor with a nomination” basis. Doubt is an “actor’s movie” and Hoffman has the Golden Globe and SAG nods already, so he’s in. Downey Jr., like Hoffman, has the double-double of SAG and Golden Globe nods, and plus it is a performance where they can put up a clip of him on the broadcast in his blackface and everybody will laugh, and the Academy loves that shit, so he’s probably in. (He gets a lot of help from the “Ledger is winning this” factor, given that his performance was the sort that, in another year with no Ledger, might not have gotten nominated because people wouldn’t actually want it to win.) Milk had three separate performances the Academy might choose to honor (Brolin, James Franco and Emile Hirsch) and Brolin has both the most cred and the most acclaim. Dev Patel is the only serious chance that Slumdog has for an acting nomination, and it’s really, really popular with the awards crowd, and he got a SAG nomination too. So he’s probably in.
Patel and Brolin are the likeliest candidates for not getting the nomination, and if they don’t it’ll probably be one of Franco (for Milk or possibly even Pineapple Express), or juuuust maybe Tom Cruise for Tropic Thunder because he was very funny and got a Golden Globe nomination for it.
BEST SUPPORTING ACTRESS:
Penelope Cruz, Vicky Cristina Barcelona
Amy Adams, Doubt
Viola Davis, Doubt
Kate Winslet, The Reader
Rosemarie Dewitt, Rachel Getting Married
Pretty straightforward. Cruz has won, like, everything for her role in Vicky Cristina (as much as I disliked that movie). Adams and Davis are both actors in the “actor’s movie” this year and both were excellent and critically hurrahed. Kate Winslet is Kate Winslet, except this time she has a Golden Globe and SAG nod. (She won’t win, because she is Kate Winslet, AKA “the Susan Lucci of the Academy Awards.”) Dewitt is the second fiddle to Anne Hathaway, which is a good place to be.
Marisa Tomei might sneak in there for The Wrestler, but other than that, it’s pretty straightforward, I think.
EDIT TO ADD:
By multiple request:
BEST ADAPTED SCREENPLAY:
Simon Beaufoy for Slumdog Millionaire (from Q and A by Vikas Swarup)
Eric Roth for The Curious Case of Benjamin Button (from F. Scott Fitzgerald’s short story)
Peter Morgan for Frost/Nixon (from his stage play)
Justin Haythe for Revolutionary Road (from the novel by Richard Yates)
David Hare for The Reader (from the novel by Bernard Schlink)
BEST ORIGINAL SCREENPLAY:
Jenny Lumet for Rachel Getting Married
Charlie Kaufman for Synecdoche, N.Y.
Andrew Stanton and Jim Reardon for Wall-E
Robert D. Siegel for The Wrestler
Thomas McCarthy for The Visitor