The envelope(s(s)), please.

Finally, my Oscar predictions! There's a little more going on here than straight-up prognostication, but it's all pretty cut-and-dried.

All 24 Oscar categories are listed below. For each category, I've made three entries. First and foremost is the person or film which most deserves to win that award. Second is the most deserving candidate from each list of nominees. And third is my actual prediction; that is, the nominee I actually expect to take the award home.

I'll be keeping track of how accurate my predictions are over the course of the show and will report back with a final tally once all is said and done. Seeing as many of my personal picks conflict with my predictions, here's hoping I don't score too many points. If you've filled out a ballot of your own, leave me a comment to let me know how you fare!

Happy viewing, everyone!


BEST ACTOR IN A LEADING ROLE
Ought to win: Philip Seymour Hoffman - Synecdoche, New York / Sean Penn - Milk
Ought to win (of those nominated): Sean Penn - Milk
WILL win: Sean Penn - Milk

BEST ACTOR IN A SUPPORTING ROLE
Ought to win: Tom Cruise - Tropic Thunder / Emile Hirsch - Milk / Heath Ledger - The Dark Knight
Ought to win (of those nominated): Heath Ledger - The Dark Knight
WILL win: Heath Ledger - The Dark Knight

BEST ACTRESS IN A LEADING ROLE
Ought to win: Juliette Binoche - Flight of the Red Balloon / Anne Hathaway - Rachel Getting Married / Meryl Streep - Doubt
Ought to win (of those nominated): Anne Hathaway - Rachel Getting Married / Meryl Streep - Doubt
WILL win: Kate Winslet - The Reader

BEST ACTRESS IN A SUPPORTING ROLE
Ought to win: Samantha Morton - Synecdoche, New York
Ought to win (of those nominated): Taraji P. Henson - The Curious Case of Benjamin Button
WILL win: Taraji P. Henson - The Curious Case of Benjamin Button
[If Penelope Cruz wins for her unimpressive turn in the unimpressive Vicky Cristina Barcelona, I'll turn the TV off right then and there. Okay, I won't really, but I'll want to.]

BEST ANIMATED FEATURE FILM
Ought to win: WALL-E
Ought to win (of those nominated): WALL-E
WILL win: WALL-E

BEST ART DIRECTION
Ought to win: Synecdoche, New York
Ought to win (of those nominated): The Dark Knight
WILL win: The Curious Case of Benjamin Button

BEST CINEMATOGRAPHY
Ought to win: Flight of the Red Balloon
Ought to win (of those nominated): Take your pick. All are decent, none extraordinary.
WILL win: Slumdog Millionaire

BEST COSTUME DESIGN
Ought to win: Don't know, don't care.
Ought to win (of those nominated): It's like I said; I don't know, and I don't care.
WILL win: The Duchess

BEST DIRECTING
Ought to win: Charlie Kaufman - Synecdoche, New York
Ought to win (of those nominated): Gus Van Sant - Milk
WILL win: Danny Boyle - Slumdog Millionaire

BEST DOCUMENTARY FEATURE
Ought to win: Man on Wire / Stranded: I've Come from a Plane That Crashed on the Mountains / Waltz with Bashir
Ought to win (of those nominated): Man on Wire
WILL win: Trouble the Water
[I still haven't been able to see Trouble the Water (hence its absence from the first two slots), but I'm not afraid to call the upset in its favor.]

BEST DOCUMENTARY SHORT
Ought to win: I wish I knew.
Ought to win (of those nominated): See above.
WILL win: Smile Pinki

BEST FILM EDITING
Ought to win: Rachel Getting Married
Ought to win (of those nominated): Milk
WILL win: Slumdog Millionaire

BEST FOREIGN LANGUAGE FILM
Ought to win: Flight of the Red Balloon
Ought to win (of those nominated): Waltz with Bashir
WILL win: Waltz with Bashir

BEST MAKEUP
Ought to win: Hellboy II: The Golden Army
Ought to win (of those nominated): Hellboy II: The Golden Army
WILL win: The Curious Case of Benjamin Button

BEST ORIGINAL SCORE
Ought to win: Synecdoche, New York
Ought to win (of those nominated): WALL-E
WILL win: Slumdog Millionaire
[Jon Brion (Synecdoche, New York) is, hands-down, the world's best active film composer. He'll probably never win an Oscar. Shame on the Academy.]

BEST ORIGINAL SONG
Ought to win: "Little Person" - Synecdoche, New York
Ought to win (of those nominated): "Down to Earth" - WALL-E
WILL win: "Jai Ho" - Slumdog Millionaire

BEST PICTURE
Ought to win: Synecdoche, New York
Ought to win (of those nominated): Milk
WILL win: Slumdog Millionaire

BEST ANIMATED SHORT FILM
Ought to win: The "Puzz & Toosh" City Arts spot that ran before a number of SIFF movies. Pure genius.
Ought to win (of those nominated): Presto is fun and clever. But I haven't seen any of the others, so...
WILL win: La Maison en Petits Cubes

BEST LIVE ACTION SHORT FILM
Ought to win: I have seen exactly zero Live Action Shorts this year. I miss you, Varsity.
Ought to win (of those nominated): ???
WILL win: Spielzeugland

BEST SOUND EDITING
Ought to win: WALL-E
Ought to win (of those nominated): WALL-E
WILL win: The Dark Knight

BEST SOUND MIXING
Ought to win: WALL-E
Ought to win (of those nominated): WALL-E
WILL win: WALL-E
[Ben Burtt deserves this one. Here's hoping the Academy gets it right.]

BEST VISUAL EFFECTS
Ought to win: The Curious Case of Benjamin Button
Ought to win (of those nominated): The Curious Case of Benjamin Button
WILL win: The Curious Case of Benjamin Button

BEST ADAPTED SCREENPLAY
Ought to win: Doubt
Ought to win (of those nominated): Doubt
WILL win: Slumdog Millionaire

BEST ORIGINAL SCREENPLAY
Ought to win: Synecdoche, New York
Ought to win (of those nominated): WALL-E
WILL win: WALL-E