Oscar Predictions, aka Recipe for Failure

As disengaged as I've been, I oughta take a stab before the big day next weekend.

BEST PICTURE
Should Win: Milk, for the fullness of its key characterizations, its prismatic yet guarded perspectives, and its expression of political fire and spirit as real, revivable, grassroots possibilities
Will Win: Slumdog Millionaire, because of its Oscarish sentimentality, its inclination to condescend just where it thinks it's paying tribute, and its ostentatious performance of Style

BEST DIRECTOR
Should Win: Gus Van Sant, for the same reasons
Will Win: Danny Boyle, for the same reasons

BEST ACTRESS
Should Win: Anne Hathaway for digging so deeply and restlessly into her character without trapping herself into a single tone or an obvious arc
Will Win: Allow me to go on a limb, but Melissa Leo. Probably a boneheaded call, but the movie has clicked with Hollywood, it would be a great dark-horse story, it has a timely emphasis on poverty and bleak moral choices, and the performance is a strong piece of work by an actor who hasn't overshadowed this character with better stuff in the past

BEST ACTOR
Should Win: I keep going back and forth between Mickey Rourke's phenomenal eloquence with a thick, hunkered-down character and Sean Penn's equal eloquence with such an uncharacteristically lively, joyfully charismatic part. It hurts me to pick either one, but I suppose I have to say Rourke, only because I never saw that 40 years of corporate back-history in Penn's characterization
Will Win: The same duel, but I'm going to resist the recent Rourke momentum and say Sean Penn, since the "Randy is Rourke" meme could easily backfire

BEST SUPPORTING ACTRESS
Should Win: Marisa Tomei basically defines the job of giving your all to a character without over-doing it and without asking for the spotlight; she enlivens and deepens the film as much as Cruz and Davis do theirs, but with less obvious assistance from her script
Will Win: Viola Davis, since Doubt appears to have so many fans, and she's come across so winningly through the season

BEST SUPPORTING ACTOR
Should Win: Heath Ledger; for what it's worth, I'm in the camp that thinks this is his best performance
Will Win: Heath Ledger, for that reason as well as all the others

BEST ORIGINAL SCREENPLAY
Should Win: I don't love any of these, as much as they all have flashes of glory or at least distinction; I'll take the consistency of Milk, finally, over the engaging but lopsided storytelling of WALL•E
Will Win: I really can't figure this out, but I'm guessing that the well-known lore of Milk's many aborted attempts will help put it over the top. Voters worried that Rourke may best Penn for Best Actor might look for some safe compensation here

BEST ADAPTED SCREENPLAY
Should Win: Moviegoers. We deserve richer, fresher, more consistent material than this. I'd be ticking the box next to The Reader if I had a ballot, but I'd be harrumphing about it
Will Win: Slumdog Millionaire, in a win that will confound the future even more than its other, "bigger" wins are likely to do.

BEST FOREIGN-LANGUAGE FILM
Should Win: It's unfair of me to say, having only seen The Class and Waltz with Bashir, but The Class would be a well-above average victor for this category
Will Win: I only hear raves about Revanche, so I'm giving that one a squeaker victory over the two strong competitors I've seen

BEST ANIMATED FEATURE
Should Win: WALL•E, and I wish he were going to be there to accept; I'd love to see him pack the trophy into his tummy. Maybe the PIXAR animators are scrambling even now to work that footage up.
Will Win: WALL•E, so their efforts won't be in vain

BEST DOCUMENTARY FEATURE
Should Win: Though I've only seen three of the entrants, I still feel comfortable singling out Trouble the Water
Will Win: I guess I'll take the safe bet and go with Man on Wire, but I feel like Encounters or Water could easily upset

BEST CINEMATOGRAPHY
Should Win: Chris Menges and Roger Deakins' ambiguously split duties on The Reader roughed up the story invaluably with cold, hard, confrontational lighting. But I forgot when I first posted this that The Dark Knight is also nominated, and it's hard to beat that one for powerfully composed, evocatively lit, and technologically ambitious lensing.
Will Win: As we learned again from Pan's Labyrinth, voters think "Cinematography" means exciting images, whether or not the lighting or framing is at the heart of what they're responding to. So, by that logic, Slumdog

BEST FILM EDITING
Should Win: Elliot Graham's engaging blend of time-frames, perspectives, and diverse genres of footage in Milk
Will Win: The flashbacks, high-energy collages, and tense, game-show staredowns of Slumdog Millionaire

BEST ART DIRECTION
Should Win: The superhero sleekness and adumbrated reality of The Dark Knight
Will Win: The expensive sepia dollhousery of The Curious Case of Benjamin Button (sorry, folks)

BEST COSTUME DESIGN
Should Win: Milk's mix of trendy peacockery and workaday outfits worn by people who don't think much about clothes
Will Win: The impressive finery The Duchess

BEST SOUND
Should Win: The soaring and diving crescendos and cackles of The Dark Knight
Will Win: The sonic splash of everyone's new favorite toy, Slumdog Millionaire

BEST ORIGINAL SCORE
Should Win: Moviegoers: there are too many coattail-riding nominations by old pros to take this list seriously as the year's best, and we deserved better than we generally got in '08
Will Win: A.R. Rahman's subcontinental pastiche in Slumdog

BEST ORIGINAL SONG
Should Win: Bruce Springsteen, by a heavy margin, except he isn't nominated
Will Win: Slumdog's "Jai Ho"

BEST SOUND EFFECTS
Should Win: The evocative, film-carrying soundscape of WALL•E
Will Win: WALL•E, breaking the Slumdog sweep

BEST VISUAL EFFECTS
Should Win: The Dark Knight, which honestly could have had sturdier work, but Iron Man looked chintzy at times and Benjamin Button just didn't convince me despite all the digital strain; plus, this guy's name is Nick Davis, so I will relish hearing it read out, except that...
Will Win: ...I assume the Benjamin Button team is going to scoop him

BEST MAKEUP
Should Win: I haven't seen the intriguing though largely carried-over character looks from Hellboy, but it's hard to imagine them being as instantly iconic as the reimagined Joker from The Dark Knight
Will Win: Benjamin Button botched the job here, too, but two studios are running heavy campaigns, and the work is so conspicuous it's bound for a consolation prize