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Predicting Oscar winners is as much a skill as an art, and it has little to do with who deserves to win. Anyone who predicts on the basis of quality is doomed to score low. The first lesson to learn when predicting Oscars (especially if you're involved in a pool - purely for entertainment, of course) is that it's sometimes a coincidence when the best man or woman takes home the prize.

When a member of the Academy votes, he or she will do one of three things: (1) Choose the film/person (s)he thinks is the most deserving, (2) Choose the film/person (s)he has a connection with, (3) Choose the film/person whose victory will be the most advantageous to him/her.

Perhaps unsurprisingly, #2 and #3 trump #1 - not always, but more often than many people in Hollywood would like to admit. Predicting winners requires that the predictor take these factors into consideration and weigh how they will impact the overall voting. It's a lot like predicting who will win an election, except there are no available polls.

Picture: Slumdog Millionaire. It's not a lock, but it rests in a comfortable position. I have long thought this movie would win based on its broad, feel-good appeal - I am on the record from before the nominations were handed out saying it would win, and nothing has changed in the past 45 days to alter that belief. The real question is: How long are its coattails?

Director: Danny Boyle, Slumdog Millionaire. Often goes in lock-step with Best Picture. No reason that should be different this year.

Lead Actor: Sean Penn, Milk. Penn is not all that well-liked in Hollywood, but I get the sense that there's a groundswell to give Milk something. If Penn loses to Mickey Rourke, expect a repeat of the outrage that erupted a few years ago when an undeserving Brokeback Mountain was passed over for an equally undeserving Crash.

Lead Actress: Kate Winslet, The Reader. Not a lock, but she has been nominated enough times that the Academy will probably figure it's time to give her an award. And if she wins… oh, the irony! But will the Academy be intimidated by Extras?

Supporting Actor: Heath Ledger, The Dark Knight. It's not a level playing field, and none of the other nominees have shown any interest in evening out the odds. (Better to be alive and have no Oscar than dead and have one.) The great unanswered (and unanswerable) question is whether a living Ledger would have been able to win this award. Anyone who argues that his death isn't a factor is fooling himself/herself. How many people have voted for him just to see the tear-jerking spectacle of his daughter (and her mother) accepting the award?

Supporting Actress: Viola Davis, Doubt. When an underdog wins, it's often in one of the Supporting categories. Since Heath Ledger's position is impregnable, that means the most likely category for an upset is this one. The favorite is Penelope Cruz, and maybe she'll win. But something tells me the front-runner could be in trouble here…

The rest (except the shorts, which I never predict), without commentary, follow. Three things that factored into these predictions: Slumdog Millionaire will have coattails, Hollywood dislikes The Dark Knight, and Hollywood really dislikes Revolutionary Road.

Animated Feature: WALL-E
Art Direction: The Curious Case of Benjamin Button
Cinematography: Slumdog Millionaire
Costume Design: The Duchess
Documentary: Man on Wire
Editing: Slumdog Millionaire
Foreign Language Film: Waltz with Bashir
Makeup: The Curious Case of Benjamin Button
Musical Score: Slumdog Millionaire
Music (Song): "Jai Ho," Slumdog Millionaire
Sound Editing: Slumdog Millionaire
Sound Mixing: Slumdog Millionaire
Visual Effects: The Dark Knight
Writing (Adapted): Slumdog Millionaire
Writing (Original): Milk

How will I do? Time will tell, but the numbers from recent years may provide a clue:
2008: 13/21 (62%)
2007: 12/21 (57%)
2006: 13/21 (62%)
2005: 17/21 (81%)
2004: 18/21 (86%)

Make of those numbers what you will…

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