I’m an Academy Award wonk and have a pretty good track record of picking the winners each year. However, this year is the most wide-open field since 1995. There are scenarios where all five best picture nominees could walk away with the top prize.
If you are interested in an unpredictable night at the Oscars, this is the one. I’ll try to take my best stab at the top categories but I’m not expecting to be overly successful.

Best Picture

Will Win–Again, I think a case can be made for all of these movies. The best I can do is a process of elimination as none of these truly stand out above the others. The Queen has a shot because of its across the board excellence and its multiple nominations. Little Miss Sunshine has great love from the acting block but it’s lack of a directing nom could be a detriment. Letters From Iwo Jima is making a late surge and it has the Eastwood cachet. Babel is an outstanding film that delivered some of the most intense scenes of the year. But ultimately I think there will finally be a much belated breakthrough for Scorcese and The Departed will be swept along with that tide.
Should Win–Babel is the one movie that has stuck with me after seeing it. The message of fractured communication in the midst of heartache and struggle is compelling.

Best Actor
Will Win–Although there seems to be a lot of sentiment for Peter O’Toole I have to give the nod to Forrest Whitaker for his stirring depiction of Idi Amin. Besides O’Toole just received an honorary award.
Should Win–It’s hard to go against those two luminaries for their performances but no actor sucked me in with a performance this year better than Leonardo DiCaprio. And he did it twice.

Best Actress
Will Win–Although Oscar is famed for its backlash, and Helen Mirren has led from the outset scooping up every award along the way, nothing stands in her way this year.
Should Win–Mirren

Best Supporting Actor
Will Win–It’s a horse race between Arkin and Murphy but I think old school gives Alan Arkin the trophy.
Should Win–It’s Eddie Murphy with a career defining role that should win the prize. A lot of talk has been about how Norbit may hurt his chances. But he shouldn’t be penalized for being Eddie Murphy. He should be awarded for how staggering this departure was.

Best Supporting Actress
Will Win–Jennifer Hudson for dominating every scene she was in in Dreamgirls.
Should Win–Hudson.

Director
Will Win-It’s finally Marty‘s year. But Eastwood is looking over his shoulder and could be the spoiler yet again.
Should Win–Martin Scorcese. If there is anyone due, it’s him.

Other Thoughts:
Children of Men should snatch up cinematography. It is the most beautifully shot movie of the year.
Babel will, inexplicably, win editing. It’s a great film but, come on, they couldn’t have trimmed 10 minutes off of it.
I’d love to see Borat win screenplay, but it won’t happen