Though I don't really agree with much Dave Karger and the EW prognostication/promoting staff says, promotes, or predicts, I thought it wouldn't be a bad idea to do what Karger is doing and making a list of my predictions for possible surprises at the Oscars.
Milk beats Slumdog (my prediction, but hard for people to take seriously) for Best Picture
Richard Jenkins or Brad Pitt beats Mickey Rourke, Sean Penn, and Frank Langella for Best Actor due to love to indies or Buttons
Josh Brolin or Michael Shannon pulls an upset on Heath Ledger and upsets thousands of viewers (not likely)
Taraji P. Henson pulls ahead of Penelope Cruz and Viola Davis
The Dark Knight wins over Slumdog for Best Cinematography
The Curious Case of Benjamin Button beats Slumdog for best Adapted Screenplay
Those are the best I can think of at the moment.