Due to time constraints I can’t do a full breakdown this year but I will post a bit of analysis. One thing is true: whenever you start hearing someone say that a film is a lock is when you really need to start wondering how true that is.

Best Picture

Will Win–Slumdog Millionaire: This is the biggest lock to win Best Picture since Brokeback Mountain. The only problem is that Brokeback did not win. The main difference here is that Slumdog peaked at just the right time whereas Brokeback had been the frontrunner for months and peaked way too early leading to the ubiquitous Oscar backlash.
Could Upset–Anything but Frost/Nixon. The Reader is a captivating tale and has the Weinstein PR machine behind it. My gut is that it peaked too late, however. Benjamin Button could move in here but overall the reception was somewhat reserved. Milk is a fabulous film and would not be just a perceived makeup for Brokeback but could win on its own merits.
Should Win–Slumdog Millionaire. As much as I like each of the other nominees, this is the best picture of the year.

Best Actor
Will Win–This could go either way between Sean Penn and Mickey Rourke. I’m going to go with Penn for bringing Harvey Milk to life.
Could Upset–I guess there is a scenario where Brad Pitt could sneak in if Penn and Rourke split votes but I don’t see that happening. A better choice would be Frank Langella for actually making Richard Nixon a sympathetic character. That is the perfomance that will be remembered in retrospect.
Should Win–Penn has won before and his role is more about the character than the performance. Rourke should be honored for such a stunning comeback.

Best Actress
Will Win–I’ve heard talk that Meryl Streep is making a tremendous surge to taking home another trophy after a long hiatus. However, this statue must belong to Kate Winslet for her indelible performance of a woman who is complex, layered and mysterious. It is her turn.
Could Upset–If Streep wins it is a huge upset in my book.
Should Win–Winslet

Best Supporting Actor
Will Win–Heath Ledger, although this could be the upset of the night. This statue was practically handed to him over a year ago when he died. The raw emotion of that passing has now subsided and Oscar voters hate being told who to vote for. With that said, he deserves the trophy based upon the merits of his performance. A win here after a huge snub for The Dark Knight is important.
Could Upset–Robert Downey, Jr. turned in an impeccable performance.
Should Win–Ledger

Best Supporting Actress
Will Win–I view this as the most wide open contest of the night. In theory the two Doubt performances should cancel each other out. However, who would not love to see an Amy Adams victory? My heart says Tomei wins and removes all doubt about her legitimacy as an Oscar winner but I am afraid that Penelope Cruz wins for her performance in the insipid Vicky Cristina Barcelona. Ugh.

Best Director–Danny Boyle
Best Original Screenplay–Dustin Lance Black
Best Adapted Screenplay–Simon Beaufoy

Best Song–Bruce Springsteen’s omission makes this category absolutely worthless.