And the Winner is…

On February 22, most of relevant Hollywood will be walking down the red carpet and a lucky few will be honored by their peers by receiving the coveted Academy Award, or Oscar.  So if you are like me, and this night is as important to you as the Super Bowl, then you have probably been paying attention to who is supposed to win, who is supposed to lose, and which races are the closest.  So far this season, Slumdog Millionaire has been sweeping the awards shows.  But at this year’s Oscars, Benjamin Button has the most nominations.  Even for folks like me that follow this closely, winning an Oscar pool can be a very challenging task.  But if you would like to have my odds of winning (trust me – they aren’t that great) while attending your big Oscar party, here is what you will need to mark down.

Best Picture: Slumdog Millionaire.  While Button just barely edged out Slumdog on my top 10 movies of the year, I think that Slumdog has the edge here.  In 10 or 20 years I think that Benjamin Button will be the movie most remembered, but it’s about this year, not 2029.  Don’t rule out Milk either which could prove to have a very successful night Sunday. 

Best Director: Danny Boyle – Slumdog Millionaire.  Let’s forget about the fact that Boyle is one of the most important directors of our time and he has never been honored by his peers.  Slumdog couldn’t have been what it is without Boyle behind the scenes.  While I love Button’s David Fincher, I honestly can’t say the same about his film. 

Best Actor: Sean Penn – Milk.  While I personally loved Mickey Rourke, and will be crossing my fingers for him, I think that Penn has too much steam going and that Hollywood will also choose to honor Milk with the Best Actor trophy rather than Best Picture.

Best Actress: Kate Winslet – The Reader.  Who doesn’t love a Nazi camp guard turned pedophile?  There is no doubt that Winslet is deserving of an Oscar (sorry for the pun).  I’m not sure it’s for this, but there is still no doubt.  But needless to say, she is the favorite to win and if enough voters saw The Reader, she probably will.  I really hope that Anne Hathaway pulls a big upset here for Rachel Getting Married as I think that she is the most deserving this year.

Best Supporting Actor: Heath Ledger – The Dark Knight.  One of the most popular questions I have gotten this past year is “do you really think Heath was that good?”  The answer is an absolute yes.  I thought he was wonderful as the maniacal Joker and would have deserved the trophy whether alive or dead. 

Best Supporting Actress: Penelope Cruz – Vicky Christina Barcelona.  This was by far the weakest category of the year and really only two of the performances turned my eye: Cruz and Marisa Tomei for The Wrestler.  But Cruz was truly fantastic in this strange romantic comedy and deserves to take home the trophy. 

As for the rest of the categories, here are the selections I plan on making: