So in honor of THE BIGGEST DAY IN HOLLYWOOD, we present to you our Oscar picks. We could be right… we could be wrong… What do we know? We're just assistants. But here's who we think will be taking home gold on Sunday.Best Actor
Will Win: Sean Penn
Should Win: Mickey Rourke
Penn's proven himself time and time again as one of the greatest actors of this generation, and his turn as Harvey Milk was at times both uplifting and heartbreaking. But Mickey runs away with The Wrestler. He breathes Randy 'The Ram' Robinson. And who doesn't love a good comeback story?
Will Win: Kate Winslet
Should Win: Melissa Leo
Kate's made this awards season her bitch and we expect her victory lap to continue on Sunday night. However, we loved Frozen River and Melissa exemplifies commitment in her portrayal of a down-on-her-luck single mom under desperate financial duress. Her performance is subtle and nuanced and makes you forget you're watching someone act.
Best Supporting Actor
Will Win: Heath Ledger
Should Win: Heath Ledger
We're still having nightmares about the Joker dressed in that nurse's outfit. Who knew someone so pretty could turn in such a sinister performance? If he doesn't win, we expect fanboys to riot in the streets.
Best Supporting Actress
Will Win: Who knows?
Should Win: Penelope Cruz
Kate Winslet took the Golden Globe and didn't get an Oscar nod in this category, and we loved all of the performances from the other nominees. So your guess is as good as ours. Cruz's turn as a completely bat-shit ex-lover hits us a little too close to home, but that's probably also why we're so drawn to it. Everyone knows you haven't experienced true love until you try to murder your boyfriend in a jealous rage.
Best Original Screenplay
Will Win: Milk
Should Win: Frozen River
This is probably one of the best categories at this year’s awards. While we think Frozen River deserves it, we’ll still be happy for Milk when it wins since it was an amazing screenplay. We also like seeing In Bruges recognized here considering it was such an underrated movie. We only wish Rachel Getting Married and Vicky Christina Barcelona were nominated too.
Best Adapted Screenplay
Will Win: Slumdog Millionaire
Should Win: Slumdog Millionaire
This category is boring. Slumdog will and should win because it has no competition. Next.
Will Win: Danny Boyle
Should Win: Danny Boyle
If Christopher Nolan were nominated this would be an entirely different race. But alas, he’s not and therefore Danny Boyle will and should win.
Will Win: Slumdog Millionaire
Should Win: Who cares?
At this point in the night we will have drunk far too much champagne and it probably won’t matter to us who wins. It’s not like our lives will be any different come Monday morning. We’ll still have to set up that conference call or stock the fridge with Arrowhead water. But we’re optimistic that one Oscar night in the future will be magical for us. Because deep down inside these bitter, stressed out souls lies an incredible film lover who one day dreams of Oscar gold.
WHERE: 5pm on ABC
COST: However much you put down for your Oscar pool. And we recommend printing these out for extra Oscar fun: http://www.thrillist.com/los-angeles/oscar-bingo-0