From ‘Slumdog Millionaire’ to ‘Milk’: HollywoodChicago.com Picks the 2009 Oscar Winners

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BEST ACTRESS

Kate Winslet in The Reader
Photo credit: The Weinstein Company

Anne Hathaway, “Rachel Getting Married”
-1st nomination; won Chicago Critics Award and National Board of Review

Angelina Jolie, “Changeling”
-2nd nomination (one win)

Melissa Leo, “Frozen River”
-1st nomination

Meryl Streep, “Doubt”
-15th nomination (two wins, none since Sophie’s Choice); won Screen Actors Guild Award

Kate Winslet, “The Reader”
-6th nomination (never won); won BAFTA for lead; won Chicago Critics, Golden Globe, and SAG Award for supporting

The transition from supporting actress to lead throws this category into disarray. Either Kate Winslet will walk home with her first prize after six nominations or Meryl Streep will take home her third Oscar but first in a quarter-century. Arguably one of the best actresses that ever lived hasn’t won since “Sophie’s Choice”.

They may be dusty, but Meryl has two Oscars already and dozens of other trophies, and we all agree that Kate Winslet will be career-honored, over Streep who has tons of gold. Harvey Weinstein’s aggressive strategy with “The Reader” will pay off with at least one major Oscar and one of the best actresses of her generation will finally have “Oscar-nominated” next to her name on future previews.

Brian would rather see Ms. Hathaway take home the trophy for her searing, raw work in “Rachel Getting Married” but Patrick and Dustin think that if the Academy goes with Streep for a third time, they’ll be getting it right. Sadly, even though Meryl Streep consistently delivers, we seem to just expect that from her.

As for who’s missing out on the party, there are a number of good candidates, but Dustin and Brian agree that Sally Hawkins got incorrectly snubbed for her amazing work in “Happy-Go-Lucky”. Patrick wishes a former winner was in there for an early-year comedy - Frances McDormand in “Miss Pettigrew Lives For a Day”.

BEST SUPPORTING ACTOR

Heath Ledger in The Dark Knight
Photo credit: Warner Brothers

Josh Brolin, “Milk”
-1st nomination; won National Board of Review and New York Critics Award

Robert Downey Jr., “Tropic Thunder”
-2nd nomination (no wins)

Philip Seymour Hoffman, “Doubt”
-3rd nomination (one win)

Heath Ledger, “The Dark Knight”
-2nd nomination (no wins); won BAFTA, Boston Critics, Chicago Critics, Golden Globe, LA Critics, and SAG Award

Michael Shannon, “Revolutionary Road”
-1st nomination (no wins)

Like the rest of the world, there’s nothing but agreement here, as the staff at HollywoodChicago.com thinks the Academy will get it right and give Mr. Ledger his last Oscar for his amazing work in “The Dark Knight”.

There’s even a bit of agreement on who should have been nominated to be another category bridesmaid for Mr. Ledger. Both Dustin and Brian would have liked to hear James Franco’s name read on nomination morning, although Mr. Levell would have voted for him for “Milk” and Mr. Tallerico for “Pineapple Express”. It makes one wonder if the split at HC wasn’t in the Academy too, causing neither performance to make the final five.

Once again, Mr. McDonald digs back deeper into early 2008, praising Haaz Sleiman’s work in “The Visitor,” a film that we would all agree wasn’t nominated enough by Oscar 2009.

BEST SUPPORTING ACTRESS

Viola Davis in Doubt
Photo credit: Miramax

Amy Adams, “Doubt”
-2nd nomination (no wins)

Penelope Cruz, “Vicky Cristina Barcelona”
-2nd nomination (no wins); won BAFTA, Boston Critics, Los Angeles Critics, National Board of Review, and New York Critics

Viola Davis, “Doubt”
-1st nomination

Taraji P. Henson, “The Curious Case of Benjmain Button”
-1st nomination

Marisa Tomei, “The Wrestler”
-3rd nomination (one win)

This is that rare category where everyone nominated is just as deserving of the win. The category that is arguably most up in the air has nearly no online consensus, but both Brian and Patrick think the smallest supporting role will be the big winner and Viola Davis’ work in “Doubt” will take home the Oscar. It’s the toughest category but Davis made the most of her screen time over Tomei’s ultimate “exposure” as a stripper.

Dustin goes with Nate Silver (the notorious election prognosticator of fivethirtyeight.com) and picks Taraji P. Henson for her touching work in “The Curious Case of Benjamin Button”.

Dustin and Patrick would like to see Marisa Tomei take home a second trophy for her daring work in “The Wrestler” and Brian certainly wouldn’t be disappointed by that win, but he’d love to see the critic’s darling win the Oscar and Penelope Cruz hear her name early in the Oscar telecast. She should have won for “Volver” anyway.

Only Amy Adams doesn’t register as a “will win” or “should win,” indicating the range of support for this category, but Patrick still finds a way to praise her, noting that she should have been nominated for “Miss Pettigrew Lives For a Day”.

Brian wishes the Academy would have recognized the title character of “Rachel Getting Married” and walked Rosemarie DeWitt down the Oscar aisle while Dustin longs for the days when Kate Winslet was still in this category for “The Reader”. At least it would be an easier pick.