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Wednesday, October 14, 2026

What Should’ve Won That Could’ve Won: 2008

The Year: 2008
What the Nominees Were: The Curious Case of Benjamin Button, Frost Nixon, Milk, The Reader, Slumdog Millionaire
Other Movies That Should Have Been Considered: How did The Wrestler and Doubt not get nominations?? They’re certainly both better than Frost Nixon (which is an okay movie, but still!)
What Did Win: Slumdog Millionaire
How It’s Aged: It certainly has dated cinematography and editing. Very melodramatic story driven by a series of huge coincidences (every single question on “Who Wants to Be a Millionaire?” can be answered by a trauma from his past?) And why would the host be rooting against him? Winners are big ratings. I didn’t get this movie.
What Should’ve Won: Milk
How Hard Was the Decision: A very hard choice between Milk, The Wrestler and Doubt. Three fantastic films, but this inspiring biopic felt the most like an Oscar winner to me.

Director: Gus Van Sant
Writer: Dustin Lance Black
Stars: Sean Penn, Emile Hirsch, Josh Brolin, Diego Luna, James Franco
The Story: Closeted New York office worker Harvey Milk turns 40 without having accomplished anything, so he gets a boyfriend, moves to San Francisco, opens a camera store, and starts running for office over and over until he finally gets a position on the Board of Supervisors. He and the mayor are assassinated by a fellow supervisor, who serves all of five years time for it.

Any Nominations or Wins: It won Actor and Original Screenplay. It lost Picture, Director, Supporting Actor for Brolin, Costume Design, Editing, and Score.
Why It Didn’t Win: Out of these five nominees it was a pretty baffling loss. One suspects that this was another Brokeback Mountain situation.

Why It Should Have Won:
  1. The (non-Oscar) success of a movie like Brokeback Mountain is great, but it always opens up a can of worms, because it becomes a danger of the “lone example.” This is our turn in the spotlight? Is that how you see us? Do we always have to be closeted? Why can’t we be out and proud? This movie became a necessary corrective, showing the other half of the story. (Of course, another question was “Do we always have to get killed by homophobes?” and this movie was very much not a corrective to that, but it’s the nature of this story.)
  2. I kept tearing up during the movie, not because of Harvey’s death but because of his speeches (stirringly scored by Danny Elfman) and the phone calls he gets from suicidal teenagers. This is an excellent old-fashioned good vs. evil movie, just with a different “good” than we normally get.
  3. None of the major cast is gay, and there’s been a cultural shift in the years since that gay characters should be played by gay actors (though still not that Jewish actors should play Jewish characters, interestingly) but it’s hard to imagine anyone finding fault with Penn’s performance. The movie is heavily indebted to the documentary The Times of Harvey Milk, and with a wealth of footage of the real Harvey, Penn was able to channel Milk to an uncanny degree. (Gone are the days of Six Degrees of Separation when Will Smith could play a gay lead and yet refuse to kiss any guys, thankfully!)
  4. Van Sant had made a series of excellent gay movies way outside the system and poised himself to be the one to get the call up when Hollywood was finally ready to tell this story. He keeps some of the independent spirit by cutting back and forth liberally between film stocks and interspersing lively tricks like this visualization of a phone tree. The movie pulses with life.
  5. Early on, Harvey gets a death threat in the mail and puts it on his fridge to show he’s not afraid. Later, as threats increase, he finally becomes scared of it, takes it off and throws it away. A great use of showing internal change through objects.

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