So this is a long read, but a good one.
The biggest snub for me was Goodfellas in 1990...losing to Dances with Wolves.
I just could not believe the best gangster flick ever made (sorry The Godfather 1/2) lost to a really crappy movie about a white man befriending and protecting native americans (insert Fern Gully reference here), but then basically leaving them.
The second was Raging Bull losing to Ordinary People. Like, on what planet do you live on if Raging Bull's cinematography isn't some of the best ever vs. Mary Tyler Moore being awful and Timothy Hutton moping through the entire flick. Yuck.
The surprises that I think they did get right are basically two of my favorite flicks ever.
If I were stuck on a desert island and I was told I could bring No Country for Old Men, There Will Be Blood, or Michael Clayton - I'd bring Michael Clayton every time.
I know that's sort of blasphemy, but Michael Clayton is one of the best flicks of the past 20 years. When I tried to write my first screenplay (horror about the catholic church and exorcism) halfway through I realized - "Yeah, they made this movie already, it's Michael Clayton". And I didn't even really like it when I saw it in the theater. It was only long after that I realized how good it really was.
The second is Moneyball. I think it's the best baseball movie ever made, and it's definitely in my list for favorite movies ever made. I read the book, and when I heard they were making a movie out of it I just thought "You guys are fucking crazy".
Instead, we got the vibe of the book - stats break though old school beliefs and biased opinions - and it's basically a story about two families, Billy Bean's (daughter, ex wife, etc), and the Oakland A's team.
The only other outlier is L.A. Confidential, which is one of the best neo noirs ever made (but I sort of get why it didn't get much love).
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