2006 stands apart as one of my favorite Oscar years because it was like this past year in a way. It’s rare that the film I personally WANT to win actually wins. It was made all the sweeter by my own instincts about it winning being right on the money, as opposed to what many of my colleagues thought – that it was too dark to win, that a movie where Leonardo DiCaprio died at the end couldn’t win, etc. But I had a feeling that if Scorsese got even remotely close to a crossover crowd pleaser he would slam dunk the thing without breaking a sweat. And that’s exactly what happened. It still makes me happy looking back on it.
I also had a great moment in the elevator at Warner Bros talking to their publicist about The Departed. He/She said “We’re not expecting it to do much.” They took out one singular FYC ad for that campaign, or maybe a few but they never went out too far on a limb with it. Perhaps because Warners had the Eastwood double Flags of Our Fathers and Letters From Iwo Jima. Both films deserved to be recognized for Best Picture, in my opinion, but the critics only went nuts for the latter, which did end up getting/winning Best Picture. A few pundits even predicted it to win, but it was always the longest shot of the five nominees.