I also agree with the last couple of people mentioning Saving Private Ryan… the movie as a whole is really pretty lackluster, and I have no problem with Shakespeare in Love winning that year.
Quick hits from a few years that were before my time, but where I’ve seen both the winner and another movie, and I’d have picked another movie (note that in all cases I’m going by movie release year rather than Academy Award Year, because it’s easier when using Wikipedia to reference):
1981: Raiders of the Lost Ark instead of Chariots of Fire
1990: Goodfellas instead of Dances with Wolves
1992: A Few Good Men instead of Unforgiven
From 1994 on, I’ve seen at least 3 and generally more of the contenders for each year, pretty much all of them since 2006 (I’ve picked up quite the movie habit over the last decade, apparently). Some more thoughts on a few years, some of which have been touched on, some of which haven’t:
1994: Anything Else That Was Nominated instead of Forrest Gump, because I don’t think that Gump was a very good movie. I actually like Quiz Show the most, but Pulp Fiction probably should have been the winner for the combination of quality and what it really meant to cinema.
1997: I get why Titanic won, and this was a kind of weird year overall, but I’d have preferred Good Will Hunting. I watched it again last week, and everything about Williams and Damon in that movie is still excellent. I also LOVE L.A. Confidential, which also holds up much better than Titanic.
2001: A few people have already mentioned LOTR: FOTR over A Beautiful Mind, but my thoughts go back more to the “animated ghetto” complaint: I would have seriously considered Monsters, Inc. that year. It was a relatively weak year in general IMO, and I see no reason why a really strong animated film shouldn’t be considered against the more traditional choices.
2003: I wish LOTR had won for one of its more deserving movies so that Lost in Translation could have pulled down this year. People seem to either really like or really dislike Lost, and I’m on the “pro” side. Also, looking at the nom list, Master and Commander and Seabiscuit? Really?! Over Finding Nemo and Kill Bill Vol. 1, among many, many others? throws hands up in frustration
I don’t totally hate Crash, and I think Brokeback Mountain has a great message and some great performances, but has a lot of weaknesses as a film.
2011: Probably The Tree of Life? How did, like, six of those nine movies even get nominated? 2009 and 2010 were so stacked, and then this is our list for 2011? This is the kind of year where if we’re listing 10, I’d think about sneaking in some really well done blockbusters like Mission Impossible: Ghost Protocol or X-Men: First Class. Also, even more seriously, Attack the Block? Drive? Shame? 2011 was not a weak year at all, but that nomination list makes it look like one.
2012: Zero Dark Thirty and Silver Linings Playbook are two dramatically different movies that both had me thinking “Wow, that’s one of the best movies I’ve ever seen” when I left the theater. I’d have voted for either one of them in about 90% of the years in the past two decades. Django Unchained was brilliant and is my favorite Tarantino movie after Pulp Fiction. Beasts of the Southern Wild was also spectacular and could have won some of the weaker years here. Argo was… a pretty good movie. I really think that in 20 years when we’re looking back, we’ll feel about 2012 the way people now feel about 1994.
Thanks for getting me to spend way too long typing about movies!