Lost To Gone With The Wind
A tough call since they've both become bona fide classics. However, in a "this movie is better than that one" contest, I'd have to give the edge to The Wizard of Oz as Gone With The Wind is plagued with sequences that just drag and make the movie seem about 18 hours longer than it actually is.
Lost To In The Heat of the Night
In The Heat of the Night is a fine film that tackles a subject that was intensely relevant in 1967, but I think Bonnie and Clyde holds up much better and had a greater impact on cinema in general.
Lost To Forrest Gump
I may be biased because I really dislike Forrest Gump, but the knowledge that it beat Pulp Fiction just makes me cringe. If any of the other nominees (Shawshank Redemption, Quiz Show, Four Weddings and a Funeral) had won, I could deal with it but for it to lose to Gump is just... ugh.
Lost To Rocky
1976 was an embarrassment of riches in terms of Best Picture nominees: Network, All The President's Men and Taxi Driver were up for the big prize along with Bound For Glory and Rocky. That Rocky came out the winner is something I just can't wrap my head around.
Lost To Ordinary People
Can you believe it? Ordinary People over Raging Bull? That's insane.