A combined list:
Those were based on real life, so the ending isn't a total surprise. The following movies, however, were entirely fictionalized:
- Bad News Bears - kthejoker says They lost the last game of the season, too, but celebrated anyway. That was the first movie where I realized winning really isn't everything.
- Mystery, Alaska - A small Alaskan ice hockey team gets the chance to play against the New York Rangers on national television and pulls their town together. You know they're likely to lose, but being a movie, you still have that spark of hope that they'll make it somehow.
- Tin Cup - A golf instructor has to overcome his macho impulses to sink the big shot instead of taking the easy win. He doesn't, but then we're asked: is that really such a bad thing?
- Rocky - He only lost in the first movie.
Why should people complain that so many movies choose the underdog to win? It is about entertainment, after all, not documentary. In ninety-five percent of all movies, plays, novels, etc., the nice guy doesn't finish last, the lone hero defeats the evil government, the small-town lawyer beats the big corporation, the heroic fighter can overcome an entire army of well-rested ninjas, the unlikely couple finds true love against all odds, and the underdog athletes win the big game.
There is a very simple reason for this: entertainment is escapism. Why pay to see or read a story that perfectly imitates what you see every day? The audience is made up of underdogs, of everymen, of nobodies who want to take down the big guys just to give them what they deserve, and they like seeing people they can relate to come out as winners. Realistic? Who cares? The movie industry hasn't been concerned with realism since its inception, and has no reason to start now.
But because of this, audiences have come to expect the underdog to win, the unlikely lovers to live happily ever after and the lone hero to save the day in the end, and so it's worth watching the last five percent of all films where this fails to happen. It's a surprise, and a plausible one to boot.
But unless there's a good story to be told despite the ending, no one is going to want to watch it. That's hard to do. And that's why it almost never happens.