Best Films About Football

I've always liked There's Only One Jimmy Grimble.

It's not really when you think about it. Football and footballers live in world of cliche. Trying to write a story based in football that doesn't play up to the tropes of the genre is very difficult. That's why the most successful of recent films is the Damned United, because the audience is at ease with the character of Brian Clough because they enter the cinema with the knowledge that he's a real person. Writing Brian Clough without him having previously existed would be extremely difficult.

If you look at the most successful sports, in terms of making successful transitions to film, Baseball and Boxing are the runaway leaders. That's because there is so much romance attributed to the people that are associated with their respective sports that the writer has a much broader canvass to paint his picture with.

The trick with a good sports film is to not actually have the crux of the film being about winning or losing.

I'm not so sure. I think pretty much every sports film, regardless of the sport, boils down to a simple underdog story. That's the nature of competition. Noone wants to watch the big team molest everyone. It can only really work if you manage to make people care about the characters. Then they'll give a fuck when the underdog comes through in the end.

I think the key word in your post is "character".
Watching the underdog means nothing if we don't care about the characters involved. And you can watch a top dog fall from grace if it's an interesting character.

Raging Bull for instance isn't necessarily about an underdog, at least not in the world of boxing. Though one could argue that it's about an underdog in society.