Great (Cynical) Sport Movies
Slap Shot
Any Given Sunday
Semi Tough
The one with Harold Lloyd
Any more?
While the original "The Longest Yard" starring Burt Reynolds in '74 was more of a cynical indictment of the prison system, than it was of the game of football. It's still a very funny and entertaining movie that will have you rooting for the inmates over the corrupt guards and warden, and is definitely worth watching.
Even though, like many sports movies before and after 74's 'The Longest Yard', the football game is ultimately used as a device of personal redemption for the ex-NFL star protagonist Burt Reynolds. And not, in any way a hard examination of the game itself.(WARNING: Avoid The Longest Yard remake in 05' at all costs)
Also, a movie that I haven't seen mentioned yet, that I think deserves consideration here is 1986's, "The Best of Times" starring Robin Williams and Kurt Russell. Written by Ron Shelton, the writer and director of 'Bull Durham' and 'White Men Can't Jump'. The Best of Times is a very funny and some what cynical film about a pair of over the hill ex-high school athletes who attempt to recapture their youth by organizing and playing in a football match-up with the towns ancient interstate rival.
One other thing, after reading through the many replies on this topic, I'm surprised to discover that so many people have actually seen the movie "One on One" starring Robby Benson way back in '77. I saw that movie when it was originally released and a few times on cable back in the early 80's, and I kind of liked it, but haven't seen it broadcasted on cable or satellite in decades since it seems. Which makes me wonder how so many people on this thread managed to catch that movie. Or, why they were interested enough to rent or buy it. WOW, kind of surprising.
Nick Nolte was terrific as the coach in Blue Chips. He learned a lot about the role from G.D. Spradlin.
I would also highly recommend Friday Night Lights, a high school football movie. I love the scene where Billy Bob Thornton's star running back has his promising college career shattered by a hit to his leg, but Coach Thornton has no time to dwell on it. He simply states, "Next man up!" and goes on with coaching the game.
Another very good and cynical sports film is The Program, which is about college football. James Caan plays a coach who is on the edge and needs to win in order to keep his job. He induces one of his linemen to get back on steroids because that's the only way the guy can play his position with success, even though the steroids are killing him. It's a very good movie.