White Men Can't Jump came out right in the middle of my basketball phase, in middle school, living in the sticks with a hoop and concrete slab and not much else to do. I bet I watched that movie 30 times.
Most of the other best sports movies are about baseball. Baseball is the subject matter that has the--by far--highest ratio of silver screen awesomeness to real life boringness. Major League, The Sandlot, Bull Durham, Field of Dreams, etc.
Most overrated sports movie of all time is Rudy. Fuck Notre Dame, and fuck that boring movie.
Biggest schlong to appear in a sports movie has to be Any Given Sunday, which I'm guessing is the #1 ranking criteria at HH.
Watched Cool Runnings with the kids a while back. I only mention it because it's a "sports" movie that I haven't seen on anyone's list yet.
The sports movie that probably had the biggest overall impact on my life is this one:
but certainly way too obscure to make this tourney.
Maybe the tourney needs a bracket for "sports" movies that are awesome. Things like Dodgeball, Baseketball, The Big Lebowski, King Pin, Happy Gilmore, Caddyshack, Blades of Glory--oh yeah, and the greatest mocumentary about rhino cum ever made: Tour de Pharmacy (how this short movie isn't yet HH canon is baffling to me).