ESPN’s list (they elaborate more than I’m going to):
- Bull Durham
- Rocky
- Raging Bull
- Hoosiers
- Slap Shot
- The Natural
- Field of Dreams
- Caddyshack
- The Hustler
- The Longest Yard
- North Dallas Forty
- Jerry Maguire
- Hoop Dreams
- Breaking Away
- White Men Can’t Jump
- Bad News Bears
- Chariots of Fire
- Brian’s Song
- Eight Men Out
- When We Were Kings
Some initial reactions I had were:
- surprise that “Bang the Drum Slowly” didn’t make the Top 20.
- I like Slapshot. And I’m a hockey nut. But it is way overrated, on this list and otherwise. It’s not even the best sports comedy of all time. That would be Caddyshack.
- Bull Durham is great. But number 1? Over some of those other movies? Come on!
- I know Raging Bull gets all the hype. And I thought it was good. But it always struck me as a little too believing in its own self-importance. It doesn’t make my top 10, as you’re about to see.
My list goes like this:
1. The Natural. This is one of my all-time favorite movies of any genre. It is beautifully filmed, written, directed, acted. It is full of unforgettable scenes. A lyrical movie.
2. Rocky. This movie doesn’t get its due now, and Stallone doesn’t get his due for his performance now, because of all the uneven sequels it spawned. Think of it standing alone, and it is a true masterpiece, that tells one of the great, human, American, underdog stories ever put on film. Rocky doesn’t win, but he does. As one of ESPN’s critics puts it, “that’s not only ground-breaking; that’s crucial.”
3. The Hustler. If you have never seen this movie (which I imagine most of you haven’t), seek it out. I own a copy. Paul Newman and Jackie Gleason are perfect as Fast Eddie Felson and Minnesota Fats. Newman reprised this role in a movie with Tom Cruise, “The Color of Money.” This black-and-white original is infinitely better.
4. Caddyshack. Still hilarious today. One of the most memorable line-spawning movies for guys ever. A sophomoric comedy that in many ways transformed how golfers look at their sport. Think about that. Happy Gilmore wishes it was Caddyshack.
5. Hoosiers. Gene Hackman is perfect as the coach. The ESPN reviewers do a great job explaining why this movie is so excellent.
And what makes it all the more powerful is, it actually happened. That last scene, where the little kid is dribbling a ball, alone, and the camera pans to a photo on the wall of the REAL team that did it, gives me chills just thinking about it.
6. North Dallas Forty. An excellent behind-the-scenes look at the dark underside of pro football. This movie really sticks with you, and it’s one of those great ones to watch and re-watch. At times hilarious, at times disturbing. Powerful. The opening scene of Nick Nolte trying to get out of bed and around, in agony, the morning after a game is haunting.
7. Rollerball. I may be cheating here, but I consider it a sports movie. And, hopefully, it goes without saying that I’m talking about the original with James Caan. A disturbing image of where sports may be headed, back to its gladiator roots. (And as a kid, you just thought the concept of that sport was so cool.)
8. Bull Durham. A funny and endearing movie. But no way should it be number one, in my book.
9. The Longest Yard. It never gets old. Funny movie, but not a shallow one.
10. Jerry Maguire. I remember thinking when this came out, “A movie about a sports agent? Why is it getting all these great reviews?” But it’s excellent. Funny, and a great love story with a great message. And enough sports to keep it from falling into the “chick flick” realm. 
Honorable Mention: The Bad News Bears in Breaking Training. I always liked this sequel better than the original. Something about the thrill of the kids going and doing it on their own really resonated with you, as a kid. You wished you were with them. “Let them play! Let them play! Let them play!”