1. Raging Bull
Without question Raging Bull is the greatest sports movie of all time. I also consider it Robert De Niro's greatest performance as well. It's brilliant in black and white and the boxing scenes, though stylized, are probably the best ever filmed. Plus, there's this scene.
I'm a huge basketball fan and I wish there were some more basketball movies on this list but at least there's Hoosiers. Gene Hackman is amazing in this movie but the actor that steals the show is Dennis Hopper. It's one of his most underrated and affecting roles. It's the only movie where a basketball practice looks like basketball practice.
3. When We Were Kings
When We Were Kings is the top documentary on the list. It's a full dose of Muhammad Ali at his verbose peak which is always fun to watch but it also has his polar opposite George Foreman. Foreman looks like he could fight a bear and rip it apart. Plus James Brown at his funky moustachioed best and expert commentary from erudite prince of American Letters, George Plimpton and idiot douchebag Norman Mailer.
4. The Hustler
I hesitate to call billiards a "sport" but I'm not making a list of the twenty best parlor game movies. Was anyone in America cooler than Paul Newman at this point in America? I doubt it.
5. Breaking Away
If you've seen this movie and didn't particularly care for it, I hate you and you're a moron.
6. This Sporting Life
It's the greatest rugby movie ever made. It's an honest look at Northern England in the early sixties and it has a gritty working class feel but This Sporting Life is also an examination of the underside of the aggression that allows Richard Harris's character to excel on the rugby field. It is sort of a predecessor to Raging Bull.
7. Hoop Dreams
Hoop Dreams is a riveting documentary about two young African American basketball players in inner city Chicago. It isn't just a basketball movie though as it delves into larger social issues such as race, class, and education. Both of the boys are recruited to an all white basketball powerhouse in suburban Chicago, the same school Isaiah Thomas attended. Neither of the boys lives up to there supposed potential, neither make it to the NBA or even a major college program but both find success in different avenues of life.
8, The Bad News Bears
I love this movie. This is probably the highest movie on the list that you don't really need to enjoy, or really even like, sports to get a kick out of. Walter Matthau gives one of the greatest performances of his career as Coach Buttermaker and Tatum O'Neil is great as the curve ball chucking Amanda.
9. Friday Night Lights
Friday Night Lights is easily the best football movie ever made. It's based on the by HG Bissinger about a high school football season in Odessa, Texas during the 1980's. Billy Bob Thornton is the coach and he's really good as he sometimes can be but he is out acted by most of the younger actors in the movie. Lucas Black plays the QB, he was the kid in Sling Blade, and Derek Luke is Boobie Miles the superstar running back who blows out his knee. Luke pretty much steals the whole movie, even from a pair of crutches.
10. Eight Men Out
Eight Men Out, aside from documentaries, is the only accurate sports period piece. It's also a John Sayles movie full of John Sayles regulars and solid actors throughout. The level of authenticity in this movie is astounding compared to other shitty period baseball movies like Babe or Cobb. It's the only movie on the list that Richard Edson is in as well.
11. The Loneliness of the Long Distance Runner
This is a really underrated movie. I'm a huge fan of the book and the movie captures the spirit completely. It's not only a great sports movie but also a great fuck authority movie.
12. Horse Feathers
The Marx Brothers are one of the few comedy outfits from a different era that I still find funny. This is one of their best. The football scenes are actually pretty good too, sure they're played for comedy but they're interesting for their period detail too.
13. Dogtown and Z-Boys
There have been a lot of skate documentaries. This one is the best. Stoked is pretty good and so is the one about Christian Hosoi but they don't have the weight of Dogtown and Z-Boys. The part when they show up at the skate contest and everyone is still doing handstands and shit while they're doing all this modern crazy shit is bad ass. Pure bad assery.
14. Killer's Kiss
This is yet another case of Stanley Kubrick being about thirty years ahead of his time. The boxing scenes in this movie are mesmerizing and I've read that Martin Scorsese took many notes from this film in making Raging Bull. Jim Thompson wrote the screenplay and it's tight and focused all the way through.
15. Chariots of Fire
It's kind of funny that this movie is about white English sprinters but it is in the 1920's. The story has an Evelyn Waugh feel, the platonic man/man love affair that the British so enjoy. It's also pretty much a storm of boaters and heavy sweaters which is awesome in its own right.
16. The Endless Summer
This is probably the first great sports documentary. I'm not sure there is a more alluring sports culture than 60's surf culture. It seems really laid back but on the edge at the same time. Plus I feel like they ate a lot of tacos and burritos before they were popular.
17. Fat City
I only recently discovered Fat City. It's a pretty amazing movie to have slipped through the cracks for this long. Susan Tyrrell was nominated for an Oscar for her role and Stacey Keach gives one of the best performances of his career. Add a young, eager Jeff Bridges as Keach's boxing protege and you've really got something.
Rudy is one of the few really uplifting movies on my list. It'sone of those "make you feel good" movies that I actually enjoy. They are a rare thing. The football scenes are pretty solid and it features a fat Jon Favreau, a skinny Vince Vaughn and the wonderful Ned Beatty and Lili Taylor in supporting roles. Joe Montana recently came out and said the actual Rudy wasn't that big a deal, he didn't work harder than anybody else. Which makes me think Joe Montana is probably an asshole.
19. Major League
I will never get tired of watching this one. It was made during the time when I was really in love with baseball and it's legit funny, not just sports movie funny. I may have seen this one more than any other movie on this list. I was legitimately sad when James Gammon died.
This almost feels cursory at this point. I suppose I have to put it on here. I still think the only reason this movie is worth anything is because he loses in the end. It's amazing that Stallone wrote it and starred in it and it is as good as it is.