[Spiny_Norman]

I will try not to repeat what others have recommended.  But I certainly would put on any list of best sports movies/documentaries some of ESPN's 30 for 30 works.  The one that still resonates is The Two Escobars.  Particularly topical since the World Cup in 1994 is such a big part of that story.

Let me add some of my favorite movies that don't seem to have been mentioned much yet:
The Adventures of Robin Hood (with Errol Flynn and Basil Rathbone)
The African Queen
Apollo 13 (I love a story where the engineers are the heroes)
Diner
History Of the World Part 1 (I met Gregory Hines once and was able to tell him that he was in one of my family's all time favorite movies)
Local Hero
The Man Who Would Be King
Mutiny On the Bounty (with Clark Gable and Charles Laughton)
North By Northwest
The Paper Chase
The Right Stuff
Some Like It Hot
Stalag 17
The Treasure of Sierra Madre
Working Girl (I still get a lump in my throat during the closing scene as Carly Simon and a gospel choir sing and the camera pans the NY skyline from the harbor and you see the World Trade Center towers).

Among baseball books, I can recommend Philip Roth's The Great American Novel (one of the players is Gil Gamesh and another is John Baal, so you can tell the epic scale of Roth's story); David Carkeet's The Greatest Slump Of All Time; and Ring Lardner's You Know Me Al.  I read Roth and Lardner for a class at Stanford called The Literature of Baseball.  Taught by a guy who worked at the post office and sold pipes in White Plaza.  I actually got 3 credits for that class.

I know there are some golfers on the board and you have to read Dan Jenkins' Dead Solid Perfect if you have not done so yet.  I think I laughed more reading that book than any other. 

[Spiny_Norman]

I will try not to repeat what others have recommended.  But I certainly would put on any list of best sports movies/documentaries some of ESPN's 30 for 30 works.  The one that still resonates is The Two Escobars.  Particularly topical since the World Cup in 1994 is such a big part of that story.

Let me add some of my favorite movies that don't seem to have been mentioned much yet:
The Adventures of Robin Hood (with Errol Flynn and Basil Rathbone)
The African Queen
Apollo 13 (I love a story where the engineers are the heroes)
Diner
History Of the World Part 1 (I met Gregory Hines once and was able to tell him that he was in one of my family's all time favorite movies)
Local Hero
The Man Who Would Be King
Mutiny On the Bounty (with Clark Gable and Charles Laughton)
North By Northwest
The Paper Chase
The Right Stuff
Some Like It Hot
Stalag 17
The Treasure of Sierra Madre
Working Girl (I still get a lump in my throat during the closing scene as Carly Simon and a gospel choir sing and the camera pans the NY skyline from the harbor and you see the World Trade Center towers).

Among baseball books, I can recommend Philip Roth's The Great American Novel (one of the players is Gil Gamesh and another is John Baal, so you can tell the epic scale of Roth's story); David Carkeet's The Greatest Slump Of All Time; and Ring Lardner's You Know Me Al.  I read Roth and Lardner for a class at Stanford called The Literature of Baseball.  Taught by a guy who worked at the post office and sold pipes in White Plaza.  I actually got 3 credits for that class.

I know there are some golfers on the board and you have to read Dan Jenkins' Dead Solid Perfect if you have not done so yet.  I think I laughed more reading that book than any other.