Hoop Dreams (1994)
Director: Steve James
Hoop Dreams, the gripping story of Chicago high-school basketball players William Gates and Arthur Agee is as much about race, class, and education as it is about sports. Those qualities make this cinematic masterpiece not just the greatest sports doc, but also one of the best documentaries in recent memory. Don't be intimated by the long run time—Steve James' achievement is thoroughly compelling. It'll be the shortest three hours of your life.