I guess it's safe at this point to mention some documentaries. The 20 pointer which was not taken (IMO) is The Sorrow and The Pity a 4 hour film from the 1960's about the German occupation of a small town in France. It remains one of the most mesmerizing films I have even seen.
Another one I would rank very highly is Don't Look Back about Bob Dylan's 1966 British concert tour. This film is completely iconic; it begins with the famous scene of Dylan holding signs and dropping them as he sings "Subterranean Homesick Blues". But it's the mystery of Dylan himself that is fascinating here.
Gimme Shelter is a film of the infamous Rolling Stones' concert in Altamont that ended with the murder of a concertgoer by Hells Angels who were incredibly hired by the Stones bodyguard. This film is a critical look at the late 1960's rock culture.
Two more personal favorites:
Let It Be chronicles the last days of the Beatles and presents the strain as they prepare and then perform their last live concert on the top of a building at Abbey Road. It's a final, all too brief look at greatness.
And finally a personal favorite, having grown up in Southern California: Endless Summer is a film completely devoted to surfing. I have trouble giving a sober evaluation of this film as I don't think I was ever sober (or without some sort of mind altering substance) when I've seen it. A true classic.
Couple more.
"Cadillac Desert" (which I've pimped in every non-fiction book and documentary list this board has done).
It's about the politics of water in the American West.
(There is a whole section dedicated to the story of L.A. and The Owens River - which was the plot backdrop for China Town).
It's an absolutely amazing documentary (actually a 4-part series), and probably and even better book.
It reads like a novel and is a page-turner.
I think it should be required reading for anyone who lives west of the Mississippi . . .
And of course, "Straight, No Chaser", which I just watched for the first time in awhile this last weekend.
Never ceases to blow me away.
Ditto on Endless Summer.
Hey Tim, what town?
What high school?
What year?