Senna is definitely one of the best in the last few years.
If you like "American Movie" you'll love "Overnight"
Overnight
http://www.imdb.com/title/tt0390336/
Quote:
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A documentary on the rise and stumble of Troy Duffy, the bartender-cum-filmmaker who was swept up by Miramax's Harvey Weinstein to turn his script for The Boondock Saints into a feature film.
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The guy who stars in the doc blew one of the biggest chances anyone will ever get because of his ego.
Other notables off the top of my head:
Man on Wire
Hoop Dreams
When We Were Kings
The Thin Blue Line
The Times of Harvey Milk
Project Nim
The Interrupters
I'm a huge Documentary fan. I have a ton more that I can't think of right now. I'll also quickly recommend pretty much anything by Louis Theroux for some light viewing.