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Grizzly Man is maybe one of the best movies of all time, let alone documentaries.
Crumb and American Movie already mentioned are great films and I actually found them very inspiring.
Another amazing documentary is called Century of the Self, about the history of the application of Freudian psychology to advertising, and further to corporate and government control of populations.
I also highly recommend Latcho Drom, a movie basically told entirely through music performances of traditional music in various cultures.
For more esoteric subjects, I really liked the Mindscape of Alan Moore, which got into a lot of his ideas about language, culture and magic.  Also in that vein is For One Week Only, a short documentary about the films and psychological theories of Alajandro Jodorowsky.
I just watched Bound to Lose, a documentary about the Holy Modal Rounders which is great but maybe not for people who aren't fans or possible fans.
If you're into movies in general, Hearts of Darkness, the documentary of the making of Apocalypse Now and Burden of Dreams, the documentary about the making of Fitzcarraldo, and Lost in La Mancha, the documentary about attempting to make Don Quixote are all very good.
Also, the Some Kind of Monster movie about Metallica is funny, painful and sad, if you're up for that.

These are the documentaries which have all changed my life in some way.  Hope I didn't ramble too much.