I got a kick out of American Movie, myself. Also springing to mind are:
Vernon, Florida- mostly slice-of-life stuff with old people and country folks. I've got relatives like some of these people though, so I got more entertainment out of it than others might.
Paradise Lost: The Child Murders at Robin Hood Hills- I don't remember if this was bankrolled by HBO, or just run as part of America Undercover (speaking of which, almost every documentary they produce under that title is worth watching) but it's about three trailer-park boys who are killed, and the blame falls on a couple of guys who supposedly dabbled in the dark arts. The most compelling thing about it is it's not really clear where the blame belongs even after the trial's over- one of the kids' stepfather manages to look pretty guilty at one point.
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Killing that robot makes me want to go home.
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