Documentaries on Unusual/Odd/Cringy Subjects

Here's an unusual documentary from 2008: "My Car is My Lover":

It explores the lives of Edward and Jordan, who are mechaphiles (ie people who have sex with cars)

Jordan is actually fairly normal (apart from the car-fucking thing, which he does in private), but Edward (who's a furry if you watch carefully) is a total creeper, getting obviously aroused at a car show and sneaking around hotel car parks at night to jerk off on the vehicles.
 
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So many dead links *sigh*

Anyway, Jefftowne.
Meet Jeff. He’s a beer-drinking, porno-consuming, wrestling fanatic with Down’s syndrome. He lies, he cheats, he steals and he fondles women. In short, he a lot more like the rest of us than we care to admit. Jeff’s days are divided between his filthy home that he shares with his 98 year old, wheel-chair bound, foster mother (who pins their financial future on the certainty that they’ll win the Publisher’s Clearance House Sweepstakes) and a mall movie theater where the employees alternately mock and care for him. They become a bizarre surrogate family for Jeff, providing him all the vices that his mother so desperately ignores – to her, Jeff is a good Christian boy with a heart of Gold. As this shocking and hilarious documentary shows, Jeff frequents strip joints, bum-rushes celebrities, cares for his horrifyingly diseased foot and gets his few remaining teeth extracted. One thing’s for sure: you’ve never seen anything like “Jefftowne”. And you’ve never met anyone like Jeff.
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Here's a short list of my own personal favorite weird documentaries

Faces of Death (1979)
What's Uptown? (1981)
Talking Feet (1986)
Dancing Outlaw (1993)
Kentucky Teenage Vampires (1999)
Six (2003)
Great American Youth (2006)
Real Talk (2007)
The Wild and Wonderful Whites of West Virginia (2009)
 
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Carts of Darkness
Carts of Darkness is a 2008 National Film Board of Canada documentary film by Murray Siple about a group of homeless men in the city of North Vancouver, who use shopping carts to collect bottles and cans to return for money and also race down the city's steep slope for thrills.

The Man Who Skied Down Everest​

The Man Who Skied Down Everest is a Canadian documentary about Yuichiro Miura, a Japanese alpinist who skied down Mount Everest in 1970.
 
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