Documentaries on Unusual/Odd/Cringy Subjects

I wasn't sure where to put this, (I know now) but its worth posting. This documentary follows some Tiffany fans (a one day fly singer from the 80s)

Full documentary:


- Guy has some sort of overpriced fake device with crystals that make him think he can talk to Tiffany in her mind brain-to-brain (Like Gail Schuler)
- One of the fans is a tranny, that isn't allowed in one of her concerts because previous felony's

I highly recommend watching this documentary, it has some top tier cringiness moments in it.

So if you're bored, sit back and enjoy an hour of craziness.
 
Here's a "YouTube Original" short documentary from the very early days of YouTube, called Great American Youth.

Directed by a guy named Daniel Wojack and originally posted around 2006-2007 back when videos on there could not exceed ten minutes in length, so it's divided into four parts.

It's about the rise and fall of the Almighty Gaylords street gang in Chicago's North Side, the violent gang wars they waged, and the racial, ethnic, and cultural tensions and disputes that led to those gang wars with all the violence, prejudice, and general ugliness that entailed.

Overall, it's a very eerie and amateurish documentary.

Maybe it's because this was one of the first videos I saw on YouTube or maybe it's the overall eerie and sometimes disturbing presentation of the subject matter, but this documentary gives me goosebumps and creeps me out, but I like it anyway for some morbid reason.




 
If you thought I Think We're Alone Now was cringey, it has nothing on I'm Your Number One Fan.

Highlights include Mike Read superfan Blue Tulip Rose Read orgasming to the sound of his voice on the radio, typing emails completely naked, singing while imitating a dog barking and freaking out because some shop assistant made an offhand comment about Mike Read being possibly gay.

Aside from Blue Tulip (who could have carried the documentary by herself) there's a mother-and-daughter Cliff Richard fan duo, a guy who wants to protect Princess Diana from the Beast (ie: the Queen, apparently she's actually Satan in disguise) and a woman who sent multiple threatening letters to snooker player Stephen Hendry.

https://www.youtube.com/watch?v=of1-vkIS5sQ

There's also Deep Water, based around a man named Donald Crowhurst who entered a race around the world sailing competition despite having never sailed before and being up against some very experienced sailors. I won't spoil it but things did not go well for him.

https://www.youtube.com/watch?v=IY2rQh8UraY

Vice did a very interesting (and grim as be fucked) documentary about teenage heroin addicts in Swansea. Following them around and listening to them talk about their lives it seems like life wouldn't be any better if they got off the skag. Notably there's a bit where the young blonde girl talks about how her boyfriend's father beat her up and caused her to miscarry with all the emotion of someone chipping a nail.

https://www.youtube.com/watch?v=aIbpt1aDFqM

On that note, there's a documentary maker who thought trying skag would make him better able to connect with the addicts he was filming, and of course he got hooked. He got his friend to film him trying to go cold turkey.

https://www.youtube.com/watch?v=1L33zkIFIaQ

Rain in my Heart is a good one if you like soul-crushing misery. It follows four alcoholics in a special unit in London. By the time the documentary is over, two are dead. One more has died since, the sole survivor seems to be doing okay.

https://www.youtube.com/watch?v=lwv7Utcf-gM

66 Months is also pretty miserable on several levels. A learning-disabled man with an alcohol problem is taken in by an elderly gay man who is abusive but pretty much the only one in his life that shows him any love. It's very shocking how intimate it is because the film-maker happened to be a close friend (ie: fellow homeless alcoholic) and they didn't hide anything. I rented it from Vimeo, it's not available otherwise.

If you have a strong stomach, The Hunt for Britain's Paedophiles is an excellent documentary. It's very graphic in places, and it shows just how hard a slog the police have to get through to secure a conviction. Bonus shock value for hearing an adult woman talk matter-of-factly about how her father promised her a pony if she made pornography with a bunch of his mates when she was no older than twelve, how it was the best-selling child porn on the market and how she never got her pony in the end.

http://www.dailymotion.com/video/x2i11al
 
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"Furries and Plushies", an old episode of an MTV show called Sex2K that talks about the furry fandom. (unfortunately, I cannot seem to find part 2)

 
an exceptional individual who loved hugging brown bears until one hugged him back. RIP his girlfriend for being dragged into that.

One of my drinking docu's... Popcorn Sutton.


Popcorn Sutton was a legend, he will be missed dearly.
 
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American Movie is about a thirtysomething alcoholic who lives with his parents, who is trying to make an independent horror film called Coven (pronounced COH-ven, because otherwise it sounds like "oven" which is not as scary) along with his friend who is addicted to scratch-off tickets. While it looks like a mockumentary everything in it is 100 percent genuine.


 
Crossing the Line (full doc is up on youtube)
About an US soldier who defected to North Korea that also tells the tales of a few other of his fellow countrymen who did the same. Pretty interesting since they get to do interviews with him, though he ofc praises the shit out of the place. The doc doesn't really hide the fact that he was a bit of a shithead before he crossed over and that the US soldiers were put into NK propaganda films to show the capitalists/westerners in a bad light. It does gloss over a few facts that maybe weren't available then, like his first wife being a kidnapped Romanian woman, but still, it was a good watch.
 
The Hunt for Britain's Paedophiles is an excellent documentary. It's very graphic in places, and it shows just how hard a slog the police have to get through to secure a conviction. Bonus shock value for hearing an adult woman talk matter-of-factly about how her father promised her a pony if she made pornography with a bunch of his mates when she was no older than twelve, how it was the best-selling child porn on the market and how she never got her pony in the end.

http://www.dailymotion.com/video/x2i11al
There is a disturbing joke to made somewhere in there, but I have too much of a heart to make one.
 
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It does gloss over a few facts that maybe weren't available then, like his first wife being a kidnapped Romanian woman,

Interesting enough another American defector (or abducted according to his family), Charles Robert Jenkins, was reported to have married a young Japanese woman who was abducted. After reading the Cleanest Race by B. R. Myers, I can understand why the North Korean government would not allow non-Korean Westerns to marry Korean woman. The book mentioned Korean woman reportedly forced to have abort their mixed race unborn children, and a black Cuban diplomat who was attack by an unruly mob with rocks reportedly because he was not Korean.
 
Interesting enough another American defector (or abducted according to his family), Charles Robert Jenkins, was reported to have married a young Japanese woman who was abducted. After reading the Cleanest Race by B. R. Myers, I can understand why the North Korean government would not allow non-Korean Westerns to marry Korean woman. The book mentioned Korean woman reportedly forced to have abort their mixed race unborn children, and a black Cuban diplomat who was attack by an unruly mob with rocks reportedly because he was not Korean.
I believe Jenkins was one of the men talked about in the doc as well (it's been a while since I've seen it, but the story seemed familiar). Interestingly enough, Dresnok (about whom the doc is mainly about) married (and had a son with) the daughter of a Korean woman and Togolese diplomat, which, considering what you said, is curious to have been allowed. They don't mention much about that in the doc, which is a shame, but I feel like that's a story worth telling as well.
 
American Movie is about a thirtysomething alcoholic who lives with his parents, who is trying to make an independent horror film called Coven (pronounced COH-ven, because otherwise it sounds like "oven" which is not as scary) along with his friend who is addicted to scratch-off tickets. While it looks like a mockumentary everything in it is 100 percent genuine.



Why do I feel like this is the next Manos: The Hands of Fate?
 
Much of Errol Morris's work seems fitting for this thread, though I'll only highlight a few:

Gates of Heaven (1978.) Morris's debut, about a group of individuals working in the pet cemetery business.

Vernon, Florida (1981), about the eccentric residents living within the titular town. "Eccentric" mostly is code for "rural and uninhibited" tbh, it's fairly tame. (As a side note, this one is worth watching with the context of the original concept for the film, "Nub City", which would've implicated residents of Vernon in an insurance scheme to cut off their own limbs and collect money. Morris's life was threatened by the townsfolk, so he reworked the film into a more standard profiling of them.)

Mr. Death: The Rise and Fall of Fred A. Leuchter Jr. (1999), about an execution technician/Holocaust denier
 
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Hate to necro this thread, but Tiger King, available on Netflix as a seven-episode series, may be the most insane doc I've ever seen. All of the primary characters in it are massive lolcows, especially the central one: Joseph Maldonado-Passage AKA "Joe Exotic": a blond-mulleted gay cowboy/C&W-singer with two husbands who rules his private big-cats zoo in Oklahoma with an iron fist (and copious amounts of firearms and explosives.)

The doc's got everything: murder plots; blackmail; unsolved disappearances; gay and straight sex cults; quixotic runs for Oklahoma Governor and US President; obnoxious nuts on both sides of the "animal rights" issue; explosions; arson; elaborate con games; and of course, plenty of footage of beautiful tigers, lions, and other exotic creatures.

 
If you thought I Think We're Alone Now was cringey, it has nothing on I'm Your Number One Fan.

Highlights include Mike Read superfan Blue Tulip Rose Read orgasming to the sound of his voice on the radio, typing emails completely naked, singing while imitating a dog barking and freaking out because some shop assistant made an offhand comment about Mike Read being possibly gay.

Aside from Blue Tulip (who could have carried the documentary by herself) there's a mother-and-daughter Cliff Richard fan duo, a guy who wants to protect Princess Diana from the Beast (ie: the Queen, apparently she's actually Satan in disguise) and a woman who sent multiple threatening letters to snooker player Stephen Hendry.

https://www.youtube.com/watch?v=of1-vkIS5sQ

There's also Deep Water, based around a man named Donald Crowhurst who entered a race around the world sailing competition despite having never sailed before and being up against some very experienced sailors. I won't spoil it but things did not go well for him.

https://www.youtube.com/watch?v=IY2rQh8UraY

Vice did a very interesting (and grim as be fucked) documentary about teenage heroin addicts in Swansea. Following them around and listening to them talk about their lives it seems like life wouldn't be any better if they got off the skag. Notably there's a bit where the young blonde girl talks about how her boyfriend's father beat her up and caused her to miscarry with all the emotion of someone chipping a nail.

https://www.youtube.com/watch?v=aIbpt1aDFqM

On that note, there's a documentary maker who thought trying skag would make him better able to connect with the addicts he was filming, and of course he got hooked. He got his friend to film him trying to go cold turkey.

https://www.youtube.com/watch?v=1L33zkIFIaQ

Rain in my Heart is a good one if you like soul-crushing misery. It follows four alcoholics in a special unit in London. By the time the documentary is over, two are dead. One more has died since, the sole survivor seems to be doing okay.

https://www.youtube.com/watch?v=lwv7Utcf-gM

66 Months is also pretty miserable on several levels. A learning-disabled man with an alcohol problem is taken in by an elderly gay man who is abusive but pretty much the only one in his life that shows him any love. It's very shocking how intimate it is because the film-maker happened to be a close friend (ie: fellow homeless alcoholic) and they didn't hide anything. I rented it from Vimeo, it's not available otherwise.

If you have a strong stomach, The Hunt for Britain's Paedophiles is an excellent documentary. It's very graphic in places, and it shows just how hard a slog the police have to get through to secure a conviction. Bonus shock value for hearing an adult woman talk matter-of-factly about how her father promised her a pony if she made pornography with a bunch of his mates when she was no older than twelve, how it was the best-selling child porn on the market and how she never got her pony in the end.

http://www.dailymotion.com/video/x2i11al

I was wondering about that. Is the young man from 66 Months still alive?
 
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