Every year there are countless documentaries that make their way into theaters or on to the various streaming services. When most people think of documentaries, they usually think of specific kinds. There are many historical, concert, and true crime documentaries that always seem to populate the awards circuit. However, if you dig deep enough, there is a myriad of options out there for extremely unique kinds of non-fiction filmmaking. Over the past two decades, many talented documentarians have tackled some of the strangest subjects. You can only watch so many documentaries about the inequalities of the justice system before you get satiated. There are only so many WWII documentaries one can watch before they are bored of the subject. Here are 10 great documentaries about strange subjects.
My Date With Drew (2004)
This neat little documentary is proof positive that no matter who you are or how insignificant your story may be, documentaries can be made about it. Brian Herzlinger had a crush on Drew Barrymore for 20 years. Being driven by her quote If you don’t take risks, you’ll have a wasted soul, Brian sets out to try and ask Ms. Barrymore on a date. My Date With Drew is the height of superficiality. However, watching this poor New Jersey Schlub come up with every idea under the sun in order to get in contact with his dream girl is pretty inspiring and fun. Do you have a monster crush on a celebrity? Why not try and pursue them? This film shows that anybody can do it.
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Resurrect Dead: The Mystery of the Toynbee Tiles (2011)
If you live in any major metropolitan city in North America, chances are you have come across one on these tiles. They are linoleum and about the size of a license plate. The tiles read:
Toynbee Idea; In Movie 2001; Resurrect Dead; On Planet Jupiter
Nobody knows what they mean and nobody knows who put them there. Resurrect Dead: The Mystery of the Toynbee Tiles follows a couple of guys who are out to solve this riddle. It is like the best of detective stories, where this group of friends is following lead after lead until they almost catch the mysterious artist actually in the act of placing a tile. Sometimes the vagueness of the tiles’ meaning can get frustrating, but the adventure the filmmakers are on is an absolute hoot.
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The Aristocrats (2005)
The Aristocrats is one the funniest documentaries ever, by far. That is because it has one of the most impressive lineups of comedians you could imagine. It was made by Paul Provenza and Penn Jillette (half of Penn & Teller). You will see the likes of George Carlin, Robin Williams, Chris Rock, Don Rickles, Bob Sagat, Drew Carey, and countless more. They are all telling their personal experience with The Aristocrats joke. The notorious joke follows a man at a talent agency who is willing to do incredibly depraved things when he is on stage. To watch each of these comics tell their own versions, their history and their opinion of this joke-amongst-comedians are hysterical. Penn states that comedy is like Jazz, where it is the singer, not the song that makes great art. Some comedians are auteurs with the joke. Some fall flat on their face. Others won’t even attempt it. The Aristocrats has more profanity and vulgarity than any movie you have likely seen in years, but it is one of the best exhibitions about the art of comedy that you will see.
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Voyeur (2017)
This film is essentially two documentaries in one. One of those documentaries follows a journalism icon, Gay Talese. It focuses on journalistic integrity, ethics, and the difficulty in obtaining the truth. There is nothing strange about this part, but the other half follows Gerald Foos. Foos’s story is one of the craziest things you have ever heard. Gerald Foos bought a Colorado motel many decades ago. He spent over a year modifying the motel by building platforms and observation ports. Throughout his life, Foos spied on his tenants every second he could. He also kept detailed ledgers about who was in what room and what they did. It is exceptionally creepy the way that this character believes that he is a researcher and not a peeping tom. Also, somehow he is 100% willing to share this revelation with a very famous journalist. Not only that, but Foos has millions of dollars worth of sports memorabilia in his basement. The twists and turns Voyeur takes are just incredible. Gerald Foos is the height of depravity, and that is fascinating.
Not currently available on Amazon.
Life, Animated (2016)
Life Animated is probably the most popular of the documentaries on this list. It was nominated for the Best Documentary Feature Oscar in 2017. It involves the incredible story of Owen Suskind. When Owen was 3-years-old, he developed extreme regressive autism. His personality shrunk back into his psyche and he becomes completely silent and non-communicative. Owen’s parents did not know what to do as therapy was not getting them anywhere. Until one day, Owen starts spouting out words in step with the animated Disney movies he was always watching. It was then that Owen began to emerge from his silence.
The way this film tells Owen’s story is truly beautiful. His autism is as huge a hurdle as anyone could overcome. Disney Movies, with their idealistic approach to living and appeal to children, allowed Owen to express himself and develop into a functional young man. It isn’t all good though. When you grow up with Disney cliches as your basis for reality, true life is bound to disappoint you. Through the use of animation and personal reflection, Life, Animated really underlines how important art is to all of us. However, it was especially important to Owen. Wait until you see his reaction when he meets the voice behind one of his favorite characters. It is magical.
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The Resurrection of Jake the Snake (2015)
Documentaries about alcohol and/or drug abuse are a dime-a-dozen. However, when they focus on an iconic WWE star with a level of access you VERY rarely see, it is something special. Jake “The Snake” Roberts was one of the most popular wrestlers of the late 80s and early 90s. He had an everyman quality and his schtick involved bringing Damien the python into the ring. Some Youtube clips surfaced of him old, out of shape, and obviously under the influence. His friend “Diamond” Dallas Page reached out to him to try and get him sober. What follows is one of the greatest recovery documentaries you will ever see. This film is not a puff-piece. It portrays Roberts is a SEVERE, pitiful alcoholic. However, the camaraderie among the wrestling community is heartwarming. Roberts gets better, gets worse, has relapses, has breakthroughs, and also reaches out to other wrestlers. The WWF angle of the alcoholic through line is infinitely interesting. Also, the finale will give you chills. This is a life-affirming documentary of the highest order.
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Room 237 (2012)
Room 237 is the second of these documentaries to involve Stanley Kubrick. Also, this film can hardly be called a documentary, but it is the only way to categorize it. The film discusses the many different themes, meanings, and interpretations of Stanley Kubrick’s 1980 Stephen King adaptation, The Shining. There are two possibilities surrounding this crazy documentary. One, that Stanley Kubrick was a mad genius whose ideas and art perfectly manipulates and pays homage to some very wacked-out ideas. Two, the Room 237 filmmakers are just obsessed with Kubrick and The Shining and they made this all up. The latter possibility seems a bit more likely, but not entirely.
The film hypothesizes things like the conspiracy that Kubrick helped fake the moon landing. It assumes that the placement of paintings and pantry food indicates sympathy for indigenous peoples’ oppression. It even goes full blown Dark Side of the Moon/The Wizard of Oz and superimposes the film playing forward and backward to find special meanings. The film is completely out of its mind, but it is never not interesting. If Room 237 does nothing else, it will at least have you watching The Shining in a whole new light.
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The Barkley Marathons (2014)
Only in America can someone like Gary “Lazarus Lake” Cantrell come up with something like the Barkley Marathons. James Earl Ray escaped in 1977 from the Brushy Mountain State Penitentiary. MLK’s assassin spent 55 hours in the Tennessee wilderness around the prison and only made it 8 miles. Inspired, Cantrell decided to create the hardest endurance race in the world.
Only 40 runners are selected to run the race every year. They must write an essay, pay $1.60, bring a license plate from their home country/state, and another item. Whatever Cantrell feels he needs that year (Flannels, socks, button-down shirts) is the additional entry fee. First, this film is a character study surrounding the eccentricities of Cantrell and his race. Second, it is a brutal exhibition of how these participants try, and mostly fail, to complete the 5-day, 100-mile course. They have to hike up mountains, cross rivers, brave prickly vines, and negotiate every kind of natural formation you can think of. There is blood, sweat, tears, blisters, disappointment, and a little bit of triumph. The Barkley Marathons is a quirky delight as well as an exhausting endeavor.
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Mommy Dead & Dearest (2017)
It was stated earlier that true crime documentaries are incredibly common. They can be good or bad depending on the filmmaker and the crime represented. Mommy Dead and Dearest is simply one of the most outrageous True Crime documentaries of all time. The crime is simple. A daughter murders her mother. But the story about what the mother put her daughter through her entire life is so ridiculously unbelievable, it has to be true.
Dee Dee was killed by her daughter Gypsy Rose, but Gypsy Rose was a prop used by her mother who was an incredible grifter. Dee Dee manipulated and abused her daughter her entire life. She made Gypsy Rose believe she was dying, unable to walk, and younger than she actually was. Dee Dee infantilized her daughter to a level that she comes across as a Gollum-esque Disney Character. With a daughter in Gypsy’s apparent condition, Dee Dee could get donations, free houses, free trips, and just overwhelming sympathy and praise for taking care of her sick child. It was all a ruse, and Mommy Dead and Dearest chronicle the story. This is the craziest Munchausen By Proxy situation you will ever hear about.
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The King of Kong: A Fistful of Quarters (2007)
It takes a certain kind of brilliant documentarian to make something as trivial as the world record of Donkey Kong so riveting. The King of Kong: A Fistful of Quarters is one of the most inspiring, follow-your-dreams, good vs. evil stories of the past two decades. Steve Wiebe was depressed and bored after losing his job. He ventured into his garage where he had an old arcade cabinet Donkey Kong machine. To distract him and give himself some sort of worth, he decided to try and beat the Donkey Kong world record.
This is when Wiebe fell down the rabbit hole of Twin Galaxies and Billy Mitchell. Twin Galaxies is the group that has been keeping track of world records since the 80s. Billy Mitchell is the egomaniac that has held many of these records and is one of cinema’s greatest villains. The King of Kong follows Steve’s journey to get the record, and the gaming communities attempt to keep him out of their little brotherhood. There are a lot of laughs, a lot of gasps, and even some tears. The film simultaneously ridicules these people because of their video game obsessions and respects them for having such important passions. Man Vs. Snake: The Long and Twisted Tale of Nibbler is a wonderful spiritual sequel to the film. It has many of the same themes but follows a different game.
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