1. Best of Enemies: Buckley vs Vidal
A good documentary can give you a peek at the way things used to be. A great documentary can show you that some things never change. Best of Enemies is the latter. It tells the stories of the televised debates between conservative William F. Buckley and liberal Gore Vidal, and shit gets INSANE. Actually, you know what? Scratch that. Shit would be insane if didn't feel so commonplace in today's political climate. Best of Enemies should have been the story of a weird blip in the history of journalism. Instead, it feels like you're watching the birth of punditry today.
2. Paris is Burning
If you've ever enjoyed an episode of Rupaul's Drag Race, you should probably set aside some time to be bummed out by Paris is Burning. You wouldn't have one without the other. Documenting the drag scene of the early 90s, the film is both uplifting and depressing as hell. You'll fall in love with the subjects then be instantly heartbroken by the life they were forced to endure. If nothing else, it's worth a watch if only so you can see, once and for all, just how much mainstream society steals from drag culture.
3. My Friend Rockefeller
True crime documentaries are something of a hot commodity these days, but given that we're a comedy website, we can't really discuss too many of them. That's not the case with My Friend Rockefeller. The documentary tells the story of con artist and eventual murderer, Christian Gerhartsreiter. Though ultimately tragic, the story is so incredibly strange that it almost feels funny at points...Almost. My Friend Rockafellar is a true crime story so breezy you almost forget it's a true crime story. In the end, that might just be the scariest thing about it.
4. The Nightmare
Alright, enough with the heavy stuff. Time to move away from murder and on to something lighter like....Crippling nightmares? Goddamnit. The Nightmare features multiple first hand of accounts of sleep paralysis, and if you don't know what that is, consider yourself lucky. Go watch it if you want to understand a terrifying part of a lot of people's everyday life, but be warned: This documentary is scarier than most horror movies.
5. What Happened Miss Simone
You probably have heard the name Nina Simone but if you don't really know what she was all about, you absolutely should. Some people are so badass that they don't deserve to be lost to time and Nina Simone is definitely one of those people. Though there's probably a LOT more to her, this biography provides you with a baseline understanding of one of the greats. If you're a fan of Simone, you'll love this film. If you've never heard of her before, give it 10 minutes and I promise you'll fall in love.
6. Room 237
Fan theories are super fun, but it takes a very special kind of mind to come up with one. Room 237 is the best insight most of us well ever get into one of those minds. The film explores multiple conflicting theories surrounding Stanley Kubrick's The Shining, which range from kinda weird to absolutely bonkers. Told entirely through voice over interviews, 237 creates an unnervingly intimate relationship between the viewer and the films subjects. By the end of it, you probably still won't buy into the conspiracies they're pedalling, but you will have a much better understanding of the brains that created them.
7. Do I Sound Gay?
Some of the best documentaries focus on topics you might not have initially assumed were big enough to sustain a full documentry. In the case of Do I Sound Gay, that topic is the "Gay voice." It may sound silly, but the film makes the most of it seemingly small subject matter, using it as a jumping off point to discuss internalized homophobia. If you've ever assumed someone's sexual orientation based on their voice (which is all of you) this film will be surprisingly eye opening.
8. Jesus Camp
When it came out, Jesus Camp was a terrifying look at religion in the Bush era. Rewatching it now, it manages to feel both like a relic of a time past, and a creepy predictor of things to come. Following a trio of kids as they attend an evangelical summer camp, the documentary manages to make you terrified of the films subjects without ever actually hating them (They are children after all). It'll occasionally make you want to cringe, but if you can power through, Jesus Camp is a rewarding experience that will stick with you well into the next election.
You might think that a movie about an old lady who dresses good would be boring as hell, but you'd be surprised. The titular character is a woman who's made a name for herself just by being really, really, really, stylish. If that sounds silly, I suggest you watch the movie, because by the time the credits roll you'll totally understand why Iris is a star. It's probably the airiest entry on this list, but if you're in the mood for some lighter fare, Iris is a fun and insightful diversion, perfect for a lazy Sunday afternoon.
10. Queen of Versailles
When the stock market crashed in 2008, billionaires David and Jackie Siegel had to stop construction on their dream home: a mansion called Versailles that, if completed, would be one of the largest in the world. Thankfully, someone was around to record it because it's good as hell. Based on that description, you'd think that the fun of Queen of Versailles would be to enjoy watching rich people suffer, and that's mostly true. What makes the film special, though, is the amount of empathy it has for its subjects. By the end of the movie, you'll be both happy to watch these people fail and hopeful that they'll get it together.
(Note: This list was last updated on 08/30/17. It will be updated to account for Netflix's changing catalogue.)
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