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.