1. I Think We're Alone Now, 2008
View this video on YouTube
This documentary follows two "super fans" of former teen icon Tiffany as they attempt to get closer to their icon. Jeff has been following Tiffany for years and believes that the two are close friends despite her having issued a restraining order again him in the past. Kelly seeks to have a relationship with Tiffany, believing the two share a special connection. More than anything else, this movie offers a fascinating (and, at times, heartbreaking) look at love, obsession, loneliness, and the struggle to belong.
Choice quotation: "The difference between me and a stalker, um, is they don't truly love the individual."
Where you can watch it: Netflix instant
2. Best Worst Movie, 2009
View this video on YouTube
Troll 2, a movie that isn't really a sequel and has nothing to do with trolls, has been dubbed the worst movie of all time, and with good reason. This documentary follows some of the movie's stars --including its affable wannabe-actor-turned-dentist leading man-- as they either embrace or struggle with having been featured in a movie where, for instance, two people sloppily make out over a corn cob and a little boy pees on enchanted goblin treats. (No, none of that makes any more sense in context.) Of special note are the movie's Italian director and writer, who are convinced that their film (a satire of... vegetarianism?) is a total work of art.
Choice quotation: "I did a very good movie."
Where you can watch it: Hulu
3. Crazy Love, 2007
View this video on YouTube
This doc tells the story of Burt Pugach and Linda Riss, a very charismatic on-and-off-again couple whose relationship takes a twisted turn after Pugach, jealous and wanting Riss to himself, hires a man to throw lye in her face, permanently scarring the object of his obsession.
Riss' reaction to the assault and to Pugach's continued erratic behavior is... unexpected, to say the least.
Choice quotation: "He said, 'If I can't have her, nobody will.'"
Where you can watch it: Netflix instant
4. Tabloid, 2010
View this video on YouTube
This film follows former pageant queen Joyce McKinney's bizarre quest to "win back" a young Mormon man with whom she's obsessed, earning her a place as a tabloid fixture amid rumors of kinky sex, kidnapping, and madness.
Choice quotation: "I knew there was only one way to get Kirk out of Mormonism, and that was to make love with him."
Where you can watch it: Netflix instant
5. In The Realms of The Unreal, 2004
View this video on YouTube
This is the beautiful, sad story of Henry Darger, an outsider artist whose work, most notably a 15,143-page manuscript he called The Story of the Vivian Girls, in What is Known as the Realms of the Unreal, of the Glandeco-Angelinnian War Storm, Caused by the Child Slave Rebellion, was found after his death. It's an unusual look at art, beauty, isolation, and imagination punctuated by animated versions of Darger's own gorgeous and strange watercolor illustrations.
Choice quotation: "This volume I hopefully say has scenes and instance no other story of usual size in the world may contain."
Where you can watch it: YouTube
6. Crumb, 1994
View this video on YouTube
Robert Crumb is an artist whose often psychosexually-tinged work has permeated pop culture. This documentary takes a look at how his style (and the sexual preferences that feature in much of his work) came to be, centering not only on Robert, but on his brothers and, of course, his mother.
Choice quotation: "At that point I was about five or six, I was sexually attracted to Bugs Bunny."
Where you can watch it: Crackle
7. The Devil and Daniel Johnston, 2005
View this video on YouTube
Daniel Johnston is an artist and musician whose genius was on track to propel him into a bigger spotlight. Even if you've never heard of his music, you're likely familiar with his "Hi, How Are You" drawing, made famous after Kurt Cobain wore it on a T-shirt. But as Johnston's creative output garnered more attention, his mental health deteriorated, which manifested in him developing an obsession with the devil.
Choice quotation: "They tell me I'm crazy here."
Where you can watch it: Crackle
8. The Imposter, 2012
View this video on YouTube
How does a 20-something, brown-haired, brown-eyed French man convince the family of a missing blond, blue-eyed American teen that he's their long-lost son? Easy: a combination of grief, denial, and... something a bit more unnerving and nefarious.
Choice quotation: "There was just something... wrong about him."
Where you can watch it: Netflix instant
9. Married to the Eiffel Tower, 2008
View this video on YouTube
This documentary offers an in-depth look at a group of people with objectophilia. Meaning: they are attracted to and form committed relationships with inanimate objects, like the titular Eiffel Tower.
Choice quotation: "I am a woman and this is a bridge."
Where you can watch it: YouTube
10. The Act of Killing, 2012
View this video on YouTube
A beautifully made, award-winning documentary that is both surreal and too real. Throughout the course of the documentary, the director (working alongside an anonymous Indonesian) has notorious gangsters Anwar Congo and Adi Zulkadry direct, design, and re-enact some of the murders they committed during the Indonesian killings of 1965–66. The two begin their project with gusto, referencing their favorite movie genres (including Westerns and musicals) and donning elaborate costumes to perform highly stylized versions of massacres. But then... the mood shifts.
Choice quotation: "It's a good family movie; plenty of humor; a great story; Wonderful scenery. It really show what's special about our country even though it's a film about death."
Where you can watch it: Netflix instant
11. The Institute, 2013
View this video on YouTube
Strange flyers start appearing around San Francisco, urging people to... well, they're not sure what, exactly. Embark on a quest? Participate in a game? Join a cult? Nothing is as it appears as more and more strangers join together to solve a mystery that blends reality and fantasy. If that sounds pretty fucking weird, it's because it really, truly is.
Choice quotation: "I saw a way to play that was entirely new. And then treating it like a game offended me."
Where you can watch it: Netflix instant
12. The Source Family, 2012
View this video on YouTube
How does a cult form? What gets people to join? This film follows The Source Family, a group led by the charismatic (and thirsty) "Father Yod," who created a utopia of sex and drugs set in '70s Hollywood. Which might sound awesome, sure. Until things begin to go awry. As they kind of tend to do with cults.
Choice quotation: "I'm the father you all wanted."
Where you can watch it: Netflix instant
13. Donor Unkown, 2010
View this video on YouTube
If your father was a sperm donor, would you seek him out? For the dozens of children of "donor 150," the answer is an emphatic yes. After finding one another online and being surprised at all they have in common --from a characteristic big toe to the way they tuck their hair behind their ears-- they decide to find their dad. Could he be a doctor? A lawyer? A scientist?
Not quite.
Choice quotation: "Is he a doctor, a lawyer? No."
Where you can watch it: Amazon