What is the Funniest Documentary of All Time?

This post was originally published on the now-defunct Documentary Channel Blog on March 27, 2013. 

In honor of the kooky new film Room 237 and also Monday being April Fool’s Day — and with that, some appropriately themed content on Documentary Channel (see down below for details) — this week’s big discussion post is focused on comedy and documentary.

There was a time when “funny” and “documentary” seemed like oppositional words, and put together they’d be considered an oxymoron. The only comedies in documentary form were fictional mockumentaries and the only docs in comedy form were concert films of stand-up shows. Maybe people laughed at or with the behavior and statements of real quirky characters in docs like Grey Gardens, The Decline of Western Civilization Part II, Sherman’s March and Vernon, Florida, but it wasn’t the primary intent of their filmmakers to get laughs from the audience. At least I hope it wasn’t. That would be cruel.*

Michael Moore helped to change the medium in many ways, one of which was adding a lot of humor in the form of sardonic political comedy employed directly and for greater influence. Political comedy was nothing new but it had mostly been just that, comedy. He sort of put the jokes in real-time in real situations to make points and, ironically, to reveal the comedy to be in fact very serious. While he had more fun for fun’s sake in his TV series, in his best films Moore’s approach is only funny until the depressing reality sets in. He’s most effective when not a clown, and his movies are hardly laugh-riots when he is.

At some point, and this would have happened with or without Moore I think, it wasn’t about political comedy anymore. It was comical politics. Particularly on the Left side of the spectrum, the approach and response to certain political issues were to have a laugh, especially because that world was becoming so absurd. You had parody on Saturday Night Live leading to true news stories treated almost like they were mockumentaries on stuff like The Daily Show. And many films followed that same model, whether they were about modern Yippie-ish pranksters like The Yes Men or about hot topics through the perspectives of jokesters like Bill Maher, Morgan Spurlock, Doug Benson and Sacha Baron Cohen, the last of whom did so by way of fictional characters.

My favorite political documentary of last decade sort of addressed the nature (and to me, problem) of the era’s reliance on comedy for political argument, influence and opposition, especially for the Democratic Party. That film is Chris Hegedus and Nick Doob‘s Al Franken: God Spoke, and it’s not really a comedy but it is humorous because it’s about a figure who is funny. Just as the documentaries Joan Rivers: A Piece of Work, Conan O’Brien Can’t Stop and To My Great Chagrin: Brother Theodore (airing on DOC this Monday) are hilarious thanks to their subjects. Each of these, too, like many films about comedians and comedy (especially the Jerry Seinfeld doc, Comedian), are also often very dark and sad.

One doc that succeeds in breaking down comedy and still being a riot is The Aristocrats, Paul Provenza‘s 2005 film about one filthy joke told by 100 different comics. You don’t have to like or get the joke every or any time, though the more often you do the funnier the film is. And if there’s not at least one version for you (there’s even mime!), then your sense of humor may be either an uncommon kind or nonexistent. Still, it’s a fascinating examination of the great variety of comedic technique and style as well as different levels of genius — or lack thereof for a few participants.

Thinking something is funny is always subjective, of course. You could certainly find some disturbing or deadly serious films funny if that’s your thing. And you may not be in tears from laughing so hard at Conan O’Brien Can’t Stop, as I was with multiple viewings. You might laugh more at goofy subjects in docs like Anvil! The Story of Anvil and American Movie and The Queen of Versailles, where I’d feel bad about doing so. And you might not get the joke that I believe to be the whole point of Room 237, which explores ludicrous theories and analyses of Stanley Kubrick’s The Shining. Of course, director Rodney Ascher might not mean for his whole film to be a big joke or even about a big joke, and my having my own interpretation would be rather fitting.

Here are 10 documentaries that I find to be the funniest, for different reasons, in no particular order (and may be switched out for something else if I think of others I’m forgetting): The Aristocrats; Crumb; Conan O’Brien Can’t Stop; Don’t Look Back; Bowling for Columbine; Borat; Joan Rivers: A Piece of Work; Super High Me; The Red Chapel; Sherman’s March.

This Monday for April Fool’s Day, Documentary Channel will be re-airing To My Great Chagrin: Brother Theodore (6pm ET), about the existential comedian, as well as the DocTalk episodes “Humorous Docs” (7:30pm ET), which features Jay Cheel‘s Beauty Day and Alexandre O. Philippe‘s The People vs. George Lucas, and “The Price of Fame” (7:45pm ET), which features Conan O’Brien Can’t Stop and Paul Williams Still Alive. Additionally, Monday is the first day of Doc Channel’s month-long attention to the planet called “Celebrate Earth,” and the first film in the program is Bag It (8pm ET), which is fittingly one of the more humor-oriented environmentalist docs out there (read more about it here).

* – See a column I wrote asking, “When is it okay to laugh at a real person?” from July 2011, which focused on Tabloid, Grey Gardens, Anvil!, The Red Chapel and more.