The documentary genre isn’t one that’s typically thought of as being funny, and for good reason. Most documentaries are grounded affairs, with many tackling important issues and real-life stories. There are certain topics where a humorous approach would feel distracting or even disrespectful to the nature of the subject at hand. Naturally, it leads to more serious documentaries than comedic ones.
However, given a documentary can document, record, or present an argument on any number of topics, sometimes, a humorous approach will work. Some of the best documentaries take a look at humorous subjects or present serious subjects in a humorous way, becoming films that balance being funny and being informative: some do their job so well they wind up being Certifed Fresh on Rotten Tomatoes, pleasing audiences, and critics.
12 ‘The Aristocrats’ (2005)
Rotten Tomatoes Rating: 79%
The Aristocrats is a documentary about the world’s most notorious joke. Without going into too much detail, the joke involves a family auditioning for a talent show, doing unspeakably inappropriate and disturbing things, before declaring that their act is called “The Aristocrats” as the punchline. It’s a challenge for comedians to try to top each other in telling a version of the joke as depraved as possible.
Those who don’t care for dirty jokes probably won’t care for The Aristocrats, but it emerges as an interesting documentary about shock humor and pushing comedic boundaries. On top of that, it also features countless comedians, all doing their take on the titular joke through interviews, which leads to a good deal of very extreme comedy, and it’s also safe to assume that with such humor comes a ton of profanity…
11 ‘The Amazing Johnathan Documentary’ (2019)
Rotten Tomatoes Rating: 80%
The Amazing Johnathan was a unique comedian/magician who is (fittingly) the subject of The Amazing Johnathan Documentary. Despite its documentary presentation – and featuring the word “documentary” in its title – it’s the kind of movie where it’s often to work out what’s genuine and what’s an act, making for a mind-bending watch.
Given The Amazing Johnathan’s act often involved surprising and confounding his audience, it’s appropriate that a documentary about the man does the same. Whether the director or The Amazing Johnathan were ultimately in control of the wild and unpredictable movie is hard to say. Like any good magic trick, it’s better if it’s kept a mystery. The Amazing Johnathan Documentary gleefully blurs the line between drama and documentary, and it’s that tension between the two that keeps it funny, surprising, and consistently engaging.
10 ‘Jackass Forever’ (2022)
Rotten Tomatoes Rating: 85%
While you might not think of the Jackass films as documentaries, they technically are. The films spun off from the MTV reality series of the same name and mostly feature crude – and shocking – stunts and pranks performed by a large group of friends. They may not be about historical events or have the sort of deep messages more traditional documentaries may have, but they serve as a time capsule for the comedy troupe.
Jackass Forever is the fourth film in the series, and so far, the highest rated on Rotten Tomatoes, too. The core Jackass members are older (and get younger newcomers to perform some stunts) but still take a ton of punishment in hilarious, wince-inducing scenarios, all for our entertainment. For anyone who enjoyed Jackass Forever and was after more, a solid sequel was released some months later called Jackass 4.5.
- Release Date
- February 1, 2022
- 1hr, 36mins
9 ‘Winnebago Man’ (2009)
Rotten Tomatoes Rating: 90%
Winnebago Man is a simple and surprisingly great documentary about a man by the name of Jack Rebney, who accidentally became a viral sensation thanks to a series of outtakes that came from an advertisement for a Winnebago motor home. The outtakes showed him getting angry and cursing in an absurd and funny way without context, which led to the outtakes becoming so popular.
Rebney’s case is interesting because these outtakes were passed around on VHS tapes before the internet and became popular on YouTube during the website’s early years. As Rebney led an otherwise isolated life, it was also quite remarkable that the filmmaker behind Winnebago Man, Ben Steinbauer, was able to track him down. It’s a good thing Steinbauer did because it created an entertaining, funny, and surprisingly interesting documentary.
8 ‘Pretend It’s a City’ (2021)
Rotten Tomatoes Rating: 91%
Martin Scorsese is a prolific filmmaker who’s made plenty of great films that get overlooked and is just as skilled at directing documentaries as he is at feature films. Pretend It’s a City is a documentary directed by Scorsese and is probably one of his more overlooked works, too, alongside being one of Scorsese’s best overall documentaries.
Whether you want to count it a miniseries (as it’s divided into several parts) or a movie (it’s just over three hours, so could be watched in one sitting), either way, it’s a solid blend of documentary and comedy. It follows writer/comedian Fran Lebowitz as she explores New York City and discusses its history with Scorsese – who serves as an informal interviewer – offering plenty of humorous observations in the process.
7 ‘Super Size Me’ (2004)
Rotten Tomatoes Rating: 92%
Back in 2004, Super Size Me was a big deal, and a critically acclaimed documentary that was even Oscar-nominated. Nowadays, there are parts of it that don’t hold up the best, as times have changed and the central premise of the documentary does feel flawed at best. Yet Super Size Me does undeniably have a good hook for its premise, following one man using himself within an experiment to see what health effects will come about from only eating fast food.
Some of the humor is intentional, while others may want to watch the film today and laugh at its expense, given the shortcomings that come with the simplicity of the experiment and some of the ways it plays with objectivity. Yet many documentaries do this for the purpose of making a point of presenting an argument, and perhaps others will argue that Super Size Me has done more good than harm, or, at the very least, is able to provoke some thought and provide a handful of funny/entertaining moments.
super size me
- Release Date
- January 17, 2004
- Morgan Spurlock , Daryl Isaacs , Lisa Ganjhu , Stephen Siegel , Bridget Bennett , Eric Rowley
6 ‘American Movie’ (1999)
Rotten Tomatoes Rating: 94%
A touching and quietly funny ode to independent, do-it-yourself filmmaking, American Movie focuses on Mark Borchardt, a filmmaker in his 30s who’s struggling to complete a short horror film he’s been working on for years. It’s a good non-fiction story and gets a healthy dose of humor thanks to Borchardt’s close friend, Mike Schank, who has plenty of great observations about his close friend and his seemingly cursed film production.
For anyone used to working in film, there’s sure to be a great deal to relate to in American Movie. Even while showing the hardships of filmmaking, American Movie ultimately celebrates it and the creativity involved in bringing any film – short or long; low or high budget – to the big screen, and it’s up there as one of the best releases of the entire 1990s (also encapsulating the feel of that decade extremely well).
5 ‘Not Quite Hollywood: The Wild, Untold Story of Ozploitation!’ (2008)
Rotten Tomatoes Rating: 95%
Not Quite Hollywood: The Wild, Untold Story of Ozploitation! is a very straightforward documentary. It takes a look at an unusual and little-known period of history in Australian cinema where, during the 1970s and 1980s, plenty of extreme and unusual exploitation films came out of Australia, with the sub-genre being dubbed “Ozploitation.”
Much of the humor comes from how bizarre the films are and how out there the behind-the-scenes stories are. The interviewees are candid and entertaining, the old movie clips are plenty of fun to watch, and Not Quite Hollywood is a great way to learn about numerous films that never received mainstream attention; some being movie hits within Australia, sure, but a number of them also not getting the attention they deserve in their country of origin either. It’s exactly what you’d want out of a comedic, light-hearted documentary.
4 ‘The King of Kong: A Fistful of Quarters’ (2007)
Rotten Tomatoes Rating: 97%
Anyone going into The King of Kong: A Fistful of Quarters hoping to see King Kong or some kind of spaghetti Western might come away disappointed, but anyone in the mood for a fast-paced and oftentimes funny documentary should come away pleased. The King of Kong plays out like something of an entertaining sports documentary, following two very different people who are fiercely competitive when it comes to the Donkey Kong arcade game.
More specifically, one is challenging the other’s world record/top score, while the other’s willing to fiercely defend that score, no matter what. You don’t have to be a huge fan of old-school video games to enjoy The King of Kong: A Fistful of Quarters, though it wouldn’t hurt… still, in any event, it’s tremendously entertaining, quite tense in parts, and fairly humorous throughout.
3 ‘Joy Ride’ (2021)
Rotten Tomatoes Rating: 100%
A TV movie that only runs a little over an hour, Joy Ride is about two middle-aged comedians: Dana Gould and Bobcat Goldthwait. The documentary follows their 2019 comedy tour together as they travel through the U.S.A.’s South and talk about their lives, which gives it the feeling of watching a stand-up special but of a more laidback variety, and one that complements its comedy with some behind-the-scenes stuff.
The documentary segments are interspersed with clips from their on-stage comedy acts, but those who enjoy their sense of humor will find both parts of Joy Ride funny. It’s a very funny and easy-to-watch comedic documentary. At 70 minutes, Joy Ride is perfect for those who want to watch a complete movie but don’t have the time or energy to sit down and commit to something more demanding.
2 ‘Swimming to Cambodia’ (1987)
Rotten Tomatoes Rating: 100%
To describe Swimming to Cambodia in a sentence or two is to run the risk of making it sound a little boring. The entire film is actor/novelist Spalding Grey sitting at a desk, talking to the camera, mostly about his experience traveling to Southeast Asia to act in the classic 1984 historical drama, The Killing Fields.
It is essentially an 85-minute-long monologue, but it’s one that’s written and told extremely well, with Grey offering plenty of interesting insights and humorous observations along the way. It’s also bolstered by Jonathan Demme‘s dynamic direction, which shouldn’t surprise anyone who’s seen the 1984 Talking Heads concert film, Stop Making Sense. Demme was undoubtedly a director who knew how to capture an on-stage show and translate it to the big screen.
1 ‘Nathan for You: Finding Frances’ (2017)
Rotten Tomatoes Rating: 100%
The final episode of Nathan for You‘s final season, Finding Frances, ultimately stands as its own separate thing, as it’s an episode that runs for almost 90 minutes. It serves then as a feature-length finale to Nathan Fielder‘s mind-bending show, and stands out among the other episodes, which are all under half-an-hour long.
It’s a hilarious, uncomfortable, and profound feature-length episode that sees Fielder helping an elderly man reconnect with a woman he knew from decades ago, yet has never been able to forget. It’s unlike anything else out there, and for as great as season 1 of Fielder’s latest show, The Rehearsal, was, Finding Frances is still probably the best thing he’s made in his career so far.
- Release Date
- February 28, 2013
- Nathan Fielder
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