Documentary filmmaking is oftentimes serious business, but not always. Such films tackle everyday stories and issues, sure, butreal life can often be funny in its own strange way, which leads to certain documentaries being naturally humorous. It often depends on the subject matter, sure, but documentaries about relatively serious things can also inject humor or be funny at times, depending on the approach taken by the filmmakers.
The following movies are all tagged as documentaries and comedy movies (among some other genres, in some instances) on Letterboxd, so per that site, they can all be considered comedic documentary films. They’re ranked below, starting with the relatively funny and informative, and ending with the best of the best for this particular genre hybrid; in other words, those documentaries that rival full-blown comedies, when it comes to delivering big laughs.
10’An Evening with Kevin Smith' (2002)
Director: J.M. Kenny
An Evening with Kevin Smithis exactly what you’d expect it to be based on the title. It’s also more of a comedy than a documentary, but qualifies as the latter because it documents a series of Q&A sessionsKevin Smithhosted as he toured the U.S., which makesAn Evening with Kevin Smithfeel likea concert movie, except without music and with plenty of crude/funny anecdotes in its place.
Anyone who doesn’t particularly like Kevin Smith or his sense of humor won’t be won over byAn Evening with Kevin Smith, but anyone who’s enjoyed his feature films – includingthe legendary 1994 filmClerks– will have a good time here. It’s extremely long, running for 224 minutes, but definitely doesn’t need to be listened to/watched in one sitting, and can more or less be treated as a high-quality podcast or clip show of the best moments from Smith’s public speaking tour.
Rent on Apple TV
9’Pretend It’s a City' (2021)
Director: Martin Scorsese
Understandably,Martin Scorsesewill always bemost well-recognized for his feature films, butthe man’s also beenresponsible for numerous great documentariesover the years. One of those is 2021’sPretend It’s a City, which was released in several parts as a miniseries on Netflix, butScorsese’s no stranger to movies 3+ hours long, soPretend It’s a Citycould well be watched as one long film.
It’s essentially a film about Martin Scorsese hanging out with and talking toFran Lebowitz, who’s a renowned public speaker, author, and humorist. She also calls New York City her home, and Scorsese’s shown his love of that location throughout his many films, too. He’s also a clear fan of Lebowitz’s sense of humor, and for as funny as she can be,Pretend It’s a Cityis largely endearing for showing Scorsese having fun (some of his recent films have been pretty heavy, after all).
Watch on Netflix
8’Roger & Me' (1989)
Director: Michael Moore
He may have become less prolific in recent years, butMichael Moore’simpact on the documentary genrecan’t be understated, with his efforts being particularly popular throughout the 2000s. He rose to prominence, however, withRoger & Me, which established his style pretty well, containing humor and a good deal of entertainment value alongside being informative and persuasive in the argument it tried to present.
Moore’s style has always been passionate and – in some cases – some would say biased, but documentaries can sometimes be more about presenting an argument than simply recounting objective facts. However, when it comes toRoger & Me, most can likely get behind the real-life underdog story, with Moore’s sometimes comedic attempts to get an interview with General Motors CEORoger Smithbeing paired with a moredramatic and empathetic look at the effects that mass lay-offs within the company had on its workers based in Flint, Michigan.
Roger & Me
7’Werner Herzog Eats His Shoe' (1980)
Director: Les Blank
Werner Herzog Eats His Shoehas a title that might sound like proto-clickbait, but it more than lives up to what’s promised in said title.Famed filmmakerWerner Herzog– who himselfhas made many great documentaries– is at the center of this amazing, simple, and hilarious documentary short, which details the aftermath of a bet Herzog lost.
Essentially, Herzog was skeptical that fellow documentarianErrol Morriswould ever finish his filmGates of Heaven, going so far as to say he would consume his footwear if it was ever released. Eventually, it was, and Herzog, being the legend he is, indeed went through with what he said he’d do, and thankfully,Werner Herzog Eats His Shoedocuments it all. It’s a quick, funny, and oddly endearing documentary, and a must-watch for anyone who’s a fan of Herzog’s larger-than-life and unique personality.
Watch on Criterion
6’Mistaken for Strangers' (2013)
Director: Tom Berninger
If you take a cursory glance atMistaken for Strangers, itmight at first look like a concert movie/documentarycentered on legendary indie rock bandThe National. There’s every chance that’s what it was intended to be, because itsees the younger brother of the band’s lead singer following them as they embark on a monumental tour, but at a point, it shifts away from being just about the band playing their songslive.
Riskily, directorTom Berningermakes himself the central subject, but it pays off, leading to some memorably awkward comedy and genuine pathos that comes from the way he uses the film to explore his life versus that of his rock star brother,Matt Berninger.Mistaken for Strangershas a good sense of humor that’s balanced well with the sadder and more introspective moments, and it overall makes for a fascinating film about the bond between brothers and the struggles of living up to one’s older siblings.
Mistaken for Strangers (2013)
Mistaken for Strangers follows The National on its biggest tour to date. Newbie roadie Tom (lead singer Matt Berninger’s younger brother) is a heavy metal and horror movie enthusiast, and can’t help but put his own spin on the experience. Inevitably, Tom’s moonlighting as an irreverent documentarian creates some drama for the band on the road. The film is a hilarious and touching look at two very different brothers, and an entertaining story of artistic aspiration.
Watch on Amazon
5’Jackass Forever' (2022)
Director: Jeff Tremaine
Some might not agree with the classification of theJackassmovies being documentaries, at least according to Letterboxd and other sources, but they do all intend to capture real-life stunts and shenanigans. If you want to be a little pretentious, you could well call the most recentJackassfilm –Jackass Forever– anexploration of middle-aged issues and shortcomings, given how much older the central crew is compared to their earlier films (and the originalJackassseries, of course).
Jackass Foreversees an added level of risk, given the main members are all in their 40s/50s here, with a workaround being some young blood brought in to do some of the more extreme stunts. The film is fairly balanced, overall, and finds plenty of entertaining things for both young and old participants to do. It won’t win over anyone who didn’t enjoy previousJackassmovies, butshould provide ample entertainment for anyone who’s ever got a kick out of the long-running series.
Jackass Forever
Watch on Paramount+
4’My Winnipeg' (2007)
Director: Guy Maddin
What isMy Winnipeg, exactly? Even after watching the film, such a question is hard to answer, because it genuinelyblurs the line between documentary and… something else. Just what that something else is proves hard to define, becauseMy Winnipegis kind of funny, sometimes bleak, and also weirdly haunting, feeling ghostly and fantastical by documentary standards.
That all seems part of the film’s intent, withMy Winnipegnot really being specific in what parts of it are fact, what parts are folklore, and what parts might be a bit of both. It retells astrange “history” of the titular Canadian city, and is one of those rare films that’s guaranteed to feel like nothing you’ve ever seen before, no matter how many movies/documentaries you think you’ve watched during your time on this planet.
3’Windy City Heat' (2003)
Director: Bobcat Goldthwait
Love it or not,cringe comedy is here to stay, and few movies embrace such a style of humor as successfully/relentlessly as the exceedingly underratedWindy City Heat. Perhaps a little like My Winnipeg, it can be a bit hard to tell how much of Windy City Heat is fact and how much is fiction, but it’s sort of incredible that it exists when viewed either way.
Essentially,Windy City Heatis a feature-length prank on the one and onlyPerry Caravello, who’s seemingly convinced that he’s the star of what he believes will bea hit gangster movie. Ordinarily, getting someone’s hopes up but being insincere all the while would feel mean-spirited, but Caravello’s behavior and some of the things he says end up alleviating the guilt one might feel from laughing at his expense. Of course, if the movie is all staged, then the joke could well be on the audience for believing any of it… but even if none of it was an actual documentary, it would still be a masterwork of uncomfortable comedy for feeling so credibly awkward, not to mention an all-time great farce.
Buy on Amazon
2’American Movie' (1999)
Director: Chris Smith
American Movieis a documentary about filmmaking that also happened to come out during one ofthe strongest ever years in cinema history. It followsMark Borchardtas he mounts the daunting task of finishing a horror film calledCoven, with the eventful production of said movie ensuring an emotional rollercoaster of a documentary, sometimes funny and sometimes surprisingly inspiring.
One of the definitive movies that should be watched by all aspiring filmmakers,American Moviewill likely also speak to anyone who’s ever had a passion for something creative. It’s a real-life underdog story that never feels overly sentimental, presenting things in an honest way throughout. It’s justfortunate that the narrative – even with its more bitter or difficult moments – was an ultimately uplifting and gently humorous one.
American Movie
1’Nathan for You: Finding Frances' (2017)
Director: Nathan Fielder
Justifiably considered one of the funniest shows of the 2010s,Nathan for Youran fora consistently hilarious four seasons, with the strongest episodes, in particular, being unlike much else out there. It memorably ended on a high with a feature-length episode, and considering it runs for almost 90 minutes and puts most other comparable documentary films to shame, it’s worth highlighting here.
The finale/film in question isFinding Frances, which sees hostNathan Fielderreconnecting with aBill Gatesimpersonator namedWilliam Heath, and journeying with him as he attempts to track down an old love. It’s funny, uncomfortable, sad, and thought-provoking in equal measure, withFinding Francesbeing genuinely brilliant on every level and undoubtedly hard to top… so it was a fitting (and epic) end for the show. Fielder’s been active since the end ofNathan for You, with projects likeThe RehearsalandThe Curse, butFinding Francesmight well remain the single best thing he’s been involved with creating.
