5 Funny Documentaries for Dark Times

In my production office, I have this embroidered sampler with the unofficial motto of my company:

In dark times, choosing to LOL can seem… kinda lame? It seems tone-deaf, or besides the point, or even callous. But, at least to my way of thinking, it is not about denying the terrible things happening in the world. I think it’s the opposite of that.

I recently read Austin Kleon’s book Keep Going: 10 Ways to Stay Creative in Good Times and Bad. The whole book was healing and inspiring and fun, but there’s a passage all the way toward the end that spoke to me so deeply (and not just because I am a gardener). Here is Austin reading it, and I’ve also transcribed the passage below:

@austinkleon

Austin Kleon on Instagram: "Plant your garden. 🌱"

The months leading up to World War II were some of the most terrible months in the life of Leonard and Virginia Woolf, as they “helplessly and hopelessly” watched events unfold. Leonard said one of the most horrible things was listening to Hitler’s rants on the radio . . .

One afternoon, he was planting purple irises in the orchard under an apple tree. “Suddenly I heard Virginia’s voice calling to me from the sitting room window.”

Hitler was making another speech.

But Leonard had had enough. “I shan’t come!” he shouted back to Virginia. “I’m planting iris and they will be flowering long after he is dead.”

He was right. Those perennial irises were still blooming long after Hitler’s death.

Every artist has their version of Leonard’s irises.
And we need every artist to keep planting them, no matter what.

I get that humor doesn’t seem “important.” Even within the realm of the virtues of art — compared to “beauty” and “inspiration” and “humanization,” how much can we really care about a joke?

I get that. But all I can say is: I would not be alive today without laughter. It’s definitely not because I take life lightly. Not even close. I actually find life pretty difficult to endure most of the time. Without my ability to laugh, I’d be a goner for sure.

So, anyway: we love a joke. We love a gag. We choose to LOL!!!

Here are 5 of my favorite laugh-out-loud documentaries:

1) BEST WORST MOVIE (2009)
This movie is so extremely my jam. I probably think about this movie once a week, or more. The gist of it is: the director Michael Stephenson was once a child actor in a B-horror movie called Troll 2. This was a movie so bad it crossed that mystical border over into “so bad it’s good” territory.¹ It’s become a cult classic — a phenomenon lovingly investigated by the adult Stephenson. I am an old-school Troll 2 fanatic, so obviously I was gonna see this. But don’t worry, you don’t need to see Troll 2 to enjoy this movie (they show you all the best parts anyway, and the rest of it is just… bad.) The best part of this movie is that Stephenson tracks down all his former cast mates and it is truly the most incredible assortment of characters you will ever meet. The Italian director of Troll 2 — who maintains the film is beloved today not because it is hilariously bad but because it is, in fact, a very good work of art which “examines very important and serious issues, like living, eating, and dying”— is unforgettable. Trust me on this one.

Related: many good funny docs have been made on the making of movies! American Movie (1999) is a stone-cold classic, of course; I’ll love it til the day I die. I just watched Megadoc (2025) and it’s very funny. Overnight (2003) is about the making of Boondock Saints and let me tell you… hoo boy! I could go on, but Nathan Rabin is the real expert on this topic.

2) TABLOID (2010)
Is it the best or most important Errol Morris doc? Nah. But I think it’s the funniest. It’s just a ridiculous romp, and he has so much fun telling the story of Joyce McKinney, who was once the center of a British tabloid frenzy. In classic Errol style, finding the truth is always the goal, but often the truth is elusive. Yes, there are many other funny docs in his body of work, and even his darkest films have more humor than an average documentary (there’s a reason he was an artistic north star for me when I was starting out). This one is simply my personal favorite. I am sure I am biased by the experience of watching it at DOC NYC with the film’s protagonist standing in the back of the theater yelling “Lies! Lies!” (A top 10 live-cinema moment for me.) Also: I am crazy about the graphics in Tabloid. One thing I don’t see enough people commenting on with Errol is his impeccable taste in graphics.²

3) DICK JOHNSON IS DEAD (2020)
A life-affirming and deeply funny documentary about death. (It feels spiritually related to Come See Me in the Good Light, the Ryan White film I’ve recommended in the past.) The premise of this film is that the director, visionary documentarian Kirsten Johnson, is trying to come to term with the fact that her beloved father is going to die. Dick has dementia. Together, Kirsten and Dick use the magic of cinema to defy, confront and accept death by acting out his death. Over and over. In increasingly outrageous and ridiculous ways, they out various deaths: being hit by a falling air conditioner, falling down the stairs, etc. These funny reenactment scenes are balanced out by footage that share the painful agony of watching a loved one slowly disappear. But the center of the film is the bond between father and daughter, and it is so alive and so full of creative energy, and — most importantly — the gags are good (we love a gag!).

4) LISTERS: A GLIMPSE INTO EXTREME BIRDWATCHING (2025)
This surprise recent hit is available for free on YouTube. Within a month of being posted, it had 1.3 million views. That’s now up to almost 3 million. I put off watching this for a while, because I am a birder and I was worried that this movie, like most movies, would just make fun of birders or be snarky about it. (That featured still above did not make me want to see it, either.) Wow, was I wrong!!! The premise is that these two brothers just decide to spend a whole year doing extreme birdwatching, kind of as a joke at first. But we watch them develop this absolutely sincere passion over the course of the film. This movie has so much heart. It’s so funny, totally original, and has that unmistakable mark of being lovingly hand-crafted. I watched it alone on my laptop, and loved it, but I wish I had seen it in a theater. (Funny movies: so good in theaters!) One YouTube viewer commented, “a work this good begs the question of what hollywood studios are even doing with their millions of dollars” and I mean… it’s hard to disagree with that.

5) EXIT THROUGH THE GIFT SHOP (2010)
A north star for me in so many ways. This manic satire of the art world, directed by the legendary street artist Banksy, concerns a ridiculous character calling himself Mr. Brainwash. MBW is making a documentary about street art, while he’s also trying to become a street artist himself. He manages to get interviews with artists like Shepard Fairey and even Banksy, but after many years of filming has yet to produce anything watchable with his footage. I don’t want to say more about the plot, because it’s truly so fun and satisfying to watch this film evolve without spoilers. (It also rewards rewatching, because it’s a tricky little thing!) One of the reasons this movie is so important to me as an artist is I saw it on Netflix back when Netflix had user reviews (anyone remember that??). The movie was a big hit on the platform, but one thing I clocked was that 95% of the reviews said something like, “I like street art it’s cool (5 stars)” as if that was really all that was going on in this film, when there’s definitely, let’s say, a number of other layers of meaning. I was inspired by that. I decided it would be the best thing ever if I could make films full of layers of meaning, but which are still enjoyable on a simpler, purer, entertainment basis, like maybe even if the viewer is not paying that much attention…

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I could easily go on for another 5, or even another 50. What are your picks?

1. A long time ago, I wrote about why it doesn’t seem like anyone loves “bad documentaries” the way they love bad movies. A question I still wonder about often! I guess it’s about ethics, again; documentaries seem too important to laugh about? But… are they? Questions for another day!

2. The artist Jeremy Landman created the graphics for this film, and many other Morris films too.