If Jerry Seinfeld’s “What’s the deal with airline food?” grew up, took mushrooms, and learned to edit in Adobe Premiere, it would become this doc.
This one is also listed on my teammate (Rob Kelly’s) list, The 30 Funniest Documentaries (Ranked with 2025 Update).
Trailer for “How To with John Wilson”
You Can’t Make This Sh!t Up
- Wilson visits the first-ever Mandela Effect Conference in Idaho. People passionately argue that shared false memories (like the Raisin Bran mascot wearing sunglasses) prove alternate realities exist.
- He crashes a baby shower at the Florida mansion of Bang Energy CEO Jack Owoc. Owoc greets him in a black robe and gold chain, gives a full hour-long tour, and proudly shows off his “Victory Gym.”
- Wilson films a full-frontal, fully nude demonstration of a foreskin restoration device. HBO gave zero warnings. He also interviews a man who self-castrated as a teen, and yes, they show everything.
Watch “How To with John Wilson”
You can watch “How To with John Wilson” on HBO Max.
Ratings:
- My Rating: 90/100
- IMDB Rating: 8.7/10
- Rotten Tomatoes: Not officially rated but widely acclaimed by critics
Director’s Note: John Wilson is the host, cinematographer, narrator, and editor. The show is a one-man documentary experiment about modern life. It’s lo-fi, deeply weird, and quietly brilliant. Nathan Fielder (known for “The Rehearsal”) served as executive producer, helping HBO greenlight this beautifully uncomfortable project.
Release Date: October 23, 2020 (Season 1 Premiere); July 28, 2023 (Final Episode of Season 3)
My Review of “How To with John Wilson”
The Setup
Each episode starts with a harmless how-to. Like “How to Cover Your Furniture” or “How to Split the Check”—but quickly turns into a deeper look at human behavior, isolation, or obsession.
John Wilson wanders through New York with a camera, capturing life’s unintentional comedy and quiet sadness. He meets strangers, follows odd tangents, and slowly reveals more of himself across the three seasons.
It’s six hours of the strangest therapy session you’ll ever witness—filmed like a diary, edited like a collage, and narrated like an anxiety spiral.
More Highlights from the Doc
- The show is made entirely from Wilson’s own footage—shot obsessively while walking around NYC with a handheld camera for years. He stitches the mundane and the surreal together into oddly profound video essays.
- Each episode starts with a simple goal (like “How to Make the Perfect Risotto”). Then it derails into strange personal encounters—like ending up at a vacuum cleaner repair convention or interviewing hoarders.
- Wilson frequently turns the camera inward—exploring his own anxiety, grief, and social awkwardness. There’s a quiet arc across the seasons as his life subtly changes off-camera.
- Season 3 takes bigger swings—questioning how documentaries are made, how we record our lives, and whether “truth” is even possible in non-fiction storytelling.
Cameos – Lesser-Known Details from the Doc
- In the scaffolding episode, Wilson interviews Kyle MacLachlan (yes, Twin Peaks’ Kyle MacLachlan) at a parking meter—purely by coincidence. They bond over how confusing the meter system is.
- The show’s editor is Alice Gregory, a longtime New Yorker contributor, and Nathan Fielder (of “Nathan for You”) is an executive producer. You can feel Fielder’s fingerprints all over the awkward genius.
- Wilson never uses voiceover recorded in a studio—his narration is always done in a whispery, off-the-cuff tone, often with flubs left in, which adds to the raw and intimate feel.
Wrap Up
If you like weird rabbit holes, uncomfortable encounters, and documentaries that feel like therapy from a guy with a camera, this one is essential. It’s like “Planet Earth” for anxious people in New York.
Thanks for reading!
Heather Fenty, Guest Writer, Daily Doc