You might think that the average person gets guarded when cameras are up and rolling, but creator and videographer John Wilson seems to have the opposite effect on his subjects. His HBO Original series, How to With John Wilson, executive produced by Nathan Fielder, is a comedic documentary series that weaves together man-on-the-street observations, interviews, and personal narratives to create a fascinating portrait of New York City, and arguably, humanity as a whole.
Each episode is filled with strange and funny moments that illustrate a larger theme. Yet it’s Wilson’s subjects that really take center stage. They’re seemingly mundane on the surface; ordinary people that you probably pass by everyday on the city’s sidewalks. But once he turns the camera on and starts asking questions, they unveil their eccentric, trivial, and deeply weird selves.
Before the show returns for its third and final season, we ranked the ridiculous — and very real — characters throughout the series so far. See our standings below, then watch the season premiere of How to With John Wilson on Friday, July 28 at 11 p.m. on Max.
10.
The Teenage Real Estate Agent (Season 2, Episode 1)
When contemplating whether or not to buy out his landlord’s — and ultimately, his own — apartment and become a landlord himself, Wilson checks out other potential rentals. After viewing the listings within his budget, like one with a bathtub in the kitchen, he decides to view a luxury rental instead. It’s listed by a teenage real estate agent who kind of looks like a child playing dress up. She says she finally passed her exam to become an agent, albeit, on her third attempt.
9.
The Casket Cruiser (Season 2, Episode 3)
In “How To Find a Spot,†Wilson explores the choreographed dance of New Yorkers trying to secure free street parking spots. He finds himself at Cruising Caskets, a company that designs and creates car-shaped coffins. The owner shares that he’ll be buried in one of his caskets, then crawls into the car (read: casket) and closes the door.
8.
The Love Leash Founder (Season 2, Episode 5)
In “How To Remember Your Dreams,†Wilson interviews an entrepreneur who dreamt up a grand business idea that he calls the Love Leash. He expresses frustration that his product is over-sexualized, when its core purpose is much more wholesome: a dog leash with handles that split into two, so two people can walk their dog at the same time.
7.
 Multiverse Man (Season 1, Episode 3)
After striking up a simple conversation with a person in a grocery store, Wilson gets invited to Idaho for a Mandela Effect conference. The man, who Wilson thought was a grocery store employee, turns out to be a conspiracy theorist, or, at the very least, a person who’s convinced the Mandela Effect is proof of the multiverse. He introduces Wilson to his community at the conference, where they all recount their experiences of every-day forgetfulness. They are convinced that they are the select few that can experience the multiverse — or maybe they just collectively have bad memory.
6.
Scaffolding Guy (Season 1, Episode 1)
A deep-dive into New York City’s scaffolding leads Wilson to interview a man who recounts having, as some might say, a night to remember against a scaffolding structure in Hawaii. The man proceeds to show how he and his romantic partner, who also happened to be a nudist, used the scaffolding during their date. He gives blunt details while reenacting the scene in front of Wilson, a complete stranger, during daylight, in public, on the city sidewalk.
5.
 The Woman Who Steals Pigeons (Season 1, Episode 1)
In a quick 10-second clip, Wilson captures footage of a woman in Herald Square who seems harmless. That is, until she opens up her shopping bag, grabs a pigeon, puts the pigeon in her bag, closes the bag, and walks away. Who knows, maybe she was bringing it to a wild bird rescue?
4.
 The Reincarnation Expert (Season 2, Episode 4)
In “How To Throw Out Your Batteries,†Wilson interviews a self-proclaimed reincarnation “expert†who believes he can identify people’s past lives. He shares famous celebrities’ past selves, then unveils that he is the reincarnation of the second president of the United States, John Adams. He says that his wife is the reincarnation of John Adams’ son, but explains it’s definitely not incestuous.
3.
Leg-in-Backpack Guy (Season 2, Episode 4)
Toward the end of the same episode, Wilson casually meets up with a man in the park, who recounts a traumatic experience that ended with one of his legs needing to be amputated. Instead of turning his leg into biological waste, he convinced medical professionals to give it back to him. Then, there in the park, he pulls his amputated leg out of his backpack, bones and all.
2.
The Man Who Eats MREs (Season 2, Episode 2)
Wilson finds a man who has made a hobby out of collecting and eating really old and expired Meals Ready-to-Eat (MREs), which are army rations that were given to soldiers during combat or in places where food wasn’t readily available. In Wilson’s honor, the hobbyist opens and heats up a beef and rice ration from 1964. It turns out, the apple doesn’t fall far from the tree. His mom shares that she too has indulged in consuming expired products, like that time she knowingly drank an expired meal replacement shake for lunch, even though it tasted like rust.
1.
Foreskin-Machine Guy (Season 1, Episode 4)
An episode that explores how Wilson can protect his armchair from his cat takes a turn, fast. In “How To Cover Your Furniture†Wilson meets with an anti-circumcision advocate. He starts off by sharing a song from his anti-circumcision concept album on the piano, “Wouldn’t Skin Be Nice?†Suddenly, the show veers into unpredictable (and disturbing) territory when the man reveals he has invented a foreskin-restoring device. He demonstrates how to use the system; a rope tied around his penis attached to a pulley system that connects to his bed … a bed that he shares with his wife.
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