How to Live with Regret

In a uniquely hilarious odyssey of self-discovery and cultural observation, documentary filmmaker and self-described "anxious New Yorker" John Wilson covertly and obsessively films the lives of his fellow New Yorkers while attempting to give everyday advice on relatable topics. The awkward contradictions of modern life are eased by Wilson’s candid, unpolished commentary. Building upon Wilson’s previously released "how to" short films, each episode takes wildly unexpected turns but is grounded in John's refreshing honesty.

A simple guide on how to end relationships before they begin.

In this engrossing and hilarious documentary, Wilson puts it all on the line to investigate the televised performances of justice and New York (the latter by Los Angeles, of course).

Or a day in the life of Ahmed Khawaja. A tutorial that forgets to be a tutorial.

In 2010, an obsessed gamer designed the perfect game of Sim City. Achieved through a repeating pattern of clustered high rises, “Magnasanti” exposes the hellish consequences of top-down civic design. In his new documentary, John Wilson explores how New York City is creeping closer and closer to realising this fictional metropolis.

Everyone’s favorite rascals, the Aqua Teens, and everyone’s favorite perverted neighbor, Carl, split up then get back together to fight everyone’s favorite corporate overlord, Amazin, led by everyone’s favorite tech mogul, Neil, and his trusty scientist sidekick, Elmer.

Vimeo hires a struggling documentarian to document a festival he can't get into.

The act of transporting an old mattress into a new walk-up apartment becomes absurdist, cinematic one-woman choreography in this wordless vignette from Adinah Dancyger, full of humor and pathos, and painfully familiar to city-dwellers.

A visit with the inimitable Mike Kuchar.

The unsung creators behind the psychedelic carpets lining casinos, offices, and hotel hallways. Chief among these textile honchos is Roderick James, a Scottish expat with a self-styled outlaw-country manner—and countless schemes to grab himself a larger share of the American dream.

An ordinary man (played by Tim Morton) lives a dull life till his friend Chet (played by Jimmy Kustes) comes over to stay for a few days. His friend ropes him to various schemes and generally makes a bunch of faux pas. His girlfriend (played by Johanna Sims) mostly runs around without alerting him of her whereabouts. He escapes his dull day-to-day existence by watching the TV show New Cops and dreaming various scenarios involving him being the President of the United States and Chet serving as his adviser. Chet recommends they hire detective Flaherty (played by David Maloney) to investigate a book heist at the local library.

A short documentary about the veiled lives of balloon fetishists.

After attending a workshop on how to write and sell a Hallmark movie, filmmaker John Wilson tries to use the same formula to sell a documentary about concrete.

At 8:55 PM on February 3, 2023, a freight train carrying hazardous materials derailed in East Palestine, Ohio. Told entirely through found footage and news archive, A DERAILMENT puts you in the center of disaster. As local news coverage and publicly circulated footage unfold in real time, the film reveals not only the immediate catastrophe but the deepening crisis that followed—raising urgent questions about oversight, accountability, and the failures that allowed it to escalate.

As the host of a long-running variety show passes away, his son is obligated to reunite a weathered cast of television performers and host the final episode. One man bands, retired cowboys and Peruvian daredevils adorn the stage as the new host protects his father's legacy from a bungling step dad. Caught somewhere in between variety and verite', People Parade is the story of a new generation paying testament to it's predecessor, as well as the narrowing chasm between reality and fiction.

A beginner’s guide to a lifetime of pleasure.