The series was created by Tim Robinson and Zach Kanin, with Robinson also starring in most of the sketches, blending cringe comedy with surreal humor.

The show is executive produced not only by Robinson and Kanin but also by Lonely Island members Andy Samberg, Akiva Schaffer and Jorma Taccone, alongside Alex Bach and Daniel Powell of Irony Point.

Recurring guest stars across all three seasons include Zach Kanin, Sam Richardson, Patti Harrison, Conner O'Malley and Tim Heidecker, joined at various points by Andy Samberg, Fred Armisen, Vanessa Bayer, Beck Bennett, Kate Berlant, Julia Butters, Ayo Edebiri, Will Forte, Paul Walter Hauser, Bob Odenkirk, Cecily Strong, Jason Schwartzman, Brandon Wardell, Fred Willard and Steven Yeun.

Production on the second season was delayed by the COVID-19 pandemic, pushing its release from a planned earlier date to July 6, 2021, two years after the first season.

A Wired contributing editor, Peter Rubin, wrote in April 2021 that he had become obsessed with the show, claiming he had watched the entire first season at least 100 times.

The show's critical reception grew stronger with each season on Rotten Tomatoes, moving from a 96% approval for season one to a perfect 100% for season two, before settling at 96% for season three.

In February 2024, Robinson and Kanin took the series on a national live tour starting at the Beacon Theatre in New York and ending at the Greek Theatre in Los Angeles, featuring unaired sketches performed live and extended sketch screenings with guest performers including Sam Richardson, Seth Meyers, Lionel Boyce, Patti Harrison and Paul Rudd.

In a 2025 interview, Akiva Schaffer revealed that Robinson and Kanin have a deal for a future season and have already been writing sketches, though a release date remains unannounced as they also work on an HBO show.