Cinco Paul had the idea for the show more than 20 years before it premiered, originally imagining that two men, like the backpackers in An American Werewolf in London, would stumble into a musical instead of a horror story.

The concept only clicked for Paul when it evolved into a couple who are trapped in the musical world until they find true love, and while the season 1 style is based on 1940s-50s musicals, the sets and costumes actually reflect 1910s America, similar to The Music Man.

The show's title and premise for season 1 parody the 1947 musical Brigadoon, while season 2's setting, Schmicago, parodies the 1975 musical Chicago.

Season 1 was written in the summer of 2019 and was originally planned to have eight episodes, but ended up with six; filming began in Vancouver on October 13, 2020 and wrapped December 10, during the COVID-19 pandemic.

Several actors played different characters across both seasons, such as Dove Cameron, Jaime Camil, Kristin Chenoweth, Alan Cumming, Ariana DeBose and Jane Krakowski, each portraying a new character inspired by different classic musicals in season 2.

Cinco Paul won the Primetime Emmy Award for Outstanding Original Music and Lyrics for the song 'Corn Puddin'', featured in the pilot episode.

Although season 2 received even more critical acclaim than season 1 (97% versus 89% on Rotten Tomatoes), Apple announced on January 18, 2024 that the series would not be renewed for a third season.

Cinco Paul revealed he had already written the scripts and songs for a planned third season titled Into the Schmoods, a play on Into the Woods, which would have parodied that musical along with Cats, Les Misérables and The Phantom of the Opera; Apple owns the unproduced scripts but Paul retains rights to the songs.

In season 2, the characters played by Jacqueline and Joyce Robbins are named the Bernstein sisters, likely a nod to composer Leonard Bernstein.