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Amitai Marmorstein as Pete, the cheerful Milkman, who is often the subject of offscreen violence, such as from Farmer McDonough's shotgun or a rock attempted to be skipped by the Mayor.Kyra Leroux as Carrie, one of Farmer McDonough's seven daughters.Bijou Brattston as Tootie McDonough, one of Farmer McDonough's seven daughters.He is based on Winthrop Paroo from The Music Man. Emma says that Carson is her kid brother, but it turns out that he is her son. Liam Quiring-Nkindi as Carson, a boy with a lisp, who announces scene changes.Aaron Tveit as Danny Bailey, the town's rapscallion, a carnival barker, based on Billy Bigelow from Carousel.Martin Short as Leprechaun, a magical imp based on Og from Finian's Rainbow.Jane Krakowski as Countess Gabriele Von Blerkom, Doc Lopez's fiancée, a rich, elegant woman, based on the Baroness from The Sound of Music.Ann Harada as Florence Menlove, the mayor's adoring but sexually frustrated wife.Ariana DeBose as Emma Tate, Schmigadoon's schoolmarm, based on Marian Paroo from The Music Man.Alan Cumming as Mayor Aloysius Menlove, the closeted gay mayor of Schmigadoon.Kristin Chenoweth as Mildred Layton, the preacher's wife, whose great-great-grandfather founded Schmigadoon, based mainly on Mrs.Jaime Camil as Doc Jorge Lopez, an attractive but judgmental widowed doctor, set in his ways, inspired by Captain von Trapp from The Sound of Music.Dove Cameron as Betsy McDonough, a waitress, one of Farmer McDonough's seven daughters, inspired by Ado Annie from Oklahoma!.Fred Armisen as Reverend Howard Layton, long-suffering husband of Mildred and leader of the Methodist church in Schmigadoon.Cecily Strong as Melissa Gimble, an OBGYN from New York City, and Josh's girlfriend.Keegan-Michael Key as Josh Skinner, an orthopedic surgeon from New York City, and Melissa's boyfriend.

The title and concept parody the 1947 musical Brigadoon. They get lost and soon discover a magical town called Schmigadoon, which is perpetually trapped in a Golden Age-style musical, and soon learn that they cannot leave the town until they find true love.

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Two New York doctors, Melissa and Josh, go on a backpacking trip in an attempt to patch up their failing relationship, only to find themselves still arguing. Paul has said that even though Schmigadoon's musical style, characters and satire are largely based on 1940s and 1950s musicals, the sets and costumes reflect 1910s America, like the setting in The Music Man. According to Paul, the concept only fully came into focus for him when it changed to 'a couple who are stuck there until they can find true love'. Cinco Paul had the idea for the show over 20 years ago, that it would be funny if two men, like the backpackers in An American Werewolf In London, stumbled upon a musical, instead of a horror story.