Stephen Colbert and Paul Dinello came up with the idea for the movie after they both saw a an after-school special/documentary entitled "The Trip Back", which featured inspirational speaker Florrie Fisher, chain smoking at a podium while screaming at high school students about her troubles with drugs and prostitution. Dinello and Colbert showed a tape of the documentary to Amy Sedaris, telling her that they wanted to make a short parodying an after-school special. Sedaris modeled the voice, mannerisms, and appearance on Fisher, and many of Jerri's lines throughout the series were taken verbatim from Fischer's speeches.
The Flatpoint High School sign reads, "Home of the Concrete Donkeys".
Most of the cast had previously been involved in Comedy Central's defunct series, Exit 57 (1995). After seeing this film, though, Comedy Central contacted Amy Sedaris, Mitch Rouse, Stephen Colbert, and Paul Dinello and asked them to return to work for them, along with the cast they'd assembled.
The only cast members who would not reprise their role for the eventual TV series was James Murtaugh, since Jerri's hospital job was written out. Sarah Thyre would return to the series, but as Mrs. Wolf the gym coach, instead of Mrs. Blank.