David Letterman jumped on board as a producer because he said that Amy Sedaris is one of the few people in this world that can actually make him laugh.
The role of Alice was originally intended for Natasha Richardson, but she was in France at the time that the scene was to be filmed. If Allison Janney hadn't been available, the next actress on their wish list was Joan Allen. They also considered the possibility of retailoring the part for Jennifer Coolidge.
Snowball 37, the band whose logo appears on apparel worn by characters in the movie, is an actual touring band, made up of three members of the infamous Fagan family, who appear as students in the movie, and all but one episode of the television series. The name of the band is a reference to a well known conversation from Kevin Smith's Clerks (1994).
According to Amy Sedaris, Larc Spies was re-cast with Joseph Cross as Derrick Blank because he had semi-retired from acting and "looks like a longshoreman now."
The pin-up model in Jerri's locker is Amy Sedaris. Sedaris also played the cocktail waitress in the "Teacher's Lounge" scene.
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