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.
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.
Some of the pictures in the lunch room were drawn by Todd Oldham, who also has a part in this movie.