Baby Gerald, Luigi Risotto, Assistant Superintendent Leopold, and Flanders' parents make their first appearances on the show in this episode. Leopold and Luigi were designed by David Silverman, one of the show's directors. Bob Anderson thought Luigi was one of the funniest characters on the show when he first read Luigi's lines in the script during a table read of the episode. When Anderson skimmed through the script and saw Luigi's lines, he said he "frightened Julie Kavner because I was laughing to myself, but trying to keep the laughter in because it was so damn funny."
When this episode first aired, stars appeared during the commercial breaks to celebrate the 100th episode.
- Luke Perry: (referring to his animated appearance) You know, I've been shot out of a lot of cannons, but there's nothing like the first time. Congratulations to the show on their 100th episode.
- Leonard Nimoy: To everyone in the sleepy town of Springfield...may you live long and prosper.
- Kelsey Grammer: Hello, Kelsey Grammer here. Felicitations to the people who bring The Simpsons to life. May you make 100 more.
The scene where Groundskeeper Willie is trying to track down Santa's Little Helper in the schools vent system is a parody of Captain Dallas' infamous death scene in the sci-fi horror classic Alien (1979)
Bill Oakley and Josh Weinstein decided to do a Skinner and Bart episode because the staff wanted to take a diversion from the relatively wacky, fast-paced episodes that had comprised Season 5 so far and, according to David Mirkin, "slow down parts of the show to take time for more emotional episodes like this one".