The part of Tom, Bart's sponsored big brother, was originally written for Tom Cruise. However, Cruise's spokesman informed the producers that the star would not do the episode. It was decided to replace Cruise with Phil Hartman providing the voice of Tom. The character pilots an F-14, in reference to Tom Cruise's role in Top Gun.
The television show Bart watches, Tuesday Night Live, is a parody of Saturday Night Live (1975). Krusty appears in a sketch called "The Big Ear Family", and says that the sketch goes on for twelve more minutes, even though the joke's punchline has already been established. That was Jon Vitti's way of criticizing SNL for having overlong sketches with thin joke premises. The sequence originally had a longer version of the Tuesday Night Live band playing into the commercial break, but it was cut because Vitti, who was a writer on Saturday Night Live during the 1985-86 season along with fellow writers, George Meyer and John Swartzwelder, did not want to come off as being bitter.
The chalkboard gag, "The Principal's toupee is not a Frisbee", is the only mention of Principal Skinner's hair being fake in the show's universe. Originally, Principal Skinner was supposed to wear a toupee and it was supposed to be a running joke, but Matt Groening thought that toupee jokes were too cliched, and scrapped the idea completely.
In the episode, Bart and Tom watch The Ren & Stimpy Show (1991). The producers contacted Nickelodeon to get authorization to use the two characters for that sequence. Nickelodeon was strict about what The Simpsons was allowed to do, and the producers were not allowed to have the savageness that they wanted. The Ren and Stimpy animators offered to do the layouts of Ren and Stimpy for the episode.
Pepi was based on the fictional character Dondi from the daily comic strip of the same name.