Dan Castellaneta inadvertently misspelled "smart" as "S-M-R-T" when Homer sang "I am so smart", and ad-libbed "I mean S-M-A-R-T". The writers found this much funnier and used the take.
Conan O'Brien, who wrote this episode, said that he based Homer's three nerdy tutors on a trio of nerds who lived in his dorm when he was at Harvard. He said he remembered that they would drop phone books on the floor at night so that girls who lived on the floor below would come up to complain wearing their nightgowns.
When Mr. Burns tells Homer that he needs to go to college, Bart jokingly asks, "College? Barber or Clown?" Coincidentally, in a later episode, Homie the Clown (1995), Homer does end up going to a clown college.
This was the final episode of the show for which Conan O'Brien received sole writing credit; his final writing credit altogether was for Treehouse of Horror IV (1993), which he co-wrote with five other writers. O'Brien would leave the series halfway through the production of the season to host his own show, Late Night with Conan O'Brien (1993) on NBC. O'Brien was informed that he had been hired by NBC not long before the recording session for this episode began, and he was forced to walk out on his contract.
The episode contains the series' first reference to the Internet, as "computer signals" being sent between the Nerds and MIT.