Homer's conductor uniform is similar to the uniforms worn by Imperial officers such as Grand Moff Tarkin, Admiral Ozzel and Admiral Piett in the Star Wars saga.
Leonard Nimoy wasn't originally supposed to appear in this episode as the grand marshal for the monorail's maiden voyage. George Takei (Sulu from the original Star Trek series) was originally picked to appear on the show, but Takei didn't want to appear in something that mocked public transportation (as Takei was on California's Board of Public Transportation at the time and was an advocate of it). William Shatner (Captain Kirk from the original Star Trek series) was also considered, but the idea was scrapped as Shatner already turned down an appearance on a previous Simpsons episode.
The chalkboard gag for this episode is "I will not eat things for money". Bart later does do this in the episode Diggs when he trying to pay Homer back.
The gag showing Homer with his mouth full of unlit cigarettes would be recreated several years later as a meme related to the video game Team Fortress 2 with the spy class, only with the cigarettes lit.
The main premise of a con man getting a town excited about something he sells but hardly knows anything about is borrowed from the musical "The Music Man".
Lanley's appearance and the musical number at the end of the town hall meeting is a nod to some of the songs in "The Music Man" as well.
A "reverse reference" occurred in 2002 when Seattle residents opposed to a proposed monorail project held a protest event called "Coming Out With Marge Simpson". The event organizers planned to show the episode as part of the protest, but were ordered not to by Fox due to copyright laws.
The scene where Mr. Burns (as Mr. Snrub) and Smithers escape town hall via grappling hook is a reference to the 1989 movie "Batman". Homer would later mistake Sebastian Cobb, the North Haverbrook contractor, for Batman
Whilst studying for the monorail conductor exam, the study book is entitled MCAT (Monorail Conductor Aptitude Test), which is a reference to the MCAT (Medical College Admission Test) taken by many medical students.
The sound-alike version of Axel F can be heard in this episode when Mr. Burns takes the toxic-waste drums to dispose of.
Doctor Hibbert was among the passengers on the monorail on the first ride, but he is seen with a pair of siamese twins in his office soon after. The person on the monorail may have been Hibbert's long lost brother that works at the Shelbyville Orphanage.
When Maggie is reaching for the possum in the monorail her pacifier changes its color.