Homer's lines "I call the big one Bitey" and "Doughnuts, is there anything they can't do?" are among Matt Groening's favorites.
George Takei was asked to guest star as he had appeared on the show once before. After demanding several script changes, Takei declined, saying he did not want to make fun of public transportation as he was a member of the board of directors of the Southern California Rapid Transit District (now the Los Angeles County Metropolitan Transit Authority). As a result, the staff went to Leonard Nimoy, who accepted.
Conan O'Brien conceived the idea when he saw a billboard in Los Angeles that just had the word "Monorail" on it, with no other details or explanation. He first pitched this episode at a story retreat to Al Jean and Mike Reiss, who said the episode was a little crazy and thought he should try some other material first. O'Brien had previously pitched episodes where Lisa had a rival and where Marge gets a job at the power plant and Mr. Burns falls in love with her; both went well. James L. Brooks "absolutely loved" this episode when O'Brien presented it.
This is the only time in the series Lurleen Lumpkin is voiced by someone other than Beverly D'Angelo. For her brief appearance here, Doris Grau provides the voice.