This episode aired in March 1995 to coincide with the premiere of The Critic on FOX. Matt Groening was against the idea of The Simpsons having a crossover with The Critic as the episode played out as an episode-long advertisement for the show. Groening removed his name from the beginning and end credits, making this the only episode (as of 2019) to not have Matt Groening credited.
Jon Lovitz speaks in the DVD commentary for the episode. He also talks about his one similarity with Jay Sherman: His testicular size.
Homer is shown to not understand the way name signs work at the airport. Instead of writing Jay Sherman's name to let him know that the Simpsons are his ride back, he writes his own name. This echoes a misunderstanding from "Mr. Lisa Goes to Washington", when Homer assumed a sign with his name meant that the person holding the sign had the same name as him.
According to a security camera in the Kwik-E-Mart on Apu's video, the videos were made on July 22, 1994. Assuming all the films were shown the next day on July 23, 1994, then the skip to six months later would be on January 23, 1995, safely within original run of Season 6, although this episode aired on March 5, 1995.
In Burns's film, current Simpsons' writer Jeff Westbrook is mentioned as one of the writers in the film's opening credits. Westbrook began writing episodes of The Simpsons about 10 years after this episode first aired.
Early in the episode Krusty is acting in a movie as a man in a wheelchair, as the movie plays, he breaks character standing up and walking toward the actress, he abruptly stops his dialogue and returns to the wheelchair; this is a parody of a scene from Dr. Strangelove Or How I Learned To Stop Worrying And Love The Bomb from Stanley Kubrick, where Peter Sellers stands from his wheelchair breaking his character and then improvise this as a miracle.
At the beginning of Mr. Burns' first appearance in this episode, the Imperial March (AKA Darth Vader's Theme) from Star Wars is played. This is used as a piece of theme music for Burns throughout the series.
The desert sequence in Mr. Burns' film is a parody of Ben-Hur, although the line, "You truly are the King of Kings," may be a recasting of a similar line delivered by John Wayne in the movie The Greatest Story Ever Told, where in a cameo as a centurion, he says, "Truly, this man was the Son of God."
McBain's "Woody Allen impression", which merely consists of him saying "I'm a neurotic nerd who likes to sleep with little girls", was a reference to the then-recent revelation that Woody Allen married his adoptive daughter Soon-Yi, as well as kept nude photographs of her while she was growing up.