The title of the episode is a homage to Hubert Selby Jr.'s controversial book Last Exit to Brooklyn. Also, the story of Homer becoming a union boss is very loosely based on the book's fifth part called 'Strike'.
The body of the union president is seen buried under a football field, a homage to the mystery surrounding the whereabouts of Jimmy Hoffa, who for years was widely believed to be buried under the now-demolished Giants' Stadium in East Rutherford, New Jersey.
Homer's imagination of a life of organized crime is based on the famous San Gennaro sequence in The Godfather Part II, accepting donuts rather than a necklace and an orange.
Lisa has a dream that echoes the Beatles movie Yellow Submarine, which Al Jean says had to be changed enough so that everything was slightly different due to legal reasons.
In that dream, George Harrison says, "Look, lads, it's Lisa in the sky." While Lisa is flying over their (purple) submarine, Paul McCartney says, "No diamonds, though." This is a reference to the famous song of the Beatles: "Lucy in the Sky with Diamonds", which also featured in the film. Another factor to the dream is that when Lisa is flying, clouds forming the word HATRED are shown (it was LOVE in the original movie).
Mr. Burns' very long and narrow corridor lined with doors is another reference to Yellow Submarine.
The scene where Lisa acquires her monstrous braces and breaks her mirror after laughing maniacally due to the trauma of witnessing her braces is based on when Jack Napier sees his new disfigured appearance during his transformation into the Joker in the 1989 film Batman.
The elaborate deadpan transition from the interior of the power plant to its main control grid is said by commentary to have been based off of Bruce Wayne's Batcave entrance scene from the 1989 film adaptation of Batman.
Rainer Wolfcastle saying the pun 'ice to meet you' is reminiscent of the film 'Batman and Robin', in which Mr. Freeze, played by Arnold Schwarzenegger, whom Wolfcastle is based on-constantly recites ice puns. However, this episode aired in 1993, four years before the release of that film.
Before Mr. Burns shuts off the power to the town in response to the strike, he says, "From Hell's heart I stab at thee" which is a reference to Captain Ahab's curse, from the film Moby Dick.
The workers' resistance to the power outage, and Mr. Burns' response, is a spoof of How the Grinch Stole Christmas. And the three final devices he names are nonsense words, which is very Dr. Seuss like.
This episode has been an Internet meme, particularly the lines "Lisa needs Braces." and "Dental Plan." which were used in some YouTube videos.
Mr. Burns has a thousand monkeys typing on a thousand typewritters to write the best novel known to man on his mansion. This is a reference to the Infinite monkey theorem, that says that a monkey typing random letters on a typewriter for an infinite amount of time will be able to write anything, from simple words to complete recreations of famous novels and books.
The scene where Mr. Burns puts his hand to his ear is a reference to the ending of the Grinch, in which he holds up his hand to his ear in order to hear the cries of Whoville, but ends up hearing their hopeful singing. Burns' subsequent rhyming is also a reference to Dr. Suess.
This is the second time in season 4 that Lisa starts dreaming/hallucinating after she take any kind of drug. The first was in Selma's Choice where she hallucinated after she drank some "water" at Duff Gardens.
When Lisa goes upstairs ashamed of her "new" braces, the flower pot and the fern that were near the staircase dissapear.
In Mr. Burns' basement, when Burns says that "he should stop ending the tour with it (the basement)", the white stripe on net of the ping pong table goes behind the electric box on the wall.
When Homer gives his speech before the strike, the orange flag on the stage disappears. The same error happens during Carl's speech.
Lisa's accoustic guitar has four strings in some scenes and six in others.
When Burns and Smithers watch Homer "exercise," the candy stuck to his back isn't visible. This is somewhat necessary for the joke to work, but in context it can be viewed as an inconsistency.
"The Big Book of British Smiles" has an extra "of" in its title.
↑Jay Kogen, The Simpsons season 4 DVD commentary for the episode "Last Exit to Springfield"
↑Matt Groening, The Simpsons season 4 DVD commentary for the episode "Last Exit to Springfield"
↑Wallace Woolodarsky, The Simpsons season 4 DVD commentary for the episode "Last Exit to Springfield"