This episode marks the first appearance of Fat Tony, along with his fellow mobsters Legs & Louie.
Chalkboard: High explosives and school don't mix
Bart: Uh, say, are you guys crooks?
Fat Tony: Bart, um, is it wrong to steal a loaf of bread to feed your starving family?
Fat Tony: Well, suppose you got a large starving family. Is it wrong to steal a truckload of bread to feed them?
Bart: Uh uh.
Fat Tony: And, what if your family don't like bread? They like...cigarettes?
Bart: I guess that's okay.
Fat Tony: Now, what if instead of giving them away, you sold them at a price that was practically giving them away. Would that be a crime, Bart?
Bart: Hell, no!
Fat Tony: Enjoy your gift.
Principal Skinner: Oh, licking envelopes can be fun! All you have to do is make a game of it.
Bart: What kind of game?
Principal Skinner: Well, for example, you could see how many you could lick in an hour, then try to break that record.
Bart: Sounds like a pretty crappy game to me.
Principal Skinner: Yes, well... Get started.
Homer: Bart!? Have you started smoking?
Homer: Don't lie to me boy. Uh huh, cigarettes, just as I thought.
Bart: But they're not mine, my boss said his warehouse was full!
Homer: Yeah right, son, I'm going to teach you a lesson! I'm going to stand here and watch you smoke every one of those cigarettes!
Fat Tony: Pick a horse, kid. We're putting two dollars on the third race. Make it a good one.
Bart: Eat my shorts!
Fat Tony: Eat My Shorts? Okay, let's see ... wait a minute, you little punk! Eat My Shorts is in the fifth race! I said the third race!
Bart: Don't have a cow.
Fat Tony: Hmm, Don't Have A Cow in the third, put a deuce on him.
When Bart crashes at the social club, his skateboard changes position in between shots.
While Homer is gambling with the gangsters, you can barely see the shoulder of an orange shirt that Bart is wearing, but in every other shot he is still wearing his tuxedo.
When the pile of newspapers fall on Principal Skinner, two garbage cans appear out of nowhere next to the door.
The Native American, in the chocolate factory film, is a parody of the Cleveland Indians' mascot Chief Wahoo.
Fat Tony is modeled much like the gangsters in the 1972 fil,. in particular, Sonny Corleone. Also, the scene when Bart wakes up screaming is a reference to Jack Woltz screaming after waking up in bed with the head of his best horse.
Principal Skinner's plan of escape from his garage--A model rocket, a vacuum cleaner cord and cord retraction switch, and a support beam--is a parody of the same kind of clever devices and gadgets devised from everyday products.