In a loose parody of the Jessica McClure incident in 1987, Bart gets an AM/FM microphone and radio set for his tenth birthday and, after Homer and Marge show him that the gift actually has some worth, Bart begins using it to trick the town into thinking a boy named Timmy O'Toole is stuck in the well.
This episode provides examples of:
- An Aesop: Practical jokes may seem cute and funny, but they can have serious consequences.
- As Himself: Sting
- Asshole Victim: Bart.
- Cutting the Knot: The townspeople come up with all sorts of weird ideas for how to free "Timmy", ranging from using a fishing line baited with chocolate, to having him carried out by a falcon, to even cryogenically freezing him. In the end, Homer is the one who comes up with the simplest and most obvious solution-just grab a shovel and dig Bart out of there.
- Fake Interactivity: The birthday stage show at Wall E. Weasel's.Wall E. Weasel: Hey there, I hear it's your birthday. How old are you?
Bart: Well, I’m—
Wall E. Weasel: (interrupting) That's great! Would you like us to sing you a special song?
Bart: Hell, no.
Wall E. Weasle: You've got it!
- Hollywood Tone-Deaf: The awful rendition of "Happy Birthday" (called "You're the Birthday Boy or Girl") by Wall E. Weasel and his cast, both the singing and the musical score. The robots are so bad that Wall E .'s mouth is clearly just moving up and down while the synthesized speech chip is playing.
- Also, Homer's (usual) off-key rendition of C.W. McCall's "Convoy."
- Laser-Guided Karma: Bart falls in the same well he fools the town into thinking he fell into earlier.
- Oh Crap!: Bart when he realized he left a clue in the well linking him to the prank (the radio that has a "Property of Bart Simpson" label on it).
- Papa Wolf: Homer is the first one to grab a shovel and try to dig Bart out.
- The Reveal: This is the first episode to show Willie's muscular build under his shirt.
- Bart scares Homer with his radio broadcast into thinking that Martians have landed, in reference to the Moral Panic that errupted after the famous 1938 radio broadcast of War of the Worlds by Orson Welles.
- America's Top 10 — Casey Kasem hosts the program, announcing "We're Sending Our Love Down the Well" reaching No. 1, and then its record-setting fall nearly off the charts.
- Walter Cronkite: Kent Brockman's announcement about the Lincoln squirrel being assassinated is copied nearly frame for frame – including a shot with Brockman removing horn-rimmed glasses while reading the news flash – with the CBS News anchorman's announcement that President John F. Kennedy had officially been pronounced dead.
- Chuck E. Cheese's: What else – Wall E. Weasel's.
- Superstar Celebrity Microphone — Based on "Mr. Microphone," a real-life version of a microphone, which could be broadcast on AM frequencies, was marketed, also via a TV commercial with 1-800 number to order.
- The tough sailor offering to bring the boy back to the surface is a reference to Quint from Jaws.
- "We are the World" by U.S.A. for Africa — "We're Sending Our Love Down the Well" and its music video is a parody.
- When Homer hears Bart crying, he exclaims, "That's all I can stands, I can't stands no more!" before grabbing a shovel and starting to dig a tunnel to reach Bart.
- Suck E. Cheese's: Wall E. Weasel's. Downplayed, as the place isn't egregiously bad, but it does have ill-maintained animatronics, crummy video games (cf. Bart playing "Larry the Looter" and losing after a shop owner shoots off his head), and a short scene shows that it's stupid easy to cheat at skeeball (Nelson standing on the game and dropping the balls in the center hole).
- Suddenly Voiced: This was the first speaking role, or rather singing role, for Sideshow Mel.
- The Unreveal: We never find out what Lisa bought for Bart with the money Homer gave her.
- Very Loosely Based on a True Story: Bart's "joke" about a boy falling down a well casing is inspired by the real-life events involving 18-month-old Jessica McClure becoming trapped in a narrow well.
- Whole Plot Reference: The concept of this episode evokes Ace in the Hole, a Billy Wilder-directed movie in which an accident trapping a shopkeeper in a cave sparks a media frenzy. Both stories even involve someone making a pop song about the victim, and a carnival becoming formed at the site of the disaster.
- Winged Soul Flies Off at Death: Happens to Scratchy in the cartoon.
- Worst News Judgment Ever: This episode provides the trope image with the Lincoln Squirrel. And later on, as the town proceeds to dig Bart out of the well, Kent Brockman reports, "This just in: the Lincoln Squirrel has been assassinated!"