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:
* ActorAllusion: When Marge tries to convince Sting to take a break from digging Bart out, Homer stops her claiming he's a good digger. Sting actually worked as a ditch digger before his music career took off.
* AnAesop: Practical jokes may seem cute and funny, but they can have serious consequences.
* AsHimself: [[Music/ThePolice Sting]]
* AssholeVictim: Bart.
* HollywoodToneDeaf: 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."
* LaserGuidedKarma: Bart falls in the same well he fools the town into thinking he fell into earlier.
* OhCrap: 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).
* PapaWolf: Homer is the first one to grab a shovel and try to dig Bart out.
* TheReveal: This is the first episode to show Willie's muscular build under his shirt.
* ShoutOut:
** Bart scares Homer with his radio broadcast into thinking that Martians have landed, in reference to the MoralPanic that errupted after the famous 1938 radio broadcast of ''Literature/WarOfTheWorlds'' by Creator/OrsonWelles.
** ''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 UsefulNotes/JohnFKennedy 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 ''Film/{{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.
* SuckECheeses: 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).
* VeryLooselyBasedOnATrueStory: 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.
* WhatCouldHaveBeen: The scene of Homer getting tricked by Bart into thinking aliens have invaded was originally supposed to have Homer mix a bowl of poisoned Kool-Aid for his family to drink. The idea was scrapped after the writers found the joke too dark and the censors complained that it would lead to copycat incidents, so instead, they have Homer grab a shotgun and run for the door.
** Bruce Springsteen was originally going to guest star in this episode in the role that went to Sting.
** During the part where Homer tries to show Bart that the microphone he got him for his birthday is worth playing with, Homer was originally supposed to sing ''The Wreck of the Edmund Fitzgerald'' instead of ''Convoy'', but Gordon Lightfoot (the singer of ''The Wreck of the Edmund Fitzgerald'') would only allow the song to be used if the producers got permission from the families of the twenty-nine crewmen who died on the ship (since the song is based on a real event). The producers found it to be too much work, so they scrapped it.
* WholePlotReference: The concept of this episode evokes ''Film/AceInTheHole'', a Creator/BillyWilder-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.
* WingedSoulFliesOffAtDeath: Happens to Scratchy in the cartoon.
* WorstNewsJudgmentEver: 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!"