In 1987, an 18-month-old girl named Jessica [=McClure=] fell down a narrow well casing and remained trapped inside for 58 hours. Her story, and the rescue effort mobilized to rescue her, got national headlines and made Jessica the darling of the media.
About 4 1/2 years later, in the fictional world of Springfield, Bart pulls a prank by finding his inspiration in the Jessica [=McClure=] story by fooling the town into believing a little boy had fallen down an uncapped abandoned well. Only this time, it potentially doesn't have a happy ending ... and it's all because Bart decided to be '''Radio Bart'''.
The whole story begins at Wall E. Weasel's, a place known for mediocre pizza, ill-maintained animatronics and bad video games. The birthday party there is even worse: Bart is annoyed at Wall E.'s attempt to sing him "Happy Birthday," the guests aren't who Bart wants at his party (Martin is one of the invitees) and he is especially disappointed in the gifts. One of those gifts (which Homer bought earlier after watching a TV commercial) is a microphone called the Superstar Celebrity Microphone, which can tap into localized AM radio systems. Homer persuades Bart about the Superstar Celebrity Microphone's potential ... and eventually, Bart realizes it can indeed be ''lots'' of fun, especially with his knack for creating practical jokes. He tricks Rod and Todd Flanders into believing God is talking to them, while he gets his dad to believe that martians are invading the Earth.
Then, one day while bored, Bart gets an idea: He thinks that, by throwing his transistor radio down narrow well shaft and – while keeping it tuned to the correct frequency – he can get people to believe that a little boy had fallen down the well. Which he does. When he begins a "crying for help" act and gets a response, he tells his potential rescuers that he is an orphan named Timmy O'Toole has fallen down the well. A rescue operation is mobilized – but it quickly becomes a circus, with people setting up a carnival, and they realize they can't get poor Timmy out. Meanwhile, Krusty the Clown gets musician Sting to join Springfield celebrities in recording a charity single, "We're Sending Our Love Down the Well." The charity single soars to No. 1 on the Billboard Hot 100.
Late one night, Lisa happens to be walking by Bart's room when she overhears him doing his "Timmy" act and then getting into a fight with Santa's Little Helper over the microphone. Lisa realizes that Bart is playing a cruel practical joke on the town and warns that he will be exposed. Bart – after hastily explaining [=SLH=]'s growling – scoffs, until Lisa reminds him that he used a label maker (one of the gifts he was bored with) to put his name on the radio. Bart knows that someone will probably find the radio and that he would be in big trouble if it were found beforehand, so he sets out to get it. As he's descending the well, Bart slips and loses the grip on his rope. The rope falls to the bottom ... and now, Bart is trapped for real.
Bart yells for help, and when he explains his predicament to the initial responders, Bart is forced to admit that Timmy O'Toole doesn't exist and that he was playing what he thought was a funny joke. Some joke – the townspeople are outraged and decide to teach him a lesson by leaving him trapped there. At the same time, "We're Sending Our Love Down The Well" dramatically falls from No. 1 to No. 97, while Bart becomes the butt of jokes in town. The actual crisis is ignored by both the media and the police, prompting a frustrated Homer to finally take action and mobilize a crew of his own to rescue his son. Although nobody helps at first, Groundskeeper Willie decides that saving a life is more important than festering on anger and decides to help Homer; other residents – including Sting – realize they must do the right thing and eventually are able to excavate Bart out of the well.
Bart is truly regretful and has learned [[AnAesop a lesson about how practical jokes can have serious consequences]]. But has the town? Instead of capping the well or having it removed, Willie decides a simple warning sign next to the well will suffice in preventing future accidents.
!!This episode provides examples of:
* 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" 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.
** ''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 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.
** "We are the World" -- "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.
* 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!"