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 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:
- An Aesop: Practical jokes may seem cute and funny, but they can have serious consequences.
- As Himself: Sting
- Asshole Victim: Bart.
- Black Comedy: Marge knits Bart a sweater to wear in the well, which is too big for him, to which Homer replies "You'll grow into it," much to Marge's chagrin.
- Charity Motivation Song: "We're Sending Our Love Down the Well." The bulk of the profits go to the benefit of its many expensive celebrity singers; the rest gets tossed down the well.
- 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. As Willie lampshades:Willie: Now why didn't I think of that?
- 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.
- Refuse to Rescue the Disliked: Practically everyone in town is so upset at Bart's prank they refuse to rescue him.
- 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!"