About 4 1/2 years later, in the fictional world of Springfield, Bart pulls a prank inspired by the Jessica McClure story, by fooling the town into believing a little boy had fallen down an uncapped abandoned well.
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: by throwing his transistor radio down a narrow well shaft, and 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 him 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 other gifts he was bored with) to put his name on the radio. Bart realises that if the radio with his name on it is retrieved from the well, he'll be in big trouble, 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. 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. The town then takes the utmost action to ensure that no incident like this ever happens again by putting up a sign in front of the well that reads "Caution: Well."
This episode provides examples of:
- Actor Allusion: When Marge tries to convince Sting to take a break from digging Bart out, Homer stops her and claims he's a good digger. Sting actually worked as a ditch digger before his music career took off.
- An Aesop: Practical jokes may seem cute and funny, but they can have serious consequences, especially if you pretend to be God in order to get your neighbors to give you what you want and later trick the entire town into panicking over a child's safety.
- As Himself: Sting.
- Asshole Victim: Bart deserved to suffer some karmic retribution because of the prank, true, but this trope is somewhat deconstructed at the same time because a whole town full of people (initially) deciding to leave a kid to die as payback for making them look like fools is an act a whole lot more cruel in comparison.
- Birthday Party Goes Wrong: From Bart's perspective, his party at Wall E. Weasel's is incredibly lame, with unwanted presents and guests.
- 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.
- Borrowed Catchphrase: Bart says "D'oh!" when he realizes he's left a "Property of Bart Simpson" label on his radio.
- Brutal Honesty: When Eddie and Lou tell Homer and Marge the situation with Bart.Homer: [somberly] You must think we're the worst parents in the world
Eddie: Well that's the general opinion down at the station, yeah.
- Call-Back: Homer blurts out that Bart was an accident on live television, which was confirmed one episode prior.
- 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.
- Chekhov's Gun: The label maker Patty and Selma gave Bart would soon become his undoing.
- 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?
- Crying Wolf: People who play unfunny practical jokes, lie, etc. all the time — as Bart has done — tend to be ignored when a real crisis arises.
- Didn't Think This Through: No one in Springfield considered just digging "Timmy" out of the well until Homer tried, looking into other more convoluted (and less successful) methods.
- Disproportionate Retribution: A little boy makes you all look bad with a prank, is genuinely sorry for having made said prank, is suffering karmic retribution from said prank, and is tearfully begging for help because he doesn't wishes to die in the well? Well — and perhaps because Springfield residents are well aware of some of the pranks Bart has pulled in the past — he can rot down there!
- Distracted by the Sexy: Homer gets so distracted by the sexy dancers on television that when Lisa asks for money to buy Bart a birthday present, he gives her over $110.
- Early Installment Weirdness: We see an unhinged fisherman character who suggests fishing Timmy out of the well. While you might expect this role be filled by the Sea Captain, this episode was made before he was an actual character.
- Epic Fail: The song "We're Sending Our Love Down The Well" gets a literally meteoric fall down the hit charts thanks to the discovery that Timmy O'Toole is a fake, all the way to rock bottom. Casey Kasem (making a cameo on his role as the narrator of American Top 40) mentions that this is something he's never seen before.
- 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, Im—
Wall E. Weasel: [interrupting] That's great! Would you like us to sing you a special song?
Bart: Hell, no.
Wall E. Weasel: You've got it!
- Fast Tunnelling: When Bart falls down a well, the townspeople dig a parallel hole to get him out.
- Fictional Video Game: Among the arcade games at Wall E. Weasel's are Larry the Looter, Touch of Death and Time Waster.
- Get Out!: When Bart tries to cash in on his birthday coupons, he goes to the ice cream shop and after a rude employee hands him a ridiculously small sundae: "Eat it and get out!"
- Gone Horribly Right: Homer wanted to get Bart a birthday present that he'd greatly enjoy; looks like Bart enjoyed his present a little too much!
- Goodbye, Cruel World!: The Itchy and Scratchy cartoon has Scratchy find a suicide note of his roommate, Itchy, with this exact phrase written on it. Of course, it winds up being a trap to lure Scratchy to yet another violent death.
- Happy Birthday to You!: Wall E. Weasel's version:Wall E. Weasel: You're the birthday, you're the birthday, you're the birthday boy or girl....
- Hilarity Ensues: In the real world, the police and fire crews ignoring Bart's real crisis after he actually does become trapped in the well would have left them open to huge lawsuits and criminal charges. Nobody seems to suffer any legal consequences here.
- Hoist by His Own Petard: Bart gets a double whammy when he realises that the radio he's using to pull his prank has his name printed on it. His attempt to avert the trope by retrieving the radio ends with him falling down the well and getting trapped for real.
- 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.
- Homer's (usual) off-key rendition of C.W. McCall's "Convoy".
- In "We're Sending Our Love Down the Well", Krusty contributes to the chorus as a background vocalist. However, due to his scratchy voice, he's not so much singing as he is screaming.
- I Am Big Boned: When asked why he can't go down the well, Chief Wiggum says, "Well, I'm too f-... important."
- I Call It "Vera": Willie has a shovel he named Agnes.
- Invented Individual: Timmy O'Toole, the Heartwarming Orphan trapped in the well. The drama Bart endures on the third act comes from the murderous hatred the rest of Springfield feels from discovering they were fooled.
- Iron Woobie: Discussed In-Universe. Lisa doesn't believe that merely enduring suffering makes someone a hero, and Homer does.
- Laser-Guided Karma: Bart falls down the same well he fooled the town into thinking Timmy O'Toole fell into, complete with a large rock falling on his leg so can't be pulled out, just like in the story he concocted.
- Lawful Stupid: Homer despairs at the fact that there is only one can of Duff Beer remaining in the house and Bart placed a "Property of Bart Simpson" label on it, saying that this makes it Bart's even if Bart is a little kid and it's obviously a prank.
- Mass "Oh, Crap!": When a large group are digging to rescue Bart, Apu notices their canary has died, leading everyone to flee the hole screaming in terror. Up top, Dr Hibbert confirms the canary died of natural causes, leading them all to run back into the hole... screaming in terror.
- A Mistake Is Born: After Bart's ruse is discovered, Homer and Marge are interviewed on the news by Kent Brockman:Homer: We didn't want the boy; he was an accident.
Homer: Uh, can you edit that last part out, Kent?
Kent: Mr. Simpson, we're live coast-to-coast.
- Off-Model: During Bart's birthday party, Sherri is depicted with dark skin and a beige dress (though her hair color is correct, oddly enough).
- 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).
- Operators Are Standing By: The commercial Homer watches for the Superstar Celebrity Microphone, urging him to buy now since (*gasp*) "supplies are limited!" ("LIMITED???!!! AHHHH!!!") note
- Papa Wolf: Homer is the first one to grab a shovel and try to dig Bart out.
- Reasonable Authority Figure: Surprisingly, Chief Wiggum. He is one of the few citizens of Springfield not staring daggers at Bart for his prank. Instead, he is left nervously explaining to Marge that, while he knows of machinery that could rescue her son, the police lacks the needed funds and no one else in town is willing to fund it.Wiggum: Your boy picked a bad time to go fall down a well. If he'd done it at the start of the fiscal year, no problemo.
- Recycled Animation:
- 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 panic that erupted 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.
- And the biggest one of all: Timmy being stuck down a well/mine shaft/etc. is one of the cliches associated with the TV series Lassie (though ironically a well was one thing Timmy didn't fall down in the series).
- The musical sting heard briefly when Bart tries to retrieve his radio from the well is similar to "Axel F", the theme of Beverly Hills Cop (and which was also heard in season three's "Separate Vocations" and season four's "Marge vs. The Monorail").
- The Funky See, Funky Do musical duo, whose song "I Do Believe We're Naked" knocked "We're Sending Our Love Down the Well" from the number one spot, resemble a composite of members from Milli Vanilli and Kid n' Play.
- Stating the Simple Solution: When Homer finally decides he can't put up with the town's coldness and lack of effort in rescuing Bart, he just grabs a shovel and starts digging on his own.Willie: (seeing Homer digging) Ach, now why didn't I think of that?!
(goes back into his shed briefly)
Willie: (to his shovel) Agnes...we've got work to do! (rips off his shirt and top part of his overalls)
- 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.
- What Were You Thinking?: When Lisa discovers Bart's prank, she warns him that his obsession with his label maker could lead to anyone who discovers the radio's "Property of Bart Simpson" label turning on him.
- 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 Itchy & Scratchy cartoon. Or it would, if not for Itchy waiting for him at the top of the well with a shotgun.
- 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!"
- Adding to that, Brockman claims that the station will stay with this story all night if they have to. That was the exact case with the Kennedy assassination as the networks provided roughly 77 hours of coverage from around 1:30 PM Eastern time on Friday, November 22, 1963 to the following Monday evening.
- Would Hurt a Child: The town was perfectly willing and able (up until Homer took things into his own hands) to leave Bart in the well, sentencing him to a slow and painful death and an equally ignoble eternal rest, as payback for his prank.