The town come out for the funeral of one Chip Davis, a beloved man who everyone seemed to know. When Rev. Lovejoy brings up the subject of regrets in one's life. A few of Springfielden start mulling theirs over. Marge, after being chastised by Patty and Selma, thinks Bart is the way he is because of listening to KISS albums during her pregnancy. Homer regrets to selling his Apple stock for a bowling ball. Kent Brockman regrets not joining a fellow co-worker to moving to cable news, instead staying in Springfield to run the local broadcast. And Mr. Burns regrets not marrying a woman he loved due to his greedy nature. The episode follows separate stores which intersect at the end.
- Bart tries a dangerous stunt on lifting himself into the sky on a laundry basket via balloons. Only to find he can't get down.
- Kent decides to go into cable news but ultimately can't bring himself to report with them, finding he actually likes controlling the news on his station rather than having to act on what a network tells him to.
- Mr. Burns tracks down his lost love and it seems they'll reconcile. But as he prepares to have sex with her, he finds that she died waiting for him. Smithers suggest honoring her by helping the less fortunate like she wanted.
Eventually Kent spots Bart while coming back into town and does a news report. The whole town comes out to try to aid Bart in getting down. Marge once more frets over her decision during her pregnancy but Chief Wiggum assures her that wasn't the case as his wife listened to Mozart and Beethoven while pregnant with Ralph and he turned out...special. Frink comes up with a way to launch a cannonball into the basket to lower it down, but the town melted all of them down to make a statue. In comes Homer with the bowling ball which is used to lower Bart enough to rescue him. As the town celebrates, the episode closes on Kent telling his former co-worker he has no regrets.
The episode has the following tropes
- Chekhov's Gun: Homer's bowling ball.
- Credits Gag: The credits feature Chip Davis edited into the following moments in the past:note
- With the ambulance in "Bart the Daredevil".
- Performing with the Be-Sharps in "Homer's Barbershop Quartet".
- Performing with The Who in "A Tale of Two Springfields".
- Working with Cooder and Spud in "Bart Carny".
- Hiding in the bushes from Adam and Eve in "Simpsons Bible Stories".
- Attacking the dolphins in "Treehouse of Horror XI".
- Standing by Bart and Joe Namath, wearing a whistle and holding a clipboard in "Bart Star".
- As a half-gorilla in "Treehouse of Horror XIII".
- Sitting next to Ned during The Simpsons Movie's "Bountiful Penis" scene.
- Appearing in the Plow King commercial in "Mr. Plow".
- Performing with the Party Posse in "New Kids On the Blecch".
- Accompanying Homer and the astronauts in "Deep Space Homer".
- Helping Homer drag Bart out of the gay steel mill in "Homer's Phobia".
- With Lisa at the discovery of the angel skeleton in "Lisa the Skeptic".
- Part of the failed human pyramid in "Sweets and Sour Marge".
- Having his head stuck on the bridge alongside Homer in "Lost Our Lisa".
- As a kid in "The Blunder Years".
- Operating a cannon in "Homerpalooza".
- Delivering Maggie in "And Maggie Makes Three".
- Standing next to Lucius Sweet during the main event in "The Homer They Fall".
- Posing with Pie Man and Cupcake Kid in "Simple Simpson".
- Laughing with Kang and Kodos in "Treehouse of Horror II".
- Hope Spot: Burns finds his lost love, but she dies before they can have sex. If that wasn't bad enough, when he tries CPR, she turns to dust in an instant.
- It's All My Fault: Marge becomes downright determined to attribute Bart's misbehavior to her habit of listening to KISS when she was pregnant.Marge: Must find way...to blame myself.
- It Will Never Catch On: Homer sold his Apple stocks in 2001 because he thought technology wouldn't catch on.
- One Drink Will Kill the Baby: A variant. Marge is convinced that listening to Music/KISS while pregnant resuted in Bart's current behavior. Chief Wiggum assures her that's not the case, as Ralph was exposed to intelilectuallism but turned out speical.
- Product Placement: Averted, there's many jokes about Apple, but a caption comes up near the end claiming they'll stop since they're not even getting paid for it.
- Remember the New Guy?: Parodied. Chip Davis is treated as this, there's even an montage at the end where he supposedly was around in many episodes.
- Running Gag: Homer being constantly reminded of the fact it was a bad idea to sell his Apple stock in 2001.
