Documentary filmmaker Declan Desmond returns to Springfield to complete the latest follow-up to a long-running project: chronicling the lives of the same group of schoolchildren he first interviewed 32 years earlier. In flashback we see a young Homer and Wiggum on a field, playing cops and robbers. Wiggum is already acting like a policeman. Young Homer declares that someday he’ll be rich, and Wiggum predicts that he’ll be the chief of police. Time flashes forward, and we see Desmond interviewing a 16-year-old Wiggum in high school. By this time Wiggum had become a hall monitor. Eight years later Wiggum was accepted into the police academy. At age 32 Wiggum was on the fast track to becoming Chief of Police. Eventually, just as he’d predicted, Wiggum achieved his goal. We then flash back to Young Homer on the playground. Desmond tells Homer that his plans require the acquisition of a great deal of money. Unsurprisingly, by the age of 24 Homer’s plans had not come to fruition. The one ray of hope in Homer’s life was his marriage to Marge. In the present day Desmond tells Homer that his life is nothing to be ashamed of. Suddenly Homer reveals that he’s now a millionaire, and is living in a lavish mansion.

Desmond wonders how Homer managed to pull off such an astounding feat in eight short years. Homer shows him the secret to his riches: the condiment pen. The device dispenses ketchup, mustard, mayonnaise, and relish. Desmond congratulates Homer on his accomplishment. The scene flashes back to Desmond’s interview with a young Professor Frink. At the time Frink predicted he’d become a rocket scientist. At age 32 Frink got a job with the space program. In the current day Frink works hard on completing his latest device: a time machine. He uses the contraption to go back in time, and he tells his eight-year-old self to abandon his dreams of becoming a rocket scientist so he can set off on a career that will win him the heart of a beautiful woman. The grown-up Frink gets hit by a car. Desmond turns his cameras to a nearby, bright-eyed girl, Eleanor. She eventually becomes an attorney, but when she burns out at the age of 32, she takes a liking to cats and ends up as the Cat Lady. Desmond then focuses on Marge, who at age 16 was the star photographer for her school newspaper. At age 24 Marge’s dreams stalled, and she ended up working at a portrait studio in a department store. She had concluded that she needed a full-time job so Homer could pursue his dreams of getting rich with one of his crazy ideas. In the present day Desmond begins to notice something odd about the mansion where Homer and his family live. It turns out that the mansion isn’t Homer’s after all. It’s the summer home of Mr. Burns, who’s furious at the deception.

Burns discovers a bound-and-gagged Smithers inside a grandfather clock. Burns tells Smithers to “release the hounds,” but Smithers reminds him that the dogs are still at the winter house. Burns gives Smithers his car keys, and instructs him to retrieve the animals. During Smithers’ absence Mr. Burns offers Homer and the others some tea. When Smithers returns, Burns orders him to set loose the dogs. The animals chase the Simpsons and Desmond out of the mansion. Afterward Desmond wants to meet with Homer so he can explain his ruse. Homer, however, wants nothing to do with him. Eventually Desmond shows up at the front door, and asks Homer for answers. Homer says he pretended the Burns mansion was his so he could look good in the documentary. Homer concludes that all he did was make everyone else look good. A furious Marge accuses Desmond of making Homer look bad. She tells him to stay away from the house. Desmond makes his way to Moe’s bar, where he admits he feels sorry for Homer. When Moe mentions that Homer is married to “one hell of a woman,” it gives Desmond an idea. Desmond invites Homer to his editing bay, and shows him footage of people throughout Springfield saying how much they’d like to be Homer. Homer realizes he’s got a great life after all.