Lisa is named "Student of the Millennium", so Marge stresses that Homer has to attend her ceremony due to past absences at most of the kids' events. Homer then wakes up early and takes Maggie to the school auditorium. Meanwhile, Marge gets impatient waiting in line at the bank, so she strikes up a conversation with an apparently charming man named Dwight (Steve Buscemi). While talking, Dwight tells Marge to hold on. He then pulls out a gun and tells everyone to get down on the floor, just as another man walks into the bank and pulls out a rifle. Gil Gunderson then arrives, prepared for his new job as a security guard, however he is repeatedly shot by Dwight's accomplice, who then flees in a panic.
Homer is smugly waiting for Marge at the ceremony. Marge privately calls Homer, informing him she is a hostage at a bank robbery. Dwight notices Marge on the phone and cuts off the call. He then makes a compromise; he will promise to turn himself in as long as Marge promises to visit him in prison, to which she reluctantly agrees. A nervous Marge returns home. Homer attempts to convince Marge not to visit Dwight in the prison, but Marge wishes to honor her promise and visit him. However, while going to the prison, she makes continuous stops to avoid going to the prison, and misses visiting hours. At the prison, Dwight expectantly waits for Marge. While watching Snake Jailbird chatting with his girlfriend, Gloria, Dwight becomes depressed and then angry, and Marge's guilt begins to get to her while watching a depressing movie about a prisoner who was to be electrocuted. At the same moment, Dwight is breaking out of Springfield Penitentiary (in a parody way of The Shawshank Redemption). He finds Marge's address in a newspaper, and sets out to find her.
At home, while watching television, Kent Brockman makes a news report on Dwight's escape from prison. Dwight begins stalking Marge in various places, and successfully catches up to Marge and keeps her as his hostage. Dwight takes her to the same amusement park where he was abandoned by his mother, with the intention to have Marge help him repay the time he had lost, and promises to let her go afterwards, to which Marge, out of sympathy, agrees. He and Marge then ride the Viking ship ride together. Chief Wiggum arrives attempting to save Marge, but he is caught in the ride. Dwight jams the ride's gears by throwing in his own body to save Wiggum (referencing The Brave Little Toaster). He survives, fortunately, and returns to prison after being hospitalized and making a full recovery. Back at the prison, Marge finally visits Dwight, who gives her a flattened dandelion encased in a bar of soap he had carved for her with a message on the back intending to recruit her in helping him attempt another prison break. Marge does not agree to the escape attempt and Dwight, although saddened, says she can keep the token.