Marge gets kidnapped by a deranged prisoner after breaking her promise to visit him.
Tropes:
- Alliterative Name: Sergeant Serious, Dwight Diddlehopper.
- Artistic License – Physics: While spying on Marge after breaking out of prison, Dwight is able to watch her from behind a flying kite that can somehow take his weight.
- Asshole Victim: Agnes Skinner getting shot at (though it misses her), when she makes a homophobic crack.
- Bait-and-Switch: After Dwight escapes, Marge is constantly worried that he's waiting for an opportunity to catch her. When she's inside a dressing room and notices a pair of eyes looking through a hole in the door, she opens the door and finds Moe.
- Body Horror: Dwight saves Chief Wiggum from falling into the middle of the swaying ships by dropping himself into the gears to stop the attraction.
- Butt-Monkey:
- Gil turns up for his new job at the bank as a security guard, only to be repeatedly shot by Dwight's accomplice.
- Dwight himself. He was abandoned by his mother when he was a boy, he had three dye packs blow up in his face during the robbery, Marge was too nervous to visit him in prison, he escaped prison through a sewer pipe instead of a one dispensing spring water next to him, and he throws himself into the gears of the Viking ship ride to save Chief Wiggum.
- Celebrity Paradox: Steve Buscemi (Dwight) had previously played himself in Season 14's "Brake My Wife, Please".
- Danger Takes A Back Seat: Dwight waits for Marge on the back seat of a car, but it turns out he boarded the wrong car, before getting into Marge's.
- Disproportionate Retribution: Agnes Skinner references this trope when she says during the bank robbery she doesn't deserve to die, because she only went into the bank to check the date.
- Endangering News Broadcast: Dwight, after escaping prison, has a newspaper that not only has the Simpsons' home address, but also the security code for their alarm!
- Epic Fail: Dwight escapes from prison by going through the prison waste pipe. Right next to it, he finds out there was a pure mountain spring water pipe he could've gone through.Dwight: Dammit!
- Freudian Slip: Marge's line to Dwight at the amusement park: "Well, this mom is not gonna say bug-eye. I mean, good bye!"
- Heroic Sacrifice: Subverted. Dwight is willing to attempt one when he throws himself into the gears of the Viking ship ride at the amusement park to save Chief Wiggum. However, he somehow survives this and makes a full recovery, after having to be hospitalized.
- Karma Houdini: Dwight's accomplice gets away with shooting down Gil in a panic due to Wiggum's incompetence at handing the situation unfolding at the bank.
- Major Injury Underreaction: Jasper is shot in the arm by Dwight during the robbery and all he does is cover the bleeding wound and say, "You said diabetic, right?", after Dwight inquired whether anyone else was a dye pack during the robbery.
- Oh, Crap!:
- Marge's reaction when Dwight is revealed as a robber at the bank, and Homer's reaction when Marge is able to tell him she's a hostage. When Marge gets out after Dwight gives himself up, he and Marge share a very relieved hug.
- Marge again when Dwight breaks out of prison and knows that she is the "unfinished piece of business" Kent Brockman is referring to.
- Parental Neglect: Dwight's mother evidently took him to an amusement park as a child and abandoned him there. Dwight kidnaps Marge and takes her there so he can relive the time he lost.
- Plagiarism in Fiction: Krusty wonders how he can be considered a worse clown than Sergeant Serious since he stole all of Sergeant Serious' jokes.
- Police Are Useless: The police only get Dwight in the robbery because he gives himself up, and Chief Wiggum's attempt to save Marge from Dwight at the end ends up causing him to have to be rescued. The police also said that Dwight's letter that he'll return to prison after unfinished piece of business sounded fair.
- Police Code for Everything: Lou says there's a 64-G in progress. Wiggum stares blankly.Lou: Come on, chief, you know this.
Wiggum: Oh, a shooty-stealy. - Rule of Three: Hans Moleman hands over a money bag to Dwight during the robbery, and a blue dye pack explodes in his face. As he goes to use a tissue to wipe his face, the tissue box turns out to contain a dye pack too, which also blows up at him. And then when he sees a clerk staring at him, he pistol-whips him, and that clerk also turns out to be a dye pack, completely covering Dwight in blue dye. Then he turns to the hostages and irritably asks if anyone else is a dye pack.
- Screw This, I'm Outta Here: Dwight's accomplice in the robbery flees in a panic after shooting Gil.
- Shout-Out: Obviously, the title parodies I Know Why the Caged Bird Sings by Maya Angelou.
- Stupid Crooks: Implied. Dwight undergoes the bank robbery without gloves, a mask, or covering himself up, meaning that his DNA would be present at the crime scene and CCTV would capture him, though it probably wouldn't have made much difference due to how Police Are Useless. His accomplice doesn't fare better as he starts shooting everyone the moment things go differently which alert the police.
- Super Serum: The Itchy & Scratchy short in the episode parodies the controversy of baseball players taking steroids, with Scratchy doing so on advice from Itchy. He becomes a baseball superstar... only to be the focus of scandal years later when Congress grills him about it. It only gets worse for him when the muscles grow out of control.
- Too Dumb to Live: Agnes makes a homophobic crack at two armed bank robbers.
