Marge volunteers to look after the kids in a field trip to a ship, leading to her becoming involved in a jewel heist with Sarah Wiggum.
Tropes:
- Badass and Child Duo: Fat Tony takes a shine to Ralph.
- Bad Boss: Lindsay Naegle betrays Sarah and her accomplices Bette and Erin.
- Big Beautiful Woman: After being seen as nothing more than a female version of Chief Wiggum design-wise, once Sarah gets access to the limelight and more flattering clothes it quickly becomes obvious why she was "the honeypot" of the crew.
- Canon Character All Along: During her time as a jewel thief, Sarah took orders from a woman known as "Red." Her former accomplices Erin and Bette reveal that after double-crossing the gang, she took on a new identity (and a new hair color) and is now known as Lindsey Naegle.
- Dating Catwoman: Sarah tells Clancy about her criminal past.
- A Day in the Limelight: For Sarah Wiggum.
- Even Evil Has Standards: Fat Tony wouldn't harm Sarah or Ralph.
- Every Man Has His Price: Smithers manages to convince Carl from ignoring the "unkillable irradiated airborne entities" within a room by giving him two VIP tickets for Bob Seger's concert Carl requested to buy his silence.
- Funny Background Event: When Bob Seger is chewing out Homer and Wiggum for breaking a promise to their wives, a bandmate is standing behind him holding up his hand and retracting a finger every time Seger works the title of one of his songs into his lecture.
- Genius Ditz: Sarah describes her son Ralph as a kind of smart kid they're "still trying to figure out what kind of smart" he is.
- The Heist: Sarah and her former accomplices plan to steal from their former boss Lindsey Naegle for double crossing them years ago. Marge gets involved as a fan of the gala Lindsay is attending, and thus knows how to sneak into the museum.
- Hidden Depths: Sarah Wiggum used to be in a gang of jewel thieves; her boss was Lindsay Naegle, who set them up for a fall.
- Honey Trap: Sarah was the "honeypot" of the team, and she met Clancy when she was seducing him for a job. Later, she tries to seduce a museum guard as part of the heist on the gala.
- Laser-Guided Karma: Bette and Erin get back at Lindsay Naegle for her betrayal by getting her arrested for theft after she falls down a flight of stairs and gets banged up on the way down. In addition, her boyfriend, Rainier Wolfcastle, dumps her for a new girl because "she tumbled down for too long."
- Life Saving Misfortune: Sarah genuinely falling for Clancy prevented her from being set up with her old friends and going to jail.
- Love at First Sight: Sarah admits that sleeping with Clancy right after they met was not exactly planned. Clancy even asks her to marry him while he likely knew Sarah for one hour.
- New Job as the Plot Demands: Marge notes that Lindsay Naegle "works in various female executive positions around town."
- Not Me This Time: Fat Tony denies kidnapping Sarah and Marge.
- Obfuscating Stupidity: Sarah is seen as slow and boring because she likes being quiet. She's wilder than she appears.
- The Quiet One: Sarah Wiggum's acknowledged as such, and she explains the reason she's so quiet is because she's a naturally shy person who's only able to loosen up when she's not in a big crowd.
- Retcon: In "A Star Is Born Again", Clancy and Sarah met when he arrested her. But in this episode they met when he was a security guard.
- Shame If Something Happened: Fat Tony invokes this trope as the reason why he didn't kidnap Sarah, because otherwise how would he make such a threat?
- Something We Forgot: At the end of the episode, Clancy asks where Ralph is. Cut to Ralph getting ice cream with Fat Tony.
- Wham Line: Sarah calling Bette and Erin her partners in crime.
- Whole-Plot Reference: To Ocean's 8.
