'''Original air date''': January 6, 2002
During an acid rain storm, the Simpsons decide to play a game of Monopoly -- only to end up arrested on domestic disturbance charges. While in jail, a social worker helps the family get back on track to being functional, which is put to the test when Homer's and Flanders' Vegas wives from "Viva Ned Flanders" return.
It is the first episode since the end of season 4 to feature Al Jean as showrunner; he took over the position from Mike Scully, the showrunner for seasons 9-12. Jean has been showrunner ever since, making him the longest on the ''Simpsons'' staff to hold that position.
* BaitAndSwitchComment: When Gabriel claims to have earned his wings, Homer takes it for further evidence that Gabriel is an angel but Gabriel means a [=CD=] titled "The Best of Wings".
* DoesThisRemindYouOfAnything: A lot of ''Simpsons'' fans have claimed this episode is an allegory of how Mike Scully's reign as ''Simpsons'' showrunner has ruined the show (represented by the Republican Club's decision to pollute the environment, causing acid rain to destroy the town and The Simpsons' fighting during a game of Monopoly) and Al Jean (represented as the allegedly angelic social worker) is brought in to fix the show's past mistakes (represented by the social worker observing the family's behavior and calling them out on their unhealthy actions and the Vegas wives from season 10's "Viva Ned Flanders" returning)[[note]]though most Simpsons fans will attest that Al Jean's turn as showrunner is not any better than Mike Scully's, or even the Bill Oakley/Josh Weinstein era[[/note]]
* HopeSpot: The Simpsons seemingly have resolved their issues...Then Homer's Vegas wife shows up. Later, Homer says he'll get his second marriage annulled. The next scene shows Judge Harm ruling both marriages valid based on the fact that bigamy is legal in Nevada.
* LeaningOnTheFourthWall: As the Simpsons are going home, having seemingly settled their conflicts, Lisa wonders "Will this be the end of our series... of adventures?"
* MagicalNegro: Homer is convinced Gabriel is one, much to his annoyance.
* TheReasonYouSuckSpeech: Gabriel gives a very succinct, powerful one after telling Homer he has a lot of problems. It's also the only time he raises his voice:
-->'''Homer:''' Which is society's fault because-
-->'''Gabriel:''' It's your fault!
* ScrewThisImOuttaHere: The social worker when he sees Homer's Vegas wife.