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.
- The Bad Guy Wins: The story of the republican party repealing all the towns environmental laws becomes this due to the lack of resolution.
- Bait-and-Switch Comment:
- When Gabriel claims to have earned his wings, Homer thinks Gabriel admitted he actually is an angel, but Gabriel means a CD titled "The Best of Wings".
- When Grampa asks if Amber wants to have sex with him again, he sounds like he wants but he turns out to be glad when she says "no".
- Does This Remind You of Anything?: 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
- For the Evulz: The Republican Party repeals environmental laws just because they love doing evil things.
- Hope Spot: 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.
- Karma Houdini: Nobody in the Republican Party faces any sort of comeuppance for repealing environmental laws and Nelson isn't punished for what he did to that spotted owl.
- Innocent Innuendo: Subverted. Both Marge and the viewers are aware that Amber is making Homer a sandwich.
- Leaning on the Fourth Wall: As the Simpsons are going home, having seemingly settled their conflicts, Lisa wonders "Will this be the end of our series... of adventures?"
- Magical Negro: Homer is convinced Gabriel is one, much to his annoyance.
- "The Reason You Suck" Speech: 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!
- Series Continuity Error: In "Alone Again, Natura-Diddily," Homer accidentally brought up his and Ned's Vegas marriage in front of Marge in order to prove to Ned that he's a bigger ladies' man than he thinks. Here, Marge acts like she's just finding out about it for the first time.
- Screw This, I'm Outta Here!: The social worker when he sees Homer's Vegas wife.
- Homer's Vegas wife's reaction to her marriage to Grampa Abe, nullifying Homer's own Vegas marriage. Ned's Vegas wife does the same after she has had enough of the Flanders' wholesome nature.
- Skewed Priorities:
- Homer must stay inside his house to be safe from the acid rain but goes outside to rescue his TV antenna. Unable to withstand the rain long enough to reach it, Homer runs back inside and, once seeing the TV not working, tries to reach the antenna again. It goes on until Marge invites the family to play Monopoly.
- Later, Homer won't leave his beer behind to save his life until he realizes it's not a brand he likes.