The Simpsons are going on spring break in Florida to hopefully cure Homer of his insomnia-induced insanity and fear of dying caused by answering a magazine quiz...but find themselves on the run from the law for running down the town's mascot, Captain Jack.
* AFoolForAClient: Homer defends himself and his family in court -- and ends up getting everyone sentenced to hard labor in a chain gang, all because he opened with, "Drunken hicks of the jury..."
* ArtisticLicenseBiology: Captain Jack has interlocking teeth like a crocodile, instead of an overbite like a real-life alligator.
* DeusExMachina: The alligator being alive all along, allowing the Simpsons to go.
* DiabolusExMachina: Just as the Simpson Family evades being re-captured by the Sheriff with a train separating them, the car is suddenly struck by another train [[NegativeContinuity on a magically-appearing railway]].
* DisneyDeath: The alligator Homer accidentally ran over turns up alive and completely unharmed at the end.
* FauxAffablyEvil: The sheriff is pretty "aw shucks" in attitude, but he has no problem arresting an entire family and sentencing them to lifetime imprisonment and using them as slave labor with the same lassitude.
* GoingNative: Once the Simpsons accept a job at a swamp diner while hiding from the police, they quickly adapt to country life, complete with bumpkin dialect.
* {{Jerkass}}: The guy that whips Homer and Marge. Everything is whipping worthy to him. Including listening to a police officer trying to talk to them.
* JerkWithAHeartOfJerk: The sheriff is a cruel man willing to allow innocent children (including an ''infant'') to rot in prison for life because their father's crimes. His initial ReasonableAuthorityFigure is actually a lie; he's being paid by beer companies to turn the other cheek during spring break; once that's over, he'll be his true, evil self to criminals and their families.
* MadnessMantra: "Can't sleep, gonna die. Can't sleep, gonna die." (similar to the [[MemeticMutation memetic]] "Can't sleep. Clown'll eat me." in "Lisa's First Word").
* MortonsFork: When Homer gets told "No listenin', you hear me?", it's pretty obvious any answer would get Homer whipped.
* NeverSmileAtACrocodile: Averted with Captain Jack.
* PersonaNonGrata: The Simpsons are not allowed to return to Florida ever again (even though they would return later in "Catch 'Em If You Can" and "Special Edna"). As of now, the only states they're not banned from are Arizona and North Dakota, which further complicates theories on [[WhereTheHellIsSpringfield where Springfield is]].
* RunningGag: Homer constantly trying to turn whatever song's being sung at the moment to Music/{{Starship}}'s "We Built This City (On Rock and Roll)"
* SanitySlippage: Homer, as a result of insomnia brought on from a magazine quiz predicting he's gonna die (even Marge looked worried when she read the results). It escalates to Homer hopping around in a cowboy sleeping bag, completely naked, at the power plant while nursing a baby doll.
-->'''Homer''': A mother can't die, and I'm a mother.
* SinsOfOurFathers: Bart, Lisa, and Maggie are sentenced to life imprisonment by Florida for Captain Jack's (apparent) death only because they are Homer's children.
* TypicalCartoonAnimalColors: Real alligators are not as green as Captain Jack is.
* WardensAreEvil: Both the sheriff and his assistant take care of the Simpsons' sentence, and the assistant whips Homer for '''any''' reason he can find (such as saying any answer Homer gives is wrong -- when Homer actually asks about this, the man says Homer is ''forbidden of listening anything'') and use them as slave labor. Putting the ''whole family'' in lifetime imprisonment because of Homer's stupidity puts them here.