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.
- A Fool for a Client: 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..."
- Artistic License Biology: Captain Jack has interlocking teeth like a crocodile, instead of an overbite like a real-life alligator.
- Deus ex Machina: The alligator being alive all along, allowing the Simpsons to go.
- Diabolus ex Machina: 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 on a magically-appearing railway.
- Disney Death: The alligator Homer accidentally ran over turns up alive and completely unharmed at the end.
- Faux Affably Evil: 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.
- Going Native: 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.
- Halfway Plot Switch: It begins with the Simpsons going on vacation to cure Homer's insomnia, but halfway through the episode it becomes a story of the Simpsons' run from the law.
- 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.
- Jerk with a Heart of Jerk: 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 Reasonable Authority Figure 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.
- Madness Mantra: "Can't sleep, gonna die. Can't sleep, gonna die." (similar to the memetic "Can't sleep. Clown'll eat me." in "Lisa's First Word").
- Mortality Phobia: Homer gets hit with this one hard, leading to increasingly weird attempts to prevent dying (even pretending to be a mother) throughout the first act.
- Morton's Fork: When Homer gets told "No listenin', you hear me?", it's pretty obvious any answer would get Homer whipped.
- Never Smile at a Crocodile: Averted with Captain Jack.
- Noodle Incident: Homer hates his psychiatrist's dad for a reason the man brought up during their session. Whatever it was he regrets mentioning it.
- Persona Non Grata: 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 where Springfield is.
- Running Gag: Homer constantly trying to turn whatever song's being sung at the moment to Starship's "We Built This City (On Rock and Roll)"
"Hey, you're stealin' my trailer!... I like that.
- The café owner saying, "I like that." Culminates with:
- Sanity Slippage: 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.
- Shout-Out: The alligator being named "Captain Jack" is a reference to Leave It to Beaver, Marge even mentions that she wouldn't mind if the animal crawled up her toilet.
- Sins of Our Fathers: Bart, Lisa, and Maggie are sentenced to life imprisonment by Florida for Captain Jack's (apparent) death only because they are Homer's children.
- Steam Never Dies: An unusual variation: the freight train and the Amtrak passenger train described in the below trope have diesel locomotives (the freight has what resembles an EMD GP 7 or GP 9, while the Amtrak train has an F 40 PH locomotive), but the sound of a steam locomotive whistle is used with them!
- Train Escape: Just like in "Homer the Heretic", Homer manages to evade the sheriff by driving his car across a railroad crossing and just missing a freight train. But then it's a Double Subversion as it was revealed to be a double-track crossing, and the family ends up hit by an Amtrak train going the other direction.
- Typical Cartoon Animal Colors: Real alligators are not as green as Captain Jack is.
- Wardens Are Evil: 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.