Original Airdate: May 20, 2001
The family rides the rails to travel to Delaware, and while on the train, a hobo tells them some famous tall tales, casting them and other Simpsons characters into the stories.
- Call-Back: The family's lines at the beginning ("The Simpsons are going to Delaware") were taken from the end of "Behind the Laughter" where Homer edits together the next new episode of the show.
- False Reassurance: The hobo assuages the Simpsons' fears by telling them that he's "a singing hobo, not a stabbing hobo." He then starts singing about how much he likes to stab people with his hobo knife.
- Fan Disservice: The Hobo's requested compensation after each story was getting a sponge bath by Homer. In the last one, Homer groans at the massive amounts of glass between the hobo's toes.
- Not Allowed to Grow Up: Lampshaded at the chalkboard gag when Bart writes "I should not be twenty-one by now".
- The Stinger: Homer's line "Oh boy, buffalo testicles!" is heard over the Gracie Films vanity plate.
- Take That!: This Simpsons episode has this pot-shot at Delaware's supposed boring nature:Marge: I can't believe it! We won another contest!
Homer: The Simpsons are going to Delaware!
Lisa: I wanna see Wilmington!
Bart: I wanna visit a screen door factory!
- Wait a minute, this sounds kind of familiar...
- All of the Other Reindeer: The townspeople drag Paul out of town for always clumsily crushing everything, but then need him to save them from an oncoming meteor.Paul: When I'm crushing and killing you, you hate me. But suddenly, when I can save your life, I'm Mr. Popular?Lenny: Yep, that's pretty much it.Paul: Woo-hoo! I'm Mr. Popular!
- Anachronism Stew: While taking place in the 19th century, Paul and Babe are seen fighting Rodan in a modern metropolis. Lisa points this out, but is ignored.
- Historical In-Joke: The Chicago Fire of 1871 was started by Paul throwing the flaming asteroid from his pants.
- Hot Skitty-on-Wailord Action: Implied. Marge tells Bunyan!Homer that she needs to take a few more yoga classes when he hints at the possibility of sex.
- I Need A Drink: When asked by her husband how birthing a baby the size of a small building was, all Mrs Bunyan can do is ask for whiskey.
- Reality Ensues: Dealing with a giant living in your town would be a nightmare to take care of and feed even if he wasn't a clumsy oaf who regularly killed people without noticing.
- Rump Roast: Paul gets a flaming asteroid down his pants.
- Screaming Birth: Hilariously (and horrifically) implied. When Paul's (normal-sized) father see's his giant son, he asks his wife how she took it. She weakly replies "Whiskey...please".
- Shout-Out: When Bunyan!Homer tears open and pours out the contents of a toy factory for Marge, one of the stuffed animals that falls by her side is of Binkie from creator Matt Groening's Life in Hell.
- Slipping a Mickey: Paul drinks one carriage full of beer and instantly gets knocked out cold. Moe reveals that he slipped a couple of giant pills into the beer, then remarks he's off to the barn dance while carrying a pill.
- Your Size May Vary: Paul's size isn't very consistent. Lisa points this out as well.Lisa: His size seems to be really inconsistent. I mean, one minute he's ten feet tall, the next, his feet are as big as a lake.Hobo: Hey hey hey, who's the hobo here?Lisa: Just sayin'.
- Comically Missing the Point: When Bart points the last two Buffalo out he, and the settlers realize they can use them as a breeding pair to restore their food supply. All Homer sees is two more Buffalo to kill and does so without a moments hesitation.
- Gender Flip: The Johnny Appleseed legend is changed to a female to fit animal-lover Lisa into the story.
- I Ate WHAT?!: Parodied; when Connie offers her father an apple, he mistakes it for a buffalo testicle and happily chows down, but when she tells him it's an apple, he spits it out in disgust.
- My God, What Have I Done?: Connie's father says this when he realizes that he's been shooting the buffalo to extinction. When his son says there are two more left, he shoots them both and repeats the line.
- No Party Like a Donner Party: With all the buffalo gone, the settlers decide they should eat Homer until Connie brings apples. Although Moe had already taken a bite out of him.
- Reality Ensues: The Simpson's (now the Buffalkill's) kill so many Buffalo that it drives the species to extinction, and as they had taken to using Buffalo as their sole food source the settlers are at risk of starvation
Tom and Huck
- Attending Your Own Funeral/Bait-and-Switch: During Tom and Huck's funeral, the camera pans upward to the two looking down from wooden beams, implying they survived. It turns out the townspeople stuffed their corpses and they're being lowered into the caskets.
- Cake Toppers: The wedding cake for the Shotgun Wedding has a father figurine pointing a shotgun at the groom.
- Downer Ending: Tom and Huck are caught and killed.
- Little Useless Gun: After Tom and Huck escape their pursuers to a riverboat, they order some whiskey from Moe: Huck drinks his and claims it's watered down, calling him a "cheat". This results in everyone in the room pulling out their Derringers and starting a shootout, but the bullets they shoot are so weak and ineffective that Tom and Huck can't even feel the numerous stray shots hitting them that they're not even trying to avoid while sitting on the barstools and they bounce off equally harmlessly off the ship windows and the rack of bottles behind Moe.Huck: Man, those Derringer bullets are weak!
Tom: Powerful weak!
- Long List:Nelson: We got any food left?
Bart: Hmm. Looks like we're out of corn pone, fatback, hardtack, fat pone, corntack.
Nelson: Any "tackback"?
Nelson: I mean "backtack".
Bart: Plumb out.
- Off-Model: Barney's hair is briefly colored grey at one point during the showboat scene.
- Ridiculous Future Inflation: There's a 99 cent store that sells grand pianos, and Tom and Huck are shocked that a few days' worth of supplies cost 2 cents.
- Shotgun Wedding: Becky's father does this to Tom for holding hands with Becky. He also remarks how he and his wife got together via this method, with a hilarious Gender Flip version of it being Homer's father who forced Marge to marry his son at gunpoint, and is still behind her with the shotgun. When Marge remarks that they've been married for 10 years and that Grampa can put the gun down now, he relents... and Marge immediately bolts out the door.Grampa: DANGIT ALL!!
- Shout-Out: Dr. Hibbert is seen singing "Ol' Man River".
- The Last of These Is Not Like the Others: As Lisa points out, Tom Sawyer is a novel by Mark Twain as opposed to a tall tale; the hobo insists on telling the story anyway.
- Whole Plot Reference: Tom Sawyer.