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 were taken from the end of "Behind the Laughter".
- Fan Disservice: The Hobo's requested compensation after each story was getting a sponge bath by Homer.
- The Stinger: Homer's line "Oh boy, buffalo testicles!" is heard over the Gracie Films vanity plate.
- What Could Have Been: Jim Carrey was considered to play the hobo (and Carrey really wanted to voice a character on The Simpsons), but he would up being played by Hank Azaria since Jim Carrey had a busy schedule.
- 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.
- Historical In-Joke: The Chicago Fire of 1871 was started by Paul throwing the flaming asteroid from his pants.
- 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. All she can mutter is "Whiskey...please".
- 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.
- 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.
- Gender Flip: The Johnny Appleseed legend is changed to a female to fit animal-lover Lisa into the story.
- 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.
Tom and Huck
- 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 are being lowered into their caskets.
- Downer Ending
- 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 immediatly bolts out the door.
Grampa: DANGIT ALL!!
- Shout-Out: Dr. Hibbert is seen singing "Ol' Man River".
- Whole Plot Reference: Tom Sawyer.