[[caption-width-right:320:Just another day when your son meets an eccentric man in strange clothing who offers to sell his novelty t-shirts across the country.]]

When the last of his baby teeth fall out, Bart is hit with a sobering realization: he's getting older. After giving a Viking funeral to his toys, Bart becomes depressed about growing up, but combats it by writing sarcastic slogans on -shirts and selling them, prompting a Willy Wonka-esque salesman to buy them off him.
!!This episode contains examples of:
* AlliterativeName: Goose Gladwell.
* ArtisticLicenseGeography: Goose Gladwell claims to own 20 stores in ''30'' states. This means his math is wrong too.
* BitingTheHandHumor: Homer's beard mouth detaches from his face for a few minutes after he states that it should be easy to make a nuclear weapon since Korea did it, despite their reputation for crappy overseas animation.
* BunnyEarsLawyer: Gladwell's lawyers wear stuff that seem as silly as the bunny ears but it's thanks to them he doesn't need to give Bart a share of the money he obtained from selling the novelty t-shirts' rights to Disney.
* CallBack: The T-shirt reading "Pobody's Sherfect, Nithead" is similar to the cap reading "Pobody's Nerfect" from season six's "Bart vs. Australia."
* {{Expy}}: Goose Gladwell is an expy of [[Literature/CharlieAndTheChocolateFactory Willy Wonka]].
* GettingCrapPastTheRadar: One of Bart's T-shirts read "Pobody's Sherfect, Nithead".
* GrowingUpSucks: Bart experiences this first hand when it seems like all of his childhood wonder has vanished, leading him to become cynical enough to make parody T-shirts. By the end of the episode though, he's back to being a kid.
* {{Irony}}: After some failed attempts to make his last baby tooth fall, Marge accidentally made it happen.
* MeaningfulFuneral: Parodied. Bart says farewell to his childhood possessions by imitating a Viking funeral, pushing the box out into the lake and burning it.
* OlderThanTheyLook: Gladwell looks to be in his late 30s, but since he served in the Vietnam War, he would have been in his 50s at the time the episode aired.
* PermaStubble: Homer indicates how in the right light, Bart is starting to get one as a sign of adulthood. Bart remarks that he thought it was chocolate milk.
* ShellShockedVeteran: Apparently, Gladwell was driven nuts in Vietnam.
* YourMom: As the credits roll, we learn that one of Bart's failed attempts to get his last baby tooth to fall consisted on insulting Nelson's mother so he'd punch Bart. It failed because Nelson decided to think about the things Bart said.