Billy signs up to sell Chocolate Sailor brand chocolates he found in a supernatural catalog. However, he begins voraciously eating through his stock and soon turns into living chocolate.
"Chocolate Sailor" provides examples of:
- Big Eater: Billy eats his way through thousands of units of chocolate and literally eats himself to death.
- Getting High on Their Own Supply: Instead of selling the Chocolate Sailor chocolate bars, Billy keeps eating them. This causes himself to turn into a Chocolate Sailor.
- I'm a Humanitarian: Mandy has no problem eating the chocolate syrup that was originally Billy.
- I Taste Delicious: Billy keeps eating himself after turning into chocolate, until nothing is left but his head. The Chocolate Sailor admits this happens every time.
- Mail-Order Novelty: Billy finds the ad for Chocolate Sailors in the back of one of Grim's comic books from the underworld.
- Mathematician's Answer: After finding out Billy ate all ten thousand units of chocolate on his own, the captain Chocolate Sailor exclaims "He ain't human!" Mandy responds, "Not anymore he ain't," pointing out how it turned him chocolate himself.
- Negative Continuity: Billy seemingly dies by the end of the episode, but of course this doesn't stick and he's fine in the next one.
- Oh, No... Not Again!: After hearing how Billy ate himself after turning into chocolate until only his head was left, the captain Chocolate Sailor exclaims "It happens every time!" while asking how he's supposed to make a crew when they keep eating themselves.
- Too Dumb to Live: Billy is so stupid he keeps eating himself after he turns to chocolate, and instead of choosing the obviously named antidote, he eats all of the options causing him to explode into chocolate syrup. In his defense, eating yourself is evidently a common problem for even the veteran Chocolate Sailor employees.
Billy has a dream of meeting the Tooth Fairy in the Wild West.
"The Good, the Bad, and the Toothless" provides examples of:
- Actor Allusion: Pairing up two characters played by Rob Paulsen and Bill Farmer is a nod to their frequent collaborations on Disney properties like Goof Troop and A Goofy Movie.
- No-Sell: The Tooth Fairy can't win against Mandy because she doesn't believe in him.
- Overly Long Gag: "Well I'll be a barbecue bacon cheeseburger supreme, with two golden onion rings, three different kinds of cheeses, crisp lettuce, a fresh tomato, pickles, onions, all on a sesame seed bun!"
