Ash is battling with another Trainer by the waterfront, not realizing he is being watched by a mysterious sailor. After he wins, Ash is confident and boastful. The kids decide to grab something to eat.
Team Rocket is currently working in a small restaurant when the old sailor walks in and demands some hot milk. While he is there, Ash and his friends sit down outside and talk about battling. The man approaches them and Max recognizes him as Drake of the Elite Four!
Drake invites all of them (including the disguised Team Rocket) to his boat where he challenges Ash to a battle. Drake sends out his Shelgon, and though it is slower, it waits for Pikachu to get just close enough to take it down with DragonBreath and Dragon Claw.
Ash calls out Grovyle against Drake's Altaria, and though Grovyle has a better time leaping on the masts of the ship, it gets knocked out by some powerful moves from Altaria, including Aerial Ace and SolarBeam.
Team Rocket takes the advantage of a weakened Pikachu to steal it, but Drake calls out his Salamence. It uses Dragon Claw and Flamethrower to send the thieves blasting off. With Team Rocket thwarted and a few lessons learned, Ash and friends have dinner with Drake and his crew on the boat.
- This episode was initially intended to be the 102nd episode of the Advanced Generation series and the 376th episode of the Pokémon anime, but was moved up in the schedule due to strong earthquakes in Niigata Prefecture nearly a week before the airing of AG100. For the skipped episode, see [[AG101: Battle of the Shaking Island! Barboach vs. Whiscash!!!|AG101 (unaired).
- The title is a pun on the fashion magazine "Vanity Fair".
- This episode marks the only time a member of the Hoenn Elite Four appears in the anime.
- After Scizor has dodged Torkoal's Flamethrower, it lands for a second and jumps for more speed. But when it leaves the screen, its foot gets stuck on the corner of the screen, even though Brock's, Max's and May's faces can be seen moving after this, clearly following Scizor.