In between the island of giant Pokemon and Tentacool and Tentacruel

episode 18 -Holiday at Acapulco-

After escaping the sinking of the St. Anne, the Island of Giant Pokemon, and the clutches of the Team Rocket, Ash and his companions find their way to the resort town of Acapulco, and settle down to a well-deserved vacation. But James, Jessie, and Meowth are still intent on making life miserable for the young trainers; Ash and the others have a run-in with them (pun intended) and accidentally destroy a dock belonging to a old fellow by the name of Ryu. Ryu doesn't make enough money from his business, a seaside restaurant, to repair the dock, but Ash enlists the aid of his Pokemon and his friends to help make a little extra money.
At the same time, the Team Rocket is enlisted by an old hag who happens to be the cousin of Nastina (from the English Episode 19:
Tentacool and Tentacruel). Meowth uses every trick in his arsenal to sabotage Ryu's operation, and Ryu loses hope that he'll be able to rebuild his dock. Suddenly, Professor Oak and Ash's mom pay a surprise visit; they bring news of a swimsuit competition where they might be able to get enough money to repay Ryu. Misty enters the show, but she is quickly eclipsed in the competition by James and  Jessie (the latter of whom is wearing an inflatable body suit-- however because of this scene the whole episode was not included in the American showing of Pokemon.); they, in turn, are put to shame by none other than... Gary's cheerleading squad!
The competition degrades into a battle as the Team Rocket, sore losers as always, launch an attack on the show. Gary generously lets Ash fight them off, and as usual, the Team Rocket (and the old gang) get royally trounced. The winner of the competition ends up being Ash's mom, and Ash and the others manage to pay back Ryu for the damages. Ash and his mother, along with Professor Oak, say their goodbyes, and then Ash is off on his journey to become the world's best Pokemon master once again...

He's even wearing lipstick!! and he's got bigger boobs than Jesse!!