Japanese Title: Battle on the St. Anne!
Original Airdate: July 8th, 1997
US Airdate: September 7th, 1998
After winning a Thunder Badge, Ash and his friends want to go on a cruise but know they can't afford it. Out of nowhere two girls show up and give them free tickets, saying that they don't need them anymore. While our heroes leave to the port, excited by their lucky prize, these two girls are revealed to be Jessie and James in disguise, and they enter into their secret base where Meowth briefs their success to a shadowy figure they call the Boss. It turns out that the St. Anne cruise is really a ploy devised by him to lure trainers in and steal their Pokémon.
Ash and company get on board the boat and Ash has a Pokémon battle with a rich, older man who later convinces Ash to trade his Butterfree for a Ratticate. Meanwhile, James encounters a salesman selling a Pokémon known as Magikarp. The salesman tells James that Magikarp can make him rich by laying a thousand eggs that hatch into more Magikarp laying another thousand eggs each. Lured by the salesman's words, James eagerly spends all of his and Jessie's salary advances to buy Magikarp, unaware that the salesman had sold him a worthless Pokémon.
As the ship sails through dark clouds, the Boss gives the signal. Doors are shut, and various crew members reveal themselves to be Team Rocket grunts. Led by the trio, they attempt to steal all the Pokémon on board, but Ash convinces the passengers to fight back. During the battle, Ash begins to regret his decision to trade Butterfree after realizing that Ratticate wasn't the same. The Rocket grunts are thwarted and blasted off save for the trio, and in the aftermath, Ash decides to trade back Ratticate for his Butterfree. Unfortunately the ship has sailed into a storm during the fight, and the rough waves knock Ash, Misty, Brock, Pikachu, and Team Rocket out cold. When the ship sinks, Ash and his friends are still on board.
- Abandon Ship: Everyone except Ash, his friends, and Team Rocket manage to get out and on board inflatable life rafts. The rest fail to escape due to falling and knocking themselves out.
- Big Badass Battle Sequence: It's the first instance of many trainers battle each other at the same time. The trainers aboard the St. Anne repel Team Rocket's attack.
- Bond Villain Stupidity: Team Rocket didn't bring any of their own Pokémon, apparently believing they could force the passengers into surrender via intimidation alone. Reality Ensues.
- Cliffhanger: The St. Anne sinks with Ash, Pikachu, Brock, Misty, Jessie, James, and Meowth still aboard.
- Didn't Think This Through: Apparently, Team Rocket figured that the trainers wouldn't fight back when they attempted to steal their Pokemon. They were wrong big time.
- Dirty Coward: The Captain of the St. Anne, who claimed the ship wouldn't sink, but decided to test out the lifeboats.
- Disguised in Drag: This episode features the first of many times James would dress like a woman.
- Drop the Hammer: After James' line at the top, Jessie hits him with a sledgehammer.Jessie: Stop acting like an ignoramus.
- Eye Catch: The featured Who's That Pokémon? this episode is Raticate.
- Foreshadowing: Ash nearly trading off Butterfree would foreshadow his departure six episodes later.
- Get Rich Quick Scheme: The Magikarp salesman sells James a Magikarp for an exorbitant price by telling him he can get insanely rich because Magikarp breed very fast and are worth a great deal of money. This is bogus as Magikarp are very common and not very useful so selling thousands of them is quite unlikely.
- Going Down with the Ship: Averted—The Captain is the first one in a lifeboat when the sea gets rough.
- Greater-Scope Villain: This episode reveals that the Team Rocket trio is only a small part of a larger criminal organization led by their boss, Giovanni. This also marks the first time where he takes a more direct role as the Big Bad of the anime. Unfortunately, it also reveals that your garden-variety Rocket grunt is about as competent as the Trio.
- Harmless Electrocution: While Pikachu electrocuting people without doing a realistic amount of actual damage is common at this point, this episode kicks it up a notch by Ash actually requesting that Pikachu shock someone.
- Hit Flash: In the dub, it replaced an extreme close-up of James' face the moment Jessie hits him with a sledgehammer.
- Imagine Spot: James has two visible fantasies in this episode, one of him lying on top of a pile of Pokémon and another of him on a throne surrounded by piles of money.
- No OSHA Compliance: Apparently, lifeboat drills don't exist in the Pokémon world, otherwise everyone would have been prepared for the storm and the impending sinking.
- Out of Order: When Pokémon premiered in the United States, this episode aired as a 'sneak peek' one day before the actual first episode, Pokémon - I Choose You!. The only difference between the 'sneak peek' version and the regular version is that the preview version has a different opening and closing narration.
- Recurring Extra: First appearance of the Magikarp salesman, who would go on to make sporadic appearances throughout the series.
- Right-Hand Cat: The Boss is shown stroking the head of a Persian, a cat Pokémon and the evolved form of Meowth. Meowth takes issue with that as he wants to be the Boss's top-cat.
- Rite of Passage: Ash makes his first Pokémon trade here, trading his Butterfree for the gentleman's Ratticate. Being his first time trading, Ash worries about his Butterfree's wellbeing in the hands of a stranger he never met, and soon realizes that Ratticate doesn't have same emotional bond he had with his first Pokémon. He eventually decides to trade back.
- Shout-Out: The captain of the ST Anne refers to her as being "Unsinkable"
- Totally Radical: Lampshaded by Ash.Jessie: (disguised as a Valley Girl) It'll be a radical party! All of the most radical Pokémon trainers will be there!Ash: (to Misty) Do you know anyone who says "radical" anymore?
- Valley Girl: James talks like one until Jessie whacks him on the head. Ash even lampshades how ridiculous he sounds.
- Vile Villain, Saccharine Show: The Rocket Boss. When Team Rocket first contacts him, his appearance and voice are distorted in a shadowy, almost demonic fashion. Unlike Team Rocket, he is not Played for Laughs in this episode, save for making one small pun on purrfection.
- Villain Decay: In full-swing for Team Rocket by this episode, especially James. Jessie calls him out on staying in character as a ganguro after giving Ash and his friends tickets aboard the St. Anne. Later, he uses his salary advance and Jessie's to buy a worthless Magikarp from a con salesman.
- What Happened to the Mouse?: After Ash trades back the gentleman's Ratticate for his Butterfree, the gentleman was never seen, heard, or mentioned again.
- You Have Failed Me: The Boss reveals that he had replaced Meowth with his evolved form Persian because he was growing tired of Team Rocket's constant failures. He promises to restore Meowth's position as top-cat if their latest scheme is successful.