Japanese Title: Gardie and Kojirō
Original Airdate: June 11, 1998
US Airdate: March 13, 1999
Ash and company continue their journey when they spot a missing persons sign. They are shocked to see that the child on the sign looks like James of Team Rocket. They later discover that James comes from a rich family and ran away when he was a just a boy. His parents are dead and James can only inherit his fortune if he marries his fiancee Jessebelle. Jessie and Meowth overhear this and while James resists they restrain him and march him like a puppet to his family's manor to claim his money.
Unfortunately, it turns out that this is a trap; his parents are not dead and Jessebelle is violently aggressive in controlling everything James does. With the aid of Growlie, James' pet Growlith from childhood, Team Rocket escapes with their freedom, but none of James' fortune.
This episode contains examples of the following tropes:
- Abusive Parents: James' parents are overly controlling and demanding, forcing James to act "properly" in every area of his life. When they tried to force him into an Arranged Marriage with a clear yandere, he ran away. The fact that he wasn't the least bit surprised that they would fake their deaths to lure him back likely means they were emotionally manipulative as well.
- Big Damn Heroes: Growlie coming to James' rescue.
- Continuity Nod: When James is pretending that he cannot remember his childhood he claims that all he does remember is flunking out of Pokemon Tech and joining a bicycle gang, two things earlier episodes mention him and Jessie doing together.
- Did You Die?: When recalling his fake childhood memories, James tells the tale of what happened to him as a child, when he and his Growlithe were caught out in the cold and James tragically froze to death. This gets a tearfully heartfelt reaction from the listeners... with the exception of Misty, who immediately points out that James is alive and standing right here, knowing that his story is only a fake.James: I'm all mixed up!
- Double Standard: Abuse, Female on Male: Jessebelle is shown as shockingly violent towards James, paralyzing him with her Vileplume and beating him with a whip. James is not happy about it, but mostly complains about how controlling she is, and his parents seems to think it's great. There is a lot of slapstick comedy in Pokemon in general, but they certainly have never portrayed James smacking a woman around like Jessebelle is shown smacking him around. Although everyone except James' parents and their butler think Jessiebelle is horrible.
- End-of-Episode Silliness: In an ironic role-reversal, the episode ends with Ash and his friends being chased by Jessebelle, who is demanding them to take her to James.
- Enemy Mine: Pikachu and Growlie team up to take on Jessebelle's Vileplume.
- Eye Catch: The "Who's that Pokémon" was Vileplume for this episode, since Jessebelle uses one.
- Faking Amnesia: James pretends he can't remember his childhood in order to avoid Jessie and Meowth's questions about it, hoping he can get away without them forcing him to claim his inheritance.
- Identical Stranger: Jessebelle looks and sounds just like Jessie, only talking with a Southern Belle accent.
- Never Say "Die": Apparently, 4Kids is okay with averting this trope if it's ultimately Played for Laughs.
- No Indoor Voice: Hopkins the butler frequently speaks through a megaphone—even when talking to someone five feet away.
- Ojou Ringlets: Jessebelle looks like Jessie except her hair is in several large "drill curls." This is a pretty quick way to indicate her higher social status.
- Runaway Fiancé: James was betrothed to Jessebelle when he was only barely a child and her controlling attitude and penchant for violence was enough to cause him to run away from home even then. At the end of the episode he runs away again and Jessebelle declares that she is not going to give up on him that easily (although it takes over 500 episodes before she shows up again).
- Say My Name: Finally at his wits' end, James calls for his only friend at the estate:"GROWWWWWLIIIIEEEEEE!"
- Secretly Wealthy: James never told his teammates that he came from a rich family, probably fearing they would make him go back to claim his money.
- Ship Tease: Probably the most significant amount for Rocketshipping (Jessie X James) the show ever had.
- Shout-Out: James' fake story about him and Growlie dying in the show and being carried off by angels is a direct reference to A Dog of Flanders.
- Take That!: Meowth gets some of his best Cats Are Snarkers moments in this episode.
- It's equal opportunity, too. This, when Team Rocket happens upon the missing sign:Jessie: Hmm, this kid looks a lot like you.
James: You think so? He looks pathetic.
Meowth: That's what she means, James.
- And later, when discussing Jessebelle:Jessie: Well, James, that fiancée of yours is truly despicable.
Meowth: Told ya she's just like Jessie.
Jessie: I'll make your mouth even bigger!
- It's equal opportunity, too. This, when Team Rocket happens upon the missing sign:
- Team Rocket Wins: While this trope would recur in later episodes, this still stands as the only episode to date that Ash and his friends fall victim to the End-of-Episode Silliness instead of Jessie and James, which this is the first and only time the villains win in this episode.