After the events that transpired at the Weather Station, Ash and co. finally arrive at Fortree City. Ash couldn't wait to challenge the Gym Leader, unfortunately the Gym Leader is helping with the Feather Carnival. Later they meet the Gym Leader, Winona, who scheduled in Ash's request for a Gym Battle, but in the meantime they should have some fun. Meanwhile Team Rocket has plans of their own. What sinister plot are they up to this time, and why does the carnival bring back such bad memories for James?
The gang climbs atop the Fortree City's Gym. May spots the city behind them. They see houses atop the trees. They continue (wishing for an elevator to get them up). A man appears, by the name of Zachary, telling them that the Gym Leader is in Fortree City for the Feather Carnival - a tradition of the city. Ash goes down to get to the Gym Leader. They see lots of food and girls (pleasing Brock). Max spots 2 people riding a Skarmory, so they go to the center to check the people.
Team Rocket appears as well in the City, with Jessie and Meowth eating food. James is depressed and makes a flashback - he was travelling in car through a carnival when he saw a Chimecho. His parents wouldn't allow him get one, so one night he snuck out to get it, but the carnival ended already. He begins to cry, but stops when he sees Jessie and Meowth aren't present. The woman (named Winona) goes to pick another child to the flight, but Brock appears with his flirting scheme, following Max who pulls his ear. Ash introduces himself and wants her to challenge to a Gym battle. Winona accepts, but after ending the duty she has to do first. A woman and her climb up on Skarmory and ride off.
Ash allows them to stay for a while at the carnival, so they bring their Pokémon out. They have some fun for a while. Team Rocket comments on James' tale, thinking this Chimecho he so much wants will never appear again (despite one passing near them). Everyone has some more fun. Brock says that Fortree citizens have respect for the sky, so thinks Ash might have difficult time challenging her. James is annoyed when Jessie and Meowth abandoned him. He sees some Chimecho and goes to the trader. However, he feels something is actually familiar. The trader gives him the Chimecho, but James sees it is that Magikarp trader! James does not believe him that he is fair, but is convinced when he sees the Chimecho ad hears some facts about it.
James buys the Chimecho. Later, Jessie and Meowth arrive near him. Meowth feels something is wrong, but Chimecho sings for them. Meowth heard a bell, actually. Soon, the "wings" tied on back of the Chimecho free themselves and its tail falls down. James rubs it a little, seeing it is a Hoppip. Jessie demands how much James spent, so he says he spent all money. Meowth spots a real Chimecho. Chimecho makes a sound, soothing Team Rocket. James befriends the Chimecho (although easily). They go to their original plan. The gang arrives to the battlefield - an open field, perfect for Flying Pokémon. However, they spot trouble at the carnival, so Winona sends Skarmory to ride it, so the gang goes down.
Team Rocket causes trouble in a machine, catching the Flying Pokémon. Skarmory uses Steel Wing, pushing the machine. The gang spots the Chimecho, but nevertheless, Pikachu electrocutes them. However, Chimecho heals them all with Healing Pulse. James thanks Chimecho, who in return folds his eyes with its tail. Meowth attacks using the machine, damaging Swellow. Swellow frees itself from the attack and uses Wing Attack, pushing the machine. Meowth releases another attack, defeating Swellow and Pikachu. Skarmory attacks with Drill Peck, releasing the Pokémon.
As Winona's Skarmory uses another Drill Peck, Jessie and Meowth advise to heal them, but they aren't hurt. So, they advise it to use Double Edge, but Skarmory hit the machine. As they are blasting off, James thinks Double Edge is dangerous to use for someone like Chimecho. The gang thanks Winona for assistance. Winona apologizes for not having battle with Ash, but proposes to battle him tomorrow, so he accepts. At the end of the carnival, they see Winona and the Flying Pokémon fly amidst the fireworks.
- From this episode, Chimcho will be be featured in Team Rocket's motto.
- Featured Pokémon: Magby, Lombre, Solrock, Ponyta
- In this episode, Ash pulled Brock's ear.
- Also, Wobbuffet did not speak at the end of the Team Rocket chant, but Chimecho did.
- At the beginning of the episode, a classic Pokémon identification can be seen. In this episode, it is a Gengar.
- James' Chimecho was the second Pokémon to be caught by friendship. The first being Cacnea and the third being his new Yamask.
- The title could be referencing the 1981 song "Who's Crying Now" by Journey. It can also reference the phrase "Who's Laughing Now?".