Chimecho was caught by James in Who's Flying Now?. In the episode, Team Rocket followed Ash and his friends to the Fortree City Feather Carnival. James remarked that he did not care for carnivals, and when asked why, he told a story of how when he was younger, he would ride past carnivals in his parents' limo, unable to attend. One day as he rode by, he saw a Chimecho for sale at a carnival; he instantly wanted it. Later that night, he ran to the carnival to buy it, but he was too late; the carnival was already packing up. He was very disappointed, missing his chance at getting what he called his "first love."
Later in the festival, James came across the Magikarp salesman selling strange-looking Chimecho. He was narrowly tricked into buying one, but it later turned out to be a Hoppip disguised as a Chimecho, and it flew away. Depressed by losing his chance again, James was instantly cheered up when a real Chimecho flew up to him, Jessie, and Meowth, using its Heal Bell technique on them. James asked Chimecho if it wanted to be his Pokémon, and it agreed, wrapping itself around his head in excitement.
In Lessons in Lilycove, Jessie borrowed Chimecho to use in the Lilycove CityPokémon Contest. In the Appeals Round, it first used Heal Bell, but Jessie subsequently abused it by grabbing it by the tail, causing Chimecho to use Astonish instead. However, the judges admired the contrast and gave Jessie a perfect score, placing Jessie among the Coordinators moving on to the Contest Battles. There, Chimecho was pitted against May's Combusken, ultimately using Double-Edge, causing Chimecho to faint from recoil damage. Throughout the Contest, James was extremely worried about Chimecho and expressed much discontent over its suffering. Another time, James whispered to Chimecho that it should have flown away when Team Rocket was about to stage an attack.
Chimecho appeared in a fantasy in The Bells Are Singing!, after James saw Francesca's Chingling. He even took one of the three stolen Bell Pokémon and battled it with Mime Jr. in order to make it evolve into a new Chimecho. Unfortunately for him, Ash and his friends managed to get the Chingling back before that could happen.
Personality and characteristics
James absolutely adores his Chimecho, and it is often seen out of its Poké Ball, either near James or being held in his arms similar to the way that Misty held her Togepi. It has a place in the Team Rocket motto after Wobbuffet. James refuses to put Chimecho in any sort of danger; thus, it does not battle physically. However, it did heal the Team Rocket Pokémon, as well as Jessie and James, with Heal Bell during battles.
Chimecho's personality is quite cheerful and upbeat, and it is apparent that it cares about James very much. It is sometimes overly affectionate, like Carnivine and Cacnea. In those cases, it wraps its tail around James, making him unable to see. Since it does not battle, it rarely interacts with any of Team Rocket's other Pokémon, except during the motto when it says its line after Meowth and Wobbuffet.