James had wanted a Chimecho ever since he was young after seeing the Pokémon being sold at a local festival. 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."
James finally caught himself a Chimecho in Who's Flying Now?. While attending the Fortree CityFeather Carnival, 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 its tail, causing Chimecho to use Astonish instead. However, the judges admired the contrast in sound 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 adored his Chimecho, and it was often seen out of its Poké Ball, either floating near James or being held in his arms. Its melodic voice instantly calmed situations between the often quarreling Team Rocket trio. It had a place in the Team Rocket motto after Wobbuffet. James refused to put Chimecho in any sort of danger, particularly battles. 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. Though this irritated Jessie and Meowth, James appreciated Chimecho's soothing nature. It was sometimes overly affectionate, like Carnivine and Cacnea. In those cases, it would wrap its tail around James, making him unable to see. It deeply cares for James, as expressed during its tearful goodbye in Sweet Baby James. Despite its departure from traveling, Chimecho was reassured that its dear friend would be fine, even smiling as Mime Jr. decided to join James's team.