Jessie/Anime/Main series/History/AG

Starting in Hoenn, Jessie became a Pokémon Coordinator, entering every Contest that she could. She frequently made it to the battle round, but usually lost there. Although Jessie entered mostly every Contest in Hoenn and Kanto, she lost in all of them, whether it was the first match of the Battle Rounds or the finals.

In the Kanto Contests, Jessie disguised herself as Jessebella (Japanese: ムサぴょん Musa-pyon) wearing a red dress and glasses. Eventually, Ash, Brock, Max and May found out her true identity in the last Contest.

During the Kanto Grand Festival, Jessie dressed up as Jessadia (Japanese: プリティ・ムサリン Pretty Musalin) and wore glasses, long white socks, a yellow and orange dress, and had her hair in pigtails. She worked there as an announcer and Lilian Meridian's assistant; Lilian herself said she did not really like Jessadia's style, but recognized her talent.

In Off the Unbeaten Path, Jessie entered Potpourri Island's Pokémon Orienteering with as her partner Pokémon. The duo had trouble finding the checkpoints and decided to drop out of the competition. They planned on letting James and his collect the five stamps, thinking James would share the sample of fruit prize with them. To assure James's victory, they dug several pitfall traps throughout the island so as to slow down the other contestants. When James was declared the winner, Jessie was certain she would get to eat some fruits. However, James was more interested in the Pokémon Teamwork Medal and he agreed to donate the fruits after Nurse Joy asked him to, much to Jessie's disappointment.

Jessie's odd Contest style had caught the eye of Harley, and they quickly struck up a friendship of sorts during the Mulberry City Contest. Harley was determined to sabotage May's chances of getting her final Ribbon, and paired up with Team Rocket, even giving Jessie his Pokémon to borrow for the event. Jessie lost to May in the final round, much to Harley's annoyance. Later in The Unbeatable Lightness of Seeing!, Harley suggested that Jessie should accompany him to Johto to compete in Contests. She refused his offer, admitting that she was already committed to Team Rocket.