Jessie repeated the disguise method during the Kalos Showcases, using the alias Jessilee. Using Meowth, Gourgeist, and Wobbuffet, she won at least three Princess Keys (at least one was obtained through legitimate means), allowing her to participate in the Kalos Master Class. Much like the Grand Festival, Jessie made it to the semi-finals, but lost to Serena. She later performed again with Serena and Shauna at a performance exhibition during the rebuilding of Lumiose City. When they encounter villains opposed to their personal or organizational goals, the three are usually more than willing to sabotage the evil team, even to the point of assisting Ash and his allies when they finally recognize the threat. In Mimikyu Unmasked!, while shopping, Jessie wears a light purple elaborate modern sleeveless gown with frill designs and purple heels. She also wears a summer hat on this occasion. Elena Ramírez ( EP159- EP167, EP169, EP192- EP205, EP230- EP233, EP274- AG017, AG033- AG034, AG093- AG100, one scene of AG133)

Throughout these episodes, they are seen trying to steal others' Pokémon, including Pikachu and Pokémon that are able to Mega evolve. However, they are blasted off by Ash and his group or other Trainer's Pokémon . They also fight against the evil Malamar group on several occasions. Jessie and Meowth are also disappointed when James successfully catches Inkay by luring it in with food. Therefore, when she tripped into a wild Pumpkaboo, she decided to capture it. She won at least two other showcases off screen, though the towns and methods are left undisclosed. Like many female characters in the manga, Jessie is depicted with an oversized bust, though this is edited down for VIZ Media's English translation. Scalchop King Competition - Disqualified (with James as "Jesty" and "Jacen"; Crowning the Scalchop King!)In Party Dancecapades!, Jessie and her team members decided to attend a dance party hosted by Monsieur Pierre. After seeing Serena and her friends go inside, Meowth noted that it would be a perfect chance to catch Pikachu. Jessie, however, decided to let go of these plans in favor of attending the dance party and decided on James being her date while Gourgeist decided Inkay to be hers. Later, she was seen flailing James during their dance. With the dance party over, Monsieur Pierre announced a Tag Battle and Miette and James were partnered against Ash and Serena. Despite James's chagrin, Jessie sternly told him to win the battle but he lost, leading to her and her Gourgeist eating from the table behind them out of frustration. Reason: Missing overworld and in-battle models and story info from LGPE; need higher-quality VS model from LGPE In the Movie Pokémon The Movie 2000: The Power of One, Jessie's age was said to be 25 in the Japanese cut. This was, however, missing in the English dub. This age of hers is not confirmed either as, in the anime, her age has been mentioned several times, almost all of them being different. In Pokémon the Series: Sword & Shield, Jessie's appearance remains unchanged and her magenta hair appears in a glossy style. Jessie began to compete as a Pokémon Coordinator in the Hoenn region. Although she was not successful, she continued to participate in each Pokémon Contest she could.

Finally, at Silph Co. in Saffron City, Jessie and James make their final appearance, once again trying to stall the main character from reaching their Boss. Along with James and Meowth, Jessie reappeared in New Places... Familiar Faces!, returning to their original plan of catching Ash's Pikachu. They've also added new Pokémon to their team, with Jessie catching a Frillish sometime before meeting up with Ash and company. However, she is forced to give it and her Woobat away to Giovanni in The Dream Continues! under the pretense that she captured them for him. She also regained Wobbuffet as part of her team in the episode. Jessie is one of only two human characters, and the only one that is a main character, to appear in Dare da? or its English equivalent, "Who's That Pokémon?", having dressed as a Venomoth in the Dare da? for EP161. The other is Brutella. In Mimikyu Unmasked!, Jessie can be a shopaholic and spent all of her team's money at a shopping mall. She also has a talent for sewing and used her skill to fix Mimikyu's costume. Jessie also loves popularity when she aspires to become a Kalos Queen and became popular with many people.Jessie is prone to vanity and explosive anger. She values her appearance, and she can get furious when her face or hair is damaged, such as in The Tower of Terror, Tracey Gets Bugged, Don't Touch That 'dile!, A Tail with a Twist, Maxxed Out!, A Meteoric Rise to Excellence!, One for the Goomy!, and Good Friends, Great Training!. When this happens, she may do things like beat up a Pokémon such as Meowth or her Seviper. Furthermore, Jessie goes into a violent outrage whenever someone insults her beauty by calling her old, such as in the episode The Battling Eevee Brothers when Misty calls Jessie an "old hag" (Japanese: oba-san). She shares this trait with James, who hates being referred to as an old man. She is also angered (compared to her companions, who are usually depressed when they fail at something) when missions are either failed or botched, which is a regular thing. At times, her anger is also shown to scare James and Meowth, usually when they are expecting it or if she really loses her temper. This intense anger was demonstrated in the Indigo League, Orange Islands, and part of the Johto League story arcs. However, her anger tantrums have become less frequent and eruptive over the next story arcs. In The Ultimate Test, Jessie decided to take the Pokémon League Admissions Exam to see if she could enter the Indigo Plateau Conference and add that achievement to her résumé. However, during the theory test, she rose from her seat and started to argue with the instructor, which led to her being expelled. In DP 171 Jessie lost in the contest. Princess Salvia, disguised as Dawn, gave her the ribbon for the performance she gave during their battle in the Final round. In The Battlefield of Truth and Love!, Jessie and Wobbuffet battled James and his Mareanie. Fully confident in her own victory, she allowed Wobbuffet to act however he pleased, which he did by repeatedly using Counter and Mirror Coat against Mareanie's Spike Cannon and Sludge Bomb. However, Mareanie ultimately managed to defeat Wobbuffet with a relentless Spike Cannon barrage after James gained a newfound resolve to win, thus eliminating Jessie from the competition.

Elena Ramírez ( GS043- GS051, GS053; GS076- GS089; GS114- GS117; GS156- GS158; RS001- RS017; RS093- RS100) In Master Class Is in Session!, having gained the two Princess Keys needed to enter the Master Class, she entered the Gloire City Pokémon Showcase Master Class. In the first round, she performed against Nini and Concetta, where she dazzled the audience with Shadow Ball from her Gourgeist. When the second part of the first round began, she chose to strike a series of poses with her Gourgeist while Nini and Concetta appealed to the audience, but later joined the appeals, commanding Shadow Ball from her Gourgeist which enveloped the stage in a lilac smoke. Due to her appeals, she managed to advance to the next round in which she participated with Meowth, and made it through to the top three semi-finalists. Jessilee seemed pleased when Monsieur Pierre announced the rules for the semi-final round in the next episode, claiming she just has to do what she has been since doing. Despite putting up a good performance with Meowth and her Gourgeist, she was defeated, and despite her partners' fear, did not seem sad about it, instead being happy that Kalos could see her beauty. When the Master Class was over, she was seen walking through Gloire City rather silently, causing James, Meowth, Inkay and her Pokémon to worry and fear her wrath. However, she shrugged their fears and decided that she just wanted to give a feast to them, which shall be financed by James, for supporting her. She is based on a combination of Takeshi Shudō's old girlfriend from when he was in school, and Majo, the female antagonist of the Time Bokan anime series. Jessie uses a team of three Shadow Pokémon in a Trainer Battle. Green-colored cells denote the Pokémon that may be encountered during the bonus challenge. The Shadow Pokémon Jessie leaves behind also has a chance of becoming Shiny, as denoted by the icon. In Our Cup Runneth Over!, Jessie announced her plans to enter the Wallace Cup and said she would dedicate her performance to her released Dustox. She also decided to go looking for Wallace, thinking that meeting Wallace would increase her chances of winning the special Pokémon Contest bearing his name. After finding him, she showed him her Seviper dressed up as a Milotic and asked him to award her some bonus points during the Wallace Cup. She later watched as Wallace delivered a performance with his Milotic, and asked him to teach Aqua Ring to her Seviper, but Wallace said Seviper could not learn the move.Though they are dedicated, the trio is not entirely loyal to Giovanni, and instead, treat the assignments he gives them as means to their own ends. Jessie functions as their confident leader, who allows them the freedom to have side jobs and hobbies and doesn't flinch when lying to their boss' face. As a child, she also had a doll that she adored, but was taken away by a Jynx to be repaired by Santa. She thought that Santa was actually a Jynx and that Santa (Jynx) stole her doll. At the end of the episode, the trio decided to capture Santa for Jessie's gifts, but instead, a Jynx came to their window and used Sweet Kiss, causing them to fall into a deep sleep.