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. Jessie forms a sync pair with Arbok in Pokémon Masters EX. Jessie became a playable sync pair on July 9, 2020. Jessie, James, and Meowth wore Nurse Joy costumes as they sneaked into the Coumarine City Pokémon Center and kidnapped a wild Vanillite. This is notably the first time James has cross-dressed since Pokémon the Series: Diamond and Pearl. In An Elite Coverup!, the trio wore similar outfits, with orange aprons instead, while they posed as Pokémon Breeders running a phony Pokémon Day Care. The trio posed as a repair crew and rigged the local Pokémon Center's Poké Ball Transporter machine to transfer the Poké Balls directly to them, with the Trainers receiving empty ones in return.

Jessidia" returned during the Wallace Cup from Staging a Heroes' Welcome! to Strategy with a Smile!, and again in Playing the Leveling Field!. Jessie was disguised as a lady who has lost her Piplup, while James and Meowth were disguised as gentlemen. In Vanity Affair, the trio wore these outfits while working at a waterfront café. Later they, Ash, and his friends were invited onto Drake's ship. Their café apparel proved to be the perfect disguise as the trio kidnapped Pikachu with ease. 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.While setting up a pop-up cafe, Jessie and Wobbuffet wore French maid outfits, while James posed as a butler and Meowth as a baby. However, their overbearingly nice service and poor products scared customers away. 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. 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.

In the games, Jessie and James are supposed to be the same age as Ash. However, according to a special CD available only in Japan, Jessie and James are in their 20's in the second episode of Anime. Jessie and James, with Meowth in disguise as a Sunflora, stole the Adamant Orb from the Eterna Historical Museum in broad daylight. The trio disguised themselves as a ventriloquist act called "The Dugtrio Trio", with Meowth as the dummy. Both Misty and Jessie were voiced by Rachael Lillis in the 4Kids dub, then they switched to Michele Knotz when TPCi took over.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. Professor Oak • Professor Ivy • Professor Elm • Professor Birch • Professor Rowan • Professor Carolina • Professor Juniper • Dr. Fennel • Cedric Juniper • Professor Sycamore • Professor Kukui • Professor Burnet • Professor Cerise • Professor Magnolia • Sonia • Professor Amaranth In the Japanese version of The Power of One, Jessie tells Ash and Misty, who are 10 years old, that they're 10 years too young to talk about love, and James adds that he and Jessie are five years older than that, placing them both at 25 years old.

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. Jessie and James disguised themselves as waiting staff aboard the S.S. St. Flower in the hopes of stealing the precious Ribbon Cup. In A Battle of Aerial Mobility!, Giovanni approved the trio's plan to steal as many rare and powerful Pokémon as they could in Kalos. The trio disguised themselves as an entertainer's group aboard a steamboat. Jessie posed as a pop idol, while Meowth and James wore Minun and Plusle costumes, respectively.Jessie and James wore Sumo wrestler costumes and entered the Sumo Conference, with Wobbuffet disguised as a Miltank. These outfits were later burned by Jupiter's Skuntank with it's Flamethrower, exposing their identity. In Loading the Dex!, the trio arrived in the Alola region to obtain some rare Alolan Pokémon for Giovanni, as well as Ash's Pikachu, which they were surprised to find on Melemele Island. They had also left Inkay and Gourgeist behind at headquarters. They allied with a Mimikyu, which hated Pikachu, but at the end of the episode, a wild Bewear kidnapped Jessie and James. In First Catch in Alola, Ketchum-Style!, the Bewear looked after the trio, giving them food and shelter at its den. Jessie used James's Luxury Ball to capture Mimikyu. 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. Tempest. The plan continued in All for the Love of Meloetta!, where they were able to injure Meloetta before it was found by Ash and Cynthia. In Meloetta and the Undersea Temple!, the operation began in full, with the trio capturing Ash, Pikachu, and Meloetta and bringing them to the Abyssal Ruins.