Jessie seems to have a special preference for snake-like Pokémon, owning both an Arbok and a Seviper. In The Ninja-Poké Showdown, she expressed a preference for Poison-type Pokémon in general, though several Bug-type and Ghost-type Pokémon have since appeared on her team including Yanmega, Gourgeist, and Mimikyu. Jessidia" returned during the Wallace Cup from Staging a Heroes' Welcome! to Strategy with a Smile!, and again in Playing the Leveling Field!. Jessie and James reused their casual outfits while competing in the Pastoria Croagunk Festival in Cream of the Croagunk Crop!.

In this game, Jessie, from the alternate movie continuity, somehow got transported to Pasio while chasing a Shiny Celebi. Unlike most characters in Pokémon Masters EX, Jessie's appearance is based directly on her anime incarnation, and retains her Japanese and English voice actors.Jessie then became eligible to participate in the Sinnoh Grand Festival, and she made it into the semi-finals, but lost to Dawn. She also participated in the Pokémon Summer Camp and got a diploma/credit for having studied (she was disguised as Jessilina). After the Sinnoh Grand Festival, Jessie abandoned the Jessilina alias. Jessie and James, with Meowth in disguise as a Sunflora, stole the Adamant Orb from the Eterna Historical Museum in broad daylight. After the disaster, she and her teammates claimed sole credit for defeating Team Flare to Giovanni. Jessie competed against several Coordinators in the Neighborly Town Pokémon Contest in Teaching the Student Teacher!. She made it through the Performance Stage and managed to defeat each one of her opponents in the Battle Stage, winning the event with the help of her Seviper and earning the Neighborly Ribbon, her fourth Contest Ribbon overall.

Jessie and James took a pair of blimp attendant uniforms to remain undercover while they stole the passengers' jewelry and Pokémon. The trio wore these outfits again while running a souvenir stall during the Lily of the Valley Conference, held from League Unleashed! to The Semi-Final Frontier!. In Kalos, Jessie started to compete as a Pokémon Performer, and like in Sinnoh contests she was successful enough to become a semi finalist. Her main goal was to be Kalos Queen like Aria and take over the Kalos region. This time, she uses fair methods to participate in showcases.

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 The First Day of the Rest of Your Life!, she and Gourgeist participated in an Exhibition Showcase held in Lumiose City, specifically planned to help the citizens recover from the gloom of the disaster by spreading happiness and excitement. This might have been caused by the change in medium when the series switched from hand-drawn to digital animation. 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. 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.

Although she is shown to be very mean to her own Pokémon such as punching or shouting rudely at them, she does care for them. For example, she along with James and Meowth helped Arbok to escape with Weezing, and a group of Koffing and the Ekans, by taking hits from Rico's Pokémon. She also let Dustox follow her true love by smashing Dustox's Poké Ball. Jessie and James posed as excavators in the hopes of finding a hot spring that they can earn money from. The trio disguised themselves as the "C-Button League". Aside from shirts with the letter "C", they wore sunglasses with the letter "C" making up the frames.

Yellow, Let's Go, Pikachu! and Let's Go, Eevee!, Masters EX, Pokémon GO, Mezastar, Puzzle League, Zany Cards 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. Jessie and James disguised Meowth as a Volbeat to snatch Juliet's Illumise. They later performed their motto as an Illumise and Volbeat, respectively. Like the actual Pokémon species, the costumes' tails light up. 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.

In Mean with Envy and Pacifidlog Jam, Jessie competed in the Pacifidlog Town Contest as "The Jester", using this disguise paired with dark sunglasses.

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. Jessie posed as "La Grande Dame Brûlée", a prestigious dance choreographer who has trained many Pokémon Performers. Using this disguise, the trio managed to steal Serena and Nini's Pokémon during a fake dance class. Jessie and James performed an operatic version of their motto in the Mossdeep Gym, complete with costumes. Jessie and James posed as an elderly couple with their ill Snorlax, which was actually Wobbuffet and Meowth in a costume, to steal from Katie's pharmacy. Like Serena, Jessie also enters the Pokémon Showcase as a disguised Jessiliee but both are eliminated in their debut. Jessie and James are also thoroughly outmatched during their encounters with Kalos' Team Flare.