Jessiebelle

Jessiebelle is the main antagonist in the Pokémon episodes "Holy Matrimony!" and "The Treasure is All Mine!". She was in an arranged marriage with James which was arranged from a young age causing the latter to flee from his home upon realising how controlling and psychotic she was. In both of her appearances she is seen attempting to force him into their marriage and morph him into a "proper gentleman".

She was voiced by Rachael Lillis in her first appearance and by Michele Knotz in her second appearance both of whom voiced Jessie as well.

Childhood
Jessiebelle and James surprisingly spent a lot of time together as children, however after their parents decided to do an arranged marriage between them James found out the truth about Jessiebelle with her being a snobby, controlling person with a horrible personality and because of this he fled only leaving behind his beloved Growlithe known as Growlie.

Holy Matrimony
She appeared in this episode after James' parents faked their deaths in order to trick him into returning home. Upon hearing of the fortune he would inherit Jessie and Meowth come with a plan and dress in awful "invisible suits" in order to steal the fortune however upon entering they realise James' parents where still alive which James angrily tells them he knew since they always do schemes like that to force him to return. His parents play along with the act for a while until they reveal Jessiebelle much to James horror. Meowth comments on the resemblance between her and Jessie which Jessie angrily scolds him for. Later they remove Jessie and Meowth from the premises as well as Ash, Brock and Misty who were watching from a higher level. In the dungeon and begins to whip James who in return runs and dodges the whip. This causes Jessiebelle to release her Vileplume which paralyzes James stopping him from fleeing and escaping. Before preparing for their wedding James is rescued from an unlikely source his old Growlithe named Growlie who saves him. Jessiebelle puts up one final fight with her Vileplume however Growlie and Pikachu burn her Vileplume alive causing it to chase Jessibelle until she accidentally knocks Jame's parents and herself into a pond giving James time to flee.

The Treasure is All Mine
After her previous defeat Jessiebelle visits one of James' family summer homes after being alerted by the butler Sebastian about James being there. After her confrontation with him involving her Vileplume (now healthy again) attacking him, Ash, Brock, Jessie and Meowth James tells Ash to make Pikachu blast him off which he does however he doesn't realise that Jessiebelle actually went with him and Meowth instead of James. Her final appearance is her chasing James and Meowth down the beach. She probably gave up on her pursuit however she could possibly reappear in a future season or episode.

Personality
Despite being sophisticated and polite Jessiebelle is also a vicious, cruel, obsessed, mentally unstable and psychotic. She will stop at nothing to marry James and this her primary goal which she is seen using in both of her appearances. She shares traits with both Jessie and James with her being calm, calculating and flamboyant as well as short fused and controlling as well as quite abusive and psychotic.

Appearance
Jessiebelle bears a striking resemblance to Jessie with the only differences being Jessiebelle's hair which is slightly crimson and held up in pigtails and her dress sense which usually consists of fancy and expensive looking dresses. She is also seen holding a fan quite a lot.

Trivia

 * Jessiebelle is one of darkest and most vile Pokémon villains.


 * Jessiebelle is also possibly the smartest and most strategic villain from Pokémon with her always coming up with grand plans and schemes to reach her way to James however since he always considers the possibility of his parents or Jessiebelle tricking him it's usually Jessie or Meowth that fall for her schemes.