Jessie was born to a high-ranking Team Rocket member (named Miyamoto in the Japanese version), but she grew up very poor. Because there wasn't enough food in the house, her mother would make Snowgasboard - elaborate meals made entirely out of snow, topped with a touch of soy sauce - whenever there was freshly-fallen snow on the ground. There were Sushi Snow Rolls, Snow Loaf, Ida-Snow potatoes with snow sour cream, and Snow Pudding for dessert. Jessie claims that "snow food is low in fat and helped me maintain my fabulous figure".
When Jessie was very young, her mother was called out on a special TR mission by Madam Boss (Giovanni's mother, and the founder of Team Rocket). Jessie's mom was the leader of a special expedition to find Mew on a snow-covered mountain. It is unknown whether she survived the trip; she is reported to have perished in an avalanche, but rumors suggest that she was saved by an Articuno.
Meanwhile, Jessie was growing up (presumably alone, or with another relative), but still without money. She had very bad luck with all holidays. First, her favorite (and only?) doll was "stolen" by a Jynx on Christmas Eve, and she never got any presents from Santa Claus since. Then, on Kids' Day, she didn't have the day off school, never had a swimming pool, and the only sandwiches she ever had were baloney with one slice. She was also the only girl who NEVER had a Princess Doll on Princess Day.
Jessie is very proud that she began her "acting career" very young... in first grade she portrayed a worm who lived inside a rotten apple. She can also sing (as heard in "The Song of Jigglypuff" and the song "Double Trouble") and dance, but she probably never had official lessons.
When Jessie was a young teenager, she tried to become a nurse for Pokemon, but for some reason, her application couldn't be accepted. Determined to make her dream come true, she enrolled at a school for Pokemon Nurses (Chanseys) and attempted to learn Pokemon medicine. There, she befriended a clumsy but well-meaning Chansey whom she helped pass its education. However, the teacher at the school was very mean to Jessie. Even though Jessie had a knack for wrapping bandages, she fell asleep when the Chanseys were using their "sing" attack to relax patients. The teacher yelled at her, which made Jessie very frustrated. Realizing that she could never become a Pokemon nurse, Jessie left the school. Before she left, however, her Chansey friend gave her half of its official nurse necklace, which Jessie still keeps.
After this upset, Jessie somehow enrolled in Pokemon Tech. It is totally unknown how this happened, since Jessie was so poor and Pokemon Tech is an elite school only for millionaires' kids. Maybe she had a wealthy relative, or perhaps the Team Rocket organization paid for her education after her mother vanished. There's also the question of Jessie's other relatives. Perhaps she's related to Giovanni, the Boss... maybe she's even his daughter! At any rate, she attended Pokemon Tech where she met James. They were both promising students, and were very confident in their abilities. They were "so sure they would beat all the rest" that, the night before the big test, they "frolicked all night, for their futures seemed bright" and as a result, "got the lowest scores in the history of the school".
Flunking out of Pokemon Tech, Jessie (along with James) joined the SunnyTown Bridge Bike Gang. There she was known as "Big Jess" or "Chainer Jessie"... since she rode her bicycle while swinging a chain above her head. It's possible that the only reason why James (using his training wheels) was accepted into the Bike Gang was because Jessie stood up for him. Maybe she kept the other Gang members from picking on him?
After this, she and James joined up with Team Rocket, and along with Meowth, formed the terrific trio we know and love today!
In "The Ultimate Test", Jessie gives her age on the application as 17 (and her occupation as "diva"), but she's obviously lying about her age. In the CD Drama, "The Story of Mewtwo's Origin", the action takes place 18 years before Giovanni owns a Mewtwo. In the story, when Jessie's mom is sent on her mission, her daughter is several years old. (I read that her age in Japan is supposed to be mid-twenties.) And when she and James attempted to enter National Park's Bug-Catching Contest, the contest helper refused to let them in. He claimed the contest was open to children 16 and under "and you two look a LOT older than that to me!" Obviously, then, Jessie is older than 17.
Jessie has owned a number of Pokemon: she received an Ekans for her birthday, which evolved into Arbok in "Dig Those Diglett!" She also caught a Lickitung on Princess Day after it ate the presents she bought for the Boss. She caught a Shellder on the Seafoam Islands but, it clamped onto a Slowpoke's tail, evolving it into Slowbro, and she lost it. Jessie's Pokemon got her to the finals in the Queen of the Princess Festival Contest. If Misty had used her Starmie (as she had planned to), Jessie would have won.
Lickitung accidentally was traded for a young boy's Wobbuffet. Wobbuffet always pops out of his Pokeball at inopportune moments, often spoiling TR's disguises. This patient Pokemon has become Jessie's equivalent of Psyduck, always coming out before being called. However, Wobbuffet isn't completely useless; his Counter and Mirror Coat attacks have had some minor successes. Still, TR is often annoyed by the fact that Wobbuffet can't initiate attacks, but can only return another attack.
After Arbok and Weezing bravely rescued the poacher's Ekans and Koffing in "A Poached Ego", Jessie was sad to see her old friend go. However, she quickly captured another poisonous snake when she met Seviper (known for his devastating Poison Tail attack). She also captured a Wurmple in the Hoenn region, and was instantly thrilled with how cute it was. She and May would often get into heated disputes regarding whose Wurmple was the smartest, cutest, most talented, etc. When Jessie's Wurmple evolved into a Cascoon, she argued that it was really a Silcoon (despite protests by James and Meowth). Surprisingly, she was delighted when it finally evolved into a toxic Dustox (which she plans to enter in Pokemon contests).
Jessie is a Rocket of many talents: she is an accomplished hairstylist, fashion consultant, wine taster, florist, costume designer, etc. but she would like to add "Pokemon Master" to her resume (which is why she tried to pass the Pokemon Academy exam). She attempted to compete in the Indigo League competition by re-stealing the badges that she, James, and Meowth initially stole from another trainer whose name I can't remember.
Jessie gives most of the orders in her team, bossing around James and Meowth. She carries a paper fan and a large mallet with her which she occasionally uses on her teammates. She is also quite skilled with firearms, particularly bazookas. More than any other member of her team, Jessie wants to be exceedingly wealthy (probably because she grew up with nothing). She is very concerned with her appearance, and becomes irate whenever Meowth Fury Swipes her face. She is also incredibly proud of her long red hair, calling it her "crowning glory", and claiming that her hair was her only friend when she was growing up. Jessie's only known fear is roller coasters. On the Island of Giant Pokemon, Jessie panics when the whole gang is trapped on a runaway roller coaster that is about to turn upside down.
Before she met James, Jessie had been "friends" with Cassidy, who is now her arch-rival. Jessie claims their friendship ended for one reason: "She was jealous because I was so beautiful." Upon their second recent meeting, Cassidy maliciously hints that Jessie's getting kicked off Team Rocket.
Somewhere along the way, Jessie had a boyfriend. It seems like she knew a brown-haired boy when she was very young, and she carried his picture around with her for awhile. She claims he was her "first love" but this is uncertain.
Jessie did have a short romance with a brown-haired guy before she met James; this may be the same person as in the picture. She suffered a heartbreak from this guy (as seen in "Wherefore Art Thou, Pokemon") and wonders why she hasn't found love.
Of course, Jessie and James are always together, which suggests that they're each other's perfect match, but we'll see what happens...
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