James was born to a rich family and spent his childhood years having everything his heart desired. However, he always hated how upper-class society had rules for absolutely everything, and his only friend on the stuffy estate was Growly, his loyal Growlithe.
As a boy, James loved Kids' Day: he used to have the day off school, and would swim in his Olympic swimming pool and eat nothing but ice cream sandwiches all day. James also enjoyed eating candied grapefruit peels, given to him by the family's servants. When James would become bored on the estate, the servants would take him fishing in the pool, which he found very upsetting because he never caught anything. James had a run-in with Stun Spore as a child, and his grandpapa cured his illness with Salveo Weed. His grandma used to grow Sunflora on her estate, which is how James knows so much about them.
Needless to say, James had the best of everything growing up. Nearly every stitch of clothing he owned was made of expensive Mareep wool. As a result, he was beat up by his envious schoolmates almost every day.
At a young age, James was engaged to Jessibelle, a respectable girl from the "proper South", through an arranged marriage. Jessibelle, who bears a disturbing resemblance to Jessie, was even more obsessed with society's rules than his parents were. She followed him around constantly, trying to change him; nothing he did was refined enough for her. Finally, James couldn't take it anymore and fled the luxurious estate with Jessibelle screaming after him, "You're not runnin' properly!"
Several years later, James attended Pokemon Tech, an elite school for future Pokemon trainers, where he met Jessie. The two of them became good friends, and were confident that they would score higher than anyone else. They were so confident that they "frolicked all night, for their future seemed bright". As a result, they "got the lowest scores in the history of the school".
After flunking out of Pokemon Tech, the pair headed for SunnyTown, where they joined the Bridge Bike Gang. James was known as "Little Jim" or "Trainer James" because he was the only member of the bike gang who had to use training wheels.
James is not the smartest member of his team (actually, he's a bit stupid), and usually does most of the actual physical work. (Jessie gives the orders, and Meowth comes up with the plans.) He has also been known to go berserk at times ("All Fired Up" and "A Chansey Operation"). He is also the most "fashionable" member of the team. Whenever Team Rocket has to come up with a clever new disguise, James occasionally has to dress up like a girl, but it makes sense given the situation. Think about it: if you were a twerp who was constantly being pursued by a red-haired girl and a blue-haired guy, you'd never guess that a red-haired GUY and a blue-haired GIRL would cause problems, right? Remember, Ash isn't noted for his observational skills nor his intellect. Hence TR's disguises usually work.
James loves to eat, and is even more obsessive about food than Jessie and Meowth (particularly when it comes to donuts!) James adores expensive bon-bons, but due to Team Rocket's lack of financial success, he has had to make due with cheap hard candy instead.
James received Koffing as a Christmas present, and this poisonous Pokemon evolved into Weezing in "Dig Those Diglett". James acquired a Weepinbell from somewhere (maybe he stole it from Dr. Proctor's hospital?), and it evolved into a very nasty Victreebel in Butch and Cassidy's Breeding Center ("The Breeding Center Secret"). Weezing is a pretty good Pokemon, who usually provides "Smokescreens" that enable TR to make their getaways. Victreebel is pretty useless, since it always begins a battle by trying to chomp on James (or someone else) and gets knocked out very quickly. His only decent Pokemon, Growly, stayed behind at the estate to look after James's parents.
James lost his Victreebel, and Weezing left with Arbok to help a lost group of Ekans and Koffing that a poacher had stolen ("A Poached Ego"). However, James soon made a new friend in Cacnea. This lovable little cactus joined James after he fed it some cookies, and it's been trying to repay him with prickly hugs ever since! Cacnea's signature attack is his Pin Missle move, often used in conjunction with Seviper's Poison Tail.
Besides his desire to steal lots of Pokemon and become rich, James has a secret wish to become a Pokemon Master (which is why he enrolled at the Pokemon Academy). He collects bottlecaps and is very proud of his collection. He also carries with him a strange collection of junk that has "sentimental value", such as photos of himself ("I like to look at myself in my spare time!"), pogs, the rings from soda cans, broken sunglasses, and of course, his rose.
James is a "triple threat", able to sing, dance, and act. We've all heard his singing voice (in "The Song of Jigglypuff" and the song, "Double Trouble") but he's also "accomplished" in acting and dance. He took three semesters of stage movement at a respected correspondence school, and his parents enrolled him in modern dance classes when he was a young boy.
James seems to be the only member of his team who can actually drive (although Meowth has tried a few times), although he doesn't have a driver's license. James is also the only member of his team to have ever stolen a Pokemon: in "A Chansey Operation", he gets away with a Voltorb, which promptly self-destructs and sends them all blasting off again. At least he got something!
James seems to have a magic touch, er, kick when it comes to evolving Pokemon. Twice, his kick caused a Pokemon to evolve: in "Pokemon Shipwreck" he kicked his useless and expensive Magikarp, evolving it into Gyarados, and in "Primeape Goes Bananas", he kicked a Mankey, evolving it into Primeape. But maybe it's more than just his kick... in "The Wacky Watcher", the Magikarp that gets stuck on his head evolves into Gyarados as well. Too bad none of these evolutions ever help out Team Rocket!
James and Jessie are never far apart, but the question remains: how does he REALLY feel about her???
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