Team Rocket are one of Pokemon's most memorable villains, with the Rocket trio standing as the most iconic members of the group. Together alongside Meowth, Jessie and James have gone on numerous adventures to capture Ash's beloved Pikachu. Forever "blasting off again", Team Rocket continuously tries and fails to grab the elusive Electric-type.
Team Rocket are not all there is to Jessie and James, they did have other ventures in their lives before joining forces. Before becoming a member of Team Rocket, Meowth came from a poor background and learned how to speak like humans. So what were Jessie and James up to during this time?
Jessie's Rise from Poverty
Jessie describes her childhood as "wretched". Her mother Miyamoto was also a former member of Team Rocket. Miyamoto was the first person to record the voice of Mew, the world's rarest Pokemon. She left Jessie in foster care while she and a team searched to find Mew. Jessie's father is not mentioned in the anime.
Jessie recounts her mother's "snowgasboard" meals as one of her few cherished memories. Her mother made her a variety of her favorite foods from snow because they had to make do with what was available to them, this is evidence of her family's struggle with poverty. Making lemons out of lemonade, a teary-eyed young Jessie exclaims that "this is the best snowgasboard any mommy ever made".
A little older now, Jessie decided to seek stardom as a pop star with two of her friends. She also met Astin around this time, a boy who asked her to leave town with him to become a Pokemon Coordinator. Jessie declined this offer, as she chose to chase her singing dreams with her friends. All three of them auditioned, but only Jessie did not make the cut. This naturally left Jessie feeling absolutely crushed and wondering how her life would have ended up if she left town with Astin.
Her next goal was to become a Pokemon Nurse. She was told it would be extremely hard for her to do so and was thus rejected by the school she was applying to. She noticed a flyer for a Pokemon nursing school for Chanseys and decided to train as a nurse there, depsite the fact that she was the only human there. While she did well, for the most part, the school was designed for Chanseys and their unique abilities. For example, Jessie cannot sing in the special way Chanseys do to make the patient fall asleep. Unfortunately, Jessie did not manage to graduate from nursing school. She did manage to make one friend at school with a fellow Chansey student, who she is later reunited with as an adult.
It has also been hinted that Jessie tried her hand at numerous things before ending up at Team Rocket. She was a ninja, a weather girl, and even a model at some point.
James' Escape from High Society
In a stark contrast to Jessie, James was raised in the absolute lap of luxury. His childhood home is an entire estate with lavish mansions, gorgeous gardens and more. His family have a tradition that they must marry in order to continue the family line.
When he was a young boy, James' parents arranged for him to marry a girl named Jessebelle, who is humerously a doppleganger of Jessie. He names Jessebelle as the reason he ran away. She would chase him all over the place and try to change him into the perfect husband material (at least, according to her standards). Nothing he did was refined enough for her. He hated how upper class society had rules for everything and did not want to be a part of it anymore. Growlithe, his favorite Pokemon, was his only friend as a child.
James soon ran away from home with Growlie, leaving his parents heartbroken. As they were wandering the town in a snowstorm starving and cold, he ended up being unconscious and frozen. He even remembers seeing angels, thinking he was not going to survive. He also briefly mentioned that he flunked out Pokemon Tech and joining a bicycle gang at some point during his new life as a runaway.
In the present time of the anime, James' parents faked their deaths and pretended to bequeathe their entire estate to him provided that he marries Jessebelle. This was all a ruse to make sure that he marries her. After putting up a fight with his parents and Jessebelle (quite literally), he decided to leave his old life behind for good. He always felt out of place in that environment and enjoys his own freedom astronomically more.