James is probably near the top of most lovable villains. From his cross-dressing trend to his goofy personality, all these quirks have made him beloved by the Pokémon fandom. Having known him from the beginning of the show till now, it can easy to forget he plays a villain role.

We’ve seen that he loves his Pokémon to the point where some fans even think he would make a better protagonist than Ash. A lot of fans love and even look up to the Team Rocket gang due to the fact that they never give up. When they accomplish something, it actually feels like they accomplished something instead of just doing what’s expected of them like when Ash succeeds.

Like what was revealed in our Jessie article, there is more to James that meets the eye. With about one thousand episodes of Pokémon, it can be easy to miss the certain episodes that touch on James’ past and present. As you will see from this list, in a way, he’s the exact opposite of Jessie.

He has a different backstory than any of the other main characters, starting off with what one would consider a comfortable life. Despite that, he constantly challenges himself and gets out of his comfort zone.

So let’s see what more there is to know about this caring underdog of a villain.

30 He Has Millionaire Parents

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You would never expect a grunt to come from the one percent, but James is that guy. Much about his family history was revealed in the episode, “Holy Matrimony!” We learned the parents are oblivious to James’ feelings and constantly forced him to do things he did not care about to develop him the perfect aristocrat.

They even set up a marriage for him as a kid, but we will get more into that later.

It’s still unknown what the parents did to become millionaires. It’s all probably old money.

29 His Pokémon Show Him Affection By Hurting Him

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James is loved by his Pokémon, but that’s not necessarily a good thing for his health, since they usually show affection by hurting the man. The list of Pokémon that lovingly attack him includes Mareanie, Cacnea, Carnivine, and Victreebel. Why does this happen? Well, it’s for humor’s sake.

It is a kid’s show and like Tom and Jerry has proven: pain can be funny.

The Pokémon usually can’t help it either. Cacnea is a cactus so it can’t help but hurt James when it wants to give him a hug.

28 Marries Jessie In The Manga

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The fandom is pretty split apart when it comes to this fact. In the manga, The Electric Tale of Pikachu, James and Jessie are shown as a married couple by the end. That’s not all either, Jessie is pregnant.

This is not canon anywhere else, yet. What got a lot of fans upset was that Jessie is shown to be a bossy to James. In the contenxt of Pokémon, it's kinda funny (and cute) — after all, these are the villains!

27 He Is 25 Years Old

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According to his wiki page, it was revealed that James is 25-years-old in the un-dubbed version of the Pokémon Movie 2000. In the scheme of things, the age of most of these characters is pretty arbitrary.

There are enough theories about Ash’s age to fill a thick book.

Though it does make one wonder how old James was when he ran away from home. He was definitely younger than ten, which is Ash’s age when he begins his journey. In other words, James hasn’t felt the comforts of home for a very long time.

26 Was Engaged Before Joining Team Rocket

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A big factor in James running away from his millionaire life was an arranged marriage created by his parents. James was to marry Jessebelle, a bossy rich girl who tormented James. What’s interesting about Jessebelle is that she’s a doppelgänger of Jessie. They look alike; have similar names, and similar personalities. Both are controlling, obsessive, and stuck-up.

In the episode, “The Treasure is all Mine,” it’s revealed that child James did once have an interest in Jessebelle before finding out about her personality.

25 Failed Pokémon Tech School

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Pokémon Tech School is a place for Pokémon trainers to study, train, and battle their Pokémon in preparation for taking on the Pokémon League without having go to on a journey and collect badges like Ash.

Makes sense that not all kids can go out camping for years.

James went and failed with miserable grades and met Jessie, who also failed. What’s confusing is that if he ran away while still so young, he could have easily gone on a Pokémon journey of his own without the school. Why didn’t he?

24 Was Part Of A Biker Gang

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This likely occurred right after failing tech school since James and Jessie did this together. In the episode, “The Bridge Bike Gang,” James and Jessie reveal their past as part of a biker gang in Sunnytown. Jessie was known for swinging a chain above her, giving her the name, “Chainer Jessie.”

James hilariously was known for using training wheels, which got him the name, “Little Jim.” Why they left the biker gang was never revealed and some Johto episodes retconned this information by having Jessie and James meet differently in different flashbacks.

23 Has Loving Grandparents

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While the relationship with his controlling parents is shaky, James is very close to his grandparents. Adorably called Nanny and Pop-Pop, they first appeared in the episode, “Sweet Baby James.”

They live in one of the family’s vacation cottages and take care of sick Pokémon and the mansion's greenhouse and garden.

We learn in the episode that James loved to visit them because they did not force him to be proper like his parents did. He also kept his job in Team Rocket secret from them for a long time.

22 He Doesn't Think His Hair Is Blue

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There is a mix of opinions from fans as to the colors of James’ hair. Some think it’s purple and others think it’s blue. Many say that the shade has changed throughout the series.

In one episode, however, James reveals to think his hair color is “lavender.”

Meowth tells James not to worry his little blue head about an issue to which James, obviously offend, quickly interjects, “Its lavender.” The most detailed of fans though, still think his hair is periwinkle.

21 Wore A Hat In His Concept Art

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Ken Sugimori, the lead artist for the original 151 Pokémon, also did concept work for Team Rocket that he later released on his Twitter page. In his drawing of James, James is wearing a hat that makes him more similar looking to the other Team Rocket grunts.

The shadow the hat makes on James’ face make him look more evil and serious.

Why the hat was dumped is not known. What we do know is that back then, Sugimori had no idea how recognized his creations would become.

20 Least Villainous Member Of The Trio

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Out of the Team Rocket trio, James has proven time and time again that he has the kindest heart. He considers his Pokémon as friends, usually crying when having to release one and babying them like they are his kids. The feeling is obviously mutual, as his Pokémon often hug him (usually hurting him in the process) when they are supposed to be battling.

His submissive personality might have been why a kind guy like him got into Team Rocket in the first place.

19 Sometimes Called Jimmy

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Including being known as “Little Jim,” turning his training wheel biker gang days, he is sometimes called Jimmy by Meowth. This is not an unusual nickname for a James, though why is it only Meowth that calls him that?

Meowth is known to view his companions as inferior, so it’s possible this nickname is used to just infantilize James.

James being the most submissive of the trio, would allow that nickname. Jessie would probably beat up Meowth if he tried a cute nickname for her.

18 Has Won A Pokémon Orienteering Contest

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It’s easy to overlook times when Team Rocket is competent when there is a sea of failures under their names. However, some episodes have hinted upon James’ talents. Due to how he was raised, he has a skill for Pokémon orienteering and won a competition with his Mime Jr. in the episode, “Off the Unbeaten Path.” He even gives part of his prize to Ash with no hesitation, much to Jessie and Meowth’s dismay.

The contest consisted of exploring an island and finding checkpoints.

17 History Of Dres Up

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This man is a cross-dressing champion. When it comes to disguises, he typically plays the part of a woman even though that’s not even required.

He has dressed as nurses, schoolgirls, brides, ballerinas, and even as Jessie.

James typically steals the show when he cross-dresses, with some episodes even getting banned due to his level of dedication. While cartoons typically dressed men in women’s clothes just for humor, it also made James an inspiration in defying gender norms and just doing what makes him happy.

16 Won A Contest Ribbon For Jessie

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In the episode, “Dressed for Jess Success,” James cross-dresses as Jessie and wins the Lilypad Town Pokémon Contest for her. The reason Jessie could not go in the first place is due to sickness and James and Meowth convince her to rest instead of attending the contest.

That’s so sweet, but Jessie does get mad at James by the end because the crowd liked him more than they ever did with her and vows to never miss a contest again.

15 Has Deep Bonds With Pokémon

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Many fans have argued that James one of the best Pokémon trainers on the show. This could be because his best and only friend as a child was a Pokémon, his Growlithe. He has rescued Pokémon numerous times including Carnivine and Mareanie.

When he releases his Pokémon, he is very emotional about it.

He also often asks permission before catching his Pokémon. We also can’t forget when he took care of his sick Chimecho when it had a fever. He loved Chemecho so much that it often was outside of its ball. He also cried like a baby when Inkay wanted to stay with him.

14 His Cross-Dressing Got An Episode Banned

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James is nothing if not dedicated. In the episode, “Beauty and the Beach,” he went as far as to buy some inflatables so he could pull off a swimsuit. This aired in Japan without any question, but it was deemed too racy for Western audiences. In fact, it was banned in all countries outside of Asia.

The episode took three years to air in dub with the questionable scene edited out. Since it’s centered on a swimsuit contest, there are other low-key creepy elements other than James’ level of dedication to his craft.

13 His Mareanie Has A Crush On Him

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James’ Pokémon are known to love him, but Mareanie takes it a step further. It acts more like it has a crush on him than anything. During Professor Burnet and Kukui’s wedding, we even see Mareanie daydreaming about marrying James.

She even gets jealous of other Pokémon, thinking they also want James.

This crush formed when Mareanie saw James look purple like her kind after he was poisoned. The whole thing is very weird. It’s not the first time though, as Ash’s Bayleef had a crush on him too.

12 Has Appeared In Every Pokémon Movie

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With 18 Pokémon movies and counting, it’s impressive that every single one has James and his gang. In many ways, they are just as consistent as the main protagonist. Their appearances in every film are due to their dedication to stalking Ash.

Their role in the movies is typically not big ones. In fact, the Team Rocket trio are typically in the background and only used for humor. Sometimes they are very useful though, like when Meowth was Mew’s translator in the first movie.

11 Hasn't Evolved A Pokémon Since 2003

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The last time James evolved a Pokémon was in the episode, “Here's Lookin' at You, Elekid.” That was 15 years ago. In the episode, James trades his Victreebel for a Weepinbell with the Magikarp Salesman. The new Weepinbell evolves and that’s the last time James evolved a Pokémon.

This also makes James the only character in the show to trade a Pokémon and then get another of the exact same species.

Other Pokémon he evolved in the past included his original Victreebel, Weezing, and a Gyarados.