While a lot of things about the Pokémon anime have changed over the twenty years it's been on the air, one thing has remained constant: the presence of Team Rocket. Jessie, James, and their talking Meowth have followed Ash Ketchum and his friends across numerous Pokémon regions in the pursuit of his prized Pikachu. Admittedly, they're not exactly very good at their jobs, since none of their schemes have actually succeeded. Still, Jessie and James did recently manage to defeat Ash in a battle for the very first time! Their fortunes could be changing!
All three members of the anime's Team Rocket trio have become characters that Pokémon fans love to hate. While they're all amusing characters in their own right, the pink-haired Poison-type trainer Jessie is perhaps the most fascinating. She's a hardened criminal with a secret passion for entering Pokémon Contests. She's clearly a hopeless romantic, but she's also incredibly rude to pretty much every guy she meets. Jessie has a mysterious and pretty sad past, which maybe explains why she chose a life of crime. Does she have a heart of gold behind her tough-girl persona, though? That's still up for debate!
We've been watching Jessie's Pokémon anime antics for over two decades now, so it's perhaps unsurprising that a few plot holes and confusing continuity errors have cropped up over the years. As much as we all love the anime, there are certain things about it that are a bit confusing—including some of its characters! Prepare to be baffled by these things about Jessie that make no sense.
25 What Happened To Her Mother?
All things considered, poor Jessie has a bit of a sad backstory. Her tale of woe begins with the disappearance of her mother when Jessie is still a young child. The story goes that Jessie's mom, a Team Rocket agent, went missing in action while on a mission to find the legendary Pokémon Mew.
However, her fate is still a point of confusion.
Some episodes of the anime hint that she's passed away; others suggest that she's still out there. If the latter is true, though, why hasn't she tried to contact Jessie? It's all very mysterious.
24 Her Gravity-Defying Hair
Jessie's most distinguishing physical feature has to be her bright pink, incredibly long hair. Jessie simply wouldn't be Jessie without it! Still, we have a lot of questions about her perfectly coiffed and curved locks. How on earth do they manage to stay in shape throughout all of Team Rocket's energetic and madcap antics? How much hairspray must Jessie have to use to keep her hair in its signature shape? Anyone who's had long hair will know that gravity takes its toll on every style eventually—except Jessie's, apparently.
23 Her Time At Pokémon Nurse School
In an episode of the original Pokémon anime series, Jessie reveals that back in the day, she actually trained to become a Pokémon nurse.
However, she failed her final exams thanks to one crucial issue.
The programme of study was designed for Chansey, whereas Jessie was a human who lacked this Pokémon's natural healing powers. To be honest, this whole situation begs a lot of questions. For one, who actually let a human enroll on a course meant for Pokémon? Was there a huge administrative failure on the school's part? What a bizarre situation!
22 Her Pre-Team Rocket Careers
Jessie's brief stint as a trainee nurse isn't the only career she pursued in her pre-Team Rocket days. In fact, for a young woman, she's had an awful lot of incredibly varied jobs. Various episodes of the Pokémon anime reveal that Jessie has worked as a professional singer; a model; a ninja; and a TV weather presenter. How did Jessie have the time to pursue all of these different careers before deciding to join Team Rocket? She's still in her early twenties if Pokémon canon is anything to go by! Or is she? More on Jessie's age later...
21 Her History With James
How exactly Jessie and James came to be literal partners in crime is a point of some contention amongst Pokémon anime fans. The show has actually contradicted itself when it comes to how and when this duo met. One episode claimed that they'd become friends when they were both in the same biker gang, way before either of them joined Team Rocket. However, another episode suggests that they first met as Team Rocket Grunts—and actually didn't get on to begin with! Which origin story is the real one? It's still unclear.
20 Her Unconvincing "Disguises"
From the very beginning of the Pokémon anime's run, one thing about Team Rocket has remained constant: their habit of using absolutely bad "disguises". What's worse is the fact that everyone seems to fall for Jessie, James, and Meowth's frankly terrible attempts at blending in! It's like Ash, his companions, and even Officer Jenny have some form of amnesia that means they're unable to recognize the same three criminals they've been dealing with for years. All these guys do is throw on a new outfit or a fake mustache! You can totally still tell it's them!
19 Her Choice Of Pokémon
To be honest, this is a complaint that's relevant to a lot of Trainers in the Pokémon anime. Why does nobody actually think to use truly powerful Pokémon in battle or in their daily lives? Everyone from Officer Jenny to Ash himself is guilty of this.
Jessie is no exception.
Her grand plans and schemes would run a lot more smoothly if she had some genuinely amazing Pokémon backing her up. Instead, she insists on keeping Wobbuffet around. Just get a Mega Blaziken or something, Jessie!
18 Her Obsession With Pikachu
Speaking of Pokémon that aren't that great... Why is Jessie still so obsessed with stealing Ash's Pikachu? There are so many amazingly powerful Pokémon out there that she and James could seek out, but instead, they're obsessed with an honestly mediocre electric mouse. Plus, Pikachu is hardly a rare Pokémon—Jessie could have caught her own by now. Basically, both she and James need to seriously re-evaluate their life and career choices. If they're going to bee Pokémon thieves, they might as well target some more impressive ones!
17 That Time She Became "Queen Of All Pokémon"
There have been dozens and dozens of slightly bizarre Pokémon anime episodes over the years, but the one where Jessie becomes the "Queen of Pokémon" has to be one of the strangest. For anyone who's forgotten about this particular storyline, Jessie comes across an ancient mask that enables her to channel the power of a long-gone queen and thus control the majority of Pokémon. However, the mask only works in a particular small village in Johto. Ummm... What? Not only is the existence of this mask frankly confusing, the fact that Jessie got hold of it is more than a bit spooky.
16 Her Blatant Fake Names In Contests
As we've already mentioned, one of Jessie's biggest passions—outside of being a Team Rocket member, of course—is participating in Pokémon Contests. When Jessie decides to join the contest scene, she realizes that her awful Team Rocket reputation might put her at a disadvantage. So, she uses a fake name while competing!
Good plan, right?
Well... almost. Instead of coming up with an imaginative pseudonym that's totally different from her real name, she uses Jessilina. She just sticks "lina" on the end of her actual name. Still, it somehow manages to fool basically everyone!
15 That Time She Borrowed Ash's Aipom
You don't have to watch the Pokémon anime for long to realize that Ash and Team Rocket aren't exactly on the best of terms. For one, Jessie and James have been trying to steal Ash's beloved Pikachu for years now! You can see why they might not get on. Despite this, though, Jessie once managed to convince Ash to lend her one of his Pokémon! She has the audacity to ask for Ash's Aipom to use in a contest—and he agrees! Why on earth would he trust Jessie with his Pokémon after all she's put him through?
14 Why She's Still In Team Rocket
After years and years of botched plans and failed attempts to steal Pikachu, you've got to wonder why Jessie is still a member of Team Rocket. For one, you'd think Giovanni would have sacked her by now!
She and James don't exactly have a very good track record.
Plus, surely having such an impressively long list of failures would lead Jessie to the conclusion that thieving isn't for her? Why hasn't she just quit and become a full-time Pokémon Co-ordinator already? She has a talent for participating in contests—surely she should pursue that?
13 Her "Relationship" With Dr. White
In the X and Y series of the anime, Jessie meets and briefly falls in love with a man named Dr. White. Dr. White saves Jessie and her Wobbuffet from drowning, and after spending about five minutes with the guy, Jessie is smitten. In fact, she's even willing to quit Team Rocket for good in order to pursue a relationship with Dr. White! Yep, that's right: she's willing to abandon her two best friends and quit her career to be with a guy she's known for around five minutes. Surely even Jessie isn't that much of a hopeless romantic?
12 Why Everyone Is Okay With Her Violent Temper
In the early series of the Pokémon anime, one of Jessie's defining characteristics was her volatile and often violent temper. She would frequently have extreme episodes of anger in response to seemingly minor events, and would even physically attack James, Meowth, and her Pokémon at times. Thing is, nobody ever tries to call her out on this behavior—they just sit back and let Jessie explode! That's not exactly the best example to set to children, which the anime's producers seem to have realized. Jessie's temper is much more moderate in newer seasons!
11 Her Incredibly Impractical Outfit
Now, don't get us wrong: we love Jessie's Team Rocket outfit. Those thigh-high boots are the height of fashion, and the general ensemble makes her look like a total badass. However, you've got to wonder just how practical the crop top/miniskirt/boots look is when you're a Team Rocket operative working in the field. Jessie and James are pretty active people—they're always dashing about here and there, trying to steal Ash's Pikachu. Surely a slightly more comfortable outfit would be more in Jessie's interests? Just a thought!
10 Her Change In Personality In Unova
In the Best Wishes season of the Pokémon anime, Jessie and James both undergo a pretty marked personality change. They've been assigned a new, super-secret mission in the Unova region, and for some reason, that leads them to totally lose their sense of humor. They both turn into pretty competent and also incredibly boring characters! Who thought that was a good idea?! The shift was so pronounced compared to Jessie and James' previous personalities that fans began to complain. Eventually, the anime's writers decided to revert Team Rocket to their old, slightly goofy selves.
9 Why Her Pokémon Even Obey Her
Throughout both the Pokémon anime and the video game series, it's made pretty clear that in order for your Pokémon to perform well in battle, a Trainer has to have some kind of emotional bond with them. It's impressed on Ash and his friends again and again by Pokémon professors and experts that they should love and cherish their Pokémon—if not, the likes of Pikachu and Charmander might not actually obey their trainer! This begs a pretty huge question: why do Jessie's Pokémon actually fight for her? She's consistently rude to them, and pretty mean too! Not cool...
8 Her Actual Age
Jessie's real age is one of the great mysteries of the Pokémon anime. At one point in the original anime series, it's suggested that she and James are the same age as Ash. However, that seems unlikely.
Neither of them exactly look ten years old!
Plus, a piece of merchandise available only in Japan suggests that Jessie and James are in their twenties, which seems more likely. Still, in different anime episodes, Jessie tries to claim that she's 12 or 17. Which is the true number? Nobody knows!
7 Her Real Feelings For James
While Pokémon is very much a child-friendly TV show, its fans still love to speculate about romantic entanglements between many of its main characters. A lot of viewers are totally convinced that Jessie and James are secretly in love, and honestly, we can see why! These two are clearly very fond of each other, and Jessie becomes very jealous when it emerges that James has a long-lost fiancée. Seriously... Can they just admit their feelings for each other already? It probably won't happen, but hey—fans can dream!
6 Her Minimal Role In The Games
Despite the fact that Team Rocket feature in a number of Pokémon games, Jessie has only cropped up in one so far: Pokémon Yellow. To be honest, the fact she and James appear in Yellow makes sense. This game deliberately incorporated elements of the anime into its storyline. However, you'd think that Game Freak would have utilized these popular characters a bit more throughout the series! Instead, we're faced with legions of generic Team Rocket Grunts. At least it's been confirmed that Jessie and James will feature in the upcoming Switch games Let's Go, Eeeve and Let's Go, Pikachu!
5 Her Resemblance To James' Mother (And Fiancée)
You know how we mentioned that James has a secret fiancée who crops up in a couple of anime episodes? Well, there's one other thing about this mystery woman that you should know. She's basically a carbon copy of Jessie! Not only is her name Jessebelle, her hair color is very similar to Jessie's and her facial features are identical. On top of that, James' mother also has basically the same face as Jessie and Jessebelle! Is this a coincidence, corner-cutting by the show's animators, or some kind of deliberate, hidden connection? Nobody's quite sure...
4 Jessie's Overprotectiveness Of Her Hair
While Jessie's hairdo is undoubtedly very impressive, Jessie frequently takes things a bit far when it comes to protecting it. Many of her outbursts of violence in early anime episodes related to characters attempting to mess with her locks. One time, Jessie has actually lost some of her hair thanks to an errant Scyther chopping it off, and she totally lost it. That's fair enough, in a way... But if she loved her hair that much, wouldn't Jessie take the time to tie it back when around a Pokémon that's a walking pair of scissors? Apparently not...
3 Her Lack Of Pokémon Knowledge
Considering both Jessie and James have made it their life's mission to capture, steal, and make money from Pokémon, neither of them actually know much about the creatures they seek to catch.
To be honest, their lack of Pokémon knowledge is pretty striking!
Jessie and James often show little awareness of type matchups, how evolution works, and what moves certain Pokémon learn. We know from one anime episode that they failed out of the Pokémon School, but surely Team Rocket would have given them some training, right? Apparently not!
2 Her Constantly On-Point Lipstick
It's very rare that Jessie is seen without her trademark red lipstick. Come rain or shine, whether she's in disguise or not, that lipstick is present—and it's perfect! Honestly, it's both impressive and a bit confusing. Jessie regularly "blasts off", crashes into things, and generally makes a mess... but her lipstick remains pristine.
There's no smudging at all!
Where can we get ourselves a product like that? A lipstick that can withstand explosions, Pokémon attacks, and other extreme conditions: that's the dream!
1 Her Actual Opinion Of Ash
As we've already mentioned, Team Rocket and Ash are basically straight-up enemies. After all, it's difficult to have a positive relationship with somebody if your aim in life is to make their life a misery. Still, there have been plenty of occasions in the anime when viewers have been left wondering whether Jessie and James really hate Ash or not. They've supported him in his major battles, help to save his life on a number of occasions, and seem to care about his welfare. Perhaps they're both great big softies at heart!