Ever since Ash first set off from Pallet Town to become a Pokémon Master, he's been relentlessly pursued by a trio of hapless Team Rocket agents: Jessie, James, and their talking Meowth. The group made their debut in the Pokémon anime in the episode, "Pokémon Emergency," when Ash's beloved partner, Pikachu, was sent to the Viridian Pokémon Center for urgent medical treatment. Jessie and James set their sights on nabbing the wounded Pokémon inside in the name of Team Rocket's leader, Giovanni. (Kidnapping Pokémon is Team Rocket's M.O.) But, their plans were foiled when Ash's Pikachu galvanized a whole bunch of sick Pikachu to overload the Center with electricity. The resulting explosion led the threesome to believe that Ash's Pikachu must be a particularly strong one, and they've been chasing the little, yellow electric mouse ever since.
While Jessie and James had a limited role in the Pokémon video games and manga, they've become Ash and company's most consistent antagonists in the TV series, as well the show's main source of comic relief. The animated series has been on the air since 1997 and in that time Jessie has set her sights on many other goals outside of Pikachu and the "twerps." She enjoyed a season-long career as a Pokémon Contest competitor and even tried to make it into Kanto's Pokémon League. (Unfortunately, during the admissions exam, she couldn't control her legendary temper in front of one of the theory examiners and was promptly ejected.) She's even attempted to strike out on her own a couple of times, but her bond with James and Meowth always proves too tight to break.
20 ALL THAT HAIR IS ALL-NATURAL
Anime fans are well-acquainted with the medium's ridiculous hair trope. Usually, it's easy to spot who our main cast will be: just look for the neon-colored, impossibly styled hair in the crowd of ordinary brown and black heads. Pokémon's Rocket trio are no exception and James' purple bob and Jessie's long magenta side-do help distinguish them from their Team Rocket colleagues.
As viewers, we're supposed to accept that these looks are completely natural, evidenced by flashbacks to Jessie as a child, where her hair looks exactly the same as it does when she's an adult. We also learn that Jessie grew up extremely poor, so she couldn't have been able to afford to style her hair that way every day. It may seem impossible, but that's just anime for you.
19 HAIR TODAY, GONE TOMORROW
While we're on the subject of what's on Jessie's head, it's worth talking about the hair-related mishaps she's endured during the Pokémon animated series. Because of the close relationship people and Pokémon share, it's sometimes easy to forget that they are actually wild animals, particularly the ones that are actually wild. This makes them somewhat unpredictable — even dangerous.
Jessie learns this the hard way... twice. In the episode, "Tracey Gets Bugged," a group of wild Scyther attack the Rocket trio and lop off a huge chunk of her hair, taking it from hip-sweeping to just above her shoulders. Then in "A Tail With A Twist," a wild Seviper pulls most of it off with its mouth. Ouch! Jessie is understandably enraged both times.
18 WHAT'S IN A NAME?
Most Pokémon fans know that Jessie and James' English names were taken from the famous American outlaw, Jessie James. (Their rival Team Rocket colleagues, Butch and Cassidy were similarly named after... Well, you can guess.) Lesser known is the origin of their original Japanese names. Just like in the English dub of the anime, the names were taken from real historical figures.
Jessie's name, Musashi, comes from the legendary Japanese warrior, Miyamoto Musashi, whose most well-known battle was against Sasaki Kojirō, after whom James was named. Some fans reckon Musashi could also be a reference to a WWII-era Japanese battleship of the same name, because Cassidy's Japanese name, Yamato, also sounds like a naval warfare reference.
17 SEEING DOUBLE
While Jessie came from an impoverished background, James was born with a silver spoon in his mouth. His millionaire parents made sure he wanted for nothing, but young James resented the restrictive rules and formalities of the high-class society they were apart of. These restrictions included who to marry, and James was forcibly engaged at a young age to a girl named Jessebelle.
Sounds familiar, right? Well, not only did Jessebelle's name echo his future Team Rocket partner, but she looked exactly like her, too. Even weirder, so was James' mother. Though James initially liked his fiancee, her arrogance began to grate on him. Eventually, he ran away, but his choice of life-partner in Jessie clearly shows he's haunted by his past.
16 A HARD KNOCK LIFE
Jessie's appetite in the Pokémon animated series is almost as legendary as her temper, and there's a heartbreaking reason behind this. Jessie's mother, Miyamoto, was a Team Rocket agent who was sent off on a Mew-related mission when Jessie was just five-years-old. Sadly, Miyamoto never returned, leaving her daughter to go into foster care.
The home she lived in was very poor and food was scarce. Remembering how her mother would make sushi for her, Jessie decided snow would make an affordable substitute for rice — desperate to recreate the happy memories she had of her. It's a tragic detail that belongs more in something like Grave of the Fireflies, not the innocuous Pokémon anime.
15 AGE IS BUT SEVERAL NUMBERS
Jessie's age is a bit of a Poke-mystery. In Pokémon: The Power of One, she and James are claimed to be 25-years-old, but when it comes to the series — which has had many soft reboots over the years — finer details like age have become very inconsistent, evidenced by a main protagonist who doesn't seem to have aged a day in over a decade.
In one episode, "The Ultimate Test," Jessie writes down her age as 17 on a form. But, in "Plant It Now... Diglett Later," she tells an elderly woman that she's "ten times" her age. As the woman is 120-years-old, that would make Jessie just 12. Seeing as she received record-low scores at the Pokémon Tech School, we probably can't rely on her math skills, though.
14 HAIR-RAISING COLOR
You might not have even noticed it, but Jessie's distinctive hair hasn't always been the same color. At the start of the Pokémon anime, it was red, matching the black, white and red color palette of Team Rocket. Then from the episode, "Here's Lookin' At You, Elekid," her hair suddenly changed from scarlet to dark pink, a change that was rolled out around across all tie-in media, too.
The change coincided with the show's production switching from cel-shaded to digitally-colored animation, but it's not clear why the subtle alteration was made. Perhaps the animators just decided that magenta popped a lot more than red did, or perhaps, in-universe, Jessie fancied freshening up her old look a little.
13 MISTAKEN IDENTITY
When she's not rocking the Team Rocket colors, Jessie has branched out into many other fields, assuming many false identities to do it. The thing is, none of them are particularly convincing. For one thing, she never bothers to hide the giveaway color of hair, and for another, she never strays too far away from her own name.
Jessebella, Jesslina, Jessadia... Is Jessie really that vain? Of course, this is all part of the joke, especially given that Ash and the gang normally fail to clock her through these disguises, despite Jessie being a part of Ash's life for longer than any of his traveling buddies. Jessie's most successful endeavor as a Coordinator took her all the way to the Pokémon Contest semi-finals in Sinnoh.
12 SHE'S THE MAN
If it wasn't already clear through her copious alter egos, Jessie loves to dress up. As does her partner-in-crime, James. The duo often poses as a couple or double-act, usually to try and trick Ash or one of his friends into handing one of their Pokémon to them. This gives the pair the opportunity to engage in what seems to be one of their favorite past times: drag.
Whether they're pretending to be magicians, a bride and groom, chicken farmers or Gandalf impersonators, Jessie and James can't resist breaking down gender norms and having a bit of fun in the process. The most notorious case of this — involving James donning a bikini — resulted in the first banned Pokémon episode outside of Japan.
11 LIP-SMACKING COLOR
Jessie might live the life of an outlaw but she still finds the time to make sure she always looks her best. And, for her, that means a full face of make-up, including lipstick. As well as her uniquely-styled hair and green earrings, Jessie is rarely seen without bright red lipstick. Even when she switches costumes, the ruby red lips remain in place.
In fact, the only times we haven't seen her wearing it are in flashbacks to when she was very young, or the rare moments where we see her getting changed. This is more than an aesthetic decision — it emphasizes Jessie's obsession with appearance, which is both a key part of her backstory and a comedic flaw in her character.
10 SHARED VOICES
We can thank actress Rachael Lillis for giving Jessie such a recognizable voice. Lillis played the character during Pokémon's first eight seasons before being replaced by Michelle Knotz when the US distribution rights switched hands. It's not uncommon for voice actors to play multiple roles, but playing multiple main character roles is a little more unusual.
In this case, Lillis extended her talents to voice Misty — the first friend Ash made after starting his Pokémon journey— as well as Jessie, which you'd probably never have worked out on your own given how different they both sound. It also means that for certain scenes, Lillis would have been having conversations with herself in the recording booth.
9 ONE WOMAN, MANY VOICES
As well as Jessie and Misty, voice actress Rachael Lillis lent her talents to many non-human characters while she worked on the Pokémon animated series. This included fan favorites like Clefairy, Ninetales and Vaporeon. Lillis also provided the voices of some more notable Pocket Monsters, such as Brock's Vulpix, Misty's Staryu, Tracey's Venonat and Nurse Joy's Chansey.
She even spent a short stint providing the English voice for the most famous Pokémon companion of them all, Ash's Pikachu. Usually, the English dubbed version just reuses Ikue Ohtani's recordings, who has long been the Japanese voice actress for the Pokémon mascot. Ohtani has become such an integral part of the franchise that she's even had cameos in the video games and anime.
8 A MODEL EMPLOYEE
As a kid, Jessie dreamed of being an idol, and while she never achieved this, she did try out a few other jobs — mostly centered around her looks. In the episode "Spring Fever," Ash, Misty and Brock are traveling with Pokémon photographer Todd Snap, who is — yep, you guessed it — the main protagonist of Pokémon Snap.
As Todd tries to capture some shots of a battle, Jessie suddenly feels compelled to step out in front of the camera, explaining to a bemused James that she used to be a model. We also discover in "Xatu The Future" that she had a career as a TV weather girl, too, which undoubtedly would have been another opportunity to strike some more poses rather than bother with accurate forecasting.
7 NURSING SCHOOL DROP-OUT
Another of Jessie's aspirations before the start of the Pokémon animated series was a surprisingly selfless one. When she was much younger, she set her sights on becoming a nurse, leading her to enroll in the Pokémon Nursing School, the student body of which was entirely filled with Chansey.
An eager Jessie continued with her studies, even befriending one of her classmates and helping others who were struggling with the lessons. Unfortunately, she eventually flunked out because, well, the course was designed specifically for Chansey — not humans, meaning there were certain things she naturally couldn't do. Jessie and her Chansey study buddy were later reunited — with Chansey now a Blissey — in the episode, "Ignorance Is Blissey."
6 BAD GIRL FOR LIFE
Jessie's early life was full of promise, leading us to wonder how she ended up being pulled into a gang like Team Rocket. Was she just following in her mother's footsteps? In the Pokémon anime episode "The Bridge Bike Gang," some light is shed onto her miscreant origins.
As Ash, Brock and Misty attempt to cross a bridge into Sunnytown, they're trapped by a group of people on bicycles demanding Pokémon battles. Half-way through the fighting, Team Rocket shows up and are warmly welcomed by the gang who reveals that Jessie and James are ex-members. Jessie earned the nickname "Chainer Jessie" because she'd swing a chain around her head while riding her bike.
5 IT'S ALL BLACK AND WHITE
Ever since they first started tailing Ash and Pikachu, Jessie and James have never strayed from their white Team Rocket uniforms — unless they're trying to disguise themselves. In the Rocket hierarchy, the color of your uniform reflects your ranking. White is only one step above the "grunt" position.
When the gang travel to Unova, they suddenly get a promotion from Giovanni, meaning an upgraded wardrobe too — from white to black. This darker change also affected the tone of their characters, going from comedic to more villainous. It was definitely weird seeing Jessie stray from her usual Rocket white, but the switch didn't become permanent.
4 A LOOSE CANNON
As her job history reflects, Jessie is very looks-orientated. She's also incredibly hot-headed, and the two personality traits combined should make anyone wary about saying anything negative concerning her appearance. Misty bears the brunt of this in the episode, "The Battling Eevee Brother" in the animated series.
After calling Jessie an "old hag," the female member of the Rocket trio flies into a furious rage. Had Misty been a Pokémon this rage might have turned physically violent, as Jessie's been known to attack creatures that damage her body or hair. By now, James and Meowth know to run for cover whenever she feels unjustly insulted.
Jessie has donned many different disguises over the years to manipulate people, but her brief time as the "Queen of all Pokémon" is the closest she's come to having it all. In the episode "Control Freak" of the animated series, Ash, Brock and Misty come across an ancient mask and scepter unearthed at an archaeological dig site.
After learning that the objects once belonged to a long-gone monarch rumored to be able to make any Pokémon submit to her will, Jessie swipes the items for herself and confirms that the rumors are indeed true. Finally, with Ash's Pikachu under her spell, it seemed Team Rocket might have won — until Brock's new Crobat separates her from her new supernatural accessories.
2 TWO ROCKETS AND A BABY
In the anime, Jessie and James' relationship has so far been nothing but platonic. In fact, Jessie values her friendship with James and Meowth so highly that she's always pulled back to them even when other opportunities for happiness present themselves. Jessie wears her heart on her sleeve, after all.
In the Pokémon manga, things turned out very differently for her and James. They're far more touchy-feely with one another and are even shown sharing a bed. Eventually, James admits he has romantic feelings for his long-time partner in crime, which she clearly returns as the last time we see the pair, they've tied the knot — and are even expecting a child together.
1 THE LOOK OF LOVE
Series creator Takeshi Shudo was a big fan of James and Jessie as characters. So much so, in fact, that when the show moved onto the "Advanced" generation in the early '00s, he favored cutting Misty out rather than the Team Rocket trio, believing Ash's female companion to be more expendable than them.
Shudo might have also felt compelled to keep them in the show as Jessie is rumored to have been modeled on his high school sweetheart, as well as the villainous female character, Majo from Time Bokan, a classic anime series from the '70s. You can certainly see the resemblance in Majo's long, sweeping hair.