Every good hero should have their own iconic foe for which the hero is always trying to thwart. For Batman, there was the Joker. For Harry Potter, there was Voldemort He Who Must Not Be Named. And for Ash Ketchum, there is Team Rocket.

Team Rocket consists of Jessie, James, and Meowth. Their main objective is to try and steal rare and powerful Pokémon for the Team Rocket organization that they work for. They have a memorable catchphrase that everyone can recite, they are great at insulting others, and they come up with intricate plans to steal Pokémon pretty much every episode. They should be the perfect villains for everyone in the Pokémon world to fear.

Unfortunately for them though, Team Rocket's plans always seem to fail because Ash and his friends are around to save the day. So, rather than impressing their boss with stolen Pokémon, they seem to just find themselves "blasting off again"  (which could have its very own list, I may add).

But, as the series went on, they became less of an evil laughingstock and more of a villainous group that demanded more respect. Heck, just recently, Jessie and James pretty much defeated Ash for the first time ever (you'll find out why I say "pretty much" later on). Plus, they have also shown that they are not evil all the time! They have even helped Ash to save the world on occasion, making their characters way more developed and fleshed-out in the process.

For all the good though, there is still a long recorded list of bad things that have happened to the group. So for this list, I will be focusing on Jessie and James (sorry Meowth) and all of the awful, embarrassing, sad, and tragic moments to happen to the Team Rocket duo in the show's history.

Here are the 20 worst things that have ever happened to Jessie and James.

20 Team Rocket's Worst Nightmare Came True In One Single Episode

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Jessie and James are no strangers when it comes to "blasting off again". For the majority of Pokémon's episodes, the running gag of the show would have the Team Rocket members flying through the air in a number of hilarious ways after they were defeated by Ash and his friends. The thing is though, this would usually only happen once per episode. In the episode "Malice in Wonderland!" though, Team Rocket finds themselves hypnotized by a Mismagius and they all find themselves in a dream-like state. Their dream quickly turns into a nightmare as they end up being "blasted off" by multiple Pokémon EIGHT TIMES on-screen in the episode, and it was implied that they were continuing to be blasted off even more times off-screen! This is definitely a record for them, and probably one that Jessie and James are not particularly proud of (or wanting to relive).

19 Learning To Never Kick A Magikarp When It's Down

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Perhaps James was putting too much faith into his Magikarp when he expected it to save him and the rest of Team Rocket when they were going down with a sinking ship. Not knowing that Magikarp are bad swimmers, Team Rocket almost ended up drowning because they thought Magikarp could pull them to safety, only to find out it can only splash around pathetically. After Ash's Pidgeotto saved Team Rocket and brought them to a floating platform that Ash and his friends were staying on, James' frustration with Magikarp's seeming uselessness came to a boil when he decided to kick the Pokémon off of the platform. James would ultimately regret this decision though, as his Magikarp would end up evolving into a terrifyingly powerful Gyarados, and it was not ready to forgive James. Instead of obeying his owner, the Gyarados decided to attack James and everyone else on the makeshift raft. With the help of a few more Gyarados showing up, James' Gyarados would use its Dragon Rage ability on James and the others, sending them flying off on to a remote island where they would be marooned. If only James had been nicer.

18 Suffering An Attack At The Hands Of Their Own Pokémon

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When Jessie and James end up on Mandarin Island, they quickly uncover a scheme by Butch and Cassidy (two other members of Team Rocket) to steal Pokémon on the island. When they learn about this, Jessie and James decide that they want to steal all of the stolen Pokémon so that they can take the credit, so they send out their Pokémon. Only problem, as they quickly discover, is that Butch and Cassidy have a Drowsee hooked up to a machine that broadcasts out across the island, giving the Drowsee the ability to take control of any Pokémon on the island. Unfortunately, this includes Jessie and James' Pokémon, who are then ordered by Butch and Cassidy to attack Jessie and James! It's one thing to be attacked by a wild Pokémon, but for them to be attacked by their very own Pokémon, that must have been an awful feeling.

17 Team Rocket Members, No More

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There's no denying that Jessie and James are really passionate about their work. Even though the results are not always there, you can tell that they really put a lot of effort into stealing Pokémon so that the Team Rocket organization can succeed. So it must have been an awful feeling for them when they found out that the organization they gave their all for had actually fired them. Even worse was the way in which they found out they were fired. When Jessie and James found an abandoned Delibird in the woods, they decided they wanted to take it for themselves. After defeating it, a Team Rocket scout appears out of nowhere and tells Jessie and James that they passed a test to become Team Rocket members themselves. After explaining they were already members, the scout looked them up and told them that they had been kicked out because they had a hefty amount of unpaid dues and loans owed to the organization. They would be re-instated later in the episode, but for them to hear they were fired from Team Rocket by a stranger rather than their boss just shows how little respect they get from the organization.

16 Sacrificing Themselves For Their Pokémon's Safety

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Even though Jessie and James are technically villains and they both steal Pokémon for a living, the two of them have shown that they have the ability to show compassion and care for Pokémon on certain occasions. This was most apparent when they decided to save a group of captured Pokémon, consisting of multiple Ekans and Koffing, from an evil poacher named Rico. In an attempt to thwart this rescue, Rico uses his ultra-powerful, freshly-evolved Tyranitar to attack Team Rocket and their Pokémon. Knowing that their Pokémon can't defeat the Tyranitar, Jessie and James decide to sacrifice themselves and fight the Tyranitar themselves so that their Pokémon can lead the poached Ekans/Koffing away to safety. It is truly a touching and sad moment for the Team Rocket duo. They distract the poacher long enough for the poached Pokémon to make an escape, but they get badly hurt in the process, which makes their heroic moment all but bittersweet.

15 Why Can't We Get Jetpacks Too?

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It is a pretty disheartening to find out someone does not respect you. But, it is an even worse to find out the very organization you work for does not respect you! That is exactly what happened to Jessie and James when they paid Team Rocket headquarters a visit to see their boss, Giovanni. Upon visiting him, Giovanni assigns Jessie and James a "mission" to Antarctica, which in actuality it was Giovanni just trying to keep them busy so that they are not in the way of the organization's plans. To make matters worse, when they find out that Butch and Cassidy (other Team Rocket members) are getting cool tech for their missions in the form of motorized scooters and flying jet packs, they demand that they also get to use cool gadgets also. Instead of jet packs though, they receive pogo sticks for their mission. POGO STICKS! They suck it up and obliviously go on the mission, but deep down they have to know that the Team Rocket organization does not take them seriously at all.

14 Becoming As Obese As A Snorlax

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Being in Team Rocket is pretty active work. In order to steal Pokémon and make a clean getaway, you would have to be in good physical shape, I'd imagine. So, when Jessie and James spent their time at Pokémon Summer Academy stuffing their faces with food everyday, they realized that they were not in the right physical shape to be performing Team Rocket tasks. They were so out of shape, that they would get winded by simply walking up a hill with a slight incline! Does that sound like somebody who has the ability to steal Pokémon? Definitely not. This forced Jessie and James to both work out in an attempt to drop all of the weight that they had put on, and fast! That had to have been rough. I think the majority of us knows that it's easier to put on weight then to lose it, and if there's "no pain" than there's "no gain". For the Team Rocket duo to lose as much weight as they did, especially in such a short time period, their muscles must have been sore to the max! Which is never a fun time.

13 Runaway Groom

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Before he chose a life of villainy and Pokémon-stealing, James was actually a child whose parents were millionaires. Even though he had no interest, James had to take part in activities to learn how to properly live like everyone else in the upper-class did. James was even arranged by his parents to become engaged to a girl named Jessebelle. At first, James was open to the idea of marrying her, but when he found out how controlling and bossy she was, James decided to run away from his lavish lifestyle just so that he could avoid her. Since then, Jessebelle is still determined to marry James. She even went as far as to lie about James' parents passing away in order to get him to return so that she can marry him! She is obviously someone that will do anything to try and control James, so it was probably a good call that he left her at a young age (although he will have to continue worrying about her in his adult years still, which is terrifying). The creepiest part is that Jessebelle bears an almost exact resemblance to Jessie! Which has got to be super awkward for James.

12 Owning Wobbuffet

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Jessie obtained Wobbuffet completely by mistake, with her accidentally trading away her Lickitung for the aforementioned Wobbuffet in one of the episodes. And I'm sure if she could do it over again, she would have ensured that she would not make the same mistake again if she knew what she was getting into. So why is owning a Pokémon one of the worst things to happen to Jessie? Well, Wobbuffet is kind of a lame Pokémon. He has no real offensive moves. He has a counter ability that uses other Pokémon's attacks against them, but even that back-fired in his debut Pokémon battle. Wobbuffet was fighting Pikachu, and he countered Pikachu's Thunderbolt move wrong, which sent him and Team Rocket blasting off as a result. As well, Wobbuffet has a penchant for escaping his Poké Ball unannounced, and will usually just annoy Jessie, rather than contributing anything really of use for Team Rocket.

11 Runner-Up Beauties

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Jessie and James were both confident that they would win when they both entered the Beach Beauty and Pokémon Costume Contest. With both of them donning swimsuits and James utilizing an inflatable chest for his outift, the two Team Rocket members bragged to Misty about how their beautiful appearances would give them an easy win in the eyes of the judges. Perhaps they boasted too prematurely though. Later on in the competition, Gary Oak appeared in the contest with his beautiful cheerleaders backing him up, and the cheerleaders were grabbing all of the attention from both the audience members and the judge (which was Brock) alike. This infuriated Jessie and James, as they could not believe that people thought the cheerleaders were more attractive-looking than them. And because they have shown in the past how much they care about their appearances, it must have hurt them, finding out that they were not the most beautiful people on the planet.

10 Quitting Time!

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In the episode, titled "Noodles! Roamin' Off!", after a plan involving the use of a massive robot made of ramen went terribly, Jessie and James decided to blame Meowth for the result. Feeling hurt and underappreciated, Meowth decides to quit Team Rocket and chooses to work at a noodle shop instead. On top of this, Jessie also decides to quit as well to become a Coordinator. This just left a lonely James who lost his two best friends in the world. Without his pals by his side, James decides to go catch a rare Metagross (because of its unique colors) to try and show the Team Rocket organization that he could work effectively alone. Unfortunately, James does not know that the Metagross is a very dangerous Pokémon, so his Pokémon are easily defeated and he is in potential danger himself. Jessie and Meowth would show up to help him out eventually, and the gang gets back together in the end. Although I would say that losing your best friends and being attacked by a crazy strong Pokémon all in one episode is definitely a low-point for James.

9 Forced To Attack Their Friend

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Meowth is definitely more of a friend to Jessie and James, rather than their Pokémon. He travels with them without inhabiting a Poké Ball, speaks English so that he can assist in their plans, and he even has the same villainous mindset as Jessie and James. They are perfect for each other! So, the fact they are all friends must have made it all the more worse when Meowth became brainwashed by Colress (a Team Plasma Boss/scientist) and forced to attack Jessie and James! He swipes at them furiously with his sharp claws, trying to hurt them. After dodging his attacks, Jessie and James decide to send out their own Pokémon to attack Meowth, much to surprise of Colress. After hurting and stunning Meowth, Jessie and James hold on to Meowth and get him to snap out of the mind control successfully. Although I would wager that it probably was not easy for them to attack their Pokémon companion.

8 Sad Childhood

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When Jessie decided to enter the Queen of the Princess Festival contest, we find out why she is so determined to win the grand prize, which is a set of Pokémon Princess Dolls. The reason is because growing up, Jessie hated the Princess Festival because she was the only girl that she knew who had a Princess Doll, which made her sad because the festival was just a constant reminder that she would never receive a doll. Up until this point, I never thought of Jessie as someone who could be hurt by something as small as simply not owning a doll, but you can really tell from the scene that it really affected her in a negative way. Hopefully she finds her perfect Princess Doll set one day.

7 Be The Kakuna

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In an effort to avoid being attacked by a group of Beedrill, Jessie comes up with an idea for Team Rocket to disguise themselves as Kakuna so that they will not be stung. They would all end up regretting this plan though, especially when Jessie and James decide to argue about the effectiveness of Jessie's plan, which catches the attention of the wild Beedrill and Kakuna surrounding them. I guess the wild Pokémon were smart enough to figure out that their own kind cannot speak English. This leads to the wild Beedrill to swarm the hanging Team Rocket members and attack them continuously, which I'd imagine must sting quite a bit. I'm guessing they probably regret not deciding on an alternative plan, such as simply running away or something less embarrassing.

6 Drowning Was Almost A Reality

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In the same episode where James kicks his Magikarp, which then evolves into an angry/disobedient Gyarados, earlier on in the episode James thinks that Magikarp has the ability to pull the members of Team Rocket to safety after they found themselves on a sinking ship. Unfortunately, James soon learns that Magikarps are not good swimmers at all, and they can only merely splash about and hope to be carried by a current. The Magikarp and Team Rocket somehow make it out of the ship that was plummeting to the bottom of the ocean, but what we end up seeing is the members of Team Rocket floating motionless and tied to a struggling Magikarp trying to pull them. Ash's Pidgeotto would spot them while flying and save them, but if Ash did not send his Pokémon out to scan the area, there's no doubt in my mind that drowning would have been the fates of Jessie, James, and Meowth. Next time find a Pokémon that can actually swim, guys!

5 Beware Of Bewear

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Bewear is a wild Pokémon who apparently really likes Team Rocket. Not only does it carry them off to safety whenever they are in danger of blasting off, but it also lets them stay in its cave and even feeds them honey! So why is this hospitable Pokémon one of the worst things to happen to Jessie and James? Well, when Jessie and James found themselves in another Pokémon battle against Ash, the Team Rocket members found help in the form of a wild Mareanie who took a liking to James. This Mareanie packed quite a punch too, as its assisted attacks helped take down Ash's Pikachu and Rowlet. It looked like Jessie and James were about to defeat Ash in a Pokémon battle for the first time ever! Just when they were about to claim victory, Bewear arrives on the scene suddenly, picks up the angry Team Rocket members, and carries them away. Bewear literally prevented a very winnable battle for Team Rocket, and the fact that it would have come against their biggest adversary in Ash, makes what Bewear did almost unforgivable.

4 Assault At The Paws Of Meowth

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There's no doubt that James and Meowth are friends, but not even James could have expected Meowth to make unwanted advances at him. After James drank Shuckle juice, unbeknownst to him that it would cause his body to give off pheromones which would attract Pokémon to his scent, this caused Meowth to announce his undying and intense affection for James. This would lead to Meowth pouncing on James, holding him down and continuously licking his face, even though James is obviously uncomfortable and not okay with the situation. In other words, Meowth essentially commits an assault against James. Sure, it's because of the pheromones that Meowth is acting this way, but James does not know that at this point! In his eyes, it's his feline-Pokémon friend who is taking advantage of him and his body. I would expect this to happen in a messed-up fan fiction on the internet, but not actually happening to him on the show!

3 Jessie Parting Ways With The Ones She Loved

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With such an villainous and angry demeanor, who would have thought that Jessie was capable feeling affections and love for others? Well, I'll let you know that it has happened to her on two separate occasions. When Jessie was a child, she had a crush on a boy at her school named Astin. He would later make the decision to leave school and become a Pokémon Coordinator, and he even asked Jessie to go with him! Jessie would decline him though, deciding to stay at the school, ending the budding romance in the process.

The second love in Jessie's life was a doctor named Dr. White. After the doctor saved Jessie from drowning (earlier on she fell off a cliff into the water below), he decided to take Jessie to his clinic so that she could get better. Jessie would end up offering to help out the doctor as he treated various Pokémon. The more time she spent with him, the more Jessie was starting to fall in love with the doctor, and even considered leaving her life with Team Rocket for him. But ultimately, Jessie decided to leave the doctor for Team Rocket.  Two potential romances leading to heartbreak. Maybe Jessie just was not cut out for relationships.

2 Team Rocket Is Blasting Off Again... And Again... And Again...

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As it was pointed out earlier, Jessie and James have been blasted off many times in the show's history. Actually to be more specific, Jessie and James have both been blasted off over 500 times each! To the average viewer, it is nothing more than a hilarious physical gag because it is happening in an animated kid's show. But think about it, though. If you were to be launched high up in the air and then crash back down to earth, it would probably hurt a lot. Especially if it happened OVER 500 TIMES! I cannot even imagine the physical pain that Jessie and James have to endure everyday as a result of all these blast offs. They must have broken bones or accumulated internal injuries, right? I don't care that it's a cartoon, they are humans still! And these injuries will probably affect them well into old age. They might as well keep Nurse Joy on speed dial for the rest of their lives.

1 Working With The Enemy

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It's crazy to think about all of the times that Ash and his friends have foiled Team Rocket's plans. Had Ash not been in the picture, there has to have been a strong probability that a lot more of Team Rocket's dastardly plans would have actually succeeded, which is most likely the reason why they hate Ash so much. What's even worse is that even though Ash is Team Rocket's biggest enemy and the reason for their failures, they have been forced to team up and work with Ash and his friends on many different occasions.

The best example of this was from the movie Pokémon The Movie 2000. In the film, Jessie and James help get Ash to an important sphere using a speedboat they acquired. As well, when they were all trying to escape on the back of Lugia, we find out that there is too much weight and it is slowing Lugia down while trying to fly away from danger. In a very noble and sacrificial move, Jessie and James decide to jump off so that Ash, Pikachu and Lugia could fly faster and save the world. They risked their own lives to help out their enemy. And after the movie was over, Ash continued to thwart their plans! Even when they helped save the world! Honestly, this just proves that Jessie and James are destined for a life of defeat.