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 Team𒅌 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 other💙s, 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 ag🐬ain"  (which could have its v𒆙ery own list, I may add).

But, as the series went on, 🌳they became less of an e𓂃vil 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 aw𝕴ful, 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

Jessie and James are no strangers when it comes to "blasting off again". For the majority of Pokémon's ep♋isodes, 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 𒀰episode "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 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 ♚

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 h🔯ad been nicer.

18 Suffering An At🐻tack At The Hands Of Their Own Pokémon ✱

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 thin🐼g 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

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 defeati⭕ng 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 lꦆoans 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 ꦓ Sacrificing Thems💎elves For Their Pokémon's Safety

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 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?

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 fl🌼ying 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

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

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 th🔜at 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 ꦚ Owning Wobbuffet

Jessie obtained 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 kn🎉ew 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 𒐪

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 wไould 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.