Longtime Pokemon fans faithfully recognize the regular characters from the anime, and Team Rocket are without question on that list. In the Gen 1 games, the whole of Team Rocket is the big bad, and you work tirelessly to stop their antics. In the anime, we were more accustomed to seeing two specific grunts: Jessie, James, and their Pokemon sidekick, Meowth.
The trio serve not only as Ash’s continual adversaries, trying in most episodes to steal his Pikachu, but as comic relief, too. Their disguises are always ridiculous, and while we the viewer know it’s them, Ash and friends have occasionally been fooled.
The anime has been airing since 1997, and I spent my childhood coming home from school and plopping down to watch the day’s episode. So, missing the series, I wanted to look back and give credit where credit is due to our bumbling anti-heroes and check out the times their elaborate disguises almost worked.
10 Mewtwo Strikes Back
This movie was the first time we got to see Pokemon on the big screen, and I remember weeping at the end of the film (and I’m judging you a little if you didn’t). There’s a big battle happening on Mewtwo’s island, but a huge storm cancels the ferry there. Trainers begin using their Pokemon to go out to sea anyway, but none of Ash’s are strong enough.
No matter, because Team Rocket shows up in a rowboat disguised as Vikings and offer to row the gang across. So Meowth didn’t stand out, he’s tethered to the front of the ship as its figurehead.
9 Showdown At The Po-Ke Corral
Okay, maybe this one is a little unfair to give to Team Rocket, since I can’t think of a reason why Delia Ketchum, Ash’s doting mother, would recognize them. After being admonished by their boss Giovanni and told to start doing their jobs, they find a renewed spirit and are more determined than ever to get Pikachu.
But since they’re not sure where Ash has gone, they disguise themselves as newscasters and head to his home in Pallet Town. Delia answers the door, and they tell her they’d like to interview Ash for a feature. Delighted by what she believes to be an opportunity for her son, she tells Jessie and James exactly where they can find him.
8 All Fired Up!
This episode begins with a standard trap, when Ash is tasked with running a torch (very much like the Olympic Flame) to a massive stadium, where the Moltres Flame the torch carries will burn for the entirety of the Indigo Pleateu Conference being held there. By trapping Ash in a hole along his running route, the Team is able to steal the torch, although the flame goes out on them.
The event organizer has kept a tiny flicker of the original Moltres Flame and restarts the event with a new torch, but Jessie and James show up at the stadium, too, dressed as traditional Greek maidens. The torchbearer passes off the flame to them, and Jessie uses it to light the main flame.
7 A Friend In Deed
At long last, Ash has made it to the Pokemon League. All that remains to do before he can challenge it to become a tried and true Pokemon Master it is handing over all his Pokemon to the two physical examiners who definitely don’t look like his longtime adversaries to be looked over before the battle.
Wait, what? Nobody told the participants about this, which Ash comments on as Jessie and James begin collecting Pokemon from the trainers. It almost works, until James says Jessie’s name by accident.
6 Entei At Your Own Risk
For a very brief moment in the anime, Ash had a Larvitar, which he hatched from an egg that Professor Elm gave him. Team Rocket is watching and hears how often the sensitive little Pokemon cries, and although they don’t want someone loud on the team, they decide to steal it from Ash anyway.
While the gang is checking out a hot spring, Jessie and James show up in their brand-new food truck and perform a food-centric version of their motto as a pitch to get Ash to come try their fruit smoothies for free. Misty and Brock are apprehensive, but Ash brushes them off and gets in the van with Team Rocket anyway, because who doesn’t want free smoothies?
5 Vanity Affair
In the earliest parts of this episode, we listen in as Team Rocket gripes about the current state of things, saying that they’re running out of money for their schemes, and that’s why they’re working at a seaside café. Elite Four Dragon-type trainer Drake shows up, as does Ash and gang, and when the two battle, Pikachu faints.
Jessie and James distract May while she’s holding the injured Pokemon, and they manage to steal him from her and hop into their balloon. Drake sends his Salamence out to use Dragon Claw on the balloon to get them to drop Pikachu, and it uses Flamethrower to send them blasting off before returning Pikachu to Ash.
4 The Light Fantastic
Ash and friends have arrived at the outskirts of what was once Remoraid Lake. Nurse Joy delivers a stern warning about depleting natural resources, declaring that there are no Remoraid in the dried-up lake, but that once every 12 years, mysterious lights appear in the sky above the lakebed. And wouldn’t you know it, Ash is right in time to see them.
But he’s not the only one interested in the possibility of Remoraid – Team Rocket show up to inquire as well, dressed as archaeologists with a mummified Meowth slung over James’ shoulder. The gang agrees to let them come on the journey to the lake, and they revert to trying to catch Pikachu instead of focusing on Remoraid when they get kind of bored on the trek there.
3 Ring Masters
There’s a Pokemon sumo wrestling competition happening, and neither Ash nor Team Rocket have Pokemon heavy enough to enter. They solve this problem in their own ways: Ash borrows Snorlax from Professor Oak, while Jessie and James dress up like sumo wrestlers and stick Wobbuffet in a hilarious Miltank costume.
And they almost proceed through the contest like this, too, and would have made it further if not for the eagle-eyed director of the event, who definitely knows his Pokemon. Jessie wins her match after “Miltank” used Counter, but real Miltank can’t actually learn that move. Upon revealing themselves as Team Rocket, they’re promptly blasted off out of the stadium before they can even attack.
2 Battle Aboard The St. Anne
Team Rocket manages to pull off their disguises not once, but twice in this episode. The first time, they find Ash and friends moping about being unable to afford tickets aboard the St. Anne, so they dress as ganguro girls and offer them tickets for free.
It’s not out of the kindness of their hearts, though – the bulk of Team Rocket is planning a massive heist during the cruise, with dozens of grunts dressing as the waitstaff to steal the Pokemon aboard the boat. A massive battle ensues as the ship hits bad weather and capsizes, leaving Ash, Misty, Brock, Team Rocket, and their Pokemon trapped aboard the sinking vessel.
1 The Ultimate Test
This episode saw Ash trying to take the Pokemon League Admissions Exam, which removes the need for taking on the gym challenge. There are a few sets of not entirely practical questions, as well as a randomized battle that each trainer must win in order to pass.
Jessie and James don’t tell one another they’re attempting the exam, and stumble upon the other during registration. James insults Jessie until she drags him outside and removes her glasses to reveal herself to him. This disguise, while not their most creative, had to get the top spot because they managed to fool absolutely everyone wearing them – even themselves.
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