Wobbuffet's first appearance, under the ownership of Benny
Wobbuffet originally belonged to a Trainer named Benny. In Tricks of the Trade, Benny was searching for someone to trade Wobbuffet with for a stronger Pokémon at the Pokémon Swap Meet in Palmpona. He was not successful at first, though a Trainer with a Stantler seemed to like his offer, but then bailed for a Hoothoot at the last minute. Jessie's Poké Ball containing her Lickitung then accidentally fell into the machine instead when she crashed into it. Unbeknownst to her, Lickitung got swapped for Wobbuffet.
Jessie unaware that her Lickitung had been traded to Benny for his Wobbuffet
Later, after the trade had commenced, Jessie wanted to send out her Lickitung to battle Ash and his friends. But, much to her surprise, Wobbuffet appeared instead. James then immediately looked up his moves for Jessie. Even though Wobbuffet had no offensive attacks, he managed to counter Chikorita's attacks back to her. Wobbuffet was still blasted off along with the Team Rocket trio by Pikachu's Thunderbolt.
Since the episode Tunnel Vision, Wobbuffet had his place in the Team Rocket motto, first before Meowth (which usually left him very upset) and some episodes later, right after Meowth. He could often be heard crying out subsequent to the "Team Rocket is blasting off again!" line, even if he was not out of his Poké Ball when the team was sent blasting off. Wobbuffet was thus somewhat a fourth team member.
When Wobbuffet popped out of his Poké Ball in Power Play!, and redirected Meowth's attack back to himself, Jessie had the idea of building a Robo-Mecha Wobbuffet, which would counter any attack back to the user similar to Wobbuffet's Counter.
In Wobbu-Palooza!, Ash, his friends and Team Rocket came across a festival honoring Wobbuffet. Jessie's Wobbuffet popped out of his Poké Ball much to the villagers's excitement. The Wobbuffet Festival crashers then showed up to attack the Wobbuffet and Jessie sent out her Wobbuffet to battle them. Jessie's single-handedly took out the Wobbuffet Festival crashers's Pokémon with the use of Counter and Mirror Coat.
In Imitation Confrontation, Wobbuffet battled Duplica's Ditto, Mini-Dit. Mini-Dit transformed into Wobbuffet and used the same moveset to battle Wobbuffet and Arbok. As a result, Wobbuffet ended up losing to his miniature counterpart.
In The Wayward Wobbuffet, Wobbuffet was tasked with guarding the Poké Pod containing Ash's Pikachu. During the chase to get the Pod, Wobbuffet, along with the Pod and the key to it, was separated from Jessie and went on an action-packed adventure. He bumped into a thief named Goneff who was not happy with Wobbuffet bumping into his vehicle. However, Goneff took Wobbuffet hostage. Team Rocket then dug a hole and headed to the warehouse Goneff was hiding from underground to rescue Wobbuffet. Ash and his Totodile went with them only for Totodile to get badly hurt by Golem. When Golem was about to finish off Totodile, Wobbuffet jumped in the way and sent Golem flying to its Trainer. Ash was then able to get the Poké Pod back but Wobbuffet still had the key as he flew away along with the Team Rocket trio on the Wobbuffet-shaped balloon. Ash sent out Noctowl to get the key from Wobbuffet, however. Noctowl was successful, and Pikachu was freed from the Poké Pod.
Advanced Generation series
In A Poached Ego!, Wobbuffet was sent out to battle Rico's Tyranitar. He was getting ready to counter Tyranitar's Hyper Beam but fainted as the Hyper Beam was too strong.
In Claydol Big and Tall, Wobbuffet put on the disguise of a maid which made a humongous Claydol fall in love with him. This was part of a plan to get this dangerous Claydol back inside its stone Poké Ball. When Wobbuffet's disguise was revealed, Claydol was angry, but Claydol was returned to its stone Poké Ball before Wobbuffet was hurt.
Kanto Battle Frontier
Wobbuffet participated in his first Contest onscreen in A Hurdle for Squirtle. Jessie planned for him to use the countering technique against Harley's Ariados. However, this backfired, as Ariados's String Shot manipulated him into a puppet. Since then, he was used in other Contests, but would usually cause the elimination of Jessie for one reason or another.
Wobbuffet ran away from the group in Fear Factor Phony after a fake ghost made by some Ghost Pokémon scared him off. While he was running away he saw a Kirlia dancing and fell in love with it. When Team Rocket caught Pikachu and Kirlia, Wobbuffet jumped into the mecha after it and broke the Kirlia and its Psychic Pokémon friends free from Team Rocket's capture. Entirely thanks to Wobbuffet, Team Rocket's plan was completely ruined.
Diamond & Pearl series
Jessilina with her Wobbuffet
Wobbuffet went with Jessie, James, and Meowth to Sinnoh in Following A Maiden's Voyage! where he countered Meowth's Fury Swipes after an argument with Jessie. As a result, he sent Team Rocket blasting off and Pikachu falling in the forest. In One Big Happiny Family!, Wobbuffet participated in catching Brock's Happiny and accidentally tugged on Team Rocket's balloon after trying to pull her down. After the balloon fell to the ground, Wobbuffet, Meowth, and Mime Jr. made funny faces at Happiny but she was not happy about it. Later in the episode, Wobbuffet, Meowth, and Mime Jr. prevented Happiny from reuniting with Brock but she single-handedly defeated them by throwing them in the air.
In Staging a Heroes' Welcome! Jessie used Wobbuffet in the appeals round in the Wallace Cup. After being sent out Jessie had Wobbuffet run straight towards her and use Counter, which sent her flying sky high. The judges were not impressed by this which caused Jessie to be eliminated. In Double-Time Battle Training!, she sent out Wobbuffet and Yanmega to perform double moves by having Wobbuffet deflect Yanmega's Silver Wind with Mirror Coat. However, this failed as Team Rocket were sent blasting off.
Best Wishes series
Wobbuffet popping out behind, and reuniting with Jessie, James, and Meowth
Following the Team Rocket trio's journey in Sinnoh, Jessie was forced to leave Wobbuffet at Team Rocket's headquarters as he is not a Pokémon native in the Unova region and would attract attention.
Since then, Wobbuffet made appearances along with Meowth in the Pikachu short, PK23, Meloetta's Moonlight Senerade and Eevee & Friends. Strangely, the three of these shorts take place during the Best Wishes series, which Wobbuffet is normally absent from for the aforementioned reasons. It should be noted, however, that these shorts call into question their canonicity with the main anime series altogether.
Wobbuffet's only appearance in a Best Wishes series episode was in The Dream Continues!. After returning to Kanto and giving away their Unova Pokémon to Giovanni at the headquarters, the Team Rocket trio walked through a corridor only for Wobbuffet to pop up, surprising them. Wobbuffet was later seen with Team Rocket as they eavesdropped on Ash from the roof of his house in Pallet Town, leaving for Kalos with them and marking his return to Jessie's team.
Wobbuffet reappeared as a member of Jessie's team in the XY series, where he was shown to be much more competent in battle. In Kalos, Where Dreams and Adventures Begin!, Wobbuffet was used in a battle against Pikachu, where he almost defeated Pikachu by returning his Thunderbolt right back at him with Mirror Coat. However, a wild Froakie came in and defended Pikachu from a reflected Electro Ball. Froakie helped defeat Wobbuffet by using its Frubbles to knock Wobbuffet on his back due to its inability to reflect moves that aren't attacks. Wobbuffet was soon blasted off by Pikachu, Froakie, and Clemont's Bunnelby.
In A Fork in the Road! A Parting of the Ways!, Wobbuffet was separated from Team Rocket along with Jessie after being blasted off by Pikachu. After falling into the sea due to a Gloom, he was rescued by Dr. White. He subsequently got romantically involved with Dr. White's female Wobbuffet. After Jessie tried to leave him behind with the Wobbuffet and Dr. White's Wynaut to help Team Rocket to fight a Pokémon hunter, he appeared at the last second to deflect the Pokémon hunter's Rhyperior's attacks. Afterwards, Team Rocket's Pokémon, as well as Pikachu and Fennekin combined their attacks to defeat Rhyperior. The Pokémon hunter was arrested by Dr. White and Beatrice, and Wobbuffet and Team Rocket left to continue following Ash and his friends.
Wobbuffet is used occasionally for battles. Wobbuffet's knowledge of moves like Counter and Mirror Coat comes in handy, since Team Rocket often finds itself on the receiving end of powerful attacks.
Wobbuffet usually serves as a comic relief character. He emerges from his Poké Ball
frequently as a running gag, and often at inappropriate times which frustrated Jessie at times. Team Rocket has also had various vehicles and robots
based on him.
Wobbuffet popping out of his Poké Ball
Even though Jessie often seems annoyed with Wobbuffet, she was shown to truly care for him. This is showcased in a handful of episodes, including Who, What, When, Where, Wynaut?, in which Wobbuffet temporarily went missing. Jessie was very worried and desperately went searching for him on the island. Another instance was in Dealing With a Fierce Double Ditto Drama! where Jessie was upset at James's idea to send Wobbuffet to Giovanni since they couldn't tell him apart from Narissa's Ditto. Even though Wobbuffet has been absent, he still been shown to be doing his comical pose every time Team Rocket do their motto.
Wobbuffet also seems to care for Jessie deeply and see her as a motherly figure. This can be seen in The Wayward Wobbuffet, when he was lost and imagined a cloud in the shape of Jessie, childishly clapping with joy after noticing it. Even so, his loyalty has sometimes been in question, such as in Fear Factor Phony, where he temporarily left the group to hang out with some Psychic-type Pokémon and even single-handedly stopped Team Rocket's plan to steal Pokémon. Since his return, Wobbuffet has taken back his role as the "fourth member" of the team. He also seems to get more battling time now, and his capability of reflecting attacks has proven useful many times. Before Jessie caught her Pumpkaboo, Wobbuffet was her major battler, and did rather well, despite his incapability of using offensive moves. By A Fork in the Road! A Parting of the Ways!, he was shown to have become very close to Jessie, as seen when he chose to stay with her over a female Wobbuffet.