Longtime fans of the Pokemon animated series have a certain affinity for Ash Ketchum's original traveling companions: Pewter City Gym Leader Brock and Cerulean City Gym Leader Misty. However, Brock is the one with a much longer arc in the show. Brock accompanied Ash's journeys in Kanto, Johto, Hoenn, and Sinnoh.

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Even after Brock and Ash part ways following Pokemon the Series: Diamond & Pearl, he still makes cameo appearances in future seasons. He's even had several Japan-only specials air that catch viewers up on Brock's latest solo adventures. These ten Pokemon episodes are must-watches for any fans of this goofy, hopeless romantic.

10 Heart Of Fire! Heart Of Stone!

Brock and Olivia charging Lycanroc's Z-Move together

Brock and Misty finally reappeared together during Pokemon the Series: Sun & Moon. After a trip Ash and his classmates take to Kanto, Brock and Misty make a surprise visit to the Alola region. There, they encounter many of Ash's Alolan companions, which of course for Brock means new women he can flirt with.

It's predictable for Brock to easily fall in love with Olivia, Alola's Rock-type Kahuna. Desperate to prove himself to her, Brock accepts Olivia's challenge of a Pokemon battle. When Team Rocket interrupts as part of their usual scheming, Brock and Olivia even join forces to power Lycanroc's Z-Move.

9 Grating Spaces!

Ash and Brock standing in the redesigned Pewter City Gym

This episode of Pokemon the Series: Ruby & Sapphire finds Ash, Brock, May, and Max arriving in Pewter City to visit Brock's family. As a pit stop on the road to Kanto's Battle Pyramid, Brock finds his familiar gym going through fashionable changes. Brock, his siblings, and his friends later discover that this is all an elaborate ruse.

Brock, Ash, May, and Max are forced to defend Pewter Gym from the nefarious Jessie, James, and Meowth of Team Rocket. It's also a chance for Brock to test out his newly-evolved Steelix. Afterward, Brock forgives his parents for falling for Team Rocket's scheme, making this episode a big moment in learning about Brock's family dynamics.

8 What I Did For Love!

Brock and Misty facing each other against action lines

Earlier in Brock, Ash, May, and Max's visit to the Kanto region, the gang arrives in the anime-exclusive Gardenia Town. There, Brock decides to enter a Pokemon Contest for the first time. Of course, he does this in the pursuit of a woman, who this time happens to be Yuma, an experienced Pokemon Coordinator offering to take him under her wing.

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Unfortunately, Brock's rash decision puts him up against May in the Pokemon Contest. May and Brock participate in a Pokemon battle against each other, where May's Eevee outperforms Brock's Marshtomp. Sadly, Yuma takes a different Coordinator under her wing, making this yet another time when an episode leaves Brock heartbroken.

7 When Regions Collide!

Brock facing off against Kiawe in a battle

During Ash and his classmates' visit to Kanto, Misty and Brock participate in several Pokemon battles against them. This episode features plenty of epic battling, which is a rare sight from Brock, who spent most of his travels with Ash as a Pokemon caretaker. Here, Brock has a battle with Kiawe, a Fire-type specialist.

As anyone with the Pokemon type chart memorized can probably guess, Kiawe's battle against Brock doesn't go so well. Even with his Steelix's type disadvantage, Brock flexes his battling skills by Mega-Evolving it. At the end of the episode, Ash invites Misty and Brock to visit Alola, which they accept later in the series.

6 Leave It To Brocko!

Brock giving a berry to a wild Nuzleaf

Brock's journey of rediscovering his desired career takes place over the course of Pokemon the Series: Diamond & Pearl. In this episode from early in the season, Brock shows off his selflessness that eventually leads to his decision to become a Pokemon Doctor. Here, he takes care of an injured Nuzleaf found by Nurse Joy.

While trying to return the lost Nuzleaf to its home, Brock, Ash, and Dawn are ambushed by Team Rocket. During the ensuing battle, Brock's Bonsly also evolves into Sudowoodo! Finally, through Brock's bravery, they defeat Team Rocket and reunite the Nuzleaf with its parent, a Shiftry.

5 Malice In Wonderland!

Brock surrounded by an affectionate Nurse Joy and Officer Jenny

This episode isn't as Brock-centric as some others on this list, but it contains a pretty key moment for Brock's character. After arriving at a Pokemon Center, Brock finds himself the object of affection by many Nurse Joys and Officer Jennys. Not only that, but Ash and Dawn receive a tournament and Contest invite, respectively.

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While audiences may expect Brock to give in to this dream scenario, it only makes Brock realize that's exactly what it is: a dream. Realizing that Ash and his friends have been hypnotized by a Mismagius, they attempt to escape the dream. Thanks to Brock's heroism, the gang wakes up in a field, able to continue their journey.

4 The Brockster Is In!

Ash, Dawn, Piplup, and Pikachu watching Brock and Happiny take care of a Pichu

If Brock's adventure with Nuzleaf was a sign that Brock has what it takes to be a Pokemon Doctor, this episode marks the discovery. After a Tentacruel poisons a Pokemon Nurse-in-training's Pokemon, Brock comes to the rescue! By the time Nurse Joy arrives on the scene, Brock has cured almost all of them.

Brock's Happiny evolves into a Chansey after taking care of that many patients. Impressed by his good work, Nurse Joy encourages Brock to become a Pokemon Doctor. Even Ash and Dawn encourage Brock to pursue this, with Dawn even admitting that she admires how much Brock cares for Pokemon.

3 Showdown In Pewter City!

Brock holding out a Poke Ball during his gym battle with Ash

Of course, discussing Brock's best episodes wouldn't be right without mention of his first appearance in the anime. In only the fifth episode ever, Ash and Misty arrive in Pewter City, so that Ash can challenge Brock for a Gym Badge. However, Ash's initial battle with Brock results in his first-ever loss after Pikachu becomes too injured.

After meeting Brock's family, Ash challenges Brock to a rematch. This time, victory is in sight as the gym's overhead sprinklers go off, weakening Brock's Onix. However, Ash forfeits the match, thinking it would be unfair if he won this way. For displaying his kindness, Brock awards Ash with the badge, and then decides to join Ash and Misty on their journeys.

2 Pokemon Fashion Flash!

Brock looking flustered as Suzie talks to him

Later during their travels in Kanto, Brock takes Ash and Misty to Breeder's Lane, a street of high-end Pokemon fashion shops and salons. There, they meet Suzie, a Pokemon Breeder, who Brock wants to learn from. Suzie is reluctant, though warms up to Brock after her disobedient Vulpix tries his Pokemon food.

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After an encounter with Team Rocket masquerading as Pokemon beauticians, Suzie thanks Ash and his friends for their support of her business. Suzie also gives Brock her Vulpix, noting that it is much more affectionate with Brock than it is with her. Brock happily accepts the Vulpix, a sign of his new friendship with Suzie.

1 Smells Like Team Spirit!

Brock standing with his team battle partner Holly, who looks anxious

In Brock's most impressive episode, the gang find themselves competing in Hearthome City's tag battle tournament. Ash is paired up with Paul, his rival; Dawn is paired with a Trainer named Conway; Brock is paired with Holly. Holly, surprisingly, becomes one of the few women in the anime who returns Brock's affections.

Brock and Holly end up performing well together, making it to the Top 4 in the tournament. However, she becomes devastated by their joint loss against Ash and Paul. Brock is heartbroken when he learns from Nurse Joy that she left without saying goodbye, determined to become a better Trainer and partner to Brock.

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