Pokemon: 10 Most Heartbreaking Moments In The Anime, Ranked

For the most part, Pokemon is a lighthearted anime about making lifelong friendships and chasing after your dreams. In traveling from Kanto all the way to Alola, Ash Ketchum was able to befriend countless Pokemon and trainers and ultimately become the champion he'd always hoped to be.

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But along the way, it wasn't always sunshine and rainbows for Ash. At the young age of ten, he has had to make some tough decisions regarding his friendships and responsibilities as a trainer. Many of these decisions either followed or created a heartbreaking story worth being told. Here are ten of the most heartbreaking moments in Pokemon.

10 Sabrina's Story

Sabrina is the mysterious Gym Leader of Saffron City. She initially comes across as cold and heartless, but there's a tragic reason behind her personality.

As a Gym Leader who specializes in Psychic Pokemon like Kadabra, Sabrina herself has had psychic abilities since she was a child. Because of how intense her psychic training was, she began to exhibit an extremely closed-off behavior to the point where she turned her own mother into a doll. In reality, however, it is later revealed to Ash that Sabrina just wanted to make friends after a scarring childhood. Thankfully, Ash is able to bring Sabrina a playful Haunter that makes her laugh.

9 Squirtle And The Squirtle Squad

Before Ash met his Squirtle, it was the leader of the infamous Squirtle Squad. The Squirtle Squad was made up of troublemaking Squirtles with sunglasses who partook in criminal shenanigans until Ash taught them otherwise. Ever since their leader joined Ash's team, the Squad became firefighters who assist Officer Jenny.

The sad part comes when Ash's Squirtle reunites with the Squad after the trainer and Pokemon had grown quite attached to one another. Despite their strong bond, Ash feels that his Squirtle would be better off fighting fires and saving lives with the Squad than traveling along with him, so they decide to part ways for good.

8 When Ash Turned To Stone

One of the most iconic moments in Pokemon took place in the classic 90's film, Pokemon the Movie: Mewtwo Strikes Back. In the movie, the legendary Mewtwo seeks revenge on humanity for making it their experiment. Mewtwo goes to war with its army of cloned Pokemon against humans and their trained Pokemon.

In the midst of all the fighting, Ash takes initiative and decides to sacrifice himself. He throws himself into a fatal blast between Mew and Mewtwo's power, turning him into stone. When Pikachu is unable to revive its partner, all of the Pokemon begin to cry. The tears are ultimately what allow Mewtwo to realize and atone for his sins, using his psychic powers to revive Ash and return everything back to normal.

7 Meowth's Story

Meowth is the sassy cat Pokemon who aids Jessie and James in their crimes as Team Rocket. While Team Rocket is infamous for attempting to steal Ash's Pikachu, they aren't the worst villains out there. In particular, Meowth has a backstory that is sure to get the tears flowing.

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Back in his days as a young kitten, Meowth fell in love with a luxurious female Meowth who quickly rejected him for being poor and not good enough. He then began learning how to be more humanlike just to impress his crush but was brutally rejected again for being a freak. In the end, he resorted to joining Team Rocket where he was accepted for who he was.

6 When Charmander Was Abandoned

Most trainers shower their Pokemon with love as if they were part of the family. Some nasty trainers, however, opt to abuse or throw away their Pokemon if they aren't living up to their expectations. This was the case for Ash's Charmander and its previous owner.

Charmander is a small Fire-type Pokemon who is extremely weak to water. When its previous owner, Damian, felt that it wasn't strong enough for his liking, it was abandoned out in the rain where it could've died. Even after Charmander was saved and brought to the Pokemon Center, it still loyally waited for Damian to take it back. It was only after it battled alongside Pikachu that Charmander decided to join Ash's team instead.

5 When Charizard Refused To Listen To Ash

Charmander might have been an adorable and reliable Pokemon when it first joined Ash's team, but after evolving into a powerful Charmeleon and an even stronger Charizard, its personality changed drastically.

Quickly becoming one of Ash's strongest Pokemon, Charizard turned extremely arrogant and full of itself to the point where it no longer respected Ash as its trainer. Charizard would completely ignore Ash during battles and opt to take a nap or scratch its belly. This has unfortunately resulted in Ash losing major battles, including one in the Indigo League Competition.

4 Ash's Farewell To Pikachu

Since the very beginning, Pikachu has always been at Ash's side through their adventures in exploring new places. While Pikachu initially hated Ash, the two quickly became best friends who could never be separated.

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That being said, there was one instance when the iconic duo almost went separate ways. When Ash's Pikachu befriends a group of wild Pikachu, it seems like it may be better off with its own species and without Ash. After seeing how happy his Pikachu was with the rest of the Pikachu, Ash believes he is doing the right thing in saying goodbye and letting his friend stay there. But of course, we all know Pikachu eventually ends up chasing after Ash several seconds later.

3 When Ash Gets Caught In A Snowstorm

In the midst of an intense snowstorm one day, Ash and his Pokemon wind up stuck in the cave of a cliff. There, friendships are put to the test.

In an effort to not freeze to death, Ash first calls upon his Charmander to warm up the cave with its flame on its tail. When Charmander gets tired, Ash calls all of his Pokemon back to their Pokeballs to rest and stay warm. Pikachu is the only Pokemon who resists the Pokeball until the others pop back out to huddle around their trainer, bringing Ash to tears. Altogether, Ash's Pokemon show their unconditional love by keeping him warm until the storm subsides the following morning.

2 Saying Goodbye To Butterfree

Similar to how Ash allowed his Squirtle to rejoin the Squirtle Squad and nearly left his Pikachu with its own kind, he also had to say goodbye to his beloved Butterfree.

This particular moment was arguably Ash's most difficult farewell due to his fond memories with Butterfree. As a tiny Caterpie, it was the first Pokemon that Ash ever caught on his journey. Despite its severe weakness, Caterpie was raised with patience and love until it evolved into a Metapod and then a beautiful Butterfree. When Butterfree found true love with a pink Butterfree, Ash knew it was only right to let it go, never to meet again.

1 When Pikachu Spoke

For years, Pikachu has always been the cute little electric mouse who squeals its name while communicating or attacking. Although it could never speak the human language like Team Rocket's Meowth, Pikachu seems to have an unspoken way of understanding its forever partner, Ash.

However, there is a moment in Pokemon the Movie: I Choose You! that may be more heartbreaking to hardcore Pokemon fans than Pikachu and Ash--when Pikachu surprised everyone and said more than its usual "pika pika." In what appears to be the end for Ash, he asks Pikachu why it refuses to get in its Pokeball. An emotional Pikachu replies by saying it always wants to be with him.

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