Top 10 Saddest Moments from the Pokemon Anime

Misty and Brock leave

Don't forget to check out their return episodes in the Sun and Moon anime. I didn't like the episode when Misty left. It will always be my least favorite because Misty's sisters were not letting her travel with Ash.

This is an episode that made me cry so much. Why did the franchise do this to Misty and Brock? But we shouldn't worry because Ash, Misty, and Brock will always be best friends forever. Nobody else, not even the Kalos gang.

I stopped watching after this episode. I simply couldn't take it. This is the saddest moment without question.

Pikachu and the other Pokémon cry after Ash is turned to stone

Only moment in Pokémon I cried at.

I was crying and crying, then what?... I got my life back when Ash woke up. But seriously. Why on earth, WHY the hell were the clones crying? And then that MEW... guess what? Was LITERALLY LAUGHING. Like WHY the freak? Dude, the anime is full of idiots...

Bye Bye Butterfree

Caterpie was the first Pokemon Ash caught. After the full evolution to Butterfree, Ash releases Butterfree into the wild. Yay, dumb Ash!

The first of many emotional times Ash has had to say goodbye to one of his Pokemon.

Boy, did this episode make me emotional when I first saw it.

Charmander is abandoned by his trainer

Stoutland dies

This is so sad because Litten is so cute and confused. It doesn't directly tell you that Stoutland died. But I loved that Meowth talked to Litten to try and help it get over its sadness and worry.

The leaves were falling from the tree one by one. When the leaf fell, Litten caught it and kept it until it blew away. Then Litten saw a cloud that looked like Stoutland. When the Stoutland cloud ran away, Litten knew it was time for him to move on. What's sadder than that!?

And they started hating Litten when Incineroar was introduced. Ha! Water type fans.

Pikachu's goodbye

Sad episode where I thought Pikachu would stay with the other wild Pikachu. Ash's Pikachu returned to Ash, so heartwarming.

What the heck is a Pickachu?!
The first time I watched this episode, I had to turn the volume off as the song made me nearly cry. But now I can watch it without getting teary.

I did not cry for Bye Bye Butterfree, but I did for this. Just shows how sad it is.

Tommy's parents almost die

Butterfree's goodbye was sad, but watch the Japanese episode of the Kangaskhan Kid. It is SO far for a kids' show in Tokyo!

This refers to the kid from the episode The Kangaskhan Kid.

Pikachu chooses Ash over freedom

Goodra leaves

Pikachu is turned into stone

I loved the movie even though Diancie is a spoiled brat. Honestly, I nearly cried. Pikachu means so much to me and Ash.

I ABSOLUTELY LOVED Diancie and the Cocoon of Destruction. When Pikachu was slowly turning into stone, I cried for hours. It was sad seeing Ash talk to it while it was dying. It was also sad seeing Serena and Clemont cry for the first time.

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Pichu leaves Kangaskhan

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Mallow sees her mother again

Weezing and Arbok leave

Team Rocket are the nicest people in the anime, and they have the biggest heart. Ash and his sad moments are overrated. Team Rocket > Ash and Friends.

It's not only that Arbok and Weezing leave. It's also watching Jessie and James battle the hunter and his Tyranitar to save those Ekans and Koffings.

They had to watch their own trainers get beaten up while trying to protect them. God, this is sad.

Serena cries after failing to make it past the first round of the Pokémon Showcase

Hey Serena haters, just a little note from a Serena lover. Have you ever actually paid attention to the show? Obviously not. Every time I get on this website, there's always people saying bad stuff about Serena. Once, when I got on here, I looked at the top ten reasons to hate Serena from Pokémon. Somebody said she was a spoiled brat. She is NOT spoiled. Her mother treats her LIKE CRAP. If you think not, go to episodes 1-5 to be corrected.
One of the reasons on that list was "because she doesn't take care of her Pokémon." I'm sorry, WHAT!? She was lucky enough to evolve her Eevee into Sylveon, which REQUIRES love and affection. Do I really need more proof than that? Apparently, I do.
I got a little off-topic there, but I wanted to share my feelings. This scene made me cry FOR HOURS. I was sad that her Fennekin and Pancham were crying too. For all those Serena haters out there, just know that Serena has feelings too.

Ash loses to Ritchie after Charizard refuses to battle

After everything Ash did for Charizard, saving him from an abusive trainer and saving him from death, this is the gratitude he gets from Charizard by costing him one of the most important matches of his young career.

Ash says goodbye to Charizard

Saddest episode for me. It's been 15 years, and I still cry when I watch this.

Ash was so sad, he couldn't even say goodbye to Charizard!

Jessie and Blissey

Very touching side story on Jessie. Blissey/Chansey may be clumsy but the most lovable Pokémon ever.

Espurr drives off to grandmother's gravesite

This was really sad, especially the flashback of Espurr's life with the grandmother.

Dawn and Brock leave

It was sad because Dawn wanted to go back to Kanto with them, but she couldn't because she had an opportunity in Sinnoh. Buneary and Piplup got upset and ran off after learning they would never see Pikachu again.

Greninja leaves

Manaphy says goodbye to May

Lucario's death in Lucario and the Mystery of Mew

Pikachu decides not to evolve

Jessie leaves Dustox

100% better than Bye Bye Butterfree. So much more emotion, and the fact that it's Team Rocket and Jessie of all people is everything. The crushing of the Pokeball, the Dustox montage, even before where we see Jessie fall in love in early childhood and then lose that someone because they had to move.
Now Jessie letting Dustox go for love, despite how much Jessie cares about Dustox, is just heartbreaking and truly emotional.

James leaves Cacnea

Max gets upset over Norman's loss to Ash

Bonnie says goodbye to Squishy

In episode 43, this scene brings tears to my eyes when she says, "Squishy! I love you!"