Top 10 Saddest Moments from the Pokemon Anime

The Top Ten
1 Misty and Brock Leave

I was cheering that Misty finally left. My god! You guys are too attached. Serena was way better than this. Y'all saw Misty bore Ash with a log! Not cool! So I cheered and laughed while Misty was leaving. Definitely the best moment in Pokemon ever.

P.S. The sun and moon goodbye was way sadder. Also, Serena, Bonnie and Clemont should have come back in sun and moon, not Misty and Brock. We see to much of them and its really annoying.

Don't forget to check out their return episodes in 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.

2 Bye Bye Butterfree

Caterpie was the first Pokemon Ash caught. After the full eveloution 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.

It's sad until you realize that butterfree leaves to get laid.

3 Pikachu and the Other Pokemon Cry After Ash is Turned to Stone

Only moment in pokemon I cried at.

I was cing 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...

4 Charmander is Abandoned by His Trainer
5 Ash is Turned to Stone and Brought Back by Pikachu’s Tears
6 Pickachu's Goodbye

Sad episode where I thought Pikachu would stay with the other wild Pikachu. Ash"s Pikachu returned to Ash so heart warming.

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

7 Pikachu Chooses Ash Over Freedom
8 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!

9 Stoutland Dies

This is so sad because litten is so cute and confused and it doesn't directly tell you that stoutland died. But I loved that meowth talked to litten to try and get it over its sadness and worry.

The leaves where falling from the tree one by one and when the leaf fell litten caught it and kept it until it blew away and then litten saw a cloud that was like stoutland then the stoutland cloud rad away and that point litten knew that it was time for him to move on... what's sadder then that!?

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

10 Goodra Leaves
The Contenders
11 Ash Sends Butterfree Off with His Mate
12 Pikachu is Turned Into Stone

I loved the movie even though dancie is a spoilt brat. Honestly, I nearly cried. Pikachu means so much to me and ash

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

13 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 over rated. Team Rocket>Ash and Friends.

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

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

14 Ash Loses to Ritchie After Charizard Refuses to Battle

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

15 Ash Says Goodbye to Charizard

Saddest episode for me. Its been 15 years still I cry when I watch this

16 Serena Cries After Failing to Make It Past the First Round of the Pokemon Showcase

Serena annoys me. She cries easily after losses. Take Jessie for example, she has gone through lots of worse things throughout her life. Serena needs some backbone. And people call Jessie selfish, why do you think she is how she is today? I can definitely see how most people watching the show are young as young people don't understand complicted characters with complicated emotions. Well, usually.

Hey Serena's haters just a little note from a Serena lover. Have you ever actually payed 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 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 tink 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 to. And for all those Serena haters out there just know that Serena has feelings too.

17 Jessie and Blissey

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

What happened in this episode?

18 Espurr Drives Off to Grandmother’s Gravesite

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

19 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 for Buneary and Piplup got upset anand ran off after learning it would never see pikachu again.

20 Greninja leaves
21 Manaphy Says Goodbye to May
22 Pikachu Decides Not to Evolve
23 Lucario's Death in Movie 8
24 Jessie leaves Dustox

100% better than bye bye butterfree. so much more emotion and the fact that its 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 just truly emotional.

25 Pikachu Almost Dies

Pikachu died in Detective Pikachu... Luckily he got bought back to life by Morelull.

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