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Saddest goodbye in the anime?

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Whether it's a pokemon being released or a former traveling companion leaving towards the end of the series, there have been quite a few emotional goodbyes in the anime.

For me, the top 2 saddest goodbyes were James leaving Cacnea with Gardenia and Jessie releasing Dustox. These two episodes were the first times that I actually cried watching Pokemon. For Cacnea getting left behind, it was more of Zoppi's delivery. I have to give him props for being able to handle emotional scenes with James.

And with Dustox, the second Jessie shattered its pokeball is when the tears came rolling down. Hell, I'm getting teary just thinking about it again.

I didn't cry watching this, but when the original trio parted ways at the end of Johto was probably the saddest goodbye to me out of Ash's companions. I mean, Ash even cried after saying goodbye to his friends. It was hard for me not to get emotional during that scene. Plus the song that 4Kids played during Misty's flashback made it sadder for me because of the "Knowing that I won't see you again" line.

There have been a few other emotional goodbyes for me, but the first two I listed actually made me cry so I had to put those down as my saddest.
 
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Out of the ones I have seen, I have to say it was Misty's goodbye for me. That song made me cry unusually hard.
 
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Jessie releasing Dustox in the original version. The voice acting and musical choices for the entire episode made it a genuinely sad moment, too bad the dub didn't translate those feelings very well.
 
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Misty and Dustox's goodbyes.
 
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James leaving Chimeco.
TR leaving Weezing and Arbok
Ash leaving Misty
 
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Ash released Butterfree...

And Dustox... whoooaaaa T.T
 
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When ash left pikachu with the wild pikachu tribe. Even if it was only for a short time, i still teared up
 
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#1 Mistys

"What makes me misty most of all
In this final curtain call
is knowing that i
wont see you again"

I loved the duo of Ash and Misty, and while Iris was similar in personality, they have just never been able to recreate that amazing chemistry Ash and Misty had.

#2 Arbok/Weezing and Jessie and James getting seriously hurt to protect them and showing their true good spirit.

#3 Dustox just as it had been around so long, and was like Jessies main contest Pokemon.
 
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Butterfree for me. Right in the damn feels everytime I watch that episode. Also when TR said goodbye to Arbok and Weezing.
 
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The saddest goodbye for me was when Ash left Misty and Brock(for the first time). It was just sad to see the original group split up at the end of Johto...It probably had a bigger impact on me when Ash said his goodbyes at the end of AG, DP, and BW.
 
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Pikachu's goodbye was really sad and touching even though it was like, only for a few minutes. Butterfree and Charizard's goodbyes were pretty sad too. Jessie and James leaving behind Arbok and Weezing was another emotional moment.
And amongst Ash's friends, I think Misty's goodbye at the end of Johto and Brock's goodbyes at the end of DP and when he decided to live with Prof. Ivy were really touching and well-written.
I had found May and Max's goodbye to be quite touching as well, but maybe it was just because they are my favorites. Tbh, I think they deserved a better goodbye instead of making it look really rushed.
Also, Misty saying goodbye to Togetic at the end of the Mirage Kingdom episodes. That surely was a pretty sad moment for all the Togepi fans.
And, another one would be Max saying goodbye to Ralts.
 
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I haven't seen any 100% human ones except for Iris + Cilan, so, yeah. I would rank Charizard as #1, Iris/Cilan as #2, and Butterfree as #3.
 
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Brock and Butterfree. ;_;

Edit: Oh yeah, and Jessie's Dustox. Goes to show that even evil has standards.
 
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All of the above^^

I also she'd a tear when Ambipom revealed the ball capsule and Make a wish played. That was a sad goodbye
 
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The saddest goodbye episode for me would have to be the one where Misty left. I cried an ocean for that one. When the time May, Brock, and Max had to leave, I had expectations for a real sad ending, but in return I reacted with a :|
There were a few other goodbyes and episodes that were quite sad, but I haven't seen any that topped the one I mentioned.
 
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Well the saddest moment to me was when Butterfree was left in a island since Ash Ketchum left him in the middle of nowhere with other of it's kind but maybe he never survived while I also vaguely remember an episode that Ash had an Ivysaur that when it evolved into Venusaur in a forest filled with others of it's kind he left him in the middle of nowhere (same theme here right).
 
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There have bee many sad moments and goodbyes in pokemon. Max parting with Ralts, Misty releasing Togetic, Ash dying in dirst movie, Jessie crushing pokeball to let Dustox fly away with its true mate, Butterfree departure etc were all memorable, impacting and saddening moments. Making you feel sorry for characters, relate to their pain and harsh times or draw valuable lesson from it.

But if there was one goodbye which could really invoke in me sentimentaliry, heartwarming feelings and sadness making you teary eyed was Misty goodbye.

I am within pokemon anime ever since its beginning and so far no other episode in my opinion beats level of emotion, memorability and moving like separation between Ash, Misty and Brock did.

Surrounding and dialogue was really well written brimming with beautiful and strong characterization between three friends which at that point became more than friends. They were like family to each other becoming strongly attached and caring and when time to say goodbye came it was doleful and very touching.

Misty cried and was visibly upset not wanting to leave her friends, Ash broke down being first and only time he cried when companions left with those two meaning a lot to him. Even Brock showed manly tears with all three trying to delay parting away for longest as they could showing to viewers powere of bonds and strong relationship which can get developed between humans.
And when Misty goodbye song started to play you couldn't stay indifferent to emotion present there.

Another reason why this goodbye was especially impacting for me is because it marked end of Misty time in show as main character which is unfortunate. Because she was great character with her sarcasm, with, caring nature and romantic, flirty side making interactions truly great. Having lot of untapped potential, unfinished things in story about her goals in becoming water master, feelings and interests.
Becoming forgotten and irrelevant.
 
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I would say the Espurr saying good bye to the woman that took care of it in the one X/Y episode above all else. Why? Espurr will never see this woman again, because she passed away, and it never got to give a proper good bye because it never knew the woman had died. That really gave me huge feels...

In all of the other good bye scenes, it's entirely possible for the parties to meet up again. But not in this scenario.
 
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I wish the Japanese version was made easily available to you guys because the Kasumi farewell flashback at the end of the original series is freaking fantastic. The combination of the clips used and the amazing music track from the second movie (which I ironically associate more with this flashback than I do with movie in which it debuted) really made the whole thing seem like an actual parting of friends.
 
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A couple of months ago I watched the episode where Misty and Brock leave at the end of the Johto Journeys for the first time despite being an original watcher when it aired and I cried. So I'm going with that.
 
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