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Saddest goodbye in the anime?

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For me it was A Poached Ego with Jessie and James having to let go of Arbok and Weezing. Seeing them getting pulverized by the Tyranitar while the Pokemon left in tears was heartbreaking, with the Tears of Life theme adding to it. The human goodbyes like the original team at the end of Johto didn't get me as much because they can always see each other again even if they won't travel together anymore, especially since I had already seen Brock leave and come back once before. But this was pretty much it for TR and their original Pokemon.
 
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- Cried a river watching OS trio split up(yes, the dub, I hear it's more sad in Japanese though, would cry an ocean.)
(Same result with Bye Bye Butterfree of course.)

DP trio split up, the music is what gets me...and the montage in the Japanese version...yeah..(so beautiful ;_;)

Every 'TRio releases a Pokemon' episode, gets me everytime q.q

AG farewell was rushed(in my opinion)..they could've done a little montage like they did with Misty.

BW farewell was eh, didn't really...uh..idk >.>
 
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honestly, the only goodbye (if you can call it that) that really had me almost bawling was Lucario's in movie 8, don't know if that counts. Other than that, TRio leaving behind Arbok and Weezing teared me up.
 
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The saddest goodbye was Team Rocket saying goodbye to Arbok and Weezing, those 2 were the best Pokemon Team Rocket had.
 
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All the mentioned. I see no one mentioned Best Wishes ending though, no surprise. It was like: "oh they left, I forgot they had been there to begin with" feeling.
I don't miss Iris much at all. She had a few redeeming qualities and good moments, but was stale and annoying imo with her constant: "what a kid/you are such a little kid"

In fact I miss the rivals (except Trip) more than Iris.
For Cilan, I liked him in fact. He was the better thing about Best Wishes, otherwise it was the worst "series" of Pokemon anime.
 
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I'd have to say the saddest goodbyes IMO, were when Ash left Charizard, the OS trio splitting up at the end of OS, Pikachu nearly leaving Ash in Pikachu's Goodbye, Ash dying in M01/M14, and oddly enough, the DP trio goodbye. Even though I thought that the DP trio as a whole had bad chemistry, it was my first series that I watched fully. I never thought that Ash and Brock would ever spilt forever like that, and it overrall, I thought it was great, if you looked past the awful dubbing.
 
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I don't think the DP chemistry was as bad. It was just conflict between the directors of the episodes. One episode made it seem as if Dawn had deeper feelings for Ash, only for another episode to completely deny that. For Brock, he had a few scenes with Dawn, like Takeshi's paradise with her for the Psyducks etc. :D
 
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By far and away, Misty's departure. Although my username might suggest a fanatical loyalty to the AG and its associated characters, it's undeniable how genuinely sad it was when the original trio was to be no more. As others have already pointed out, nearly every aspect of the parting made it feel so legitimate. Ash's Butterfree is a close second.
 
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Oh my gawd... I was just thinking this lol. To me its Jessie and dustox. That was like the worst kind of feel in the anime. My heart exploded with tears when she crushed its pokeball. I hope I'm not the only one >_<
 
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Misty's leaving was just so depressing for me. The whole episode was really emotional, and as some have said, that flashback scene is the part I remember making me just want to burst out into tears. I actually cried when it aired, and I'd probably still get emotional if I watched it again. :bawl:
 
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Team Rocket releasing their Arbok, Weezing, Chimecho, Dustox and Cacnea with Dustox's being the most emotional release.
 
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Charizard didnt really stay away long, it returned later in series, several times, burning Ash affectionately with Flamethrower, also, in the first time he returned, which was in the time when the heroes tried to get the Dragon Fang back from Team Rocket, Charizard, after burning Ash and Pikachu, landed on the both of them, and licked theit faces until the soot was gone

Also, there were lots of sad moments, but I never cried about them
 
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