Saddest Episode?

The episode when Misty released Togetic was pretty sad because everyone loved Togepi
 
Diamond & Pearl Episode 117 - Noodles Roamin' Off!

I thought it was so sad that James wanted to keep Team Rocket going but Meowth and Jesse were ready to give up. I almost cried :(
 
For me it would be when Jessie and James let go of Arbok and Weezing (I LOVED Jessie's Arbok they made such a great team), watching the expression's on the Pokémon's faces as their former trainers were being all valiant really got to me.


Also, when Ash left Charizard and ran away without looking back and Charizard was just roaring... ARGH that was really bad for me as well.


I may as well do a top three haha - I'm also kinda sad that Ash never reunited with his Pidgeot, when he said goodbye to it I felt like he'd come back again and he never has.
 
Gotta Catch Ya Later, definitely. It was the saddest departure episode in my opinion, although I can't say for the finale of Unova. It's really sad, but now that I remember it, Memories Made Of Bliss was really sad as well. As a PearlShipper during the time, the last high-five killed me. :( Home is Where the Start is never really captured me, despite me growing up with May for some reason.

I guess it's a tie between Gotta Catch Ya Later and Memories are Made of Bliss, haha.
(Also what was the track used in Gotta Catch YL the part where Ash, Brock and Misty were walking together and Misty was walking with her bike. I recall it was used prominently in that episodes and in other episodes as well, haha.)
 
Bye bye butterfree, all day every day. Still gets me sad even having seen it a load of times. Not ashamed to say, but I shed a tear the first time I rewatched it as an adult.

I don't know the episode name, but the departure of Max and may at the end off battle frontier was quite emotional.
 
Peitharchia said:
Don't remember which episode it was, but I was pretty saddened when Misty left Ash and Brock in their journey. ): She was later replaced by May, though, thankfully, who was equally as awesome. When I'd first seen her, I actually thought it was Misty but only with a different outfit and hairdo, haha. Their designs were extremely similar; I'm sure I'm not the only one who felt this way.
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OMG!! Season 5, one of the last episode where Brock and Misty go their own ways and Ash goes back to Pallet Town!! That was soo sad, almost cried!! I thought I would never see Brock or Misty, and I didn't see Misty!
Also the episode where Ash leaves Pikachu in season 1 with the wild Pikachu, that was too much as well... So happy when Pikachu came back!!
 
For me, there are quite a lot, but my biggest one, was when James gave cacnea to gardenia. Even if it was for Cacnea's benefit. I remember when Ash and the others met Barry, and he talked about Cacnea when TR showed up, that made me sad all over again
 
Aside from League loss episodes, contests/Grand Festival loss episodes, episodes where trainer and Pokemon part ways, episodes where trainer and Pokemon seemingly part ways, the famous "Bye Bye Butterfree" and "Charizard's Burning Ambition", a specific mentioning goes to "Do I Hear a Ralts?"
 
I'd say Pikachu's Goodbye, Bye Bye Butterfree. The episode when Ash says goodbye to Lapras, when he says goodbye to Charizard, whenever Team Rocket releases Pokemon. Of course Pokemon Movie 1. But I've seen recently very sad episode. It was Pokemon Origins episode 2. This poor Cubone! If I tried to make my top 5 of saddest Pokemon episodes it should go like this:
1. Bye Bye Butterfree
2. Pokemon Origins: Cubone
3. Pikachu's Goodbye
4. Memories are Made of Bliss
5. Charizard's Burning Desire.
 
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