Bye, Bye, Butterfree (Season 1)
Let's start with when Ash let his Butterfree return to the wild to be with his little girlfriend. This one hurt extra bad because not only was it the first wild Pokemon Ash ever caught, it was also the first time he parted ways with one of his companions. And in addition to a heart-wrenching final look back as Butterfree flew away, we were also treated to a montage of their journey together set to the most ridiculously dramatic music possible. But you know what, Butterfree had a cool scarf and found love. We should be happy for him.Pikachu's Goodbye (Season 1)
Keeping on the topic of goodbyes, there are absolutely none that come close to when Pikachu met all the other little Pikachus in the forest. Ash had to make the hardest decision of his life to leave his partner behind with his new friends. This turns into a Pikachu-Ash tear-fest that ends up with Ash literally running away crying while we're treated to yet another dramatic montage. Luckily the episode ends with the triumphant Pikachu making the right call and returning to Ash while his friends cheered on.Charmander, The Stray Pokemon (Season 1)
Charmander originally belonged to a horrible trainer named Damian who got tired of Charmander being weak and abandoned him in the forest, telling him that he would come back later. Charmander was stuck out in the rain loyally waiting for Damian to return and his health deteriorated as his flame started to go out. Ash rushed him to the Pokemon center, sheltering his poor little tail. Thankfully Nurse Joy worked her magic and Charmander was nursed back to perfect health. Guys, this is serious stuff.Friend of Foe Alike (Season 1)
So this one's a whole different type of sad. We see Ash completely dominate gym after gym, obstacle after obstacle, and then he blows it at the Pokemon League. There wasn't a single one of us out there that wasn't upset at Ash's Charizard ignoring him, and his crushing loss to Ritchie and his Pikachu Sparky was just sad. Come on Ash, only top 16?Pokemon Origins (Episode 2)
Now this isn't from the original anime but actually from the excellent, recently released Pokemon Origins. The series followed the original games to a T, including the Marowak ghost haunting the tower in Lavender Town. The show introduces a baby Cubone who reunites with his mother one last time before she finds peace with her passing. If you're a Pokemon fan, make sure you check out this four-part special because it is awesome.Pokemon: The First Movie
Okay, we all knew it was coming to this, the granddaddy of them all: Pokemon: The First Movie. So we see Pokemon struggling to fight their clones, which is difficult to watch. But then we see Pikachu simply unwilling to fight back, just taking slap after slap standing up for what he believes in. But then it all goes to the next level when Ash seemingly dies and is turned to stone. Seeing Pikachu cry over his best friend is just wrong. And then every Pokemon starts crying, and then all the kids watching start crying, and then Ash wakes up and then the tears save him. Why is this so emotional!?So what's your saddest Pokemon moment? Let us know in the comments and share this article on Facebook or Twitter to see if your friends agree with you. For more on everything Pokemon, hit up IGN. Brandin Tyrrel is a freelance writer covering games and tech. There's absolutely no reason to follow him on Twitter.
