Top 10 Saddest Moments from the Pokemon Anime

1Misty and Brock Leave

Misty and Brock Leave


2Bye Bye Butterfree

Bye Bye Butterfree


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


4Charmander is Abandoned by His Trainer


5Ash is Turned to Stone and Brought Back by Pikachu's Tears


6Pickachu's Goodbye

Pickachu


7Pikachu Chooses Ash Over Freedom

Pikachu Chooses Ash Over Freedom


8Tommy's Parents Almost Die

Tommy


9Stoutland Dies

Stoutland Dies


10Goodra Leaves

Goodra Leaves


11Ash Sends Butterfree Off with His Mate


12Pikachu is Turned Into Stone


13Weezing and Arbok Leave

Weezing and Arbok Leave


14Ash Loses to Ritchie After Charizard Refuses to Battle


15Ash Says Goodbye to Charizard


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


17Jessie and Blissey


18Espurr Drives Off to Grandmother's Gravesite


19Dawn and Brock Leave

Dawn and Brock Leave


20Greninja leaves


21Manaphy Says Goodbye to May


22Pikachu Decides Not to Evolve


23Lucario's Death in Movie 8

Lucario


24Jessie leaves Dustox


25Pikachu Almost Dies


26James leaves Cacnea


27Max Gets Upset Over Norman's Loss to Ash


28Bonnie Says Goodbye to Squishy


29Ash leaves Greninja for Sun and Moon


30Pikachu Talks


31Pikachu Almost Dies After Being Attacked by a Flock of Spearows


32When Serena leaves at the end of XY


33Ash yells at Serena because he wanted to be alone (Pokemon XYZ Episode 28)


34Dawn's Piplup Runs Away


35When James left his Chimecho with his grandparents