7. "Bye Bye Butterfree"
For any watcher of Pokemon as a child, they will know this episode to be one of the most depressing things about it, in which Ash after many months of training his Butterfree which instantly became a fan favourite, departs. The episode entails a love story between Ash's Butterfree and another, except this one is PINK (A rare Pokemon in the game on Gold & Silver) and Ash, faces the decision of either keeping the Butterfree he loves, or releasing him, to his despair. Ash decides to do the WRONG thing and let Butterfree go, causing himself and thousands of viewers to break up and sob uncontrollably as this heartbreaking scene. A childhood truly scarred.