Tear Jerker / Hercules: The Animated Series

The episode "Hercules and the Phil Factor" has these moments in Phil's scenes. Phil has to deal with the fact that his rival Chiron is not just more successful than him as a hero trainer, but was also a hero in his own right, telling him that if he's not a hero, he's not worthy of training heroes, which causes him to try to be better than him by being a hero himself, but despite Hercules attempting to help him, it didn't work. After several failures, a tearful Phil has an identity crisis and starts questioning himself as a trainer, thinking that if his previous students failed, it wasn't because they were disappointing, but because he was inept and a second-rate trainer. Despite Hercules insisting that he never failed him and protesting against his decision to just give up hero business and leave, he resigns as his trainer, saying that he'll fail him too if he stays. Phil then sadly hugs him good-bye as he leaves to go working at his uncle's spear-selling business, but he has no success in this either.