The original books
- Mowgli leaving the jungle for the very first time. He just witnessed almost the entire wolf pack, who had always been his family, turn against him because of Shere Khan's manipulations, and try to kill both him and Akela. It's even the first time Mowgli actually cries in his entire life."What is happening to me? What is wrong with my eyes? Bagheera... am I dying?"
- In "Red Dog", Akela's death. After helping the Seonee Pack fight off the dhole, he succumbs to his wounds but not before telling Mowgli his debt to the wolf pack is repaid and he must return to men.
- "Lukannon." Hoooo boy.
- When Mowgli leaves the jungle for the last time to return to the world of men and must say good-bye to his animal friends.
- Grey Brother can't let Mowgli go and constantly howls with sadness. Bagheera only comes for a little bit to see Mowgli off because he's afraid he'll do the same thing, and Mowgli has the same thought about Bagheera.
The 1976 Chuck Jones short.
- After Mowgli scared off Shere Khan and the traitorous wolves, he start to cry and say goodbye to his jungle friends and family. Cue sad music.
- Mowgli getting picked on by the other wolves, resulting in him running away from the pack and his mother.