The dream of the octopus

Found in a high-school notebook.

I see four separate things going on:

  • At left is a sideways mineshaft.
  • At center is an octopus riding on an alien companion. He desires to be human. (He will change his mind once he realizes how cool it is to have eight arms.)
  • At bottom right is a mustachioed depiction of a high-school classmate. Christy was her name.
  • At top is a nomadic ladder. He wanders the desert, seeking out treasure that’s out of reach to the average adventurer.