Vice Principal Plum was the main antagonist of the Annoying Orange episode Cruel Middle School. While Orange and the gang looked through their old middle school yearbook, Orange explained that he always used to prank Vice Principal Plum every chance he got. Some examples of this was when he superglued his hairpiece to the ceiling and when he locked him in a vending machine. Vice Principal Plum, however, returned to the kitchen after he saw a Fruit-book post that Midget Apple made to issue a long-overdue reunion between Pear and Liz Lizard, and figured that the couple needed a chaperone. He then proceeded to look for Orange and get revenge on him for all of his pranks. Orange quickly disguised himself with a fake mustache and told Vice Principal Plum that he went into a nearby vending machine, but by the time he was trapped inside, he realized that he had been fooled once again, and everyone proceeded to have a dance party while Vice Principal Plum tried to escape.