Harold Gloom, also known as the Hobo Candyman Magician or just Gloom, is Wallis Gloom's younger brother and Petunia's son. He lived on the streets in a cardboard box, living next to Mooching Hobo until he stole money from Wallis and was forced to work for him in order to pay him back. He didn't get his magic until he was seventeen, which is considered a late age to get your magic, and is the most likely reason that Wallis hired Assistant.
Wallis Gloom Edit
Harold is Wallis's younger brother. They were really close when they were younger, but after Wallis accidentally turned Harold's limbs invisible their relationship has been strained. Wallis blamed himself for the incident and distanced himself from Harold.
Harold and Assistant quickly bonded while undergoing training to work for Wallis. They are friendly with each other, and Wallis often teases them by implying they are a couple or that Harold is romantically interested in her.
Mooching Hobo Edit
While Harold was homeless, he lived next to Mooching Hobo, who he became good friends with. He would often give him candy, though he would never let Mooching Hobo eat one of his lemon kids.
The Dark Overlord Edit
The Dark Overlord has only been seen by Harold, Seaweed, and Assistant. According to Seaweed, Harold has made many attempts to contact the Dark Overlord, all of which have been unsuccessful. Although Mooching Hobo hasn't seen the Dark Overlord himself, he believes Harold because they are good friends.
Lemon Kids Edit
The Lemon Kids are sentient creatures formed from Harold's magic that live in his hat. Although it isn't unheard of for people to make golems using their magic, golems are unable to think or speak on their own. According to Harold, he has no idea how he creates them, they just appear on their own and he has no control over them. So far four lemon kids have made an appearance, the original Lemon Kid, Lemon Geek (wears glasses and has a calculator), Lemon Chap (wears a top hat and monocle), and an unnamed lemon kid with a mustache. Although they have a cute appearance and joyful attitude, they often make creepy comments and worship the dark overlord. It upsets Harold when they make creepy statements, such as, "The dark lord will be pleased," or, "I hear human flesh is delicious."
- Harold has a stuffed pink bear with a top hat and monocle named Mr. Monocle. Wallis uses it in The Battle Between Brothers to mock him. It also makes an appearance in Hereafter when Assistant dreams about the kid versions of herself, Wallis, and Harold during her coma.
- Although Harold/Assistant is a popular ship, Harold is asexual and aromantic.
- Petunia's nickname for Harold is Gloomy Bear