From Homestar Runner Wiki
Lotionman is The King of Town's dunce cap, as shown in origins. When Strong Bad, Strong Mad, and The Cheat relocated from hanging out at The Stick to hanging out behind Bubs' Concession Stand, they began calling themselves the On Point Kings. However, The King of Town thought that they were mentioning a "pointy king", and so he arrived, donning the dunce cap and apparently expecting to be part of the gang. According to Strong Bad, the On Point Kings eventually stole the dunce cap and named it Lotionman. Strong Bad does not elaborate on the history of Lotionman, and only says that "It was Strong Mad's idea."
- Debut: Email origins