Homeschool Winner is a rejected character, appearing visually similar to Homestar Runner. Though never properly appearing with a significant, identifiable role in a toon, Homeschool Winner has been the most frequently referenced of the site's rejected characters — likely due to his resemblance to the site's title character. He was described as being a big nerd, with a possible creepy edge to him.
The name "Homeschool Winner" came about when a friend of the Brothers Chaps misremembered homestarrunner.com as "HomeschoolWinner.com". In keeping with the connection to Homestar Runner, his design is an intentional distortion of Homestar's: similar white skin, lack of arms, and general proportions; but with an overbite instead of an underbite, blue shirt and red-soled feet rather than a red shirt and blue-soled feet, and speech bubble rather than star on his shirt. This parodic design is somewhat similar to Homsar, another joke character inspired by an incorrect version of Homestar's name.
In Dangeresque Roomisode 2, the silhouette of the arcade game player in the window bears a striking resemblance to Homeschool Winner, and has a voice vaguely similar to Homestar's without the rhotacism. In addition, Dangeresque mentions the silhouette's behavior being "creepo", presumably referencing the aforementioned "creepy edge" to Homeschool's character. If this figure is indeed Homeschool, the game would be the first time he has been heard speaking.
