John, Why? is a user who signed up in the beginning era of Drawception. He is very popular and many regard him as one of the best artists on Drawception. He is known for his high-quality and often disturbing drawings.
With this game https://drawception.com/viewgame/229hnC5ON3/drawception-otps/ an inside joke started to go around Drawception about the "Desolation x John why" ship. They even have a love child which looks like a mix of Desolation and John as a baby.
John, Why? announced leaving Drawception for the US Air Force. As evident by this game: https://drawception.com/game/xTKD4SafZ8/john-bye/ . Shortly after in February 16th re-appeared, participating in more games explaining "I'm no longer entirely cut of from the outside world, and I'm trying to play a little with an iPad. No tablet right now." and has since been fairly active on the site taking part from time to time.