The cruelest thing i've ever done to Pennywise was put my roommate's ushanka on his head for a photo op. The second cruelest was when he was a kitten I chased him until he was terrified and cowering, but that was less cruel, because it was necessary. He was getting too cocky.
This is a really rare and unique sitting style. It was actualy pioneered by Penny himself and has only been successfully replicated a handful of times by his many protegés. Don't try this style at home, it's for experts only!!