Thanks for the thoughtful comment, Riley. I'm not sure he enjoys hurting the most marginalized as much as he enjoys being an instigator and is careless with his targets. Your second point is definitely true. He acknowledges his own hypocrisy in hurting others when battling his Shady alter ego in Guilty Conscience 2: "ain't you the same one who hated bullies callin' you bad names / then you turned around and did the exact same?" It seems to be a "hurt people hurt people" situation. The difference between him and those he ridicules, though, is millions of dollars and fame.