I think there’s a bad logical fallacy that some comedians make. They think that being transgressive and cutting-edge and iconoclastic typically means offending people… and that therefore, if you’re offending people, it somehow automatically makes you transgressive and cutting-edge and iconoclastic. They think that because they’re offending people and making them angry, it means they’re Lenny Bruce.
It doesn’t work that way. To be iconoclastic, you have to destroy icons. To be cutting-edge, you have to push cultural boundaries in a way that moves society forward. To be transgressive — at least, to be transgressive in a meaningful way — you have to cross lines and break rules that deserve to be broken and crossed.