Until recently, shame culture was considered a powerful weapon for maintaining the status quo. Furthermore, it was also considered anti-democratic. Yet nowadays, in the hands of the weak, it has become a powerful weapon for challenging the status quo. It appears that the efficiency of shame has increased in an allegedly shameless society. This article seeks to clarify such conundrums by employing the largely forgotten dialectic of the self to highlight the difference between “being ashamed” within one’s inner self and “feeling shamed” in one’s outer self, as evinced in the usages of two different words for “shame” in Hebrew and Greek. By contrasting Socrates with Diogenes the Cynic, this approach shows not only why not being able to be ashamed within one’s inner self is a sign of a totalitarian self but also why such a self can become more vulnerable to external acts of shaming.