Plato's Gorgias might as well have been named On Shame. The word appears sixty-nine times in the course of the dialogue with a lion's share of references to shame being made by Socrates’ character. Callicles comes in second in his use of the term. Cairns notes that in the corpus of the lyric poet Theognis of Megara (sixth century BC) we have ‘the first instance of the noun aischunē.’ Cairns goes on to comment on Theognis’ use of αἰσχύνη and says that ‘[h]ere it appears in the objective sense, but later it will also be found in a subjective sense, as the reaction to or mental picture of disgrace and so as equivalent of aidōs.’ Although it is important to differentiate αἰσχύνη and αἰδώς, the terms, as Cairns suggests, are capable of expressing interchangeable meanings. Hence, in our comparative study of shame in the Gorgias and in the Clouds, we pay close attention to and examine the context in which a given term appears. The central role that shame plays in the Gorgias is the subject matter of analyses by Race, Bensen Cain, McKim, and Dodds. Race is confident that ‘of all the motifs running through the work, the most insistent is that of shame, for the word aischyne (along with verbal forms of aischynomai and the adjective aischros) occurs over 75 times.’ In line with the view that shame is central in the Gorgias, we offer a further contribution, which focuses on the affinity between the treatment of shame in that dialogue and in Aristophanes’ Clouds. We argue that either the ostensible subject of the Gorgias, which is usually identified as rhetoric, is not the dialogue's true concern or the explicit subject matter cannot be understood without its accompanying element, which is shame. To support this thesis, we undertake a comparative analysis of the thematic, heuristic, and conceptual use of shame in the Gorgias in view of Aristophanes’ play. We argue that the characters in the Clouds portray the same perennial attitudes to life as do the interlocutors in the Gorgias and, what is more, the characters in both works evoke with more than incidental clarity certain historical figures (Alcibiades and Pericles). Thus, both works, as we claim, are commenting on and, even though the Clouds is a comedy, serve as the ground for our philosophical reflection on the political, educational, and cultural ideals of ancient Greece. Moreover, the Clouds makes light of, instead of endorsing, such distinctions as shameful/laudable, natural/conventional, old/new, education/didacticism, and moral/prudish. We draw on the humor of the Clouds, which allows us to withhold immediate judgment about these dichotomies in order to then examine these same notions which are problematized in the Gorgias.