This article deals with the ‘problem’ of flattery (kolakeia) as a specific form of activity, contrasted to parrhesia. Who is the flatterer? In which ethical-political contexts does the flatterer act? With what cultural, social, and political consequences? Discussing such questions, the article revitalizes the concept of flattery, showing its enduring constitutive role in social life. I start with giving an account of flattery in ancient literature, focusing on Aristotle, Plato, and Aristophanes. Then I move to early modernity and discuss Machiavelli’s and Castiglione’s approach to flattery. Finally, I turn to flattery in late modernity. This analysis is coupled with a discussion of de Certeau’s concept of ‘tactics’ and the concept of ‘profanation’ in Spinoza and Agamben – concepts that are apparently comparable to flattery but are very different. To end with, the article synthesizes its arguments and relates different styles of flattery to each other systematically, discussing some practical-political consequences of flattery.