This article concentrates on the transformative potential of the Millennial generation within the framework of the political landscapes of the United States, several European countries and Russia. Generational experiences frame the context for the comparative examination of the democratic order and the perspectives for democratic transition. In Western countries, the group is a potentially powerful political force, yet its members do not pursue traditional forms of civic engagement - they are sceptical about institutional forms of participation and have little trust in public authority. Embedded in a youth-marginalization discourse, the public identities of the Millennials are seen rather as a manifestation of the failures of democratic representation, rather than as forms of agency seeking new ways of political expression. The orientations of this distinct group also present a puzzle when the future of authoritarian regimes is discussed: Millennials’ openness to political change is often questioned, despite the prominent role they play in the rise of the opposition forces that gained influence during Vladimir Putin’s third term. Nevertheless, in both contexts, the ongoing generational shift has become an increasingly important area for social-scientific investigation and it is being directly related to broader arguments about the nature of political change.