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Chile has usually been considered a particularly successful post-1990 case of democratic consolidation, with fairly high-quality democratic functioning (at least by regional standards). Nonetheless, a series of symptoms- such as the massive 2011 student demonstrations, severely declining electoral participation and a deep and sustained drop in party identification, among many others- suggest its democratic institutions face serious challenges of representation that could imperil its long-term legitimacy. In this paper, I argue that a generational change perspective is particularly useful for illuminating the causes of these symptoms, and thus helps to frame and explain the nature of current democratic change in Chile. In particular, I systematically examine continuities and discontinuities in political attitudes, preferences and behavior between an ‘older’ generation that was politically aware by the time of the 1988 plebiscite that defeated General Pinochet’s dictatorial regime, and a ‘younger’ generation that became politically aware after the return to democracy in 1990. Using LAPOP survey data, as well as local polls and disaggregated electoral data (that allows comparisons between younger and older voters), I show that from a comparative perspective there is an unusually sharp discontinuity in some key dimensions between the younger and older political generations, particularly as relates to actual political behavior (as opposed to mere attitudes and preferences). I suggest these differences herald significant changes for Chile’s political dynamics and particularly for its so-far-stable party system, with uncertain consequences for the long-term functioning of its democratic system as a whole.