Left and right are viewed as social constructs that serve to orient and to bind people to political choices over the last two centuries mostly within established Western liberal democracies. Their contents and functions, however, have not been invariant across polities but were largely shaped in accordance with the distinctive characteristics of societies and of political systems in which they operated. Thus, one can't avoid addressing left and right under an historical perspective to make sense of their different expressions and to better appreciate their functions. Recent findings have shown that individual differences in personality traits, basic values, and core political values account for a significant portion of preference for left and right across several polities. It has been argued that affinities between individual differences in personality and political preferences have developed over time under conditions of choice in which people's dispositions and value priorities could meet contingent political offers. Time and opportunities of free choice made possible the establishment of distinctive ideological identities that ultimately find their roots in people's personalities. Novel findings document the function that left and right still can play in predicting political preference and in summarizing political attitudes as stable social postures that account for the encounter of personality and politics.KEY WORDS: personality, left-right ideology, democracy, historical accountsThe decline of sociostructural factors as shapers of political preferences and the emergence of person-centered issues has been a striking change for contemporary democracies. Traditional social cleavages like religion, class, occupation, income, and education account for political orientation less than in the past (e.g., Dalton & Wattenberg, 2000;Jansen, De Graaf, & Need, 2011;Van der Brug, 2010), in concomitance with the secularization of societies and with the access of most of citizens to decent conditions of life.Likely this does not occur to the same degree across political contexts where the functioning of democratic institution results from different vicissitudes and current contingencies. Neither should we overlook the severe tolls that poverty, racial divisions, and social exclusion may impose over the full realization of democracy, even in the wealthiest countries (Manza & Brooks, 1999;McCarty, Poole, & Rosenthal, 2006 Yet a major concern with respect to individuals' rights and the full expression of their personalities appears to be a unique feature of the political offer that appeals to citizens' preferences, the more they attain the freedom to voice their needs and aspirations (Inglehart & Welzel, 2005).The traditional compasses of political navigation, like party identifications and political ideologies, appear less constraining than in the past, particularly in multiparty democracies where political parties change names and constituencies, form coalitions, and endorse political programs that are barely distinctive, w...