Political scientists traditionally have analyzed the effect of politics on subjective well-being (SWB) at the collective level, finding that more liberal countries report greater SWB. Conversely, psychologists have focused primarily on SWB at the individual level and shown that being more conservative corresponds in greater SWB. We integrate the theoretical foundations of these 2 literatures (e.g., livability and system justification theories) to compare and contrast the effects of country- and individual-level political orientation on SWB simultaneously. Using a panel of 16 West European countries representative of 1,134,384 individuals from 1970 to 2002, we demonstrated this SWB political paradox: More liberal countries and more conservative individuals had higher levels of SWB. More important, we explored measurement as a moderator of the political orientation-SWB relationship to shed some light on why this paradox exists. When orientation is measured in terms of enacted values (i.e., what the government actually does), liberalism corresponds in higher SWB, but when politics is measured in terms of espoused values (i.e., what individuals believe), greater conservatism coincided in higher SWB. (PsycINFO Database Record (c) 2014 APA, all rights reserved).