The relationship between political conservatism and left–right orientation was examined in 15 Western European and 13 former communist Central and Eastern European countries using the data from European Social Survey Round 3 (N = 46,103) and Round 4 (N = 50,601). Cross-culturally validated values were used to measure the two potential aspects of conservatism: resistance to change and acceptance of inequality. Both of these aspects were positively related to right-wing orientation in Western countries. In the former communist countries, the relationships were positive, negative, and nonexistent; they differed between the countries and varied between 2006 and 2008. The results indicate that conservatism can be related to left-wing or right-wing orientation depending on the cultural, political, and economic situation of the society in question. The results also show that despite the shared communist past, former communist Central and Eastern Europe is a diverse region that should be treated as such also in research.