The possible impacts of contextual effects on political behaviour have long been studied and analysed by political scientists and geographers. We review previous relevant literature and extend it by incorporating the recent rise of populism and developments of socio-economic determinants of the political economy of discontent and the geography of happiness and well-being across the European Union. In particular, the research presented in this paper is aimed at analysing the impact of individual and contextual variables on political behaviour across European regions. Additionally, this paper examines links between subjective well-being and political preferences, while at the same time considers contextual factors at the regional level across Europe. Methodologically, we adopt a multilevel modelling approach to analyse voting behaviour and to also examine subjective happiness indicators in relation to factors of political geography. We employ data from the European Social Survey (ESS) to estimate the effects of economic and non-economic factors across Europe on the geography of subjective happiness and discontent using individual social values and cultural norms. We find that not only are individual level characteristics significant, but so too are regional characteristics.