This paper explores the relationship between happiness and inequality. It does so firstly through an analysis of how "classical" authors of political economy and philosophy have linked these two issues. Secondly, major findings of "happiness economics" are discussed in the context of new insights about how happiness is influenced by inequality. This paper also addresses whether these findings provide any substantial arguments for combatting inequality on the grounds of promoting "happiness". It will be seen that although some empirical research shows that the prevalent levels of inequality influence happiness in society, the main argument in favor of tackling inequality for the sake of happiness is normative. In this interpretation, happiness is closely related to John Stuart Mill's neo-Aristotelian idea of "self-fulfillment" and less so to the neo-Benthamite notion of "hedonic pleasure". In the wake of an ever greater emphasis on analyzing people’s "subjective well-being" within national statistics, this has political implications as it calls for the importance of allowing free and broad discussions on the "fairness" of the prevailing political systems as an important prerequisite to promote happiness – and combat inequality.