This chapter explores the utility of the concept of hypermasculinity for studies of gender and power relations. We draw centrally on the work of Norbert Elias and R.W. Connell to advance the argument that while the concept of hypermasculinity is somewhat equivocal, it is useful in highlighting the development of absolutist masculine values, attitudes, and behaviours which entails a panoply of complex power balances between different sexes, social classes, ethnic groups, sexualities, and other established–outsider figurations. To develop this argument, we divide the chapter into two sections. First, we review recent debates surrounding gender and hypermasculinity in the academic literature, with a particular focus on the tandem sociogenetic ascendancy of what are here termed hypermasculine attributes and hypermasculine attributions. Then, we offer a tentative application of an Eliasian approach to hypermasculinity by tracing the ‘sociogenetic’ ascendancy and demise of ‘canons’ of hypermasculinity using an array of historical sources. We argue that hypermasculine developments are founded in a set of processes that pre-date the specific terminology of hypermasculinity, and which articulate a series of longer-term ‘integration conflicts’ and interrelated rising and falling levels of fear, particularly in response to perceived threats from ‘outsider’ groups to the power chances of historically ‘established’ hegemonic groups.