This chapter will include a brief historical account of masculinity and summarise the underpinning pathway of masculinity in relation to its current positionality in Western culture. It will detail multiple masculinities and outline how hegemonic masculinity and patriarchal systems are interlinked. This chapter will also discuss male identities that sit outside the expected hegemonic norms for males and how this has reinforced the masculine identity. Links with sex, sexuality, abortion and control of women’s bodies will be discussed in the light of the contemporary males and the landscape that they have to negotiate.