This article explores the gender politics of heterosexual masculinity by detailing the practices of masculinity and heterosexuality among a group of Thai men working in the tourism industry in Thailand's south. The research is based on ethnographic data obtained during a number of field visits between October 2000 and January 2007 to Pha-ngan Island in southern Thailand. It is positioned within the geography literature on masculinities and heterosexuality, extending the current literature on cross-cultural negotiations of masculinity by exploring negotiations of heterosexual masculinity in a context where differing cultural notions of hegemonic masculinity come into dialogue. Specifically, I detail the articulation of heterosexual masculinity by Thai bar workers through their encounters with three key 'Others': Thai transgendered people; tourist women; and tourist men. These encounters provide a context through which the complexity and instability of both hegemonic and subordinated masculinity can be explored. In particular, I argue that the delineation of these masculinities is both contextually and culturally specific. The encounters also provide an opportunity to investigate the importance of spatiality to the performance of heterosexual identities.