This dissertation examines the conception and performance of masculinities amongst two groups of Russian men, half of whom live in Russia and the other half in the United Kingdom. A total of forty in-depth biographical interviews were carried out, twenty in each country, with men of different ages and highly different social backgrounds. On the basis of these interviews, the thesis portrays contemporary Russian masculinities as a complex, socially and historically constructed phenomenon, situated within large-scale social and political processes. It explores the most prominent reference points and social hierarchies employed by the respondents in order to negotiate their individual gender projects, and shows how these are culture-specific, context-specific, and rooted both in individual life history and in the social, economical and political realities of different historical periods. While the respondents play an active role in defining and constructing their own masculinities, they do so within the macro-parameters laid down by the state, in accordance with broader socio-cultural and political factors. Shifts in the macro-parameters (such as the collapse of the Soviet Union or migration to another country) change the environment in which an individual lives and give rise to new resources for negotiating masculinity. Like the reference points and social hierarchies referred to above, these new resources are rooted in specific historical, cultural, political and personal events. Each resource belongs to a particular social topography that orients people towards the places, practices and discourses which they need to realise their masculinity. The main empirical findings in the thesis are ordered in accordance with the contexts, reference points and hierarchies for making masculinity which were referred to by the research participants themselves. The dissertation is structured around four contexts which emerged from the data: (i) the Soviet past; (ii) the first post-Soviet decade (the 1990s); (iii) the second post-Soviet decade (the 2000s); (iv) the immigration period. I explore different masculinity construction strategies and the reference points on which they rely as the site of a socio-cultural power struggle that offers a unique prism through which to understand how Russian masculinities and gender relations are validated and contested, and how they change.