Even though there is evidence that public acceptance of homosexuality continues to improve in a growing number of Western countries, gay men continue to face challenges across the life course in relation to material inequality, lack of cultural recognition, and inadequate or problematic political representation. These experiences are intersected by other dimensions of advantage and disadvantage – not least gender and age – that play out differently in different contexts. This chapter explores the treatment of older gay men by society, generally, and in comparison with other population groups. It also examines gay men’s own experience of ageing and, in particular, how gay men themselves regard ageing and older gay men. Our analysis highlights not only the extent to which ageism shapes societal views of older gay men but also how ageing experiences affect gay men’s view of themselves as older and eventually old men. The chapter considers gay men’s understanding of their own advantage or disadvantage in their specific cultural contexts and the transformative strategies they are involved in and that link to a wider politics of material redistribution, cultural recognition and political representation.