Despite having a significant impact on how we perceive ageing, cultural representations of old age, particularly depictions of old men, have received little attention. This is especially true regarding the cinemas of small nations and Eastern European film. Some authors claim that this gap in knowledge unintentionally repeats a widespread cultural assumption of associating masculinity with young and middle age men (Saxton & Cole, 2012, pp. 97–98). Old age has a complex relationship with the hegemonic variant of masculinity, which, as defined by R. W. Connell and James W. Messerschmidt, opposes itself to femininities and oppresses alternative forms of masculinities (Connell & Messerschmidt, 2005, p. 832). As hegemonic masculinity presupposes that one is physically and/or socioeconomically in their prime, old age appears to be inversely correlated with it, offering an opportunity to rethink masculinities. At the same time, as the films analysed in this article will show, becoming marginalised in old age, often due to hegemonic masculinity, does not necessarily lead one to abandon its principles.Caring masculinity has recently been discussed as a non-hierarchical alternative to hegemonic masculinity (Hanlon, 2012; Elliott, 2016; Ruby & Scholz, 2018; Chatzidakis et al., 2020; Hyvönen, 2021). So far, caring is socially constructed as feminine (see also Reskin, 1988). Despite the growing labour market participation of females, the gender care gap is not closing at the same speed and remains the chief source of the ‘patriarchal dividend’ (Connell, 1995). Men's changing relation to care, at least regarding one's own children, has been the focus of policy reform, but less so men's relation to care more broadly. Theories that aim to explain the gender inequality in care work usually do not engage with critical studies of men and masculinity along with the concept of hegemonic masculinity (Connell & Messerschmidt, 2005). Care's intersectionality with ageing and masculinities especially merits further study. This article will frame caring masculinity as well as the social context regarding care and old age in Estonia. Following this, the representation of these topics will be analysed in two Estonian films: A Friend of Mine (Kivastik, 2011) and Tangerines (Urushadze, 2013), in which such concerns are central.