Gender is an important axis around which societies are organized. Gender norms carry implications for men, women, and others, shaping behaviors and practices, and access to opportunities. Limited research to date has focused on how men belonging to distinct social generations conduct their lives and how men’s enactment of gender may influence their health. To address this gap, a critical review of international research conducted in different countries including the USA, Canada, Australia, and Denmark was undertaken. In addition, a qualitative study was designed to examine men’s enactment of masculinities for their health problems. A social generational lens, drawing upon Mannheim’s classic work, was applied to acknowledge diversity in men and their understandings of masculinities across space and time. A total of 34 men were recruited for the study and they were living in three separate cities in Bangladesh. The semi-structured interview method was used to elicit men’s responses concerning their life histories, their enactment of masculinities, sexual practices, and their health status. A thematic analysis was conducted to derive conclusions. Men’s enactment of masculinities was found to be multiple, situational, and varied across social generations. The construction of hegemonic masculinities, men’s provider role, engagement in respectable professions, “caring” masculinities, masculinities demonstrated through self-reliance, sexual prowess, and risk-taking were some of the major themes that emerged from the data analysis. Importantly, there were both social generational similarities and differences in the construction and enactment of masculinities. Furthermore, the enactment of masculinities can carry both positive and negative health consequences. Thus, this chapter highlights the need for applying a generation-specific masculinities lens to men’s health policies and programs.