Masculinity Studies remains an emerging field within Middle Eastern studies, especially in the discipline of history. The case study of Lebanon serves as a compelling example to adapt, refine and further approaches to Masculinity Studies, which has attained prominence in other research fields over the past twenty years, particularly those focused on the global North. Situated within this unfolding scholarship, my paper deconstructs the terms of masculinity that emerged in Lebanon during the last years of the Ottoman Empire. Drawing on recently released archival material and private family papers, I contrast the lives of three Beiruti men of the early twentieth century: Alfred Sursock (1870-1924), an elite cosmopolitan, and Ottoman ambassador to Italy; Vahan Kalbian (1887-1968), an Armenian medical student at the Syrian Protestant College; and Muhammad Bakr (1894-1973), a Shia’ born, Sunni raised, Iranian-Beiruti journalist. These case studies serve as evidence of an entanglement of identity between men who would otherwise be categorized as carrying distinctly different identities based on sect or ethnicity (for example, a Catholic Melkite, an Armenian and a Sunni). To grasp this entanglement effectively, I move away from established approaches in Masculinity Studies (such as hegemonic masculinities and tendencies to focus on male characteristics) by investigating the intersections and divergences in social dynamics such as class, race, religion and even age. I argue that employing innovative historical methods, such as histoire croisée, or adapting interdisciplinary methods, such as intersectionality, exposes these intersections and thus offers a more complex understanding of male identity. These findings determine a new perspective of the meaning of Ottomanism as a lived experience, and consequently raise questions over normative terms of identity in the late Ottoman period in Lebanon. Rather than a wane in Ottomanism versus a rise in national identities, as the dominant historical narrative presents, identities from the perspective of masculinity present a map of heterogeneous yet simultaneously linked identities that were negotiated across a range of social dynamics.