The legacy of a compromised hegemonic masculinity that came to define the persona of the male European colonizer became the benchmark by which masculinity was measured during the British Empire. Such a legacy, however, has not been upheld through subsequent years. This is due largely to a near impossible correlation between the pioneering European plantation-owner and, initially, the indigenous peoples, then the transplanted and, subsequently, the creolized, inhabitant of the West Indies. Rather, a ‘dishonoured’ hegemonic masculinity has resulted due to the negativities associated with imperial dominance. Moreover, a series of counter-hegemonic ‘positive’ masculinities materialized. These either slipped into a warrior-type rebellion at one end of the male gender identity spectrum, or a passivity traditionally associated with Western femininity at the other end, accompanied by a highly complex gamut of intervening masculine identities along the continuum. In this chapter, I explore early Caribbean men’s bourgeoning masculine and sexual identities with inflections of class, ethnicity and culture. My aim is to understand the tensions, contentions and collisions Caribbean men experience in forging their dynamic masculine and sexual identities, through the twin interrogation of scholarship and selected works of canonical Anglophone Caribbean prose. I utilize intersectionalities of historical, sociological, psychological, theoretical and literary frames while dimensions of biology, psychoanalysis, deconstruction, postcolonialism, feminism and masculinity studies inform this interdisciplinary chapter. Decisively, early Caribbean men have grappled with the particularities of complex politico-historical and sociocultural arrangements, facilitating masculinities that become interlocked with sexual performance.