Lamb’s (1975) seminal work on the contribution of fathers to children’s development provided the context for research attention to fathers. Scholars conceptualized father involvement with a primary focus on behavioural involvement, leading to criticism that involvement should also include affective and cognitive domains. Moreover, the theoretical understanding of fatherlessness has received less consideration, primarily focusing on family structure (e.g., the residential status of biological fathers). Thus, the conceptualization of fathering, or the lack thereof, resulted in the stereotype and/or overgeneralization of ethnic and minority fathering. The present study extended the current literature on ethnic fathers, particularly of Afro-Caribbean fathers, to challenge assumed stereotypes and to contextualize these fathers in their unique historical and sociocultural context based on the bioecological perspective (Bronfenbrenner & Morris, 2006). The current study employs a qualitative methodology from a social constructivist perspective to explore fathering and fatherlessness in Afro-Caribbean families to gain insights into these phenomena. Thematic analysis was used to analyze semi-structured interviews involving 24 Afro-Jamaican fathers (27 to 37 years of age) with at least one child in middle childhood. The findings revealed that fathering and fatherlessness were conceptualized as multidimensional, including behavioural, affective, cognitive, and spiritual domains, extending Palkovitz’s (1997) conceptualization. Also, fathering and fatherlessness were regarded as opposite concepts that included biological and social fathers. The findings also revealed that intergenerational transmission of fathering was reflective of change and stability over time. These findings reinforce the notion of there are features of fathering that may be regarded as universal and provide insights into the culturalized aspects of fathering such as fathering roles and barriers. Implications for research and practice are discussed.