It is widely argued that in contemporary Western societies, masculinity is in crisis. Whether or not this alleged `crisis' represents a shift towards more positive and reflexive masculinities has been the focus of much debate. Such debate provides the context for this thesis. The thesis offers new insights into the psychic and cultural shaping of masculinities by examining the possibilities for `good-enough' masculinities within the shifting conditions of Western postmodern culture. It uses psychoanalytic, cultural and social theories to explore contemporary masculinities through a study of male jealousies and their representation in popular cinema. Jealousy provides a useful case study to explore the alleged crisis of contemporary masculinities because it indicates a capacity to tolerate the complex emotions of wounded narcissism and feelings of loss that are said to characterise this crisis. The thesis argues that jealousy occupies a central place in the psychosocial shaping of Western masculinities. Historically, it has played a key role in guarding and defining men's social and emotional boundaries. However, the cultural rules of entitlement and possession are in flux, and the cultural codes surrounding male jealousies are becoming less clear. The thesis discussion develops through the analysis of representations of male jealousies in recent popular films, where the possessive gaze of the hero and the emotional and moral outcomes of jealous triangles are often ambiguous. Such ambiguity resonates with the popular cultural trope of masculinity in crisis and the alleged feminisation of masculinity within popular culture more generally. These themes are explored in depth through case studies of four films, released in the 1990s, which examine their cultural reception in the press and the possibilities for reflexive, `good-enough' formations of masculinity in popular cinema. The thesis aims to contribute to the study of cinema and the emotions by developing an interdisciplinary mode of analysis, which captures the psychic, social and emotional nuances of the film text, and the cultural context of its reception.