The concept of a '"crisis" in masculinity' came to prominence in Britain and North America during the 1990s. This phenomenon developed out of several decades in which the notion of 'the subject' came under critical scrutiny, both from developments in postmodern and post-structuralist theory, and sociocultural shifts informed by the politicised campaigns of second-wave feminism, gay activism and civil rights movements. In this context, the discursively central position of the white, heterosexual, middle-class male subject looked to be decentred by a host of radical projects that claimed identity positions as constructed and contingent. In exploring the resonance of the 'crisis' in mainstream playwriting practice of the 1990s and early 2000s, this study centres on a range of texts by contemporary British and North American male dramatists: Closer (1997) by Patrick Marber; The Shape of Things (2001) by Neil LaBute; Alan Bennett's The History Boys (2004); Tony Kushner's Angels in America: A Gay Fantasia on National Themes (1992 and 1994); Roy Williams's Clubland (2001) and Bondage (1992), by David Henry Hwang. Through evaluating strategies by which privileged and 'marginalised' masculinities are portrayed, this thesis considers not only how far these works may appear to suggest a state of rupture in 'normative' masculinity, but whether they can be read as reaffirming or undermining binaristic and 'stable' notions of identity. These concerns take account of the various ways in which gender is articulated through 'race', sexuality, nationality and class. The primary theoretical framework is drawn from the field of poststructuralist philosophy, and, specifically, selected works by Jacques Lacan, Judith Butler and Homi Bhabha. Cultural studies and sociology provide a 'sub-strand' of theory, through analyses that interconnect the themes of masculinity and nostalgia. While the former trope enables psychoanalytic readings, the latter is apt for analyses of cultural texts produced at a time in which masculinity was deemed in a hazardous state of decline. It is in combining these threads with queer, feminist and performance theory, and philosophical accounts of the postmodern, that this thesis looks to reflect on how the male-authored dramas under discussion respond to or evoke the 'crisis' in masculinity, and what might thus be discerned about both this practice and the 'crisis' discourse itself.