This thesis offers an account of the relations between representation, sexuality, and gender at the close of the twentieth century, modelling novel theoretical framings for thinking trans as metaphor, and material reality, under and against queer’s foreclosures. As queer and transgender were crystallising into new identarian and disciplinary objects in the 1990s, this thesis observes the significance of artistic practice and visual theory as a crucial site through which these terms were negotiated and entered the academy as figuration, frequently imagined as a discursive limit in visual/literary theory and debates surrounding the politics of representation. By attending to the formal qualities of artists’ film, video and photography, this thesis elaborates on this limit as an aesthetic that also shaped articulations of the sexed subject according to corollary images of entrapment and escape. Taking up trans revisions of psychoanalysis, materialism and aesthetic theory, this thesis invigorates queer theory from a trans perspective, generating novel theoretical frameworks capable of attending to this period of artistic-theoretical practice concerned with a subject trying to escape the trap of its foreclosed condition.

This argument is made through a series of interrelated studies. In chapter one: I model a trans(femme) historical materialism via a revised intellectual history of queer theory’s foundation, as told through Isaac Julien’s 1989 film Looking for Langston and the writings of theorist Kobena Mercer. I read their ambivalent figurations of Black gay male desire against the temporality of queer theory’s racialised erotics and the animating place of sexual difference within cinematic theories of identification. In chapter two: I excavate queer and transgender’s relation under the foreclosures of the AIDS crisis via Tessa Boffin’s 1989 photographic series Angelic Rebels: Lesbians and Safer Sex and Jason Barker’s 1997 short ‘creative documentary’ St Pelagius the Penitent. These works’ shared fantasies of angelic ascension open onto an alternate trans genre that departs from biography to claim death as an aesthetic of trans life. In chapter three: through Tessa Boffin’s unfinished billboard project Queerelle, or, The King’s Trial [1993], I pursue a reading of 1990s queer transvestism as a trans epistemology of the ‘egg,’ which cracks into an archive of trans materialism found in the DIY aesthetics of Jason Barker and Hans Scheirl’s experimental short Summer of 95 [1995]. In chapter four: I argue that Hans Scheirl’s experimental feature film Dandy Dust [1998] innovates on the trope of trans life-writing to describe the horrors of trans masculinity, an object without epistemological clarity that challenges the utility of the figurative trans femme in 1990s media theory.