In 1994 Chilean culture (re)gendered of one of Latin America's founding fathers, Simón Bolívar, the Liberator, who was depicted riding onto the front of a widely circulated postcard while dressed in drag and flashing an obscene gesture to her audience. Such a gender (re)presentation, as Christopher Conway notes, challenged the nation to question the limits of a dynamic, newly negotiated freedom of expression as this transgendered hero burst onto the front pages of newspapers and into television newscasts (2–3). The question arose: was the transitioning Chile ready for the gender-bending figure par excellence to surge onto the public stage?

Doris Sommer, in Foundational Fictions: The National Romances of Latin America (1991), explores the allegorical national embodiment of female protagonists in such works as Amalia (1851), Iracema (1865) and María (1867) during Latin America's post-independence nation-building process. The permeability of strict gender expectations passed down through generations becomes apparent as a bare-breasted twentieth-century feminized twist on the nineteenth-century figure was no longer regarded as a revolutionary hero, but rather as an insult, ultimately requiring a formal apology to the Venezuelan government. The uproar caused by artist Juan Dávila's recasting of such an important historical figure reminds us, as Raquel Olea has observed, that national projects in Latin America tend to rely on the masculine, heterosexual body to organize memory and history (110). At the same time, as Nelly Richard points out, Dávila's painting exposes the Latin American tendency to retouch history (Masculine/Feminine 4). In this way the masking makeup somehow unveils an alternate truth, facilitating the cross-dressed figure's front-stage role in Chile's transition to democracy.

Such an exploration of identity felt long overdue after the oppressive seventeen-year dictatorship of Augusto Pinochet. Following the 1970 democratic election of Salvador Allende, on September 11, 1973, the United States backed a coup d’état that brought Augusto Pinochet to power.