Abstract: This dissertation studies the discursive and formal appearance of irony in architecture between the mid-1960s and the mid-1980s. In this timeframe, a number of architects and architectural historians position their theories and designs in relation to irony---as they define this notion themselves, or as they effectuate discursive transfers from literature, literary criticism, the visual arts, and philosophy (New Criticism, Pop art, philosophical existentialisms, Romantic literary theory, semiology, pragmatist philosophy, deconstruction). In these theories, architecture and irony appear persistently at odds with one another: the ensuing symbiotic clash negotiates a paradoxical space between architecture's stronghold of stability, bounded by the 'gravity' of its traditions, and irony's actions of critique, undoing and denial, related to the negative freedom of irony's author. Different architects expect irony to be operational in diverse ways, and accordingly, they adjust their ironic strategies and means of expression: Robert Venturi is more interested in the formal side of irony, Stanley Tigerman leans towards satirical comedy, John Hejduk is closer to parody, Arata Isozaki closer to Romantic tragedy, James Stirling closer to wit, Peter Eisenman closer to aporetic rhetoric, and Rem Koolhaas closer to cynicism. Notwithstanding the sometimes considerable dissimilarities of their theories and designs, they all define architecture as the expression of 'distance' from the canonical moments of 20th century modernism. I maintain that irony is the paradoxical distance-holder that generates their architectural space in reference to some implied alter ego: Venturi-Le Corbusier, Tigerman-Mies, Isozaki-Metabolism. In opposition to these instrumentalists of irony, the Marxist historian Manfredo Tafuri, who recognizes the value of irony as an operative technique of the historical avant-garde, makes himself the fervent critic of this Kunstmittel. In his view, irony's subjective bricolages of history detach the architectural discussion from its socio-political mission. Eisenman and Koolhaas emerge as two figures, who turn ironic self-reflectivity into full-fletched epistemological strategies: Eisenman puts the negative method of textual dissimulation---of 'showing in denial'---in the service of an architectural Absolute; Koolhaas develops paranoid fictions about reality as productive simulations. Both generate a 'rhetoric of distancing,' which depends on an ironic mise-en-abîme ---the dominant thematic of architectural postmodernism.