The approach of this article complements those of previous critics that account for the rise of the 'mature' style of Tin Pan Alley chiefly in terms of the internal logic of the field of American popular music. It suggests that the so-called golden age of the Alley (ca. 1920?1940) should be considered in broader cultural terms, provided by modernisation and especially the growth of a ?cool?, urban sensibility, representing a crucial reassessment of Victorian emotional style. In their contributions to this reassessment, the Alley greats stretched the conventions of popular song-writing in a number of ways, usually described vaguely in terms of wit, sophistication and the like. Qualifying these concepts by lyrical analysis, the article suggests that the self-reflexive use of irony, linguistic play and realist imperatives makes a number of songs approach contemporary high literature in such a way that it makes sense to speak of a popular modernism.