Using the literature-in-marketing approach this study explores the transition said to be occurring in contemporary culture, society and philosophy between the waning postmodern and the ascendant post-postmodern. Research gauges a complex unfolding sociocultural moment that has major implications for marketing, but which heretofore has been little described. Song lyrics of prominent pop music artists, Madonna and Taylor Swift, are suggested to illustrate respective characteristics. Lady Gaga is held up as an intermediary between Madonna’s deconstructive and Taylor’s reconstructive selves. Themes of reputation, revenge and romance highlight how Swift experiments with re-compositions of self in relation to surroundings and vice versa. Her fabulations and manipulations thereof are supported by processes of communality, publicity and transition. The rise of Taylor Swift as a post-postmodern paragon provides insight into where the post-postmodern turn might be observed and how it may impact marketing theory and practice.