In September of 1986, megastar Prince journeyed across the Atlantic to France to begin filming his second motion picture Under the Cherry Moon. Having captured the US imagination in the commercially successful Purple Rain (1984), “The Kid” (Prince’s Purple Rain alias) was eager to begin shooting his idea for a wry comedy in black and white in “homage to the B films of the 1940’s” (Goodman, 1986). Prince’s artistic, transcontinental trek was already on display with his 1985 Around the World in a Day, an album that at once pushed him forward musically by looking backward to 1960s psychedelic, Beatles-esque pop. An avant-garde experimentalist, Prince was seemingly constructing a new musical paradigm that linked past and present in kaleidoscopic fashion. The title song might have Prince playing the melodious wanderer: “Open your heart, open your mind, A train is leaving all day, A wonderful trip through our time, And laughter is all U pay.” Parade: Music from The Motion Picture “Under the Cherry Moon” continued the sauntering theme as the diminutive Prince declares in the title track, “The little 1 will escort U, 2 places within your mind.” In this manner, the wanderings of Prince’s character Christopher Tracy took him “more often to the strange corners of Paris than to its historic centre, to the strongholds of multiculturalism rather than to the classic headquarters of the Gallic tradition” (White, 2001). The purpose of the article is to present Prince as a postmodern flâneur. Beyond notions of his dandyism, most directly observed in his use of signifiers that convey gender ambiguity/bending, Prince’s urban representations, traveling imagery, solitary character, social commentary, contradictory relationships with women, and transformative creativity mark a new take on the flâneur.