<p dir="ltr">This article performs a comparative literary and cultural analysis of two enigmatic figures separated by a century: the fictional “Man in the brown macintosh” from James Joyce’s “Ulysses” (1922) and the real, anonymously performed persona of “EsDeeKid,” an underground rapper from Liverpool. It argues that both figures function as potent cultural symbols of intentional anonymity and generative mystery within their respective contexts of High Modernism and contemporary digital-era music. By examining their shared resistance to fixed identity, their cultivation of public speculation, and their status as authorial ghosts haunting their own narratives, this research contends that these parallel phenomena reveal a persistent cultural fascination with the unknown figure as a critique of celebrity, a challenge to interpretive authority, and a space for collective myth-making. The analysis moves beyond solving either mystery to explore the structural and social functions of sustained enigma.</p>