David Bowie Study - Triple Trouble is a deeply personal and technically layered work by Shepard Fairey, created specifically for the Triple Trouble collaboration using mono-engraving combined with ink and charcoal on paper — a medium that emphasises mark-making, texture, and the physicality of the artistic hand. Fairey's portrait practice draws on constructivist and street-art traditions, and his depiction of Bowie — one of popular culture's greatest icons of transformation, gender fluidity, and artistic reinvention — aligns naturally with Fairey's own interest in figures who challenge normative power structures. The choice of Bowie as subject within a collaboration titled Triple Trouble feels deliberately resonant: Bowie himself was a collaborator, a chameleon, and a disruptor whose multiple personas mirror the multi-artist nature of the project itself. The mono-engraving technique lends the work a raw, printmaking quality reminiscent of both protest art and underground music ephemera, grounding the image in the counterculture Bowie helped define. As a 2025 work, it also functions as an act of cultural memory, enshrining Bowie's legacy through the lens of street art's enduring reverence for icons of rebellion.