The world of artistic tattooing and the strict legal framework of intellectual property have clashed in an unprecedented confrontation that could forever change the rules of the game for artists worldwide. This refers to the protracted legal battle between the icon of the modern tattoo scene, Kat Von D, and renowned photographer Jeffrey Sedlik. At the heart of the dispute is the iconic portrait of jazz legend Miles Davis, which Kat transferred to her client’s skin. This case has ceased to be a mere private dispute over fees and has evolved into a large-scale discussion about where copying ends and a new art form begins, and why traditional tests for “similarity” of works no longer work in the era of social media and hyperrealism.