Street art and graffiti are on the rise and their problematic relationship with the law is becoming an increasingly pressing issue. This paper considers a series of high profile street art controversies involving famous street artists Banksy and Alice Pasquini as cases studies for illuminating such a relationship. First, by discussing the “Banksy’s Law” – a “law” protecting street artworks in the style of Banksy while condemning graffiti – and its perceived arbitrariness, I investigate what I call the structural differences between aesthetic and legal judgments. While not denying some continuity in reasoning about the law and the arts, I argue that legal judgments possess a degree of formality that cannot be found in their aesthetic counterpart. Second, in expanding my discussion, I also maintain that aesthetic considerations should not function as overriding reasons in legal determinations. By being illegal, many street artworks and graffiti acquire subversive power. If deprived of the possibility of challenging the law because of their aesthetic value, these art forms would lose much of their political value. And, more generally, a world where artworks cannot challenge the law is a world where the arts are rather superficial forms of entertainment.