Jasper Johns is one of the most provocative American artists of the twentieth century who has shaped the perception of art and has influenced generations of artists. This paper examines one of his most important works, Flag (1955), regarding it as a work defying easy categorizations as either a realist or an abstract work. Without being identified as either kind, it nevertheless displays certain traits of both. As for its suggestion of realism, the work comes up as a response to its political, cultural and artistic context, challenging Cold War aesthetics; albeit in a mocking manner. Its ridicule is evident in its allusion to the concept of ideology via its ‘kitschy’ subject matter whilst its delicately painted surface exhibits brushstrokes reminiscent of abstract expressionism. Yet the work also confronts presumptions of abstract expressionists by drawing attention to their implicit conventionalism despite their claims for authenticity and uniqueness. It will be argued that by calling the notion of identity in question, the work suspends and surpasses neat categories and sparks even further controversy by hinting at postmodern art and evoking ready-mades simultaneously.