This paper discusses art works by Suzanne Treister, Deborah Kass and Doug Fishbone. It considers the importance of their work for contemporary Jewish identity within the terms of wider conceptual questions that preoccupy contemporary art. These concerns are challenging the perceived structures of power, the “performance” of subjectivity and the questioning of authenticity. A deflationary aesthetic is central to the critique of these structures of thinking fuelled by an interest in the relationship between Jewish subjectivity and popular culture that underpins all of these art works. I argue that popular culture plays a key role as a constituting factor in the production of contemporary Anglophone subjectivity. I use the case studies to develop the argument in the three artists’ specificities and the way they all question the idea of authenticity as a stable source of self-understanding. Suzanne Treister questions history and our relationship with historical events, specifically the Holocaust. She also explores questions of the relationship between structures of power and narratives of history. Debora Kass considers the representation of Jewish women, power and iconicity. Doug Fishbone, a younger artist, takes on self-hate as a transformative tool and as a motif that destabilizes Jewishness as a category, especially in an age of the accelerated post-internet-derived subjectivity.