Culture has increasingly been analyzed ironically in relation to social conflict, emphasizing themes of ideology, co-optation, and complicity in reproducing inequalities. Arguably the most sophisticated ironic cultural critique is provided by Bourdieu. Bourdieu’s critique is often criticized for reductionism, but without pursuing what is neglected by ironic reductionism. Nietzsche provides a remarkable counterpoint, offering both seminal resources for modern social criticism, and profound reflections on culture’s potential to affirm life with integrity and authenticity. Nietzsche’s analysis of classical Greek tragedy suggests how culture can collectively affirm life through art without illusions. The relative emphases and insights of these two critics are contrasted here in relation to the cultural phenomenon of hip-hop, addressing latent ideological baggage but also its social activism and tragic-realist aesthetic. Grounded in this discussion of hip-hop as predictably compromised, but also incisively defiant and painfully honest, a challenge is posed for cultural analysis to be critical without being dismissive of existential and aesthetic questions, or blind to the potentials of popular culture. Culture is neither as derivative as much social criticism would suggest, nor as autonomous as many artists and art critics would suggest. Cultural studies therefore must find a middle way, navigating between cynicism and naiveté.