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“Young Jean Lee’s Cruel Optimism” argues that the Brown University production of Young Jean Lee’s Straight White Men stages the tensions inherent in performing white masculinity under U.S. neo-liberal capitalism. The article performs a dramaturgical analysis of the production in relationship to Raymond Williams’s conception of liberal tragedy from Modern Tragedy (1966) and Lauren Berlant’s theorization of the impasse in Cruel Optimism (2011). This analysis reveals how the reconceptualization of liberal tragedy in the neo-liberal age asks that we reconsider the relationship between debt and aspiration so crucial to Williams’s conception of Ibsen’s dramaturgy. The theatricality of the play offers a new way to understand the affect and effects of living with the spectre of labour precarity and debt in the contemporary United States.