In September 2015, Vicky Featherstone, Artistic Director of London’s Royal Court Theatre, was widely reported in the British press as commenting on the lack of female roles equivalent in stature to the tragic figures of Shakespeare’s Lear and Hamlet, or Miller’s Willy Loman. Her observation that audiences are more “comfortable” with a “male narrative” sparked considerable debate. My article engages with and develops this debate by turning a feminist gaze on two plays in Featherstone’s Royal Court repertoire: Penelope Skinner’s Linda and Zinnie Harris’s How to Hold Your Breath, both of which premiered in 2015. Mapping feminist thinking on to Raymond Williams’s reflections on “modern tragedy,” I conceive of a feminist-tragic feeling as crossing the divide between the political and the tragic. Formally, I argue this encourages a move away from the generically-bound categorisation of tragedy with its attendant definitions and theories, and makes it possible to think in more expansive, fluid, genre-crossing ways of what Rita Felski terms a “tragic sensibility.” Ultimately, through close readings of Linda and How to Hold Your Breath, I argue how each structures a feminist-tragic feeling for a world in which Western privilege has repeatedly failed to democratise.