Chapter 2 begins by looking at how medical and cultural histories of melancholy and unhappiness have traditionally defined and diagnosed such feelings as negative, unhealthy, and undesirable, even while recognizing their potentially enabling features. Freud’s essay of 1917 is seen to mark a definitive moment when melancholia becomes fully pathologized. In response to this, the chapter turns to the work of Walter Benjamin, who attempts to mine new readings of melancholic experience (and criticism) that show the latter to be profoundly social, political, and productive. This places his work at odds with the prevailing consensus, which characterizes melancholia as a personal psychological failing that is stifling, passive, and anti-social. The chapter closes with a section on ‘conscious unhappiness’. Revisiting Theodor Adorno’s work, this section affirms the importance and interconnectedness of affective and political refusal. Rather than seeking to avoid or relieve dysphoric feelings through psychic adjustment, conscious unhappiness amplifies unmet needs, giving voice to the suffering that arises from a social world in need of wholesale transformation. As part of its revolutionary critique of capitalist social relations, critical theory refuses to privatize the notion of happiness and in so doing aligns itself with the (negative) truth-content of unhappiness – the bad that cannot be made good.