The gendered maxim ‘men must work and women must weep’ comes from Charles Kingsley's 1851 ballad 'The Three Fishers'. Virginia Woolf appropriated 'Women Must Weep' for early version of Three Guineas, serialised in The Atlantic Monthly (1938). This chapter argues that the public nature of Woolf’s polemical anti-fascist essay may, concurrently, be read as a more intimate document about personal grief and grievance. For Woolf her sister, Vanessa Bell, was the weeping woman, devastated by the tragic death in 1937 of Julian Bell in the Spanish Civil War. Duncan Grant drafted posters (reproduced here) to raise money for refugee Spanish children, employing the trope of mothers cradling babies. Woolf’s contemporary, the German artist Käthe Kollwitz, a mother bereaved twice by war, repeated the poignant pietà image in numerous anti-war pieces. Picasso, inspired by Dora Maar whom he regarded privately as ‘the weeping woman’, created sixty mater dolorosa works in preparation for his immense elegiac public work, ‘Guernica’ (1937). The chapter traces the powerful aesthetic of the sorrowful mother as a European anti-war figure. It concludes by considering how this iconography has been used cross-culturally and trans-historically. The pietà has been gender-flipped, adapted and plagiarised in war photography, murals, comic books, manga, fashion, film and video.