Head of a Woman No. 5, Portrait of Dora Maar (Tête de femme No. 5, portrait de Dora Maar)

Picasso met Surrealist photographer Dora Maar in the winter of 1935–36 and the two were lovers until the early 1940s, through the turmoil of the Spanish Civil War and the outbreak of World War II. In addition to her involvement in Surrealist circles, Maar was active in leftist political causes. Her volatile personality was well–known; Picasso called her his "weeping woman."

Credit: Lily Auchincloss Fund and the Riva Castleman Endowment Fund