The aim of this paper is to explore what could be meant by modernist portraiture. On the face of it, there is a real tension about the very idea of modernist portraiture inasmuch as one key idea of modernism is negativity and self-negation, whereas portraiture is, in some very obvious sense, not negation. It is the depiction of the sitter. So there are reasons to think that modernist portraiture, in the strong sense of the term, is a contradiction in terms. Nonetheless, I argue that there is such a thing as genuine modernist portraiture – modernist portraiture in the strong sense. But it is not easy to pull it off. And the modernist act of creating portraits of people not present also reveals something important about the nature of depiction and the importance of mental imagery in picture perception.