This chapter explores interconnections among conceptualizations of mental illness, artistic genius, and emotional suffering. It does so through the extended example of Vincent Van Gogh from 1890, the year of his death, to the 1990s, a period of record-breaking sales of his work. My intention is to assess, first, how popular culture in contrast to modernist high art circles regard the place of emotionality in aesthetic activity. Second, I examine the role of emotions and emotional disorders in public perceptions of mental illness when applied to twentieth century art. Emotional disorders, as I use the term, encompass mood, anxiety, and significant aspects of personality disorders.1 The two preceding concerns link together in that modernism’s artistic persona attempts to unite madness, troubled emotionality, and aesthetic brilliance in one figure. However, as we will see in the case of Van Gogh, attempts to integrate such vastly different, complex aspects of human existence have created more controversy than clarity.