This article concerns attitudes to melancholia and melancholic painters in the literature of the arts from sixteenth-century Italy, and focuses primarily on the writings of Giorgio Vasari, with some attention also to texts by Pino, Dolce, Lomazzo, and others. Remarks made by these authors are analyzed in relation to other sources of primary evidence, ranging from a carnival song to a treatise by Marsilio Ficino on "black bile," the humor supposed to cause melancholia. The principal argument, built around the figure of Michelangelo, is that, contrary to received wisdom, there is no strong evidence that sixteenth-century artists feigned melancholy As well as rehearsing the many negative and ambivalent views on the humor expressed by Cinquecento authors, this article shows that these commentators believed that melancholy gives rise to a very specific kind of painterly flair, namely, a genius for the fantastical and grotesque.