In 1986, just months before his death, Andy Warhol created a series of Polaroid self-portraits against black backgrounds wherein the artist is obscured behind dark sunglasses-wearing his iconic un-human and an artificial fright wig. These singular portraits remain some of the artist’s most striking work: detached, disguised, and manufactured. They represent the culmination of four decades of portraiture. Around 1977–1980, the artist also created self-portraits of himself in drag, with makeup and wigs. Yet, these works owe more inspiration to the Ladies & Gentlemen series of transgender performers and gay rights activists. Warhol’s portraits of other subjects utilized a uniform process of having the subjects apply kabuki make up homogenizing the subject. By contrast to Warhol’s earlier self-portraits or his traditional portraiture work, the Self-portrait in Fright Wig is entirely the artist’s own personal creation, not reliant on artifice or uniformity, but rather constructing his own vocabulary for the viewer to understand that the artist is neither familiar nor recognizable. How ironic then it is that the resultant image has become the most recognized of all his portraits.