Although Warhol was unhappy with his appearance throughout his life, self-portraiture was a recurring theme in his oeuvre. Role-playing was a central aspect of many of his self-portraits and his Polaroid camera was an effective means of quickly documenting his changing personae. In this work he initially appears uncomfortable, sitting in profile with his hand tentatively touching his face; his eyes uneasily meet the viewer's gaze. Yet, on closer consideration, there appears to be a slight smirk on his mouth, which alters his overall demeanour to one of intrigue and even flirtatiousness. Perhaps Warhol is experimenting with his own version of the Mona Lisa’s enigmatic smile.