This paper will explore classical and contemporary methods of painting applied to the portrait. It will emphasize the metaphor of paint as flesh and the connotations of the breakdown of the painted form that stands in for flesh as it relates to our preoccupations with our own mortality. Borrowing from influences like Lucian Freud, Jenny Saville, and Francis Bacon, the artwork explores the creation of a form that is physical and confrontational, and is intended to provoke a psychological response in the viewer. This series of figuration bases its processes on traditional methods, while borrowing from modern art devices to interpret intangible human characteristics that clarify the representation of the subject and the moment being captured. The ultimate product of this two-fold approach is an image that is a tightly rendered representational portrait that simultaneously lends itself to gestural study.