Though the portrait might seem to pale in comparison to a dynamic narrative painting, this collection of 1000 portraits presents a comprehensive panorama to prove otherwise. A masterfully painted portrait can be equally, if not more, compelling and intriguing by depicting a person’s true essence. This selection of images has been juxtaposed against one another to form a chronology of the artistic timeline. Each portrait has been specifically chosen for its historical significance and influence in developing different artistic movements and periods. We hoped to create a cohesive dialogue between the images and their stylistic traits to present a comparative dissertation on the history of portraiture and the aesthetic and stylistic barriers that artists have surpassed to express their own interpretations of the portrait genre.