The purpose of this thesis project is to discuss and describe the transformation of the image of Roman Emperor through artistic representation and cultural demonstration. The ultimate goal is to determine why the presentation of the office changed so greatly. I have selected certain works of art depicting the first Roman Emperor, Gaius Octavian Caesar, best known as Augustus, and Justinianus, the greatest Roman Emperor. More than 500 years separates these two men, whose only connection, at first sight, is that both served as Roman Emperor. I will analyze each piece of art, discuss its history, determine what each piece represents and discuss the cosmetics of the Emperor in the work. Once both Emperors have been dissected artistically, I intend to answer the question of why the office of Roman Emperor changed so thoroughly over 500 years by observing cultural and world developments between the first and sixth centuries of the Common Era.