Since the often turbulent relationship between Russia and the Caucasus began around 1817, the Russian perception of the land and peoples living between the Caspian and Black Seas has been shrouded in myth. Throughout the artistic dialogue on the Caucasus, starting at the beginning of the 19th century, authors, artists, musicians, screenwriters and directors have grappled with the idea of the Caucasus as a cultural place. By the time Pushkin writes his first verse on the topic in 1820, the “myth” of the Caucasus, akin to the European myth of the Noble Savage, is already well-established. The Byronic myth both draws and repels Russians and Russian artists to the Caucasus. By focusing on Pushkin’s “Captive of the Caucasus” (1820), Lermontov’s A Hero of our Time (1839), and Mikhalkov’s 2007 film, 12, this paper explores the Russian artistic position on the Caucasus region and how it has evolved up to now. In each storyline, the authors and filmmakers use Russian characters to explore their own generation’s myths and conceptions of the Caucasus. The paper specifically analyzes how each artist struggles with the stereotypes about the region’s inherently “wild” and romantic character. It also examines the contrasting images of captivity and freedom that permeate each of these stories and many other artistic pieces relating to the Caucasus.