This study of Hunter S. Thompson's earliest published works (1965-1972), specifically Hell's Angels: The Strange and Terrible Saga of the Outlaw Motorcycle Gangs, "The Kentucky Derby is Decadent and Depraved," Fear and Loathing in Las Vegas: A Savage Journey to the Heart of the American Dream, and Fear and Loathing on the Campaign Trail '72, seeks to justify their inclusion in the modern American literary canon as examples of post-modern, countercultural works that speak to concerns and worries from that time and that still bear lessons of continuing importance to modern audiences. In order to make this case the study seeks to refute the negative interpretations of critics such as W. Ross Winterowd that fail to recognize the deeper implications of Thompson's Gonzo literary style. Thompson's works are studied from journalistic and literary critical points of view in order to illustrate how they hold true to ethical journalistic principles while operating outside of standard literary conventions for their time, and how both journalism and literature have come to embrace techniques that Thompson pioneered. The final goal of the study is to show how these sixties and seventies era texts continue to hold lessons for modern audiences, specifically when it comes to scrutinizing the information they absorb, in order to understand what is true, and what has been altered by personal bias or misinformation. It also seeks to explain why Thompson has thus far been overlooked as a literary figure by analyzing aspects of his psychology that led to him to destroy his credibility, and how these personal flaws should not affect interpretations of his best, early works.