In order to consider what the photography used within Rolling Stone magazine contributes to the history of photojournalism, Between Life and the Underground analyzes the aesthetic of the photography and conceptual layouts produced within the magazine. This study looks specifically at the period of 1967 to 1972, a time when mainstream publications like Life magazine ceased production and when over 500 underground publications were piloted. A comparative analysis of the design, economics, and production of both Rolling Stone and the underground publication the Berkeley Barb traces the influence that the underground had on the aesthetic of Rolling Stone’s photography and layout. The role that cover photography played in perpetuating the identity that Rolling Stone wanted to embody is also investigated. The influence that New Journalism had on the production of photojournalism at Life and Rolling Stone is also considered—framed around a comparison of the photographic coverage of the Woodstock Festival of 1969 and the police riots at the Democratic National Convention of 1968. This study concludes that the underground press cultivated a new photographic aesthetic and conceptual technique for laying out photographs which adhered to the ideals of the 1960s—namely informality, which Rolling Stone then adapted to create a profitable magazine.