Although frequently undetected or ignored, counterculture groups commonly face misrepresentation in popular media and, in turn, society. These subcultures are often depicted as undesirable or dangerous, creating a negative stereotype that follows the individuals who choose to express themselves in the aesthetics and lifestyles of non-normative communities. This creative project celebrates the beauty and sense of rebellion that can be seen in counterculture groups, and provides viewers with a window for viewing them in a new perspective. Considering the vastness of this topic, this project approaches it from three different directions: a series of photographic staged portraits, a series of digitally illustrated character portraits, and a written analysis to begin a discussion around the types of misrepresentation of countercultures and the potential impacts of that phenomenon. The process of planning was difficult yet rewarding, as it was important to ensure that the work would not contribute to the cycle of misinformation, but rather bring visibility to countercultures in the formal art realm. The photographed body of work recreates the composition of famous genre paintings by Judith Leyster and Johannes Vermeer, but substitutes the subjects for a model dressed in the conventional aesthetic of a particular counterculture. There are four portraits in this series, depicting Punk, Goth, Metal, and Emo cultures, using costuming as well as clues in the surrounding environments. By adopting the genre practice of depicting scenes of everyday life, the counterculture communities become normalized for the viewer as people living similar lives to their own. This portion of the thesis is largely inspired by Cindy Sherman, a visual artist who stages portraits of herself as various characters to comment on ideals of beauty and the female form. Continuing to examine the idea of personality in counterculture, the digitally illustrated body of work pulls from four other countercultures to create portraits of fictional characters. Although imaginative, their designs reflect genuine aesthetics of the communities they represent, and are combined with photographic imagery to suggest their connection to real world peoples. The images represent Grunge, Glam-Rock, Non-Binary, and Scene cultures, with each character receiving a name, location, and occupation to challenge first impressions and demonstrate their roles in society. The characters are drawn in a cartoon-like style with the intent to design them as something one might see in popular media (such as in graphic novels). Lastly, these bodies of work are complemented by a brief analytical introduction into the issues of misrepresentation of countercultures in popular media. Intended to be a catalyst for future discussions, the piece discusses the importance of representation and the harmful effects of misinformation in media, and explores contemporary examples of such issues in depictions of Punk and Goth communities in television. In combination with the two series, this analysis will guide viewers as they proceed to interpret and internalize their own meaning from the project.