The purpose of this thesis is to document the change of the vejigante mask, from a folkloric object to a contemporary icon. The research focuses on a further understanding of the mask, magnified through traditions and heritage, executed with an advanced examination of ethnographic research. The investigation theorizes the impact of clashing cultures by analyzing the impact the United States of America has had on Puerto Rico through the use of cultural assimilation. In conjunction with the research, an experimentation with my personal artwork was completed by using unconventional mediums and combinations of classical and contemporary techniques. This provided the platform to encompass the appreciation and the aftereffects of the vejigante’s encounter in contemporary contexts. Documentation on the subject is insufficient. Interviews were conducted to contribute evidence to the investigation where the literature lacked. Art historians, artisans, and artists were interviewed, and presented a local perspective and response to the undeniable changes that have taken place in the Carnival. This provided another form of research known as word-of-mouth, which is necessary in the contribution to the history of the vejigante. It is important to include the oral history that derives from word-of-mouth, stories passed down generation to generation, allowing a cultural history to thrive with limited information on the subject. The results display the vejigante mask experienced a shift in cultural depiction and representation due to the United States of America. Although, with the introduction to Western culture, the concept of the vejigante was enabled to transform from Carnival traditions to contemporary contexts.