The early years of the Kamehameha Dynasty (1795-1874) saw increased interaction between Hawaiʻi and Europe as a by-product of rapid developments in commerce, diplomatic delegation, and most overtly, colonialism. These confrontations manifest in the visual culture created by Europeans, specifically through state portraiture. In an effort to challenge traditionally held perceptions of the history of the early nineteenth-century Hawaiian Royal Family across disciplines, this thesis approaches a multi-faceted analysis of the portraits of King Kamehameha III (1814-1854) and Princess Nāhiʻenaʻena (1815-1836) by English artist Robert Dampier (1800-1874) and situates the context of their creation against the backdrop of English imperial presence in Hawai‘i. Portraits of the former monarchs, painted by French artist Eugénie Le Brun (1797-1872), are presented in contrast to enforce the realities of stipulated conformity placed upon the Kamehamehas throughout their earliest rule. Utilizing these four portraits and the exoticized symbols of Hawaiian heritage included within them, a clear understanding of the active agenda emphasized within colonial myth-making is newly acknowledged.