Focusing on a period roughly from 1865 to 1900, this dissertation utilizes close readings of paintings, illustrations, photographs, and other material culture to provide a lens on the rapid political and cultural transformation of the final decades of the Kingdom of Hawai‘i. Visual culture played a key role as a coercive tool as postbellum planters and industrialists who eyed Hawai‘i as the first Pacific outpost in an overseas American empire developed a colonial rhetoric that obscured Native authority and visibility and touted the “inevitable” extinction of the Hawaiian race. However, many images from this period which appear to illustrate Hawai‘i’s docility in the face of American supremacy do not fall as neatly into this simple interpretative framework as we might initially assume. For instance, this project observes how figures such as Queen Emma and King David Kalākaua refused to accept the threat to their sovereignty as they themselves leveraged visual culture in resistance to American imperialism. Chapter One analyzes photographs of Queen Emma as reflections on both Victorian mourning culture and Emma’s political ascendency from 1865-1885. Chapter Two explores paintings of early Maui sugar plantations by Enoch Wood Perry, Gideon Jacques Denny, and Joseph Dwight Strong as lenses on questions of slavery, Asian contract labor, and annexation. Chapter Three provides a close reading of the anti-annexation critique in Mabel Clare Craft’s illustrated book Hawaii Nei alongside the visual and literary production of other women who depicted Hawai‘i in the years surrounding annexation. Chapter Four jumps to the mid-20th century as it examines the painted portraits of late nineteenth-century Hawaiian royalty created by Fredda Burwell Holt alongside key works of literature by her husband, John Dominis Holt, a leading voice of the “Hawaiian Renaissance” that emerged in the 1960s following the resolution of Hawaiian statehood. Overall, this dissertation embraces its case studies as necessarily multivalent and open-ended as it resists the tendency to craft a narrative in which primitive indigeneity meekly yielded to the unstoppable barrage of American imperial pressure. Together, these chapters navigate a material landscape of nineteenth-century Hawai‘i that was layered with imperial control as well as opposition.