This dissertation examines the dissolution of landscape painting as a major cultural project in the late nineteenth-century United States. As a genre aligned with the goals of nation building, landscape maintained a privileged artistic status for much of the nineteenth century. Yet as frontier development, land speculation, environmental change, and other factors slowly rendered its conventions meaningless, landscape became the site through which American artists most urgently sought to come to terms with the modern world. This argument is anchored by unorthodox artworks, from landscapes resembling banknotes to paintings made out of bird feathers—limit cases that allude to the failure of landscape in sustaining American cultural goals. Chapter One concerns Albert Bierstadt's aesthetic struggles in post-frontier America. During the 1890s, Bierstadt's anxieties about landscape surfaced in the particularities of objects that fold and unfold, from butterflies painted by chance to expanding railway cars—objects that might be considered the subconscious of a genre built upon expansionist ideology. Chapter Two argues that Martin Johnson Heade's tropical and marsh paintings of the 1870s and 1880s used “groundless” conditions to express cultural insecurities about traversable land and its representation. The pictorial blockages and interferences in Heade's paintings challenge both the compositional legibility espoused in the blockbuster canvases of his mentor and rival Frederic Church and the physical accessibility promised by the period's environmental interventions. Chapter Three proposes that Ralph Blakelock's nocturnes and money paintings—produced in the context of rampant land speculation, volatile art markets, and representational doubts surrounding paper currency—attempt but fail to overcome landscape's monetary entanglements. Blakelock's paintings theorize the value of labor and material accumulation in the increasingly abstract economic world of the last decades of the nineteenth century. Chapter Four reconsiders the trope of the "figure in the landscape" using Abbott Thayer's turn-of-the-century representations of animal camouflage. In these mixed-media artworks, Thayer's attempts to visualize invisibility demonstrate the ways in which camouflage proved irreconcilable with landscape's figure-ground principles. Together, these episodes trace pictorial attempts to resolve spatial problems arising with modernity, and in so doing, they signal a shift toward new paradigms of representation. / History of Art and Architecture