My thesis centers on Lolita and The Crying of Lot 49 and the ways in which both novels defamiliarize our world and ways of thinking. Both novels use formal literary techniques as a way of making ordinary cultural artifacts, situations, and environments seem unfamiliar from our every day perceptions. This process of defamiliarizing the regular and everyday has the greater implications of estranging universal themes such as love, environment, and belonging. Both novels also question our precarious hold on corporeal reality by interpreting plot through two outside narrators whose trustworthiness is constantly placed into question. Unsurprisingly, Lolita and The Crying of Lot 49 unsettle the categories of truthfulness and reinvention in interpreting America's immediate cultural and environmental landscape. Both texts blur the distinction between recorded and imaginatively reconstructed worlds: just so, America has isolated our two narrators in the text from their immediate landscape. Interpretations of America are questioned in the thesis through the process of Shklovsky's theory of Defamiliarization interfaced with Freud's Uncanny in the novel. Language disobedience and discord also play a part and will be discussed through Bakhtin's theories on polyphonic language.