This thesis is an attempt to analyze Mark Twain's story Captain Stormfield's Visit to Heaven as well as selected paintings from the Ashcan School in terms of American exceptionalism. In the process, I also explore the stylistic affinities that reflect the times in which the works were executed, and evaluate how the styles in turn help to enhance the themes. Like Twain's Stormfield, until recent years, works by the Ashcan artists were rarely discussed: they apparently did not fit the common perception of America as a City on a Hill, an exceptional country with exceptional people. The works of the Ashcan artists and Mark Twain's Stormfield seem to contradict or at least show that there is another side to the myth of American exceptionalism. In my attempt to see how far thematic affinities and differences between Stormfield and the paintings of the Ashcan School impinge on the idea of American exceptionalism, I first explain my eclectic approach towards the works in question. Then I discuss some aspects of American exceptionalism, after which I narrate the theory on the relationship between painting and literature. Next I explore Mark Twain's Captain Stormfields Visit to Heaven in terms of American exceptionalism and use the ideas gathered to compare with the themes found in selected paintings from the Ashcan School. Finally, I analyze how the times in which the works were executed influenced the styles, besides showing how the styles enhanced the content. I hope this attempt in investigating the thematic and stylistic affinities and differences between the Sister Arts will serve to illuminate further the ongoing controversy of American exceptionalism.