This dissertation explores how two American storytellers, considered by many in their to be exemplary in their craft, rely on narrative strategies to communicate to their audiences on divisive political topics in a way that both invokes feelings of pleasure and connection and transcends party identification and ideological divides. Anna Quindlen, through her political columns and op-eds, and Aaron Sorkin, through his television show The West Wing, have won over a politically diverse fan base in spite of the fact that their writing espouses liberal political viewpoints. By telling stories that entertain, first and foremost, Quindlen and Sorkin are able to have a material impact on their audiences on both dry and controversial topics, accomplishing that which 19th Century writer and activist Harriet Farley made her practice: writing in such a way to gain the access necessary to “do good by stealth.” This dissertation will argue that it is their skilled use of storytelling elements, which capitalize on the cultural relationship humans have with storytelling, that enables Quindlen and Sorkin to achieve this. The dissertation asks: How do stories shape the beliefs, perspectives, and cognitive functions of humans? How do stories construct culture and interact with cultural values? What is the media’s role in shaping society? What gives stories their power to unite as a medium? What is the significance of the experience of reading or hearing a well-told story, of how it feels? What are the effects of Quindlen’s and Sorkin’s writing on audience members and the political world at large? What is lost when a simplistic narrative structure is followed? Who is left out and what is overlooked? The literature that informs the answers to these questions will cross over and through several academic disciplines: American Studies, British Cultural Studies, Communication, Folklore, Journalism, Literature, Media Studies, Popular Culture, and Social Psychology. The chapters will also explore scholarship on the subjects of narratology and schema theory.