This chapter begins by analyzing the relationship between the manuscript newsletters of early eighteenth-century Boston and the first regularly printed newspaper in colonial America, the Boston News-Letter. It emphasizes that the shift from manuscript to print in journalistic periodicals did not alter how the news was covered: brief paragraphs of a few sentences that did not include any explanation or context and that were known as “intelligences.” The chapter then discusses the first literary writing to appear in a colonial newspaper, the satirical essays placed in the New-England Courant in the 1720s by its printer James Franklin. These essays differed significantly from “intelligences” as they were conversational and narrative in style and were designed to entertain readers. The essays were composed by a stable of writers known as the “Couranteers,” a group that included, most famously, James Franklin’s younger brother and apprentice, Benjamin Franklin. Significantly, these essays—among the earliest examples of American literary journalism—were framed as fictional letters to the paper, to distinguish them from the more traditional “intelligences,” and this demonstrates how epistolary modes of writing were central both to the early history of American newspapers and to the development of American literary journalism.