This essay examines literary journalism’s commercial trail in the marketplace, looking for connections between its first modern period in nineteenth-century newspapers and its resurgence in twentieth-century magazines such as The New Yorker, The Smart Set, and American Mercury. This approach suggests the influence of Lincoln Steffens may be somewhat limited. The essay offers an alternative lineage for the genre that highlights the overlooked roles played by a turn-of-the-century boom in evening newspapers and the editorial influence of H. L. Mencken.