Since the early 1900s, song-poem entrepreneurs, often referred to as “song sharks,” have fueled a diffuse and largely hidden American industry that produces music to accompany the poems and lyrics of amateur writers. These entrepreneurs have long been demonized in the popular media for preying on the naiveté of their clientele. Yet despite charges of exploitation, this musical equivalent of the vanity press has survived for over a century. Although the vast majority of song-poets and their song-poems have remained in obscurity, in the 1990s, song-poems developed a cult following among record collectors; as “anonymous collaborations,” these recordings highlighted tensions between poignant personal expression and impersonal commercial rendering that appealed to listeners with a penchant for the obscure. This article draws on advertisements, sheet music, media coverage, and personal interviews to piece together a history of the song-poem industry, with particular focus on the gendered dimensions of the practice, the role of technology in the production process, and the multiplicity of meanings embedded in song-poems for both song-poets and collectors.