This chapter establishes the historical context and conditions for crooning’s increasing centrality in American popular music, specifically its development from the nineteenth and early twentieth centuries, when it was used to describe the sound made by mammies and mothers, to its use as a term of courtship in the 1910s and 1920s. The industrial developments and social dynamics that enabled and accompanied this evolution are discussed: the shift from minstrelsy to vaudeville; the rise of Tin Pan Alley’s new publishing model and changes in song content to increasingly focus on the romantic and erotic; the role of black song writers and performers in contributing to the shift in crooning’s meaning, and the growing importance of female audiences in determining content and promoting performers. Analysis of sheet music is foregrounded, as well as publisher memoirs. The racial, gender, and class implications of this shift are also examined in detail.