This chapter focuses on Rudy Vallée’s earliest fan letters to help explain and contextualize his rise as a popular idol in 1929. During this era gender and sex became the primary discursive frames for understanding American life and identity; the contexts examined here include the promotion of radio as a domestic companion, the new social acknowledgment of female sexual desire and the availability of sex advice manuals, the promotion of companionate marriage and reproduction as the focus of social life for both men and women, and the emphasis on consumerism as a source of comfort and romantic fantasy. The chapter demonstrates Vallée’s popularity with both sexes, indicating the song style’s broad appeal, and details how Vallée and these earliest fans together developed the conventions of the romantic crooning sound that would become the foundation of pop singing: direct address, sincerity, accessibility, intimacy, and listener identification.