This chapter identifies the factors surrounding Bing Crosby’s survival of the attacks against crooners and analyzes every stage of his career and media production from the 1920s through the early 1940s, from his live performances as part of the famous Rhythm Boys singing trio in Paul Whiteman’s jazz orchestra through his rise as a romantic crooner and a successful film star and national icon. This chapter provides detailed analysis of Crosby’s recordings, films, and media coverage and identifies the broader social factors that aided Crosby’s ascent, including technological and industrial changes in radio, recording, and film sound, the consolidation of mass-media machines in Hollywood, and his widely publicized adherence to middle-class norms of masculinity and assimilated Irish Catholicism: patriarchy and traditional family values, emotional detachment, earned wealth, religious devotion, and traditionally masculine hobbies.