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This chapter traces crooning’s development and increasing popularity as a new modern song style produced by the microphone in the mid- to late 1920s. Crooning exemplified and helped drive the aesthetic, industrial, and cultural shift in popular singing from the belting theatrical style to a more personal, soft, intimate style. New technologies, industrial changes, commercial interests, performer investments, and audiences’ desires (particularly those of collegians, women, and “mass” versus class audiences) helped create the context for this shift, resulting in the dominance of crooning’s nascent pop sound and attractive young male crooners in American popular music. Examined venues and modes for crooning performance include radio, recording, sweet jazz bands, cabaret, motion picture houses, and early sound films. Key performers in the early development of microphone crooning are examined, including Vaughn De Leath, Gene Austin, Whispering Jack Smith, and Waring’s Pennsylvanians.

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