First commercial recording session with Benny Goodman, cutting “Your Mother’s Son‑In‑Law” and “Riffin’ the Scotch.”
On 27 November 1933, producer John Hammond organized Billie Holiday’s first commercial recording session in New York City, pairing the 18‑year‑old singer with clarinetist Benny Goodman and his studio orchestra.
In this Brunswick session, Holiday recorded "Your Mother’s Son‑In‑Law" and "Riffin’ the Scotch." Although the records were modest sellers, the session was historically crucial. It introduced Holiday’s highly personal style—behind‑the‑beat phrasing, elastic timing, and conversational delivery—to the recording industry at a moment when most big‑band singers still functioned as straightforward, rhythm‑bound "girl vocalists." Her ability to reshape melodies and treat the band as a partner rather than mere accompaniment set her apart immediately.
The collaboration also marked the beginning of Hammond’s sustained advocacy for Holiday, helping secure further work with pianist Teddy Wilson and other leading jazz musicians. In the broader context of the early 1930s, when opportunities for young Black women in commercial recording were sharply limited, Holiday’s entrance into the studio system signaled a breach in industry barriers and presaged a new, artist‑centered approach to jazz singing that would influence generations.