"Between the Devil and The Deep Blue Sea" by The Boswell Sisters

In 1931, as America sank deeper into the Great Depression, the Boswell Sisters recorded a song about a different kind of crisis — the kind where every choice feels like a trap.

Written by Harold Arlen and Ted Koehler, “Between the Devil and the Deep Blue Sea” sounds light, even playful. The harmonies glide. The rhythm swings. But beneath the polish is a confession: sometimes you’re not choosing between right and wrong — you’re choosing between bad and worse.

In this episode of Dustbin Prophecies, we explore how the Boswell Sisters transformed a Tin Pan Alley dilemma into something quietly devastating. We’ll break down the lyrics, the harmonic tension, the 1931 recording session featuring musicians like Tommy Dorsey and Benny Goodman, and the subtle musical choices that make this record feel suspended — unresolved — nearly a century later.

Because this isn’t just a jazz standard. It’s a song about understanding the trap. And singing anyway.

Dustbin Prophecies: digging through the forgotten corners of rock history — one record at a time.