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Billie Holiday at 100

Broadcast: April 2, 2023 at 4:00 p.m.

Listen to this episode: Click here.

The astonishment about Billie Holiday in her 100th birthday summer is how differently we hear her. Back in the day — in her music, in her autobiography — Lady Day was the full catalog of suffering in a 20th-century underground: abandonment and child prostitution on the way to drink, drug addiction, and death at 44. “The most hurt and hurting singer in jazz,” said the authoritative Nat Hentoff.

But resurrection in art jumps out of the soundtrack here — starting with her breakthrough film with Duke Ellington in 1934, when she sings, at age 19, “Saddest song on land or sea, was when my man walked out on me.” Then, when we hear Billie Holiday’s recording of “I’ll Be Seeing You,” from 1944, she has stopped at our table in a small club and started speaking directly to us. There’s no other singer who ever made us cheer and cry at the same time. So Billie Holiday stands less for all that pain than for Hemingway’s dictum that a blues hero “can be destroyed but not defeated.”

In Billie Holiday: The Musician and the Myth, the meta-biographer John Szwed (also of Sun Ra, Miles Davis and Alan Lomax) traces the self-invention of an icon and finds the life and art of Billie Holiday running side-by-side with a truth-telling drive that did not quit. In our conversation, Szwed finds that to the end she was “smarter, tougher, funnier” than all but a few knew. And of the sound: "This is cubist music."