How did Anita O’Day—the legendary jazz singer who, along with Chet Baker, Miles Davis, Gerry Mulligan, and Stan Getz, led the so-called “cool school” of modern jazz—define cool?

“That means doing everything that you like to do and getting away with it, you dig?”

Her traits included a frosted tone with a dash of vinegar; a blithe, airy rhythmic sense that could make almost any band swing; an ultra-hip bebop vocabulary; and a wisecracking insouciance, as though all this were just a lark. O’Day emerged in 1941 as a big-band singer whose tough look and take-charge style established her as a musically savvy leader of men, not a begowned accessory. Thereafter, while creating a historic body of recordings on Verve Records, O’Day became “one of the boys” in another regard: She spent much of the ‘50s and ‘60s hooked on heroin. Finally clean by the ‘70s, she had a stunning renaissance, touring the world each year and releasing dozens of albums; 60 Minutes even profiled her.

Her memoir, High Times Hard Times, while vividly written (it was optioned more than once for films that didn’t happen), cuts off in 1980, and contains almost no reflections on why she sang the way she did. Author James Gavin, whose biography subjects include Chet Baker, Lena Horne, Peggy Lee, and George Michael, now turns his attention to O’Day’s mad roller-coaster life, a nonstop procession of thrills, laughs, outrageous stories, and unforgettable music-making. Gavin, a Grammy nominee and a two-time winner of ASCAP’s Deems Taylor-Virgil Thomson Award for excellence in musical journalism, will draw upon a wealth of unpublished material, including interviews with many of the people who knew her best. His book promises to be a definitive portrait of one of the great characters and innovators in jazz history.

Series: Popular Music History