5 Minutes That Will Make You Love Billie Holiday

Billie Holiday is one of the foremost vocalists in jazz, whose emotional depth and unique phrasing inspired generations of singers to experiment with form and pitch fluctuation. Nicknamed “Lady Day” by the saxophonist Lester Young, her star brightened in the 1930s behind a string of hit songs and notable live performances in Harlem. In what was the hottest jazz scene in the country, Holiday stood out, and in 1937 she joined the famed Count Basie Orchestra; a year later, the clarinetist Artie Shaw asked her to join his orchestra, making Holiday the first Black woman to work with a white big band.

Holiday’s legend grew in the late ’30s during her residency at the Café Society in Manhattan. She was introduced to “Strange Fruit,” a song by Abel Meeropol about lynching in the American South based on a poem he had written. Barney Josephson, the proprietor of Café Society, heard the song and brought it to Holiday, who first performed it there in 1939. It was a watershed moment for the singer: It’s not only the most famous song in her repertoire, it’s considered one of the most important in history, the track’s vivid imagery a strong indictment of racism in the country. Holiday was officially a star after the recording of “Strange Fruit,” and followed it with an impressive run of tracks in the early ’40s that cemented her fame.

While there’s been a notion to only associate Holiday with pain and struggle, these accounts have dimmed her light as a firebrand artist whose creative bravery encouraged others to take similar risks. We asked 10 musicians and writers to share their favorite Holiday songs: Enjoy listening to their choices, check out the playlists and be sure to leave your own selections in the comments.

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‘Autumn in New York’

José James, vocalist

Within the first two seconds of this song it’s impossible not to be drawn into the spell of Billie Holiday’s voice. Sailing confidently over lush chords by the pianist Oscar Peterson, Holiday pulls back the curtain on the beating heart of everyone who has loved, lost, loved again and (finally) lost themselves in that great city. A superb storyteller, Holiday explores every nuance of Vernon Duke’s paean to autumnal introspection in the city that never sleeps. Through her knowing delivery, every detail becomes vivid, cinematic: couples holding hands in Central Park, clouds reflecting off endless steel buildings, sundown in Greenwich Village, the wry smile of the maître d’hôtel at the Ritz, a lipstick-stained empty cocktail glass left behind at the bar. Billie was queen of it all, one of the highest-paid Black entertainers of her time, who left no stone unturned on her journey toward the self. This is beyond jazz singing; this is mastery in its highest form. With this song, Billie takes her place among the greatest of all balladeer improvisers in the jazz canon, creating the definitive version of an American classic.

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