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What are the 20 Most Essential Blues Songs?

Over the past hundred years, blues music has mutated and transformed itself repeatedly, borrowing from other styles and traditions as it migrated from the South over to Texas and up to Chicago. Winnowing such a massive catalog down to a handful of tracks would be impossible, but here are 20 songs essential to the blues and its long, storied history.

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1. โ€œCrazy Bluesโ€ by Mamie Smith (1920)

Smithโ€™s debut single looms impossibly large over popular music: Itโ€™s the first vocal recording by an African American, the first blues recording, and the first race record. Ninety-five years later, โ€œCrazy Bluesโ€ has more than history to recommend it, as Smithโ€™s jazzy delivery sounds just as sly and mighty as ever.

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2. โ€œDark Was The Night, Cold Was The Groundโ€ by Blind Willie Johnson (1927)

This itinerant preacher and musician has traveled from the dusty streets of Texas to the very edge of the solar system. One of his biggest hits, an all-but-silent prayer based on an18th-century hymn, was included on the gold record that NASA shot into space on the Voyager spacecraft in 1977.

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3. โ€œStackoleeโ€ by Mississippi John Hurt (1928)

It wasnโ€™t the first tune to recount the exploits of the notorious St. Louis pimp Lee Shelton, but Hurtโ€™s version may be definitive. He describes the violence that Shelton perpetrated in a spry sing-song melody: โ€œAt twelve o’clock they killed him,โ€ he sings, with no small relief in his voice. โ€œTheyโ€™s all glad to see him die.โ€

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4. โ€œDiddie Wah Diddieโ€ by Blind Blake (1929)

From 1926 until 1932, Blind Blake cut more than 80 records of potent Piedmont Blues, a subgenre that used deft finger-picking to mimic ragtime melodies. โ€œDiddie Wah Diddieโ€ shows off his agile fretwork as well as his winking vocal delivery. Everybody but the censors knows what diddie wah diddie means.

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5. โ€œLast Kind Word Bluesโ€ by Geeshie Wiley (1930)

Little is known about Geeshie Wiley, but the small body of work she left behind reveals the deep pain associated with blues music. โ€œLast Kind Wordsโ€ is a steely, world-weary lament of lust and loss. โ€œIf I get killed, please donโ€™t bury my soul,โ€ she sings over an ominous strum. โ€œI prefer just leave me out, let the buzzards eat me whole.โ€