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.

1. โCrazy Bluesโ by Mamie Smith (1920)
Smithโs debut single looms impossibly large over popular music: Itโs the first vocal recording by an African American, the first blues recording, and the first race record. Ninety-five years later, โCrazy Bluesโ has more than history to recommend it, as Smithโs jazzy delivery sounds just as sly and mighty as ever.

2. โDark 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.

3. โStackoleeโ by Mississippi John Hurt (1928)
It wasnโt the first tune to recount the exploits of the notorious St. Louis pimp Lee Shelton, but Hurtโs version may be definitive. He describes the violence that Shelton perpetrated in a spry sing-song melody: โAt twelve o’clock they killed him,โ he sings, with no small relief in his voice. โTheyโs all glad to see him die.โ

4. โDiddie 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. โDiddie Wah Diddieโ shows off his agile fretwork as well as his winking vocal delivery. Everybody but the censors knows what diddie wah diddie means.

5. โLast 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. โLast Kind Wordsโ is a steely, world-weary lament of lust and loss. โIf I get killed, please donโt bury my soul,โ she sings over an ominous strum. โI prefer just leave me out, let the buzzards eat me whole.โ
