Click on any song title below to play it on Spotify. The full 66-song playlist can be found on both Spotify and Apple Music.

T H E T H I R T I E S

Leadbelly, “Midnight Special” (RCA Victor reissue; original release 1934): As John Lomax and his son Alan scoured the South, gathering folk songs for the Library of Congress, they came across Huddie Ledbetter at the Louisiana State Penitentiary in Angola. Leadbelly, as his fellow inmates called him, played the 12-string guitar like a one-man band and had a head filled with colorful old tunes. On his take of the song “Midnight Special,” Leadbelly fingers the low notes in an early version of country music’s walking bassline, simultaneously strumming the chord progression that carries the melody, as—on the way to the rousing refrain—he pulls in lines from prisoners’ favorites and, more importantly, adds a few of his own. As this performance makes stunningly clear, Leadbelly was no less than the living embodiment of the oral tradition at the root of all folk music, as common songs and stories were passed along from one singer to the next. More to the point, this song was the yardstick for all American folk music to come. “‘If you want to learn something, just steal it—that’s the way I learned from Leadbelly,” Woody Guthrie admitted.

Fats Waller, “I’m Crazy ’Bout My Baby” (Victor, 1935): Fats Waller had it covered: He was a brilliant piano player who popularized stride, which moved from the regimented approach of ragtime and early jazz to a sexier, more hip-swaying style; he sang with the gritty charm of Louis Armstrong; and he was an irresistible entertainer, commanding and hilarious. From the opening verse of this love-struck romp—“I’m the world’s most happy creature/tell me, what can worry me?/I’m crazy ’bout my baby/and my baby’s crazy ’bout me!”—the sheer force of Fats’ larger-than-life personality blazes through like a meteor crashing into a nightclub roof. But that’s true of every performance by the first great piano man. Without this charismatic hepcat, there would be no Jerry Lee Lewis, no Fats Domino, no Randy Newman.

Robert Johnson, “Hellhound on My Trail” (Vocalian/Columbia, 1936): For rock ’n’ roll to truly come into being, it would require more than music—it would demand a mythic figure. The otherworldly voice and eerie themes of Robert Johnson make the powerful myth of his deal with the Devil seem totally plausible. Down at the crossroads where Highways 61 and 49 intersect in Clarksdale, Mississippi, Satan supposedly offered Johnson superhuman talent in exchange for his immortal soul. Johnson sure does sound haunted in this song, his high-lonesome voice edgy and tremulous with dread, his guitar playing taut and startlingly complex, the friction of his fingers on the strings seeming to set off sparks. The world he describes in the lyric is in tumult—blues falling down like hail, wind rising, leaves trembling on the tree, a hellhound snapping at his heels. And, as if things weren’t bad enough already, his woman has sprinkled hot foot powder around his door. No wonder he’s got to keep moving. One of the mere 29 recorded performances that make up Johnson’s towering legacy, “Hellhound” shows why he’s still worshipped as “the King of the Delta Blues.”

Count Basie, “One O’Clock Jump” (Decca, 1937): This fusion of African-American sexuality with the polite sound of big band music—which, somehow, swung while the tuxedo-encased hips crowding the dance floor remained stiff, even as they did the Lindy past midnight—cracked open the door for the collision of black and white music. On this Count Basie nugget, the brass-driven arrangement keeps spiraling tighter and tighter, like a wind-up toy, until the last half-minute, when the horn section finally steps forward and blows a melodic hook for the ages, in a key early example of the goose-bump moment. An exhilarating blend of peak-period swing and early R&B, “One O’Clock Jump” was a smash during the height of high society, as the blues rolled uptown in a long, black limousine.

Billie Holiday, “Strange Fruit” (Commodore, 1939): Unlike any other song of its time, “Strange Fruit” cut right through all metaphoric niceties to reveal the raw, brutal, horrifying face of racism, a cancer metastasizing unchecked through Jim Crow America. Written by a Jewish schoolteacher named Abel Meeropol, the song found its way to jazz singer Billie Holiday, who had the guts to sing it, and force her fans to endure every chilling detail of this picture of the country at its ugliest. Over muted horns droning a variation on the New Orleans funeral march, set against a seemingly summery piano, Billie lays out this scene of a lynching in an otherwise pastoral Southern setting with an ache in her voice, sounding like the ghost of one of its victims stepping to the mic. “Here is a fruit for the crows to pluck/for the rain to gather, for the wind to suck,” she sings deliberately and gravely, letting the words sink in. “For the sun to rot, for the tree to drop/here is a strange and bitter crop.” It’s highly unlikely that Holiday, singing of such misery in segregated Harlem, could’ve imagined a day when a black man would be elected to the highest office in the land.

Next up: The 1940s