Lady Day on Swing Street: Part I cover

Lady Day on Swing Street: Part I

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Tracing the history of Billie Holiday and NYC nightlife through the Harlem Renaissance to Café Society.


Rating: 5 out of 5 stars on 1 review

"This was a great piece about Billie Holiday's early life and ascent to the upper client clubs in Harlem. It also does a good job of painting the atmosphere of Harlem during that time." 5 stars by




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Lady Day on Swing Street: Part I

Swing Street

There are few moments more perfect than walking into a dimly lit old bar late at night and hearing a Billie Holiday song, either on the jukebox or being covered by the four-piece in the corner.

“These Foolish Things” is practically custom made for sliding onto a stool and ordering an Old Fashioned as you prop your elbows up on the bar and think about lost loves and life’s regrets.

Her discography is not composed entirely of anthems for the lonely, but few American artists seem to have captured the melancholy of 2 a.m. quite like the woman who would become known as Lady Day. And for much of her career, her unique voice could be heard in one of the many clubs that used to line Manhattan’s 52nd Street, a stretch of the city that became known as Swing Street.

Billie Holiday

Billie Holiday

Image by William P. Gottieb

Riddled Past

Confirmed details about Holiday’s early life are scant.

She was born Eleanora Fagan in Philadelphia and raised in Baltimore, but her father left his family and her mother worked such long hours that Holiday was usually left in the care of her mother’s half-sister, Eva Miller, who herself worked so much that she in turn left young Holiday in the care of her own mother-in-law.

Records from this era are sketchy, and Holiday’s own autobiography is vague and riddled with inconsistencies (it was, in fact, written by a name William Dufty, and when questioned about some seeming errors in it, Holiday once famously shrugged and replied “I ain’t never read that book.”)

Tumultuous Times

She was in and out of a reform school called House of the Good Shepherd—

first when she was caught skipping school and a second time after a neighbor attempted to rape her and the police needed to keep her somewhere with more protection than her frequently empty home.

She worked as an errand girl in a brothel, and it was there that she first heard the music of Louis Armstrong, the artist she credits as having the most profound influence on her eventual drive to become a performer.

In 1929, Holiday followed her mother to Harlem, where both of them found work in a brothel. Holiday was thirteen at the time. When police raided the house, she found herself imprisoned in the workhouse on Blackwell’s Island, later renamed Roosevelt Island.

A New Home

When she was released in October of 1929, she decided she had had enough of being Eleanora Fagan.

She sought work as a singer, taking the stage name Billie from her favorite actress, Billie Dove, and the last name Holiday from musician Clarence Holiday, the most likely candidate for being her father. She teamed up with neighbor and aspiring saxophonist Kenneth Hollan and began knocking on club doors.

It didn’t take long for club owners and talent managers to realize there was something special about this tragic young kid. She soon had a new home, on Swing Street — 133rd Street between Seventh Avenue and Lenox Avenue in Harlem.

Musical Tour

Musical Tour

Map of Harlem Renaissance clubs, first published in Manhattan Magazine (1932)

Important Dates

By the time Holiday and Hollan were looking for work as musicians, the Harlem Renaissance was in full swing and Swing Street was its artistic heart.

An event as momentous as the Renaissance doesn’t have a specific start date — such cultural shifts grow organically, and sometimes it’s only in hindsight that we can see a Movement — but if forced to chose, many people cite 1917, the year in which a white playwright named Ridgely Torrence cast black actors in a series of performances that allowed them to actually be actors — no minstrelry, no blackface.

Famous Speakeasies

In 1919, poet Claude McKay wrote the angrily political “If We Must Die,” a piece that served as a sort of clarion call to black Americans to stand up and defy the racism and subjugation that had been their lot in American life for so long.

In the final days of the 1910s, Harlem experienced a cultural, artistic, and intellectual awakening — all set to the sound of a new piano music called the Harlem Stride style. As jazz became more acceptable — it had previously been regarded as something a bit low class and “Southern,” not really the stuff for more sophisticated urbanites — clubs began to open to showcase the new sound.

With the onset of Prohibition, many of the Harlem jazz clubs — Tillie’s Chicken Shack, Pod’s and Jerry’s, the Rhythm Club, the famous LGBT friendly Harry Hansberry’s Clam House — became some of New York’s most famous speakeasies.

International Adventures

White patrons, fancying themselves adventurous, even began making the trip up to Harlem to see this once in a lifetime community of musicians that included:

Louis Armstrong, Duke Ellington, Fats Waller, and a guy named Buck Clayton, who eventually moved to Shanghai, where he partnered with a Chinese musician named Li Jinhui, resulting in the birth of “Shanghai Jazz,” an incredible melding of traditional Chinese music with modern American jazz, condemned by the government as pornographic (they branded it “yellow music”) and embraced by the masses to such a degree that, despite the hand-wringing on the part of moral watchdogs, it became the sound of Chinese pop music during the 1930s and 1940s.

Social Friction

Back in Harlem, the influx of white patrons was good and bad.

Good because it exposed whites to black culture — not just the music, but also to the social and political defiance that was growing. Good because it resulted in integrated streets. Bad because those streets sometimes integrated at the expense of black locals. Bad because some of the clubs, including Harlem’s famous Cotton Club, opened specifically to showcase black talent for white-only audiences.

52nd Street

52nd Street

Image by William P. Gottieb

First Hits

It was in this dynamic and tumultuous atmosphere that Holiday found herself performing. Her reputation grew quickly, and in 1933 producer John Hammond heard her sing for the first time.

Later that same year, he arranged for her first recording, backed by Benny Goodman and resulting in her first hit, “Riffin’ the Scotch.” Hammond — and most of America — had never heard anyone sing like Holiday.

Her voice is still today instantly recognizable. There’s something about it, something to do with smoke and shadow and sex; something that seems melancholy even when the words and melody are happy; something a little slurred, a little muddled, the exact voice you need late at night.

Leaving the Band

Hammond paired her with an increasingly impressive array of musicians and bandleaders both black and white including:

Teddy Wilson, Artie Shaw, and Count Basie, who was at the time famously in a musical duel with Chick Webb, whose lead vocalist was Ella Fitzgerald. Holiday’s working relationship with Basie and his band was tense.

They claimed she was temperamental, unprofessional, and difficult. She claimed they were cheap, and that they demanded of her artistic changes that undermined the very reason so many people were coming to see her. In the end, the differences were irreconcilable, and Billie left the band.

Changing Times

By the end of the 1930s, Swing Street was gone.

The Depression, the end of Prohibition, the rise of organized crime, and the brutal suppression of demonstrations that became the Harlem Riot of 1935 kept patrons away.

By then, though, Billie Holiday was a star, and Hammond booked her at a new place downtown, in New York’s Bohemian Greenwich Village neighborhood, called Café Society.