Billie Holiday: Heroin Hounds, ‘Whorehouse Music,’ and the Queen of Jazz

Summary

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Podcast Summary: DISGRACELAND

Episode: Billie Holiday: Heroin Hounds, ‘Whorehouse Music,’ and the Queen of Jazz

Host: Jake Brennan (Double Elvis Productions)
Date: April 5, 2022

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Main Theme

This gripping episode of DISGRACELAND dives deep into the turbulent, harrowing, and often heartbreaking life of legendary jazz vocalist Billie Holiday. Host Jake Brennan unpacks the real story behind Lady Day: her formative childhood trauma, the grinding realities of her rise from prostitution to stardom, the racism and hypocrisy she faced, her heroin addiction, and the government’s relentless campaign to bring her down. The episode centers around the iconic moment of Holiday's triumphant Carnegie Hall comeback—only ten days after being released from prison—while weaving in the personal, social, and political forces that defined her rollercoaster life.

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Key Discussion Points & Insights

1. Billie Holiday’s Childhood & First Betrayals

• Abuse and Institutionalization: At age 10, Billie was sexually assaulted and then, disturbingly, criminalized and institutionalized rather than cared for.
  • “A rape victim was thrown in jail... The cops didn’t believe her.” (05:41)
  • Sent to a Catholic reform school, she endured brutal, dehumanizing treatment and was haunted by unspeakable events—including being punished by being locked in a room overnight with a dead girl.
• Early Independence Amid Trauma:
  • “As a child, Billie Holiday didn’t have much of her own anything, save for her mother’s love. Her father, a working musician, split early. He left Billy for a life playing the banjo.” (04:41)

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2. Prostitution and the Power of Music

• Drawn to “Whorehouse Music”:
  • As a child, Billie was drawn to the lively music emanating from local brothels, which exposed her to the sounds of jazz and blues greats.
  • “By the age of six, Billy was running errands for the madam… but more than the promise of something different… there was the music… it knocked her out.” (19:13)
• Entering Sex Work:
  • Holiday’s transition into sex work at thirteen was driven by economic desperation and the lack of alternative paths for a young Black girl. The brothel also functioned as her initiation into the world of jazz performance.
  • “Billie, at 13, had house girls who also worked for the madam doing her laundry. Billie vibed on her suddenly flushed purse. The sex, however, scared the hell out of her.” (21:32)

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3. The Escalating Search for Escape: Addiction

• Beginnings of Drug Use: Holiday began with marijuana, then drank, graduated to cocaine, and ultimately heroin—a habit that both fueled and destroyed her.
  • “Stardom, adoring fans, the rush of live performing, none of it did what getting high did—liberate.” (24:21)
• Heroin Hound, Mr.:
  • Ingeniously, Billie used her dog to smuggle heroin—a risky necessity given her fame and the constant police scrutiny.
  • “Mr. was Billie’s dog… he’d get his treat. Then he’d get smothered with love from his mistress. Then she’d detach the special package Mr. had brought her. She’d sit, she’d shoot, she’d sail away wild.” (27:14)

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4. The Triumph and Perils of Fame

• Carnegie Hall Comeback:
  • Just ten days out of prison, Billie returned to the stage at Carnegie Hall—clearly still in full possession of her musical powers.
  • “The Carnegie Hall concert wasn’t her idea… 3,500 capacity seats sold, including standing room only tickets.” (03:41)
• Relentless Surveillance:
  • Federal agents attended her shows, seeking evidence of continued drug use.

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5. “Strange Fruit”: Protest, Persecution, and Legacy

• Performance as Political Act:
  • Her stirring rendition of “Strange Fruit” was a punch in the gut to American racism, making her a target for law enforcement.
  • “Strange Fruit was loaded… more potent than her sexuality… the sting of racism she experienced daily… Billy channeled every ounce of fear and disgust into her performance of Strange Fruit.” (33:08)
• Backlash from Powerful Men:
  • Harry Anslinger, Federal Bureau of Narcotics commissioner, was enraged by her outsized influence and protest music, vowing to destroy her.
  • “Strange Fruit was a protest song… what angered Anslinger more was that this particular song was being sung by a Black junkie musician.” (34:40)
• Manager’s Betrayal:
  • To avoid Armstrong’s arrest for marijuana use, her manager Joe Glaser cooperated with authorities, giving them Billie instead.
  • “So Harry aimed lower… set his sights on Joe Glazer’s other client, Billie Holiday.” (35:55)

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6. The Tragic Downward Spiral

• Legal Troubles and Endless Exploitation:
  • Holiday was repeatedly set up and betrayed by the men managing her—who acted as informants for the Feds. Even as she climbed musically, she was relentlessly surveilled, arrested, and jailed.
  • “Levy, like Joe Glazer before him, was an informant. But from way back, the feds sponsored Levy. The feds let Levy be Levy in exchange for Boku fink dirt.” (41:27)
• Final Days and Death:
  • In 1959, dying in the hospital from cirrhosis, Holiday was arrested by federal agents on her deathbed for possession.
  • “As she laid dying in her hospital bed, Henry Ainslinger and his federal agents stormed into her hospital room and arrested Billie Holiday for possession of illegal narcotics, heroin.” (46:03)

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Notable Quotes & Memorable Moments

• On the transformation of trauma into art:
  • “You listened to Billie Holiday and you knew the woman who owned that voice had seen some things… Billie Holiday would rather have done without some of that experience.” (04:25)
• On institutional cruelty:
  • “The treatment of the young girls was barbaric… For tonight anyway, 10 year old Billie Holiday will be keeping the body company.” (07:37)
• On her relationship with drugs:
  • “First it was reefer, then alcohol, cocaine, then heroin. Then cocaine and heroin at the same time. By the time Billie Holiday was 25 years old, getting high was a daily thing.” (24:34)
• On the use of Mr., her heroin hound:
  • “Mr. was smart. Smarter than some of the men in Billy’s life. And definitely smarter than some of the drummers she’d known. Mr. was capable. Mr. was trained.” (26:27)
• On ‘Strange Fruit’ as protest:
  • “Strange Fruit was Billie Holiday’s most powerful weapon… The sting of racism she experienced daily, be it in prison, on the streets of New York, on tour throughout the Jim Crow south…” (33:13)
  • “Billy channeled every ounce of fear and disgust into her performance of Strange Fruit. The audience loved it. Most of them anyway. Some didn’t want politics mixed up into their cosmopolitan nights on the town. But they were a minority.” (34:10)
• On her tragic, final arrest:
  • “As she laid dying in her hospital bed, Henry Ainslinger and his federal agents stormed into her hospital room and arrested Billie Holiday for possession of illegal narcotics, heroin.” (46:03)
  • “Billie Holiday died before being judged one more time… handcuffed, off stage, on drugs. The opposite of free.” (46:44)

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Timestamps for Important Segments

• Billie’s Early Trauma and Institutionalization — 03:23–10:30
• Life in Brothels, Prostitution, and Music Discovery — 17:57–22:00
• Descent into Heroin Use and Ingenious Drug Smuggling — 24:21–27:30
• Carnegie Hall Comeback and Federal Scrutiny — 03:23, 17:57–33:08
• The Political Power and Fallout of ‘Strange Fruit’ — 33:08–36:47
• Series of Betrayals and Exploitative Relationships — 36:47–43:50
• Final Decline, Hospitalization, and Death — 43:50–46:44

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Tone and Approach

Jake Brennan narrates with moody reverence, dark wit, and a palpable sense of outrage—balancing admiration for Holiday’s art with unflinching depictions of her pain and the many betrayals she suffered. The tone is frank, hard-edged, and cinematic, bringing Holiday’s world and struggles vividly to life.

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Conclusion

This episode paints Billie Holiday as a towering, tragic figure—an artist whose genius and resilience were matched only by the cruelty she endured from society, the law, even those closest to her. Her art was shaped by trauma and transformed into a political act. Ultimately, her life serves as both inspiration and cautionary tale: a story of survival, betrayal, addiction, and resistance, ending with the government’s final, heartless blow—arresting Lady Day on her deathbed. As Brennan laments, “So incredibly sad. Such a disgrace.” (46:44)

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Listen to the full episode for a dramatic, immersive ride through the life and legend of Billie Holiday—a journey as haunting as her music.

Transcript

[Ryan Seacrest]

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[Podcast Sponsor Announcer]

Support for the show comes from Public, the investing platform for those who take it seriously. On Public you can build a multi asset portfolio of stocks, bonds, options, crypto and now generated assets which allow you to turn any idea into an investable index with AI. It all starts with your prompt. From renewable energy companies with high free cash flow to semiconductor suppliers growing revenue over 20% year over year, you can literally type any prompt and put the AI to work. It screens thousands of stocks, builds a one of a kind index and lets you backtested against the S&P 500. Then you can invest in a few clicks. Generated assets are like ETFs with infinite possibilities, completely customizable and based on your thesis, not someone else's. Go to public.com podcast and earn an uncapped 1% bonus when you transfer your portfolio. That's public.com podcast paid for by Public Investing Brokerage Services by Open to the Public Investing Inc. Member FINRA and SIPC Advisory Services by Public Advisors llc. SEC Registered Advisor Generated Assets is an interactive analysis tool. Output is for informational purposes only and is not an investment recommendation or advice. Complete Disclosures available at public.comdisclosures

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[Jake Brennan]

Disgraceland is a production of Double Elvis. The stories about Billie Holiday are insane. She was institutionalized for being raped. She ran errands for call girls at just 6 years old and was later imprisoned for refusing to prostitute herself. She had a heroin hound that inconspicuously delivered packets of dope to her front door. Her double crossing manager helped the feds buster for narcotics. Anyway, she was a master of her own sensuality. Despite the trauma inflicted upon her as a young girl, Billie Holiday grew up fast. But her voice was slow, sweet. She sang jazz in a way that hung in the air that mesmerized millions of people. She could bring a room to a hush or a roar with a single syllable because Billie Holiday made great music. Unlike that music I played for you at the top of the show. That wasn't great music. That was a loop from my melotron called Shortcake Strut MK1. I played you that loop because I can't afford the rights to Manana Is Soon Enough for Me by Peggy Lee and why would I play you that specific slice of sultry cheese? Could I afford it? Because that was the number one song in America on March 27, 1948. And that was the day Billie Holiday performed to a sold out Carnegie hall, proving that no prison sentence, no betrayal and no drug habit could keep her down on this episode. Call girls, heroin hounds. Betrayal. Bringing down the house at Carnegie hall in Billie Holiday Jake Brennan and this is disgrace. 10 days out of prison, nothing tasted as sweet and strange as this freedom on stage. Again, lost in song. Literal blood, sweat and tears. Blood from the hat pin she used to fasten her trademark gardenias to her Hair, sweat from giving her all on stage in tears of joy. 10 months in prison and there was no telling whether she'd have a career at all afterward, never mind a rabid and supportive audience just 10 days removed from the shame of incarceration. The Carnegie hall concert wasn't her idea. It was the promoters. He must have known what he was talking about. Promoting was his business. Singing and doing time was Billie Holiday's business. Tickets moved like Harlem numbers runners quick. Billie Holiday's triumphant return was barely announced before it sold out. 3,500 capacity seats sold, including standing room only tickets, which extended to the actual stage. Come showtime, 2,000 people jammed 7th Avenue and 57th street in hopes of finding their way in to see the woman they called Lady Day. Billy hadn't sung a stitch in prison, not a note. But you wouldn't know it from listening to her on stage at Carnegie hall that night. She was in possession of all her powers. Commanding, sensual, sultry. The most unique, inexperienced voice in the business. You listened to Billie Holiday and you knew the woman who owned that voice had seen some things. It was sultry and sensual. Yes, and it was also experienced. Billie Holiday would rather have done without some of that experience. It was what led her to this point. Tonight, she tried blocking it out. She dug into the feel. She sang one of the first songs she wrote, God Bless the Child. The title was only half of it. The whole phrase, God bless the child that's got his own hinted at the full story. And the full story started with this. As a child, Billie Holiday didn't have much of her own anything, save for her mother's love. Her father, a working musician, split early. He left Billy for a life playing the banjo. But he also left behind a shared love of music. Billy had to fend for herself most days while her mother worked as a maid cleaning rich people's homes in Baltimore's white neighborhoods. There was a man, a neighborhood man, 40 and big. Mr. Dick. Billy was 10 years old. Physically, she had started developing early, before most of the other young girls in her neighborhood. Mr. Dick noticed. He told Billy her mom had asked him and his wife to watch Billy until her mom returned later that night and that Billy was supposed to go with the couple to their home down the street. Billie Holiday was 10 years old and innocent. She believed the two adults who then brought Billy into their home, locked her in their bedroom, held her down and proceeded to rape her. She screamed. She scratched. She saw her mother and a policeman Break down Mr. Dick's door. And Mr. Dick was arrested Billy and her mom gave their statements at the station. And incredibly young Billie holiday, at age 10, a rape victim was thrown in jail. The cops didn't believe her. Look at her. She must have enticed Mr. Dick. It couldn't have been all his fault. Look at this girl. Developed beyond her years. Surely she deserved some of the blame as well. So went the incredibly ignorant and insensitive thinking from authorities at the time. Billy spent two nights in jail, then court. Mr. Dick got five years in. Something approaching justice. Billie Holiday, on the other hand, got sent to Catholic Girls Reform School. She needed to be sorted out, taught a lesson, broken, of whatever wild spirit brought on this terrible incident. For it couldn't happen again. It was Billie Holiday's first taste of institutional injustice. And it was horrifying. The reform school was its own type of prison. The treatment of the young girls was barbaric. They were beaten, isolated, mentally abused. And inside the walls of the school, physical abuse wasn't beyond the realm of possibility if Billy wasn't careful. In short, it was dangerous. Danger around every corner. Even in the most seemingly innocent of places. On the playground, Billy sat on a bench, kicking her shoes, watching one of the other girls on a swing. The girl kept pushing it, pumping her legs and propelling herself higher and higher and higher until she swung so high she was dead. Even on a line with the crossbar that the swing's chain swung from. She pumped some more, higher, more, higher still. Until the swing's chains broke from the crossbar and the girl in the swing flew through the air. The girl screamed in horror as Billy watched the girl fly high over the schoolyard in what seemed like slow motion. Then over the yard's fence. The girl screamed the whole way. She flew out of the yard, into the yard next door and crashed down violently. The scream went dead. So too did the girl. Her neck broken, she died instantly. Billy saw most of it, heard it all. Something in her that day died a little too. It was traumatic, upsetting to say the least. She mouthed off to the Mother Superior and for her punishment they threw Billy in here. Locked in the front room of the reform school with the body of the dead girl. It would be a day or so before the morgue could make it out to collect the body. And for tonight anyway, 10 year old Billie Holiday will be keeping the body company. Dead girls don't make much noise. But every little sound within and in earshot of that room, every spin of the overhead fan, every creak in every floorboard of the house, every foundational shift, every scurry from every rodent inside the old home's walls, the scattering cockroaches, every distant voice, every scuffle outside on the sidewalk, every random car horn. All of it conspired to come together in a symphony of horror that soundtracked the living nightmare playing out in Billy's head at the moment she screamed bloody murder, banged on the door, pleaded, cried. None of it mattered. All that went unheard, unnoticed, unattended. To young Billie Holiday might as well have been as dead as that girl. No one cared. Not like they did now anyway. Billie Holiday was somebody. A bold faced person of note. The thousands of fans in attendance before her at Carnegie hall cared. Her fellow musicians cared. The press, the reporters who wrote about not only her music, but her legal troubles cared. And of course, just like they did back when she was 10 years old, the authorities cared. In their own way, that is. Except now it wasn't backward thinking local cops who had Billie Holiday on the brain. It was federal agents. And unlike the press or the fans who obsessed over Billy's music, her records, her stunning onstage performances and appearances on screen, the feds cared about one thing. The same thing Billy cared about. The thing that supplanted the music. Music was great. Sure. Music was the only thing that came close to restoring that innocence. That innocence that was ripped away from Billy when she was raped and subsequently institutionalized for the first time as a 10 year old. And music transported Billy out of herself and into another place. Completely. It was sublime. But that was onstage. Offstage, Billy needed something else to transport her, to take her away, to free her, to make up for that loss of innocence. And for Billie Holiday in 1948, going as far back as her addled brain would take her, that one thing was indeed the thing that federal agents cared so much about as well. Heroin.

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[Podcast Sponsor Announcer]

Support for the show comes from public, the investing platform for those who take it seriously. On public you can build a multi asset portfolio of stocks, bonds, options, crypto and now Generated Assets which allow you to turn any idea into an investable index with AI. It all starts with your prompt. From renewable energy companies with high free cash flow to semiconductor suppliers growing revenue over 20% year over year, you can literally type any prompt and put the AI to work. It screens thousands of stocks, builds a one of a kind index and lets you back test it against the S&P 500. Then you can invest in a few clicks. Generated assets are like ETFs with infinite possibilities, completely customizable and based on your thesis, not someone else's. Go to public.com podcast and earn an uncapped 1% bonus when you transfer your portfolio. That's public.com podcast paid for by Public Investing Brokerage Services by Open to the Public Investing Inc. Member FINRA and SIPC Advisory Services by Public Advisors llc SEC Registered Advisor Generated Assets is an interactive analysis tool. Output is for informational purposes only and is not an investment recommendation or advice. Complete Disclosures available at public.comdisclosures

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[Jake Brennan]

They were there in the audience that night. Federal agents clocking Billy's new post. Prison moves. As always, if she was high on stage, they couldn't tell. Compared to themselves, every jazz musician seemed at least a little high. The feds didn't understand what made these junky musicians tick, what made heroin so appealing. The drug wiped you out, rendered you unable to do anything except nod out and vomit if it was good anyway. Then when the high wore off, all you wanted was more. More drugs, more of that high. And you spent nearly every waking moment chasing it, scheming for it, stealing for it. Over your friends and your family for it. Except Billie Holiday hadn't hit that sort of bottom yet. She wasn't over anyone for heroin. Before prison, she was living large. From fat paycheck to fat paycheck. She wasn't in the position of having to steal for her drugs. Quite the opposite. She was the one being worked over. On stage. She leaned into the effortless chill of My Man. The song Cut Deep, made her think of Joe. Like most men, Billie Holiday involved herself with Joe Glazer. Her manager manipulated her. But unlike John Levy before him or Lewis McKay after, Joe's con was more complicated. He wasn't after Billy's hard earned money that she generated as one of the country's premier singing talents. Joe was up to something else. Always up to something else. Joe also represented another artist, one of Billy's favorite artists, megastar of stage and Scream, Louis Armstrong. Armstrong was no doubt the bigger of the two artists on Glazer's roster and definitely his priority. Billy felt this. She didn't like it, but she accepted it. Billy accepted a lot of things. As far back as she could remember. She accepted the fact when she was 13 years old that if she were going to make any money, that there was unfortunately only one job available to her at the the oldest profession in the prostitution. Billie Holiday was drawn to the whorehouse as a young child. It was a hub of activity in the neighborhood. Good looking men coming and going at all hours, fancy cars for pulling up and pulling out, off towards some other reality far away from the grind of the Baltimore grime Billy and her mom were struggling through. But more than the promise of something different, something else there was the music. The madam kept a big Victrola record player pumping around the clock. And out of its big horn speaker, the sounds of Bessie Smith and Billie Holiday's future colleague Louis Armstrong filled the air. The music was infectious. It flowed through the whorehouse windows onto the street. It called out to Billie Holiday. And by the age of six, Billy was running errands for the madam. Washing basins, putting out towels and soap. Billy didn't even want to get paid. She just wanted to be around the music. It knocked her out. It was jazz music, but Billie Holiday didn't know it at the time. She called it what everyone else in the neighborhood called it, whorehouse music. By the time Billy turned 13 and had relocated to Harlem from Baltimore with her mother, she knew where the action was in her new neighborhood, the whorehouse. Billy quickly found employment once again as an errand girl and then quickly elevating herself to working girl or to the status of what was commonly referred to at that time as Twenty Dollar Girl. Two regulars a week, white dudes, 20 spots a pop, five each to the madam. And now, instead of doing laundry for other people as her mother did, Billy, at 13, had house girls who also worked for the madam doing her laundry. Billie vibed on her suddenly flushed purse. The sex, however, scared the hell out of her. Two times a week with nice, polite white dudes running around behind the backs of their wives was one thing. In her autobiography, Billy told a story about a man she called Mr. Dick. She said she was still terrified from her experience with him a few years earlier, even though he was paying for it and paying for it well. A 50 spot. For Billy alone, it was way worse. He nearly put Billy in the hospital. She said she couldn't walk for two days. Her mother called the ambulance, and the ambulance man gave Billy a crooked smile. But Billy remembered the rumors. Young black girls in the late 1920s being admitted into the hospital for pneumonia and coming out sterile, having had their ovaries involuntarily removed. No, thank you. Billy told the ambulance man she wasn't going anywhere. She'd take the pain and heal on her own in her mother's home. And from then on, Billy wrote, she made a pact to herself that she'd only take work from white guys. Now, I realize that in 2021, that sounds a lot like a stereotype that we'd rather not talk about. But to understand Billie Holiday, you need to understand who she thought she was in that moment. Because that's what she told a neighborhood gangster named Big Blue Rainier. There was no way she was taking his trick. Not for 20, not for 50, not for a hundred. But Big Blue didn't want to hear it. He had connections. And he wasn't about to take this humiliation from a $20 whore. So he had Billy arrested for prostitution cuz she wouldn't take his money to sleep with him. Incredibly, the hypocritic fink move worked. And Billy, at 15 years old, was sent off to Welfare Island. Welfare Island, New York City, 1929. Lunatics, the insane, the infirm, Criminally bent. Ill fit for society. Isolated off in the middle of the east river to keep the five boys burrow safe. If real reform was actually part of the plan, you couldn't tell from the facilities. Institutional drab bordering on horror. Trash. Filth. Rats the size of house cats. Violence imbued into every nook and cranny of the island. Predatory guards, predatory inmates, predatory patients. Billy kept her head down, did her time. And when she was released four months later, she slid past the predatory pimps waiting for her and the rest of the recently freed young women who hit the shore in Manhattan to get back to their lives. Billie Holiday had other plans. Recently released from incarceration as a teenager, it was clear to her that whoring wasn't the way. But maybe, just maybe, whorehouse music was. Billy jumped into her singing career the only way she knew how. Head first. She started at Pods and Jerry's, an integrated club in Harlem where the gin flowed freely and the reefer smoke permanently hung in the air. Crooning down on 133rd street earned her $18 a week. She was 16 years old and already soaking in the speakeasy spotlight. As she branched out to covens in the Harlem Alhambra, her social circle mushroomed. Count Basie and Artie Shaw became fans. Better yet, they became her bandmates. She took the work where she could, even if it meant she had to walk through the kitchen to enter a venue. Even if she had to sleep on the bus while touring with Artie's white band, who slept in the white motel. She endured it all. By 1939, she had signed with Columbia Records, and they knew her potential. Saw the way the crowds hung on her, every low, lewd syllable. Her voice mesmerized people. It lured people. People in, ensnared them. Just like the way that cocaine and heroin had suddenly Ensnared her. Billie Holiday was on top, one of the country's biggest stars. But that feeling didn't do enough. Billy needed more. Call it senses numbed, call it stolen youth, call it some twisted idea of freedom, whatever it was, stardom, adoring fans, the rush of live performing, none of it did what getting high did liberate. First it was reefer, then alcohol, cocaine, then heroin. Then cocaine and heroin at the same time. By the time Billie Holiday was 25 years old, getting high was a daily thing. Performing didn't matter. Billy could do the gig while stoned. And then after the gig, she'd do some more. Billie Holiday's constitution was depression era tough. There was no fucking with her. But that meant she needed drugs regularly. And for a woman of her profile, that was no easy task. She knew she was being watched. Cops, locals, feds, whoever. She knew she was a potential prize scalp. A bold faced name capable of putting a shine on the name of the arresting officer in the papers. She couldn't be holding ever. It was too risky. She could be searched at any moment without cause. She was a black woman in a very white man's world at the time. So a plan was hatched. Mr. Mr. Was Billy's dog. A boxer. Mr. Was smart. Smarter than some of the men in Billy's life. And definitely smarter than some of the drummers she'd known. Mr. Was capable. Mr. Was trained. Mr. Loved Billy. Mr. Was obedient. Mr. Was crooked. As Mr. Got recruited by Joe Guy, Joe Guy was recruited by Billy. First to blow a trumpet in her band. Then to blow her away in the sack. Then to run Mr. For her. Joe Guy, every day, every day, bought an ounce of heroin up on 8th Avenue. Then he'd find Mister, give Mister a treat. Mister would sit. Joe Guy would attach that ounce of heroin to Mister's collar inconspicuously. Next time for Mister's daily walk down Morningside Drive over to the Braddock Hotel. With the Braddock sign In his sights, Mr. Would know what time it was time to see the man in the funny hat who operated the elevator for another treat. Mr. Would run around the back of the Bradock. Joe Guy, his work done, would bounce. Mr. Would scratch the door. The man in the funny hat would appear. Mr. Would follow him into the hotel and into the elevator he'd go and have his new treat tossed to him before the doors would close up. Then the doors would open and that meant another treatment. This treat from Billy, who'd be waiting for Mr. On the other side of the opening elevator doors on the top floor, out of the elevator and into Billy's arms. Mr. Would go. First he'd get his treat. Then he'd get smothered with love from his mistress. Then she'd detach the special package Mr. Had brought her. She'd sit, she'd shoot, she'd sail away wild. She was a star, a very high star. She descended from the rough and tumble streets of Baltimore, then Harlem, through reform school whorehouses, Welfare island, to the top of the music game with a bad habit, but able to satiate that habit from a penthouse suite via a trained canine who ran drugs for her on orders from a man who worked for her. Billie Holiday Stone cold surreal.

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it was time. A time in the set everyone was always waiting for. Would she or wouldn't she play it? That is Strange Fruit. The song became her trademark, its words written by Abel Meeropol. Billy first performed it back in 1939 at Cafe Society. It brought the house down then and it would bring the house down now. Strange Fruit was loaded. It was Billie Holiday's most powerful weapon, more potent than her sexuality. And Billy loaded that weapon every night with hard emotion. The sting of racism she experienced daily, be it in prison, on the streets of New York, on tour throughout the Jim Crow south, being led in through the back doors of clubs she'd headline. Forced to always pack a sandwich in her purse because you never knew when. Whichever restaurant you were forced to stop at wouldn't serve you. The countless trips into the woods on the side of the road as a woman traveling in bands that were almost entirely made up of men. To relieve yourself. So humiliating. It stung. So too did the the thought of her daddy in the wrong part of the country. When his lung disorder worsened. Dallas, Texas. They wouldn't see him at the white hospital. And by the time he found his way to the black hospital, it was too late. It was a goner. Dead at 38 and entirely preventable. And then there was the fear. The lynchings. She knew how prevalent they still were. So prevalent, in fact, that the NAACP, the ACP's fight for anti lynching legislation, was still going strong in 1939 and facing fierce resistance from Congress. She knew how white men were still peddling postcards depicting lynchings like door to door candy salesmen. It sickened her almost as much as it scared her. The song captured the outrage and the horror of seeing black bodies swinging from southern trees. Strange Fruit indeed. Billy channeled every ounce of fear and disgust into her performance of Strange Fruit. The audience loved it. Most of them anyway. Some didn't want politics mixed up into their cosmopolitan nights on the town. But they were a minority. Oddly, Count Basie was a part of this minority. Back when Billy was coming up and touring in Basie's band. Basie wouldn't let her perform the song. It was too political, he reasoned. But Basie was a bit backward. He doubled down on that mammy bullshit. Please. The white crowd, even incredibly had Billy wear blackface because she was so light skinned and that her up that made it into the performance of Strange Fruit. To this day, Harry Ainslinger was also part of the minority that didn't love Strange Fruit. The commissioner of the Federal Bureau of Narcotics didn't Want politics mixed up into anything social. Least of all politics he didn't agree with. And that's exactly what he and his federal agents intended on stopping. Strange Fruit was a protest song at a time when popular protest songs barely existed. Not in the mainstream anyway. Of course, this was before Bob Dylan, before Nina Simone, before Chuck D. When it was performed, it was even before Woody Guthrie. What angered Angziger more was the fact that this particular song. Song Was being sung by a black junkie musician. And a popular one at that. Except that's where the rub was. A Billy Holiday bust meant headlines. Headlines meant Harry got his name and maybe even his square mug in the papers. He saw an in Joe Glazer, Billy's manager. Joe also managed Louis Armstrong. Louis was a chronic reefer man. Smoked 24 7, carried constantly. He was an easy target and a massive name. Almost too big to bust. Beloved in some ways, too. Blacks and whites worshiped Louis Armstrong. They'd come up with him. And not just cosmopolitan whites. Middle America whites as well. Louis was practically an institution. Busting would bring on more headaches than was necessary. So Harry aimed lower to just a ring or two below the bullseye and set his sights on Joe Glazer's other client, Billie Holiday. A big enough name to carry the bust on the wires. A small enough name to avoid any long legal hassles or result in bad pr. And the genius move was he could leverage Louis Armstrong's Reefer Madness against the manager of both Louis Armstrong and Billie Holiday, Joe Glazer. Give us the fucking girl, Joe, or we're taking Louis down. So went thinking. Cooperate with us on busting Billie Holiday and we won't bust your bigger client, your cash cow, Louis Armstrong. Joe Glaser had no choice. He rationalized it as he was doing Billy a favor. It was the only way to get her clean, to bust her off of the stage and off to prison. To get down with the Cold Turkey Quartet. Philadelphia, 1947. The plan was to bust Billie Holiday with the heroin. The heroin was in Billy's catalog. Black, 2 ounces. But the warrant was late. Waiting on the judge, the agent stewed. Someone tipped off Billy. Chauffeur. Time to bounce out of the city of brotherly love. Billy and company vamoosed. The agents freaked. There goes their target. There goes their heroin. There goes their headlines. They pulled their pieces and fired off round after round. Billy ducked into the back seats. Bullets lodged into the passenger side door. The chauffeur gunned it. The agents gave pursuit. Chauffeur ran Backstreet hop routes the agents couldn't keep up north to NYC into Harlem. Free for the night. Billy breathed a sigh of relief. Until she was busted. The next day, Billy pleaded guilty. Possession of narcotics. The judge brought down the gavel. A year and a day in Alerson Federal Correctional Facility. Billy did her time. She bounced. And now, 10 days later, she was back in the spotlight, on stage, free, if for only a moment. Billie Holiday's Carnegie hall concert, just 10 days after being released from from prison was a success. The headline screamed Billy is back. But her time in prison did have negative ramifications. For one thing, it resulted in the loss of her cabaret card, effectively the piece of bureaucratic paper that allowed her to perform in New York City. It was small time, local politics bullshit, but it mattered. It meant Billy had to find work out of town, which was easy. But still, not being able to work in town was humiliating. Billy's reputation followed her wherever she went. So too did federal agents. Nothing changed. There was no presumption of rehabilitation and there was no real rehabilitation. Billy went back to performing and went back to getting high. This time in lockstep with her new man and manager, John Levy. He was married and had a kid, but that didn't seem to stop him or Billy from taking up an affair. Levy managed Billy as well. Then there was no fine romance. It was piss and vinegar from the start, pretty much. The two fought endlessly. Levy drank, Levy scammed side trim. Levy ignored Billy's ire. Levy beat Billy. Levy pushed Billy back up on stage. Levy collected checks. At the end of the night, Levy let Billy have just enough. Levy, like Joe Glazer before him, was an informant. But from way back, the feds sponsored Levy. The feds let Levy be Levy in exchange for Boku fink dirt. Billy was small time, an addict, a user, not a trafficker. But she had that name that Levy kept in lights. Levy ratted his woman out in San Francisco. Billie Holiday got busted again, this time for smoking hop opium. Levy vamoosed. Billy got shrink jail. Billy got out. Billy got a new man. Worse than the first, slightly better than less. Louis McKay. He may have been her husband, but he managed. Billy doped up and working. Work, work and more work. Billy's health deteriorated before everyone's eyes. Didn't matter. Those performance fees were large. Louis McKay knew how to get his girl to earn. Billy may have dodged the pimps coming off of Welfare island years ago, but she worked as hard or harder for the predatory men in her life ever since. Even as of late in her mid-40s at least. Horrors got to retire after a while. And there was no retiring for Billie Holiday. Just work, tours, sessions, press repeat. Through it all, she somehow remained a relevant and impactful artist, appearing numerous times on television. Steve Allen, Mike Wallace, Art Ford. Even with that old pain in the ass Count Basie, Billie Holiday's trademark sensual performance style was now perforated with hard earned experience. You can see it on screen and hear it on record. Billie's last recordings are some of her best, particularly 1958's all or Nothing at All. You can still hear in Billie's recorded performance that movement, that freedom, that dizzying high effect her voice was capable of conjuring whether or not she felt that freedom, that feeling she felt on stage when things were really clicking pods and Jerry's back when she was getting her start. Carnegie hall after prison was something that only she knew. Regardless, she kept using drugs, kept searching for that feeling, that freedom in the needle. And it was no secret. America was wise and America was watching and listening to see if their junkie pop songstress would nod out right there in front of them. On screen and on record, it was a slow moving train wreck. The Billie Holiday Story. Everyone knew how it was going to end. And they knew it was going to end soon. But no one knew it was going to end like this. May 31, 1959. Billie Holiday's few remaining close friends checked her into New York's Metropolitan hospital. Billy was 44 years old and in bad shape. Cirrhosis of the liver. She'd lost £20 in much of her strength. Billy wasn't going anywhere. The doctors knew it. This was the short coda before the stage exit. There'd be no encore. Death was thick in that hospital air. But that didn't stop G man Narco fucko Henry J. Anslinger. As long as Billie Holiday was above ground, Billie Holiday was a threat Ansinger hadn't forgotten. Strange fruit Protest music from a black entertainer. A black female entertainer. Ainzlinger was never going to let it go. The stakes for him were too high. He had an entire nation's social order to maintain. Everyone had their place from Ainzinger's point of view. And Billie Holiday clearly didn't know hers or her people. So judgment was swift and punishment a must. Ainsinger thought of Psalm 711. God is an honest judge. He is angry with the wicked every day. Simple. True. But that passage didn't jazz Ainzinger's ire complete. He pulled from his memory Timothy 3:1:5 but understand this that in the last days there will come times of difficulty for people will be lovers of self, lovers of money, proud, arrogant, abusive, disobedient, ungrateful, unholy, heartless, unappeasable, slanderous, without self control, control, brutal, treacherous, swollen with conceit. Lovers of pleasure rather than lovers of God avoid such people. Henry Anslinger did the opposite. He didn't avoid such people, people like Billie Holiday. He confronted and crushed such people so that America could avoid such people. Junky jazz musicians were a scourge. That was the Fed mantra, especially those with high minded ideas about equality. Billie Holiday with her fur coats, her Cadillacs, her heroin and her protest song. Who did she think she was? Ainslinger knew who she was. Uncle Sam knew who she was and sure as God knew who Billie Holiday was. As she laid dying in her hospital bed, Henry Ainslinger and his federal agents stormed into her hospital room and arrested Billie Holiday Holiday for possession of illegal narcotics, heroin. Her new arraignment would be in a few weeks. Billie Holiday died before being judged one more time in her hospital bed, handcuffed off stage on drugs. The opposite of free. So incredibly sad. Such a disgrace. I'm Jake Brennan and this is Disgraceland. Disgraceland was created by yours truly and is produced in partnership with Double Elvis. Credits for this episode can be found on the show notes [e-mail] if you're listening as a Disgraceland All Access member, thank you for supporting the show. We really appreciate it. And if not, you can become a member right now by going to Disgracelandpod.com membership members can listen to every episode of Disgraceland Ad Free. Plus you'll get one brand new exclusive episode every month, weekly unscripted bonus episodes, special audio collections, and early access to merchandise and events. Visit disgracelandpod.com membership for details, rate and review the show and follow us on Instagram, TikTok, Twitter and Facebook Disgracelandpod and on [e-mail] Disgracelandpod Rocka Rolla

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