Interview with Paul Alexander, author of Bitter Crop: The Heartache and Triumph of Billie Holiday’s Last Year

photo by Sandra Cisneros

Paul Alexander, author of Bitter Crop: The Heartache and Triumph of Billie Holiday’s Last Year [Vintage]

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Dear Readers:

…..As we know, Billie Holiday was an undisputed giant of popular music. Her influence on fellow musicians – and on listeners – is legendary. Her philosophy about singing and performing was pretty simple: “If you find a tune and it’s got something to do with you, you don’t have to evolve anything. You just feel it and when you sing it, other people can feel something, too.” This innate ability to connect her innermost emotions with listeners was the centerpiece of her artistic genius. She wore her heart on her sleeve, and the intensity of the blues she sang was easily relatable to her audience.

…..In Bitter Crop: The Heartache and Triumph of Billie Holiday’s Last Year, the author Paul Alexander – whose previous subjects include the similarly inimitable Sylvia Plath and J.D. Salinger – chronicles the important events in Lady Day’s tragically short life with empathy and in great detail, helping readers comprehend the emotional complexity of her life.

…..In addition to his heavily researched presentation of the events during the year prior to her death in July, 1959, Alexander provides a vividly written and detailed account of key periods in her life: her involvement with the Abel Meeropol song “Strange Fruit,” the emotionally searing song about lynching that helped make her famous, and which provoked the US government into an unending endeavor to harass her; her loving relationships with women (including Tallulah Bankhead), and her consistently disastrous choices in men; her ongoing challenge with drug and alcohol addiction; and her final recording session that culminated in Lady in Satin, an album that divides critics and her fans to this day.

…..In this March 24, 2026 interview, Alexander talks with me about the courage and resilience of Lady Day, and his outstanding book – an inspirational and revealing portrait of an iconic American, that, like his subject, exudes compassion and creative soul.

Joe Maita

Editor/Publisher

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photo via Smithsonian

Billie Holiday, 1943

“Billie’s contribution will always be near, for many singers carry her style on today…Lady’s voice, while very sophisticated, was coarse, soft, yet earthy. Her style and deliver were unique, all her own. The contribution she made in the American art form, jazz, was infinite and immeasurable and meant many things to many people…Generous to a fault, Billie was misused by people, many people. Loving well but not wisely, that is the story of Billie Holiday’s life. Although regal, but not ‘pale,’ Lady to me was a queen.”

-Saxophonist Dexter Gordon

Listen to a 1939 recording of Billie Holiday singing Abel Meeropol’s composition “Strange Fruit” at Cafe Society, New York

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JJM Thanks for joining, Paul.

PA My pleasure.

JJM What was your own introduction to Billie Holiday?

PA She has always been a musical interest of mine. I have an eclectic taste in music and like various forms, and one of them, of course, is jazz. Growing up in the South, as I did in Alabama, jazz and blues were always around, and as I age, I’ve found myself going back to her music more frequently. When I was given the opportunity to write this book about her, I did a deeper dive into her, but I have been a longtime fan and admirer of her work. So, I can’t pinpoint when I first heard her, but she always seems to have been in my life.

JJM What was your goal with this book?

PA Because I’d been a longtime admirer of her, I thought about doing a theater project on her for quite some time, which I ended up not doing. But in doing just very informal research I realized that all of the biographies published about her in the past had many inaccuracies in them – basic things like stories that weren’t true and dates that weren’t correct. Biographers couldn’t even agree on how many marriages she had. So, I began digging into that. And when I looked at her 1956 autobiography Lady Sings the Blues, the problem was obvious because about half of that book was completely made up. Many of the stories are fictitious, even down to her writing that she was born in Baltimore – which is not true, she was born in Philadelphia. She really didn’t care a lot about the truth as she was writing the book because she felt she’d sell more books by telling a fascinating story rather than the truth. That seems to have worked since the book has never been out of print since its first publication.

Subsequent biographers would come along and read her work and believe it since it is her own story, as told to William Dufty. So, part of what I did in the book was unpack a lot of that. I went through the autobiography carefully and determined which stories were real and which were not, and then corrected some of those in my book. But more importantly, I tried to give an account of her. Even though a focus of my book is on the final year of her life, her whole life is covered in the book, and I tried to make sure that everything I wrote about it was factually accurate.

JJM Given all the misinformation about her life, who/what were some of your reliable sources for your book?

PA I tried to interview as many people who knew Billie as I could, but since she died in 1959, that was a challenge because the people still alive were in their late 80s and early 90s. But I got the last interview with her dear friend, the singer Annie Ross, before she passed away, and it was the most revealing interview Annie had ever given. She had talked a lot about Billie over the years, but she was just so forthcoming and revealing and told me things that she hadn’t told anyone else before. I was thrilled to do two extensive interviews with Sonny Rollins because he had worked with Billie and was friends with her, so his input was really important. I talked with about 15 others who fell into that category of being friends of Billie’s – mostly older people who were close to her.

I then sought out people from the next generation. While Charles Mingus isn’t with us, his son Eric is, so I interviewed him. The disc jockey Art Ford has died, but I interviewed his son about his father and his friendship with Billie. So, the people I interviewed from that generation shared what their parents had passed on to them about Billie. One of the best examples was what I learned from the singer Mala Waldron, the daughter of Billie’s last pianist Mal Waldron. Mala had never really talked about her father before, but I was able to convince her to do so, and she shared memories and stories of her father telling her about Billie, most importantly about how they wrote a song together. From just that one interview I was able to understand what Billie’s song writing process was. So, if I could get the original source to talk about Billie, I did. If I couldn’t, I would reach into the next generation, the result is that I directly interviewed about 100 people for the book.

I also did all the library research that was possible, especially the major collections of her at Rutgers University in Newark – the gold standard for jazz research in this country – and at Emory University in Atlanta and Johns Hopkins University in Baltimore. So, the combination of the library research and the personal interviews made up the body of information allowing me to go really deep into the events of her last year. People have told me that when they read my book it feels like they’re often in the room with her, and that’s possible because of the level of research I did.

JJM It reads like a novel…

PA I wanted it to read like a nonfiction novel, and to feel like readers were in the room with her.

JJM The recording and subsequent live performances of “Strange Fruit” had the most profound effect on her life – more so than any other song she performed. How did she come upon this song?

PA Until the late 1930s, while she played elsewhere, she had played mostly in the clubs of Harlem. At the time she was known in the local jazz community as a lovely young woman with a beautiful singing voice and who was an upcoming talent, which is how the producer John Hammond – who put her career on the map – saw her. Then, in 1938 and at Hammond’s urging, she sang at the opening of a new club in the West Village called Cafe Society. People forget that the clubs in New York during the 20s and 30s were all segregated. Even the Cotton Club, the most famous Black venue in New York at the time, was segregated. While the entertainers were almost all Black, the audience on the first auditorium level was all white, and the Black audience was relegated to either the back of the first floor or into the balconies. Barney Josephson, who was a shoe salesman at the time, would go up to the Cotton Club and couldn’t believe that this world-famous club in the mecca of the Black community in America was segregated. So, he opened Cafe Society, and Hammond suggested that Billie Holiday open for him as the club’s first headliner.

Café Society was the first integrated club in America, so the entertainment on the stage was integrated and the audience was also integrated. Because of that, performing there put Billie on the map locally, and in the press. There was a lot of press coverage of this club – the New York City police department would often stake the place out, and she was surveilled all the time because an integrated club was so controversial at the time. So, that became part of the publicity.

Abel Meeropol, a songwriter and member of the Communist Party, had written this song called “Strange Fruit,” which his wife had been singing at local Party events. He wanted this song to reach a larger audience, so he took the song to Barney Josephson at Café Society, who then shared it with Billie. She was immediately taken by it. There are several stories out there about how she didn’t understand it at first, which is ridiculous. She may have asked Meeropol to explain the word “pastoral,” but she certainly understood the song. In fact, her musical soulmate Lester Young had almost been lynched himself, so she knew all about lynching. And she of course knew about racism, having been subjected to it all her life, and while touring with Artie Shaw in the South where she wasn’t allowed to stay in the same hotels or eat in the same restaurants as the white band members.

So, she immediately took to this song and started singing it during her act at Cafe Society. She would perform three sets a night, and ended each with “Strange Fruit.” She had to end with that song because singing it was such an emotional experience that she couldn’t perform another one after it, and that became her approach over her entire career. There were periods of time when she didn’t sing it, and she didn’t sing it very much in the last year of her life since it took such an emotional toll on her, but she sang it from 1939 until she died in 1959. The last song she ever sang on television, on a British show recorded in February of 1959, was “Strange Fruit,” which means the last words she ever sang on TV were “bitter crop,” which is where the title of my book comes from.

JJM She made claims to have collaborated on the composition of the song…

PA Well, several men at the time claimed that they had helped Billie write this song, so I guess it’s fitting that Billie claimed she helped write it as well. Of course she didn’t – Abel Meeropol wrote the words and the music. but in two or three paragraphs of Lady Sings the Blues, she implied that she collaborated with him, that she brought in her arranger, and that it took two or three weeks to write the song together. This is the kind of factually incorrect information I was talking about earlier that surrounds Billie Holiday. She eventually agreed to stop saying she helped write the song after Meeropol wrote a letter to the New York Times. After that, she would tell audiences that the song was written especially for her, which was also not true.

JJM What was the political establishment’s reaction to the song?

PA Oh, they hated it. They were scared of it. Her record label at the time, Columbia Records, wouldn’t record it. She was able to get a four-song release from her contract, allowing her to do a standard recording session for Commodore Records. It started getting publicity while she was singing it at Café Society, but nobody would broadcast it on the radio until after six months, when stations eventually relented and started airing it.

Edgar Hoover was terrified of the song, and he was concerned that it was such a radical song that it would cause social unrest within the Black population, which actually ended up being true. Ahmet Ertegun, the producer and co-founder of Atlantic Records, said that “Strange Fruit” was the first shot in the fight for civil rights. and, in a way, it was – Billie began singing the song in 1939, 15 years before the civil rights movement kicked into high gear.

JJM Barney Josephson and his brother Leon had links to the Communist Party, which made them and the Café Society targets of government surveillance and investigation. Did Billie know about the club’s connection to the Communist Party?

PA Yes, she absolutely had to have known since it was in the newspapers. They were all communist sympathizers, and many in the audience were communists. When I look back at the way Billie was depicted, something that really makes me angry is that they wanted her to be seen as someone who was dim-witted and didn’t know what was going on around her. There were even stories that she couldn’t read, which was so demeaning for an African-American woman at that time to be described in that way. I read many of her letters, and she had a beautiful writing style. She wrote 16 or so songs, five of which have become blues and jazz classics. She was smart enough to conquer the entertainment business in the Jim Crow era, and you don’t do that if you don’t know what you’re doing. So, the idea that Billie couldn’t write or didn’t comprehend is just insulting. But these accounts existed because they set out to demean her as a person, and much of it came from J. Edgar Hoover and his offshoot that he created, the Federal Bureau of Narcotics (FBN), which was run by Harry Anslinger. Those were the two main organizations that smeared her.

JJM FBI surveillance haunted Billie throughout her professional career and personal life…

PA Yes, and it began when Café Society opened. Since it was an integrated club, it was considered inflammatory at the time, and since she performed there, by 1939 she was being followed wherever she was going, and whatever she was doing. It wasn’t systematic, but it was consistent.

And then, in the early 40s, she literally handed them the weapon with which to hit her, and that was when she became addicted to heroin. She had dabbled with some drugs before then, and she was certainly a drinker from the time she was 12 or 13 – she never stopped drinking her entire life, which is actually what killed her. Cirrhosis of the liver triggered a heart attack, similar to the way Lester Young died. His esophagus burst, triggering his heart attack, all caused by excessive drinking. So, when it became clear that Billie had become addicted to heroin, the FBN ramped up their surveillance of her. This culminated in her being arrested in 1947 in Philadelphia and being sent to prison for a year and one day, an important sentence because that extra day kept her from being able to get a cabaret card in New York once she got out of prison. The consequence of that sentence meant that from 1948 until her death in 1959, she was unable to perform at a venue in New York City that served alcohol, which severely limited her ability to make a living. It was also the reason why she had to travel so much because clubs in cities like Philadelphia and Boston didn’t require cabaret cards in order to perform in them.

A musical interlude…Listen to the 1958 recording of Billie Holiday singing the Hoagy Carmichael composition “I Get Along Without You Very Well,” from the album Lady in Satin (orchestra arranged and conducted by Ray Ellis) [Okeh]

JJM While your book is a full life biography, an emphasis is placed on the final year of her life, including her 1958 album Lady in Satin, perhaps the most ambitious record she ever made. What was her vision for it?

PA She started thinking about the record in 1957 and it finally came together in early 1958. By that time in her career she had recorded upwards of 300 songs while working with some of the best people in the business – from Teddy Wilson to Lester Young on down. So, while she had had this huge body of work, she had never been able to record with a full orchestra. Most of the time she recorded with a trio, so her records were cheap to produce.

She had a vision to record an album like her close friend Frank Sinatra, who had full orchestras behind him on popular concept albums like In the Wee Small Hours. So, while she wasn’t recording for Columbia at the time, she offered to come back to them, but it would have to be for doing a recording with an orchestra, and the arrangements and the conducting had to be done by Ray Ellis, who was a young man and a new name known in the recording business as an arranger. He had released one record called Ellis in Wonderland, which was a great title, but as an example of the misinformation surrounding Billie Holiday, biographers called the album “Alice in Wonderland,” which of course didn’t make any sense. But Ellis in Wonderland was beautifully orchestrated and arranged, and included background singers. Billie had heard that record and thought it was just incredible, thinking Ellis could be the next Nelson Riddle. So, she wanted to work with him. Columbia contacted him, and he couldn’t imagine Billie Holiday knew who he was, but he of course agreed to work on the album that would become Lady in Satin.

Three sessions took place in February of 1958. The album was essentially a collection of American classics that she had not recorded before, performed with a 36-piece orchestra – lots of strings and a little background choir that Billie hated, but it’s it on the record nonetheless. Ellis was just stunned on the first session, because he hadn’t heard her sing recently – he knew all of her old work but her voice had changed dramatically over the years, mostly due to her alcohol use. She was also a chain smoker, which did a lot of damage to her voice, and her drug abuse from the past didn’t help either. The result was her raggedy sounding voice was recorded against this beautiful, melodic orchestra music that Ellis had worked so hard to create gorgeous charts for. So, when he listened to the playback on the first session, he got so upset that he ran to the bathroom and threw up. He felt this would be the end of the career, that he wouldn’t be able to continue in the business after this recording. He felt that way after the next two sessions as well. The other thing is that Billie was drinking heavily while they were doing the sessions, so she would peter out after about four hours, whether they were finished or not. So, for a long time, Ellis was very apprehensive about the record.

When it came out, Lady in Satin was very controversial. Many people felt that this was Billie’s worst album, and that Columbia should never have even done this project. But there was an equally large group who felt it was her masterpiece. Great art triggers those kinds of responses. And over the years, Ellis finally did come around to realizing that they had created a masterpiece together. I fall into the category that it’s a masterpiece, one of the monuments of her career. It’s just a beautifully rendered record in terms of the music, and the melodic qualities highlight the pain and suffering that’s present in her life at the time. Those two opposite forces resonate.

JJM You said she made this recording because she wanted to record an album similar to something Sinatra would do…

PA Yes, she did it because of Sinatra, who she was clearly imitating on the album. He had basically learned how to be a solo artist from Billie. She taught him phrasing – which he would admit to – and basically gave him this whole act. So, she wanted to do a “Frank” record, and when he visited her on her deathbed, he told her how much he loved Lady in Satin.

JJM Reading your book is also a reminder about the complex and awful relationships she had with men, many of whom were drawn to her by her talent, money and celebrity, but who were mostly unable to live in her shadow. So, she had a deeply disappointing love life and was lonely for much of it. But the other reminder – and to some readers likely a revelation – is that she had very significant romantic relationships with women. One of them was with the wealthy American heiress Louise Crane – which was uncomfortable for people like John Hammond, who didn’t want news of their relationship to go public and thus worked to derail it. The other one was with Tallulah Bankhead, who Billie started a romantic relationship with in 1948, while she was simultaneously dating an abusive boyfriend and manager John Levy. What connected Tallulah and Billie?

PA That was a fascinating relationship, and I think it was the most successful relationship of all that Billie had during her lifetime. They connected on so many different levels. Tallulah was born in Alabama and had been raised by a very wealthy family. Her father was in Congress – even becoming Speaker of the House in the mid-to-late 1930’s – and her uncle was a senator from Alabama during that same time. So, she considered herself a daughter of the South. And, although she was born in Philadelphia, Billie was raised in Baltimore and considered herself a southerner in many ways.

They had both, in a way, been the “other” for a while. Billie felt like an outsider, and Tallulah had such an odd life. She was a very big name in the theater, and she really wanted to be a movie star, which never really happened for her, so they both experienced disappointment concerning dreams they had for themselves. They also both wanted children, which never happened for either of them, and they both loved animals in general, but particularly dogs. So, they had all these connections.

Tallulah used to do the rounds up in Harlem, where she was picking up drugs and girls back in the late 20s and into the early 30s, which is when Billie was coming up, also in Harlem. I’m sure their paths crossed multiple times during those days, but they really didn’t connect up until they had both become name performers. In 1948, when Billie got out of prison, it was just one of those things. They had known who each other were for a while by then and ultimately connected up in a very powerful relationship that went on from the late 40s into the early 50s, when it finally ended.

JJM Why did it end?

PA Mostly because there was an incident involving Tallulah Bankhead where her maid was stealing money. Tallulah was afraid that during a trial the maid would spill the beans and talk about her drug use and her relationship with Billie. So, Tallulah, very cruelly and dramatically cut it off, which had a profound effect on Billie. She was very upset over it. When she wrote her autobiography in 1956, she wrote about Tallulah, but she made Billie take almost all of the stuff about her out of the book. They never really reconnected until she died in 1959. Tallulah’s behavior at the viewing of Billie’s body was incredibly powerful – she basically talked to Billie while she was in her coffin. Bystanders were quite aghast at her behavior. She didn’t attend the funeral but she sent 12 dozen roses to it. So, to me, it feels as if it was a relationship that ended because of the circumstances of the day. You could imagine the scandal caused by an interracial lesbian relationship between Tallulah Bankhead and Billie Holiday during the era of Jim Crow. The times were just so much different then and people were afraid of those kinds of issues. So, that’s basically what happened there. It was a wonderful relationship for Billie while it lasted, and she was able to get away from that awful John Levy.

JJM She was very busy in the year prior to her death. She traveled overseas and had work that didn’t pan out for her. She considered relocating to Europe, but she chose to return to America. And when she returned, she had another encounter with the Feds, this time with customs and immigration, who charged her with being a convicted drug addict who failed to inform the government about her comings and goings out of the country. On top of that, doctors were trying to get her to stop singing, and people like her agent/manager Joe Glaser and Leonard Feather were trying to persuade her to get to a hospital. So, many issues to contend with. Did she have an understanding about how sick she was?

PA I don’t think so. I believe that she was in denial about how ill she was, and denial can be a powerful thing. She had a good friend who was a doctor who hadn’t seen her in a while, and when he came to visit her in San Francisco, he was horrified at what she looked like – she was so clearly suffering from diseases related to alcoholism. Efforts were made by friends, including her doctor and by Glaser, to get her to take some sort of demonstrative step to address her illness, but she just refused to do it.

She tried a couple of times to get off of alcohol. There’s a story in the book where while during a visit she paid to Leonard Feather at his apartment he offered her a drink, which she refused because the doctor had her drinking only tea. Well, that didn’t last very long. When you drink alcohol virtually daily from the age of 12 or 13 up until age 44, when she died – particularly when you drink as much alcohol as she drank – it has a devastating effect on your body. She should have gotten the message when Lester Young died three months before she did, because, as I said earlier, he died of the exact same thing. She knew what alcohol had done to Lester, but she never stopped. So, I would have to say that she never realized how serious her medical condition was until it was too late, until it had taken over her. She ended up collapsing in her home and was taken to the hospital, and she never returned. She spent the last weeks of her life in the hospital.

JJM Where, true to form, she was set up by the feds…

PA Of course. Once they got her in the hospital, she very famously told a friend that they (the Feds) are going to get her while she was there. And they did. About two or three weeks into her stay, they suddenly found heroin in the Kleenex box on her nightstand. How heroin would have gotten in the hospital is hard to understand, but that was the story. Clearly, a nurse named Figueroa had planted the heroin in the Kleenex box on the nightstand next to her bed, and after “discovering” it, ran out to get someone on the hospital staff to have a witness when she confronted Billie about it. She was arrested on what turned out to be her deathbed; she was photographed and fingerprinted, but she was not chained to her bed as had been reported in some places. However, she wasn’t able to get out of her bed because she had an oxygen tank and other contraptions like intravenous feeding tubes connected to her in order to keep her alive. In the ensuing time, the authorities tried to get her to appear before a grand jury, but her lawyer wrote to the judges and said she can’t even walk, how can she possibly appear before a grand jury? So, they ultimately dropped that attempt. But she had police guards outside her door for a week or ten days, so none of her friends could get into the room to visit her. Her horrible husband, Louis McKay – who she’d been separated from a year before she died – came back from California, where he had moved. So, he was there. If there was a chance that she was going to be able to recover from her illness and get back on her feet, the arrest and all of the subsequent abuse to which she was subjected took away her spirit and life force needed to continue living. I believe that arrest is what ended up killing her.

JJM The last song that she wrote was “Left Alone”…

PA Yes, she co-wrote that with Mal Waldron.

JJM It’s an incredibly sad, moving piece. Did she view herself as a victim?

PA That’s the way she was projected in much of the literature about her, but I don’t believe she viewed herself as a victim, and people I talked to and who knew her said didn’t believe she saw herself that way either. She saw herself as a very successful and acclaimed jazz artist, which of course she was. Here was this poor little girl from Baltimore who, by the end of her life, was one of the most important jazz musicians in the world. Now, was she victimized by the federal government? Of course she was. For 20 years she was surveilled and attacked by it, resulting in four different arrests. While the local police made the arrests, they all knew it was part of a larger scheme.

So, I don’t believe she viewed herself as a victim, I believe she saw herself as a survivor who had been able to survive things like the racism of Jim Crow, and these many awful men abusing her and stealing her money. She had that spirit where you just get on with it, that you don’t worry about what’s happened in the past, or what they are trying to do to you now. For her, it was all about where the next gig was, and who do I perform with? And that’s the way she lived – even when she was so sick. She just carried on.

Mel Levine, CC BY 2.0 , via Wikimedia Commons

Billie Holiday, 1955

“She had the most unique voice and style I’d ever heard. What she felt when she sang, she felt with all she was.”

-Louis Armstrong

Click here to watch Billie Holiday singing “Strange Fruit,” which was the final television appearance of her life.

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Bitter Crop: The Heartache and Triumph of Billie Holiday’s Last Year [Vintage]

by Paul Alexander

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About Paul Alexander

Paul Alexander has published eight books, among them Rough Magic, a biography of Sylvia Plath, and Salinger, a biography of J. D. Salinger that was the basis of a documentary that appeared on American Masters on PBS, Netflix, and HBO. His nonfiction has appeared in numerous publications, including The New York Times, Los Angeles Times, The Boston Globe, Newsday, New York, The Guardian, The Nation, The Washington Post, and Rolling Stone. He teaches at Hunter College in New York.

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