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‘It was one of the greatest careers in show business’: Author Paul Alexander on Billie Holiday

Paul Alexander, author of eight books including acclaimed biographies of Sylvia Plath and J.D. Salinger, has just published a new book about the life (and death) of Billie Holiday. It’s called Bitter Crop: The Heartache and Triumph of Billie Holiday’s Last Year on Knopf and the book is about much more than her final months. The result of enormous research and numerous interviews, it may be the definitive biography of the legendary singer. With its rich and in-depth context for the last year of her life, it’s an engrossing read that I highly recommend and not just to fans of jazz or of Holiday’s music, because in essence it’s a story about her overcoming (and also failing to overcome) daunting challenges in her life. I spoke with Alexander about writing the book and about the many myths that continue to surround the iconic singer.

Listen to our conversation, above.

Interview transcript:

Lee Mergner: What led you to choose a Billie Holiday as a subject? There have been numerous books, films, and documentaries about her.

Paul Alexander: She was one of those presences with me growing up. She was always singing in the background somewhere. I've loved her work really for as long as I can remember.

As the years passed, I started reading more and more things about her life. But when I was reading them, there was just something that didn't feel right. I thought to myself, “This isn't the whole story” or “This is sort of made up.” It turns out Billie was responsible for part of that because much of, I would say about half of the book, Lady Sings the Blues, which was her autobiography, is pretty much made up.

It's fabricated with just some crazy stuff that's still in there. She still has the wrong city where she was born. There’s a paragraph in there that still claims that she wrote the music for “Strange Fruit,” which she did not and on and on. I thought, “I think there needs to be a book that can set the record straight on some of this.” Part of what I wanted to set straight was the way she had been depicted, particularly in the movies, as this loser drug addict victim, falling down high all the time. She did have a heroin problem in the ‘40s. She did go to prison for it, but except for that one episode, she was able to more or less control her heroin abuse for a good part of her life.

What she was not able to control was her alcoholism and it was really the gin that killed her. She didn't die from anything related to drugs. She died of cirrhosis of the liver, which caused her heart to stop. She had a heart attack. It's the same way that Lester Young had died three months before. It’s ironic that they both drank themselves to death.

The book’s title says it's about Billie Holiday’s last year, but actually the last year is the framework for a deeper dive into her life story. Why did you choose that approach as opposed to just a straight chronological biography?

That’s a great question. That was the very first thing I addressed when I pitched the book. I had to have an editor who would agree to go along with that framework. I wanted the present story that I'm telling of the last year of her life to be really intimate and up close so that you feel like you're in the rooms with her. You're in her dressing room, you're in the courtroom, you're in her home, the modest little apartment she was living in on the Upper West Side. I wanted that feel and to hear the conversations that she had with people. But in order to understand those things, you needed to know what had happened before in many cases.

That’s why there are lots of flashbacks through the book to put those events into biographical context. The end result I think is that by the time you get to the end of the book, you really feel like you've known her. Like you've been in her life with her. That's what I wanted the reader to come away with and I found an editor, Erroll McDonald, at Knopf who would let me do it because it's an unusual structure for a book.

Where did your research take you? Was there new material that previous writers and researchers didn't have access to?

I started the book right at the beginning of COVID lockdown so I did all of the interviews over the phone because we were all in isolation. That was a challenge. I'd never done that before. It's much more normal to go travel and interview them in person, but this was all done over the phone and so the research had to be done over the phone too.

I gathered an enormous amount of archival research on her via email. These libraries would send me these huge files of material on her. When we were coming out of lockdown, I was able to go interview a few people. One of them was a private collector in New Jersey, who let me see his fairly extensive collection of material that hasn't been made available to the public before.

There's some new material from that collection and also there was a large collection of material generated by the biographer, Linda Kuehl. I was able to access all of it from the various places where it is now located. Although I had access to all of her material. I interviewed a number of people who hadn't really talked about Billie before. I got the last interviews of several people who are advancing in age. A lot of the people who knew Billie such as Annie Ross, I got her last interview on Billie. George Wein, his last interview on Billie. There's an enormous amount of research that went into the book.

What did you learn about her that surprised you or some things that you just really didn't know until you got into it?

I think that we have this image of her based on really the two movies, but also some of the other biographical stuff that the last year of her life she was just walking around in a drug coma and then she died. That wasn't what I found at all. She was incredibly active. She was still doing gig after gig all over the country. I was able to access original stuff because of the advances in research engines that just normal people can access, like newspapers.com or newspaperarchives.com. They have vast holdings that include all these small-town newspapers, which you can readily access. It's public access and you pay for it.

I was able to go find all of the gigs that she had played during the last year. A lot of them hadn't been written about before. For example, George Wein always told everybody that her run at Storyville [in Boston] in April 1959 was her last gig. Well, it wasn't. I think George wanted it to be her last gig. I found out that Billie Holiday's last gig was a week or two later when she played a club in Lowell, Massachusetts. I found all this material on that gig so that's the chapter that opens the book, her actual last performance because it was very emblematic.

She had trouble performing the first two nights because of her physical condition, but she finally pulled it all together. By the end, she had a great run and she had an interview with a local journalist, which I used for the basis of a dialogue session in the chapter. You get a sense of just how driven she was, even at the end of all, even with all the illnesses that she was dealing with, but how she had to keep going. As Catherine Russell says in her blurb for my book, what really stood out to her was that Billie just had to sing. She couldn't stop singing. I guess if you're a singer of that caliber, that's what happens to you. You just can't stop.

Billie Holiday
Billie Holiday

One of the ongoing themes in the book, which you mentioned at the beginning here, was just how often she misrepresented her own story. Why do you think she did that?

I find it charming from the point of view as a listener or viewer. As a biographer, it's really infuriating because you're always having to go, “Well, did she really do this?” I think there were various motivations for it. Like with “Strange Fruit,” she felt so possessive of that song, she just wanted to claim it as much as she could. I think the way she sang the song really did affect the quality and the success of the song, so she felt like she was entitled to something in there. Abel Meeropool disagreed, and so finally she would stop saying that she wrote the music for the song. Instead she would say, “This is a song written especially for me,” which was also not true.

There were various reasons why she did it. Sometimes she wanted the story to be better. Sometimes she wanted the story to be different. I remember when I was doing the research, I got her prison file. Here she is, it's the mid ‘40s, and she's being admitted to the prison and they do a background interview. She made up half of it. She was describing this beautiful marriage that her parents had and this home life in Baltimore, and then they moved to Harlem because her daddy could get better work there. He was a musician. None of it was true, but that's probably the way she wanted her childhood to be, so the prison official dutifully wrote it down and wrote it up and none of it's true.

I have a friend, Miene, and she has a saying, “It's your story, make it great.”

That's it. That's why she did it. She also wanted to sell that book [Lady Sings the Blues]. She was working with William Dufty, who was a great writer. They would take a rather mundane story and then liven it up and throw in some big names. He even admitted when he wrote the first piece about her in the New York Post when she was admitted to the hospital for what became the last time, about all these celebrities sending stuff, but none of it was true.

One thing I have to say that she didn't fabricate, which you document, is the FBI’s and the police’s targeting of her as they did to a lot of jazz musicians of the ‘40s and ‘50s. Do you think it was made worse because of her association with the song “Strange Fruit,” which became sort of a touchstone for folks.

It didn’t help. This Lee Daniels movie that's on Hulu that's been out there for three or four years makes the argument that that's why she was harassed. I think it was bigger than that. She definitely was harassed but Colonel George White and the Federal Bureau of Narcotics (FBN) said privately they were harassing her because they were bothered by the fact that she had the jewelry and the clothes and the car. She was the big lady everywhere she went. She had gotten too big so they wanted to knock her down a bit.

It was the government doing it, so it wasn't organized. But it was systematic and it was at all levels. It was the FBI, the FBN, it was the local police and from 1939 on, they were just constantly on her and she knew it. Her friends knew it. I talked to Annie Ross about this before Annie died and she said, “Yeah, it was Hoover. He was out to get her. He wanted to kill her.” She was on the scene when it was happening. So yes, it was a relentless pursuit of her.

Billie Holiday - "Strange Fruit" Live 1959 [Reelin' In The Years Archives]

Part of the reason was because she was singing “Strange Fruit,” but part of it was also that Cafe Society was very much associated with the Communist Party early on. It was the first integrated nightclub in America, which offended a lot of the racists in the FDN. There was a whole variety of reasons why they were pursuing her. Her problem was when she developed the drug habit in the ‘40s, it made her an easy target because they had something they could bust her for.

The interesting thing is when I interviewed Sonny Rollins extensively for this book, he said he was pursued, Dexter Gordon was pursued, all of them. The interesting thing is that they were all arrested for drug possession. No one was ever arrested for trafficking drugs or selling drugs. It was just that they had drugs. That's why they were all arrested. It was a victimless crime and they all ended up in prison.

Another theme that runs through the book is her love of children. That's another thing that a lot of people really didn't know about because it just didn't mesh with the public persona, but she was godmother to I don't know how many friends’ kids.


She often spoke about wanting to be a mother. Do you think that void contributed to her substance abuse?

It didn't help. Also that the men that she chose to become involved with were abusive. Not the women that she chose to be involved with who were actually very supportive and nourishing of her life and career. The men that were just so abusive and it created this void in her life, this loneliness that she was always fighting. She hated to be alone. There are some people who have issues with loneliness and some people who don't. She was one of those people who just found it difficult to be by herself.

I think she wanted a child in her life. She tried to adopt at different times, but because she had a criminal record, she was not a candidate for adoption. She and Tallulah Bankhead were very close, and that was one of the things I think they had in common, because Tallulah wanted to have children too, but she never did. It's the saddest thing that happened to Billie, that she was never able to have the child she always wanted. So any friend who asked if she would be the godmother, she always said yes. Duffy’s son, Bevan Dufty, she's his godmother. Leonard Feather’s daughter, Lorraine Feather. Mal Waldron’s daughter Mala.

Characteristics that come through the narrative are her toughness, her courage, her resilience. She was unabashed about her sexuality. She fought for what she was due financially. Did you find yourself impressed by that?

Oh, absolutely. That's part of the myth, that she was terrible with money and she died penniless with 26 cents or whatever in her bank account. I was impressed at how she was able to forge a career for herself with no training, no background. She dropped out of school in the fifth grade, yet she was able to forge this career.

Let's face it. It was one of the greatest careers in show business. Who accomplished more than she did in that 20 year or so period of time with 300 songs plus, and the numerous record albums, constantly touring, playing some of the best venues in the country? She was a good songwriter too. She wrote 15 songs, and five of them are classics. That's really what impressed me. Her problem was she kept getting involved with these men who stole all her money, which happens to women in show business.

People look back at female jazz singers like Sarah Vaughan, Carmen McRae and Betty Carter, and talk about how there was an edge to them at different times. But of course they had to be tough.

Right, because the men were always trying to steal all their money. On the flip side, Billie was smart when she got involved with women. She got involved with wealthy women who were not into stealing her money.

Author Paul Alexander
Michael Lionstar
Author Paul Alexander

If you could ask her one question, if she were around today and you could say, “Billie, I just don't know about this,” what might it be?

If I got to have an interview with her, it would go on for a while, but I think the one thing, because I was drawn to her originally because of the music that is why jazz? I would want to know that because she was a young girl who early on, when she was a young teenager in Baltimore, worked at two different bordellos and that's where she first heard jazz played on the victrolas.

There was something about Louis Armstrong that spoke to her. I'd like to talk to her about that. What was it that she heard that Louis Armstrong, caused her as a young kid, uneducated in music, to be moved? She never studied music. All this was natural. She didn't know how to read music. She didn't know how to write music, but there was something about hearing Louis Armstrong that spoke to her. What was that because she then took that and that's where she developed her style of singing, which has fundamentally changed the American Songbook, I believe, in terms of her performance style. The way she spoke the songs, instead of singing the songs with a la-di-dah.

She didn't belt. She didn't riff. She had a very narrow range, but she used her skill that she was inspired from Louis Armstrong to create the singing style that Frank Sinatra was affected by. Everybody who came after her in some way has been affected by it because it was that colloquial vernacular singing that she used. If you think about it, that's what rock and roll is, that's what folk music is…an everyday language attempt at connecting with a singer. That's all Billie Holiday. How did she know that she was going to do that when she was this kid working at the bordellos in Baltimore?

What came out in your book was just how large she loomed for Frank Sinatra—that he was really enamored of her talents.

This is when he was breaking away from the big bands, which was a particular style of singing when you're fronting a big band. He wanted to go out on his own and be a solo artist. To do that, he had to create a different persona for himself, but he also had to create a different singing style. He would go, when she was playing 52nd Street, and he would sit in the front row and watch her night after night and study her night after night.

She always downplayed it. She said, “Oh, I just taught Frankie how to bend the note at the end.” That's not what she did at all. She taught him phrasing and of course, now we listen to Frank Sinatra for the phrasing. That all came from Billie. He showed up at her hospital room at the end of her life to thank her for what she had done for him. Now I don't think he knew she was going to die, but I think he thought if there was a chance, he wanted to acknowledge it because he was deeply, deeply affected by her death.

This conversation has been edited for brevity and clarity.

Billie Holiday - All of Me (Official Audio)

Read an excerpt from Bitter Crop: The Heartache and Triumph of Billie Holiday’s Last Year here.

For over 27 years, Lee Mergner served as an editor and publisher of JazzTimes until his resignation in January 2018. Thereafter, Mergner continued to regularly contribute features, profiles and interviews to the publication as a contributing editor for the next 4+ years. JazzTimes, which has won numerous ASCAP-Deems Taylor awards for music journalism, was founded in 1970 and was described by the All Music Guide, as “arguably the finest jazz magazine in the world.”