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Billie Holiday book outline

Outline for A Kiss Always Tasted: Living with the Art of Billie Holiday

Billie now

For a long time, I've known I was going to write this book. It's something I had in my sights for several years now, growing more prominent in its urgency—the need for this book to exist—with where the world is at. What we see in the social media and social justice age, where we're apt to encounter faux-activism every bit as much as real activism, with all manner of agendas and motives. This is the fake news era, when people will often say what they want to say for that reason alone, not because it's true, or they've been invested in the subject they claim to know about, and which they may be banking on for attention, a platform, what we call "clout."

I've honed these ideas in the many prominent pieces on Billie Holiday I've written in major magazines, newspapers, and op-ed sections. But there was one moment in particular that hit me hard with the real need there is for this unique book. Said book will employ light first person from time to time, in the relaying of illuminating anecdotes. Not some heavy, "I came to the gospel of Billie Holiday as a conflicted teen in high school," but a light, guiding first person on occasion. This is one example.

I was at the popular coffee shop down the street from me, where I am most days. Some days you get the good music—Louis Armstrong, Duke Ellington, Nat King Cole—other days you get heavily processed, machine-produced pop, and on other occasions it's Christopher Cross and Air Supply. I had ordered my drink and was waiting for it to be made, when Billie Holiday's 1939 song, "Strange Fruit," came on the sound system. As you'll see, there's going to be a section of this book all about that towering work of art, and I'm using it here to get into our subject, what we can also call our need: the important challenge to know what Billie Holiday, was about, and why that knowledge is so vital now, and what it adds to lives.

But some info will be provided about this number early on here, for context, before we dig deep down later. "Strange Fruit" is what I'd call one of the two most important songs ever produced in the United States, the other being Sam Cooke's "A Change Is Gonna Come," a song I wrote about at length in my 33 1/3 book on his Live at the Harlem Square Club, 1963 album, in which we can see the future anthem of the Civil Rights Movement begin to coalesce on a stage in Miami in January 1963.

The Holiday number unfurls like a dirge, but one that has been sent from a world beyond ours to impart necessary meaning, clarity, truth. The crop of the title isn’t of apples and oranges, but rather dead, Black bodies hanging from the trees. The song is shocking. It has never failed to shock me in the decades I've been listening to it. It is a sonic blow to body and soul. Performing the number made Holiday physically ill. She'd race to the bathroom after to vomit.

This is not what one expects to encounter at the Starbucks when "Sailing" had been playing the day before. Clearly whomever programmed the music had no clue about this song. It was winter, and the cafe was full. There were people in every chair. Some were working, some were reading, some were just sitting there, and many were staring at their phones. I was standing, as I said, waiting for my drink, looking around, wondering how on earth this song was playing, and not a single person seemed to notice or have any idea. I could have wept. They were oblivious. Everyone was.

I thought about these people and how Billie Holiday is regarded now, how she's used. And that's where we start: with Billie Holiday today. Because I see many people namecheck her. I see all of these Billie Holiday posters in bedrooms and dorm rooms on social media. A publisher once said to me, "Oh, she'd be really good to do that whole Black Lives Matter" thing. And no one has a clue about this artist who is as vital, and has as much to give, as she ever has.

We also have to look at how Billie Holiday has been discussed over the decades, and why. How did we com to this spot with her? She's sentimentalized, and if one knows her work—and her personality—there was never less of a sentimentalist. But people have applied that same romantic brush to Holiday that they do to Vincent Van Gogh and Edgar Allan Poe, and, to lesser but real degrees, F. Scott Fitzgerald, Jackson Pollock, James Dean, John Keats. Those artists of emotion who died young, and become more of a stand-in, a symbol, than flesh-and-blood creators of deathless, flesh-and-blood art.


This is a book that is going to be conversational, but learned. It's talking to you, with you, and sometimes will all but sit back and listen as the reader, in effect, talks with themselves. Develops their own thoughts. As such, it won't be a strict chronology. No one wants a text book. We want a book that is alive and vital, spirited and knowledgeable. A book for the ultimate Billie Holiday fan and student, but also someone who has no idea who she is, as of yet.

An editor of mine describes my writing on jazz—for he is the editor of the most prominent and respected jazz magazine—as "art about art." This book, too, will be its own work of art, but also a necessary case-maker. And a guide at the museum, so to speak, with no reader or listener left behind because of jargon, or narrow, niche-y focus. This is important stuff, and it will be talked about that way, celebrated that way, supported that way, explained that way, and, most crucially, shown to be that way.

So while we're not going chronologically, we are going to begin near the beginning, with the first recordings Holiday made for Brunswick with pianist Teddy Wilson. These are the recordings that changed popular music history. They stand out like few recordings do as recordings one remembers in terms of where they first were—and who they first were, I'd add—when they heard them. What else could I say this about? Elvis' Sun sides. Joy Division's first LP. The Sex Pistols' "Anarchy in the UK." The Beatles' "She Loves You." Ornette Coleman's Free Jazz. The Jesus and Mary Chain's "Upside Down." Charlie Parker's "Ko-Ko." So, not a lot.

Here we're going to look at larger ideas like what does it mean to sing? What did people think it meant to sing before Billie Holiday sang like this? What was she doing that was so different? She described an important early gig for her where she did her thing, and no one clapped. They didn't boo. They sat there. As she said, they didn't know if she was good or if she was bad. She added that they hadn't been told what to think yet, and what she was doing was so new, they struggled to process what their own reaction should be.

There is this persistent old saw that Holiday's music is "heavy" and dark, and everything mopey and bleak that goes along with that, which is both wrong and limiting. That music had huge swaths of range for all of the various totems that were always in place, which this book will also explore. You know them when you know her music, and she knew them, too. In fact, she explained them. The Brunswick sides musically codify joy and freshness in manners I've never heard anywhere else. They surge with the same bursting ardor for life and expression as the journals of Thoreau do.

The development of the voice

We'll look at what Billie Holiday looked at. What she wanted to be. Who she loved to listen to. This is someone who changed how a person might sing. Her voice was as much a horn as it was a voice. We'll explore her musical relationship to Louis Armstrong and Bessie Smith. Someone like Ella Fitzgerald sang with more technique than Holiday, but she's never invoked the same loyalty—that depth of passion—in the people who know her music well—and I write on her often, too—as Holiday does. Why? That's a big question, and we'll answer it. Because there are quote/unquote loads of singers with more chops than Holiday. Which isn't to say that her technique was rudimentary, or she didn't have virtuosic command. But she had something else, certainly. And it was there from the start, though it'd be further developed in time.


Holiday only lives to the age of forty-four, dying in 1959. Despite her short life, her recording career breaks down into rather convenient musical chapters, based upon the labels she was with at the time. Those labels tell us a lot of her musical story, for each label marked a distinct period, the same way that we can cite A Hard Day's Night as indicative of one mode of the Beatles, Sgt. Pepper another, the White Album a third. Here we'll explore her time at Columbia which covers most of the 1930s. For other sections of this book—for instance, the one coming up on Lester Young and Billie Holiday—there can be some overlap, and I'm going to make sure to avoid that. In other words, we'll be clever, and what we discuss at length here, won't reappear later. And if a work needs to come up in both places, it will do so differently, and be used in a biographical/background/context sense in the one, and then opened up for further exploration elsewhere, but without ever inducing a feeling for the reader that we're skipping anything. There is a lot of material to work with, so if one truly knows this music—and I do—it's not that hard.

Lady in Satin

As I said, we're not moving chronologically, but rather what I'd say logically, and narratively, creating—or revealing—relationships between different parts of Holiday's musical story in presenting this work centered around and within the fierce social and personal utility of that music. That's a big part of this section, as we talk about her controversial 1958 album, Lady in Satin, which would be the final release of her lifetime. A question I think we ask far too infrequently, especially now, when careers are made by how many followers one has on social media, awards given, book deals handed out, etc., is what is the point of art? What is art? What does it do? Why do we need it? Why is it the greatest of all gifts? I'd say—and Billie Holiday would too, I believe, as her work testifies—that the point is to help us live better. What does that mean? To live more honestly. To understand ourselves. To work on ourselves. To help others. Holiday was a giver as an artist, and also one who compelled her listeners to turn that listening into an inward process and listen to who they were, as to determine who they might better be.

The consensus with Lady in Satin is that Holiday's voice was gone at this stage. Shot. She was a physical wreck, on account of her years of drug addiction. I mentioned light first person. I had this old thesis advisor in college. He was quite old, actually. Every now and again, The Atlantic would dump him out of mothballs and he'd write a piece on white jazz musicians or some such. He was offended that I loved this album like I did. He believed it made a mockery of what it means to sing. Whereas, I have always heard a clarion call of what it means to be human, to endure, and to sing in ways as radical in their invention, as the ways in which Holiday sang back on the Brunswick sides.

My 33 1/3 book was actually going to be about this record, before the person who oversaw the series at that time changed his mind. On a Friday he committed, and then on Monday he reneged, saying, "In today's world, I'm scared to have a white male write this book, but don't tell anyone I said that." Holiday would have knocked the guy out. She hated that kind of thing. Racifying, one way or the other. She sang to connect people with themselves, so that they could better connect with other people, and the world. We will explore this approach to singing, as it's heard on Lady in Satin.

Commodore/"Strange Fruit"

Now we flow easily into the series of recordings that Holiday made in 1939 for the small, specialty label, Commodore. Why was she there? Columbia wouldn't allow her to record "Strange Fruit." During this period, she's in small band settings. There aren't that many recordings from this association, but that also allows us to get into the alternate cuts, as we try to understand Holiday's process as a singer from track to track, because she never sang a song the same way twice, and made a big deal about this—it comes up often in her writings and interviews. "Strange Fruit" will be a major area of discussion, but I want to talk about it as no one else ever has. It's a folk song, and Holiday isn't ever posited as a folk singer. It's also a blues, but a unique attempt at the blues. When she sang the song live, there were people who actually came up to her thinking it was some "sexy" number, like some ode to nudity or what have you.

We'll discuss the historical importance of the song, what she does with certain words as she sings it. Holiday spoke about words that she sang as no one else did. She talked about why that was. "Hunger" was one such word. "Love" was another. She was correct, and we can also extrapolate that idea to look at words within "Strange Fruit," among them "bitter" and "crop." Later she would "bite" her words—split them in parts when the syllables themselves didn't necessarily suggest a splitting. Her phrasing was unique, and it changed. Evolved, I'd say. Some would say devolved. I don't agree, and I think we can put that notion to rest in these pages.

We see aspects of the biting on "Strange Fruit," but a different type of that biting. We'll also explore a live version of "Strange Fruit" from 1945, which is the most emotionally intense in-concert recording I've ever heard. I used to think it was Janis Joplin singing "Ball and Chain" with Big Brother and the Holiday Company at Monterey in 1967, but the live "Strange Fruit"—which features Holiday's voice and a piano, nothing else—is a recording that a person needs to hear. It'll change your life. She introduces it, and you can tell she's nervous, but adds that the piece was written especially for her. It's not a boast, or it doesn't register that way. Her voice is an element, a force of nature unto itself in this performance. Were I to meet a pack of aliens who said to me, "What can we listen to to get an idea about you humans are all about?" I'd give them this 1945 live performance of "Strange Fruit." And so we will give it to our readers.

Lady Sings the Blues

Full stop: Billie Holiday's 1956 autobiography, Lady Sings the Blues, written with William Duffy, isn't just one of the best music books I've ever read, it's a work of literature. It's also not discussed enough, understood enough, and too much is made of some of its false claims and poetic license. Never has a book more efficaciously captured the voice and essence of its musical subject. Berlioz's memoirs don't do the job that this book does. I have no issue claiming it as one of the most humanly revealing things I've ever read. I reread it a lot—once every couple years.

During this section, will also get into the Diana Ross film from 1972 of the same name, and various Holiday documentaries that contribute to their varying degrees to the myths and misconceptions about her, and also some of the truths that we'd be wise to embrace. This book, though, will be the focus here. To read it is to have a life experience. It transposes her music into prose form. We'll spend a decent amount of time on race, too, and how Holiday experienced her life as a Black woman, and what that says about then and also now. You can get better at writing from reading this book. Get better at singing—for we all sing in some way, even if we just speak. Get better at living. At knowing what is real and what is, what matters and what doesn't.


From Commodore Holiday went to Decca, because the same man, producer Milt Gabler, was overseeing what she did at each stop. Here we can find her swathed in strings (and sometimes even with backing singers!). Do strings really work for Holiday? It's not her natural environment, and she becomes a different artist in the different setting. She makes her only recordings with Louis Armstrong, and we need to consider how their pairing works, given everything they had in common, despite paradoxically unique styles, if not their approaches and aims. Her voice was changing during this period, deepening, acquiring a huskier element. She's not as "light" as she was with Columbia, but she's learning to use that to her advantage.

Prez and Lady Day

Jazz is an intensely dyadic and dialogic medium. What I mean by that is despite the presence of groups large and small, duos have a special potency in jazz. Or they can. Look at the chief pairings: Miles and Trane, Duke Ellington and Jimmy Blanton, Charlie Parker and Dizzy Gillespie, Eric Dolphy and Booker Little, Max Roach and Clifford Brown. There is none, I'd suggest, at quite the level of Billie Holiday and tenor saxophonist Lester Young. He dubbed her Lady Day, and to her, he was Prez.

I look at them this way: he's the singer version of him with his horn, and he's the horn version of Holiday the singer. The latter had an ability that I've only ever seen in Miles Davis—I'm thinking about his recordings with his Second Great Quintet—to influence those around her in what hey played, quite apart from what she was singing. A musical leadership quality, where her essence rubbed off on others. We'll explore this more in the final part of the book, but my goodness did these two grow individually through their association. It's a kind of joint fructifying. We'll talk about the key examples, what they were to each other in "real" life, and spend time with their astounding segment on the 1957 TV special, The Sound of Jazz.

Young was ill and not long for this world—not that Holiday was either. There was doubt after rehearsals if he'd be present for the telecast. No one was expecting much, and it was surprising enough when he turned up, saying he could. This is jazz's finest moment on TV, ever, period. And a big reason is what ensues between these two. She sings "Fine and Mellow," and Young takes an early solo. After he begins, the camera pans to Holiday's face, and for whatever reason—sagacity; dumb luck; we don't know—it stays there as Young plays, so that we see all of her reactions, the internal made visible. Again, we are dealing with the question of what is art for? What does it do for us? Why is it made? Why must be come to it on its terms? Why is it so important not to just use art and artists for our Twitter beefs, our dorm posters, the copy of the book or LP we leave out on the coffee table to impress company? If ever there was a visual for what art means, can do, when we allow it into our lives, and allow our lives into it, it's this.

An evening out with Billie Holiday

What would you have experienced—and what can you experience now on record—if you went out for an evening to see Billie Holiday in concert? We will go through her various live iterations, and talk about this side of her artistry, from the earliest days until the very end right here where I live, in Boston, where her final live recordings were made. She had all manner of problems, given her legal situation due to drug issues, and then also bad management and unfair blame, so that there were stretches when she could sing at the posh joints—a Carnegie Hall—but not at a random bar or club. Live Holiday is different from studio-based Holiday. It can be hard to know where to start with all of the tapes out there. Who was at her shows? What were her own experiences like? How did people react to her? What occurred racially? What were her approaches? Verve

Holiday was at Verve for the 1950s, and this will be our big wrap-up that covers her work with the label, her association with the invaluable producer Norman Granz, and which leaves us listening to Holiday right back here in our current world, better suited for her, and up to speed. There is a lot of material here, but a special focus—a kind of grand synthesis--will be the sessions she cut for Granz in early 1957. They are—underline this—the best anything she ever did, and it's when people usually think--because they go along with lazy histories—that she was all done. Granz said, in essence, "Enough strings! Lady Day belongs with small bands!" She exerts that leadership influence that we would have commented on earlier. These are extended sessions, when it's cut after cut, and brilliant performance after brilliant performance. She's not the singer of the Brunswick/Teddy Wilson sides, but she's...more. As an artist, and a human artist. And an artist for humans. An artist whose art one can live to, and live in.

This is the point of who Billie Holiday was, and what her music remains, and why it offers so much to us right now.


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