An interview with James Kaplan – on his new book about Miles Davis, John Coltrane and Bill Evans

Veteran writer James Kaplan, author of acclaimed biographies of Frank Sinatra and other figures, has just written a book, 3 Shades of Blue: Miles Davis, John Coltrane, Bill Evans and the Lost Empire of Cool, that ties together the stories of those three jazz greats, culminating with the recording of the iconic album Kind of Blue but also with a coda on the different directions that each musician took in the years thereafter.

The book provides detailed back stories of each, as well as material on other major figures in the music at that time, including Sonny Rollins, Dizzy Gillespie, Charlie Parker, Thelonious Monk and Cannonball Adderley. With so much already written about those three figures and that popular album, Kaplan has remarkably created a fascinating and in-depth narrative about a formative time in jazz history.

Listen to our conversation, above.

Interview transcript:

Lee Mergner: What led you to focus on these specific three musicians to tell the story of jazz’s evolution during the fifties?

James Kaplan: I had gold in my pocket, Lee, and the gold was that back when I was a pup in 1989, I somehow managed to wangle my way into doing an interview of Miles Davis for Vanity Fair magazine. I had no business being sent by Vanity Fair magazine to interview Miles Davis on a couple of counts. I really hadn’t done much magazine writing at that point, and I knew zero about jazz.

But my good brother, the late Peter Kaplan, former editor of the New York Observer back in the day, knew this editor at Vanity Fair, told this editor that I knew everything there was to know about jazz. And somehow or other, Vanity Fair believed him and believed me and sent me to interview Miles. All I knew about Miles at that point was that he was terrifying. So with my knees shaking, I took the elevator up to the 17th floor of the Essex House where he had a suite at that point with his publicist and I trembled my way in the door and found a lot of surprises in there. One of which was a very, gentle and welcoming Miles Davis.

Zoot Sims once said about Stan Getz, “Oh, yeah, Stan, he’s a nice bunch of guys.”  And that might qualify as a descriptor for Miles who could be very tough and gruff, but then a lot of times would be very sweet and open. Particularly with his fellow musicians, he was very loving.

He was and I spoke to a number of people who worked with him, Black and white. By the way, race is a big part of my book. A white guy writing about jazz and a white guy writing about a lot of Black musicians. In particular, along with Miles and Trane, I’m also writing about Bill Evans, who stirred a lot of controversy by becoming the sole white guy in the biggest small jazz group in America in 1957.

The white guy with Miles was a thing then.

One of the many great musicians I interviewed from my book was Chick Corea, and he told me about being 17 years old, pretending he was 18, and going with a pal and getting into a club in Boston, where he was from, to go see Miles and the quintet. They had seats right down next to the stage. The musicians were up on a platform and Paul Chambers strolls in and Cannonball strolls in and Jimmy Cobb strolls in. Then there’s Coltrane and then Miles comes in and then Chick says, “This white guy with glasses sits down at the piano and…” I am not going to use Chick Corea’s precise language, but he said “I was so eff-ing disappointed.” But after a couple of minutes, he was disappointed no more.

It’s always a great narrative arc to start with figures from different places and to explain their background and how it comes together in this kind of magical situation. What was it about the Kind of Blue session that made you choose those three in particular? Because you also talk about Monk. And Cannonball Adderley. And Gil Evans.

I do. And in the many, many pages that fell on the cutting room floor, when I was editing my book, there were a lot of pages on Diz and Bird. A lot. It’s a bit like an iceberg. In this book, I concentrated on these three figures because one, because at that point in my life when I was supposed to know everything about jazz and knew zilch and went in to interview Miles, one of the three jazz albums I had was Kind of Blue. And like everybody else in the world, I loved that album and I love it still.

It’s the best-selling jazz album of all time. And arguably the best loved jazz album of all time. And what is it about this album? What is it that’s so mysterious and so indefinable about this album and the great musicians who put it together, six of them. Three of them arguably geniuses, Miles and Trane and Evans. Miles himself said, “I built this album around the piano playing of Bill Evans.”

There was so much there and 1959 was such a hinged year, such a meaningful, transitional year for jazz. So many things going on, so many great albums being made and such changes going on in jazz that it seemed Kind of Blue seemed like a great place to concentrate on and on these guys in particular.

James Kaplan
Avery Kaplan- James Kaplan

What’s interesting about Kind of Blue to me is that although the album is iconic and popular, all of them went in different directions. It wasn’t the beginning of a style. It was more like the beginning of something completely different for all of them.

That’s right. They were all bursting to go out in different directions. Coltrane and Evans and Cannonball were all bursting to go out on their own. And they did very shortly thereafter. Giant Steps was recorded one month after the second session for Kind of Blue.

Where did your research take you? Was there new material that previous writers and researchers hadn’t had access to?

I am a seat of the pants researcher. I did these two enormous volumes on Frank Sinatra. When I first started writing about Frank Sinatra, I knew…I guess maybe my trademark as a writer is being a know-nothing to start out with. And I certainly knew nothing, when I started doing this book. I certainly knew more about jazz than I knew when I first went to see Miles But just a little bit more and I feel that I just still know just a little bit more. But I began trying to talk to people and getting people to talk to me. It was less about going places and digging up archives or research that hadn’t been tapped before. My specialty and my love is connecting with people.

I had some huge luck at the beginning. One of the very first people I was greatly honored to speak with was Sonny Rollins. I can’t even tell you what a terrific interview Sonny Rollins was. He was so smart, so candid, so revelatory to me about the times that he played in, about the drugs that everybody used, about the music that people made, about him and Coltrane, and the rivalry or the lack of rivalry, and so many different things. But also about the end of Coltrane, and the very sad last days of Coltrane.

I started with in the present day with Sonny Rollins and it wasn’t downhill from there. I got so many more people to talk to and everybody I talked to really was a revelation to me.

It seemed like one of your important or influential sources was Wallace Roney, who served the purpose of kind of explaining Miles, because he was as much of a protege as there would be from someone like Miles.

Arguably the only protege that Miles ever had. Yes, Wallace Roney was a great man. He was a kind of genius, I think, himself. He was discovered at age four to have perfect pitch. His father used to amuse himself and his friends by doing blindfold tests with little Wallace. In effect, he would play a jazz record and he asked little Wally if he could identify who was playing and Little Wally having perfect pitch and an amazing ear and an amazing, amazingly analytical mind and a great emotional intelligence too, was almost always right on.

It was a huge boon and privilege and so informative and educational for me to sit at his feet and listen to him talk about Miles that he knew and loved—to listen to him talking about all this great music that I was writing about. He was such a great guy, such a brilliant guy. It’s so sad that we lost him so young. He died of COVID [in 2020].

What did you learn about these seminal figures in jazz that surprised you?

Everything was a surprise from the fact that Coltrane played with Eddie “Cleanhead” Vincent and that Coltrane was a great R&B saxophone player. He used to walk the bar. He was very embarrassed about walking the bar. And one time, I think was it Benny Golson who walked in on him while he’s walking the bar. I think he ran out of the club, he was so humiliated.

John Coltrane
John Coltrane

Bill Evans, early on, was trained as a classical pianist, but then he turned himself into the fastest boogie woogie player in New Jersey. He was just enraptured by jazz. He fell in love with jazz and that was the way he had to go.

Miles…everything about Miles from his privileged upbringing. The fact that his father had a horse farm and Miles used to ride horses when he was a kid. He dressed beautifully. He came to New York, under a pretense, at age 18. He told his father he was going to study at Juilliard. Well, he enrolled at Juilliard, but he very quickly got sick of Juilliard. What he really came to New York for was to find Bird and play with him, which he did.

Here you have Miles in 1947, cutting a record of Miles Davis’ All-Stars at age 21 with Charlie Parker playing, guess what, a tenor saxophone. How come Charlie Parker was playing tenor sax on Miles’ All-Stars album? Because Miles told him to. Miles is 21 years old and he is telling Bird to play tenor sax because it’s going to sound better next to Miles’ trumpet on the album. Anyway, the research for this book was an endless fountain of surprises like this.

One of the themes, unfortunately because of the time, was the drug use and how substance abuse really affected almost all of them and how they were targeted by the police and by the FBI. It really affected their lives and their livelihood.

Of course it affected their lives and their livelihood, and it was a very complicated thing. I was almost like a Pandora’s box opening and then came the heroin abuse among jazz musicians in the 1940s and 1950s. Prior to that, the big drug in jazz had been marijuana and of course, alcohol.

A lot of heroin came in through the ports after World War II. Charlie Parker was the biggest heroin addict in jazz. Like Pandora’s box, this myth sprang out of the myth of Charlie Parker, who was a mythical figure himself. He was so larger than life and such a genius. And he was a bad heroin addict and every jazz musician knew it. This lie started circulating that if you want to play like Bird, you got to do like Bird.

The Pied Piper of heroin. A reluctant one at that.

That’s right. He said, he used to say to young jazz musicians, “If you put it in your nose [meaning heroin], you’re still your own man.” He said, “The second you put it in your arm, you become a slave.” He knew what that was all about. Jazz lost so many great young talents through this terrible plague of heroin. We almost lost Miles who was badly addicted, but then he managed to kick with great difficulty in the mid-50s.

Coltrane was badly addicted. He managed to kick, but he had damaged his body. So between heroin and alcohol, it killed him at a very young age. Then also at a young age, Bill Evans, who as soon as he joined Miles’s band, feeling himself to be this nerdy professorial guy from New Jersey wearing glasses and white, set about making himself the biggest junkie in the band and stayed addicted to heroin and then cocaine for the rest of his short life. He died at age 51 in 1980.

Yeah, I think Gene Lees called it “The longest, slowest suicide in music history.” And race came into it too because it gave the police a way to take down these Black jazz musicians. And there was Red baiting at the time too.

There are all these factors going on. There was this terrible institution in New York called the Cabaret Card. What was the Cabaret Card? It was a kind of protection racket by the NYPD that you had to have in order to play in clubs that served alcohol, which meant the jazz clubs. You had to have this cabaret card and Monk got busted. It was actually Bud Powell’s drugs with Monk sitting in a car with Powell and his drugs. Monk lost his cabaret card, until he came to the Five Spot. The owners of the Five Spot, Sal and Iggy Termini, vouched for Monk, and he got his Cabaret Card back. Monk couldn’t play in clubs for years and years.

And let’s not forget about organized crime either. Organized crime were controlling the drugs and they were controlling these musicians and controlling the clubs. But the musicians were under a terrible thumb with the drugs.

Another racial factor was that most of the record execs, the producers, even just the regular business people in jazz, were all white. There were very few John Levy’s out there, a former musician and a Black manager of jazz musicians. There were very few people like him. So they had to navigate that as well.

That was rocky navigation. Just to take one example, Atlantic records, the huge label run by Ahmet and Nesuhi Ertegun that was very reputable and had a great roster of artists. This was particularly true with R&B, maybe less true with jazz, but Atlantic didn’t pay the Black artists. They just didn’t pay them. These artists had to come after Atlantic Records and sue them to get any of their profits.

Listen, jazz, except for the very few, was not a way to make money. And that very few included the three principals of my book, including Miles, Coltrane and Evans, who made a very good living out of jazz. In jazz, people weren’t in it for the money. These great artists were in it for the love of this great American art form.

They had to be out on the road 52 weeks a year, slaving away, at what was really a discipline that they loved, but working their butts off to make a living.

Another paradox is the way that we all look back on that time period in jazz as this great Renaissance era, which it was musically, but very few of them played a theater or larger venues. The jazz artists mostly played for small audiences.  

Yes, back in the day, America in the forties and fifties and into the early ‘60s was a land of nightclubs. The clubs were small for the most part—little tiny places could seat maybe 100 or 200 people tops, if everybody was jammed in like sardines. They were not big profit generators. They made their money off the drinks and paid the musicians what they could.

You got to interview Miles in 1989, but well before you became immersed in the jazz world. If you could ask him and Coltrane and Bill Evans one question now, what would it be? Were there some questions which remained unanswered for you after you did this book?

I would ask Miles how much of fusion was about trying to stay current and sell records, and how much of it was about what you really loved. When you recorded “Human nature” and “Time After Time,” were you recording music that you really loved? Or was it really about selling records? He loved to sell records. Listen, Frank Sinatra loved to sell records too, and Frank Sinatra recorded a lot of crap trying to sell records. And Miles arguably did too. So I’d ask him that.

I would ask Coltrane, forgive me for being so presumptuous, but your audience began to drift away, began to peel away when your music became less and less understandable to them. Were you, as McCoy Tyner felt, just playing for yourself and not for an audience anymore? You were on a spiritual quest. That’s a beautiful thing. On the other hand, did your spiritual quest so separate you from an audience that you became almost solipsistic.

I would ask Evans, listen, you played this trio format for the rest of your short career. Your repertoire and your style didn’t change much. Some argue that you went deeper and deeper into this limited repertoire. And Jon Batiste, another one of the great musicians I got to interview for this book, felt that, well, Bill Evans did conversations with myself. Nobody else did that. He felt that Evans really was on an exploration. But I would ask Evans, “Could you have gone farther? Could you have gone wider?”

I’d have questions for all of them, but the great editor with whom I worked at Penguin Press, Scott Moyers, originally came to me with an idea to write a book about Kind of Blue. I felt that Ashley Kahn wrote a great book about Kind of Blue. And I’m not a jazz writer. Ashley Kahn is a jazz writer.

It may surprise you for me to say that, having written this book, there’s nothing technical about my understanding of jazz. But I had the idea, since I had this interview with Miles in my pocket, what about these three guys, as men and musicians, before, during and after the making of this pivotal album in this pivotal year, that you would really have something there. You would have a book that was not just about this album, but about these three geniuses and about jazz itself at such a crucial juncture in its life.

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