Chris Entwisle and Mark Havens: authors of WAIL on the constraints that led to timeless designs for Prestige Records

1 Jul 2026 · 25 min · 12 chapters

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In short

The origins and design history behind Prestige Records’ album covers, as documented in Whale: The Visual Language of Prestige Records, focusing on how constraints and limited resources produced “timeless” design.

Guests

Mark Havens and Chris Entwisle, Philadelphia-based designers and long-time jazz/record fans who spent about 20 years tracking down original Prestige releases and researching their visual creators.

Key claims

Prestige’s cover design mythology is less documented than Blue Note’s; Prestige’s identity emerged from a shoestring, “mom and pop” operation run by Bob Weinstock, with little/no briefs or marketing oversight. Constraints drove creativity: typography-only when imagery was unaffordable; photographers shooting musicians when stock photography wasn’t funded.

Notable examples

Rudy Van Gelder’s Hackensack living-room studio discovery; Reed Miles’ typography-as-art and painterly/Warhol-era connections; Tom Hannon’s self-shot imagery; David X. Young’s rejected cover work (e.g., Lester Young purple cover). Also credited: Ira Gittler (liner notes/historian) and Dan Morgenstern (jazz studies/DownBeat editor).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

The Power of Constraints in Design

0:00 to 0:30

Learn how limitations in design can foster creativity and innovation.

“With so many things at designers' fingertips now, it's almost difficult to place limits upon a project.”

The Journey to Prestige Records

0:30 to 1:34

Discover the origins of the authors' journey into Prestige Records' design history.

“Years ago, two friends in Philadelphia, both designers, both obsessed with jazz, kept noticing the same notation on the back of their favorite records.”

Creative Freedom Through Lack of Direction

1:34 to 2:18

Explore how the absence of direction led to unique designs in album art.

“No budget, no briefs, no marketing department produced a visual identity coherent enough to still echo through design today.”

Welcoming the Authors of Whale

3:24 to 3:44

Hosts welcome guests Mark Havens and Chris Entwistle to discuss their book.

“We'll return to the conversation after this quick break.”

Welcoming the Authors of Whale

3:48 to 4:26

Hosts welcome guests Mark Havens and Chris Entwistle to discuss their book.

“That's dbtr.co slash YouTube, or just go to YouTube and search for Design Better Podcast.”

The Importance of Design History

4:26 to 5:41

Hear why understanding design history is crucial in today's landscape.

“Yeah, we are big record fans and jazz fans and graphic design book fans.”

Origins of the Whale Project

5:41 to 9:32

Get insights into how the authors' project on Prestige Records began.

“He was into the music earlier than me, definitely.”

Designers Behind Prestige Records

9:32 to 14:01

Learn about the designers and artists who shaped Prestige Records' identity.

“When we initially had conceived of the book, it was just a bunch of albums.”

The Origins of Prestige Records

14:01 to 16:46

Learn about the early days of Prestige Records and its unique working environment.

“He talks about packing boxes of records for shipping and sweeping the floors and writing promo copy and delivering records to DJs, just about everything.”

Interdisciplinary Design Approaches

16:47 to 19:15

Discover how a multidisciplinary approach influenced the timeless designs of album covers.

“And if you talk about silos, when you think about the art world of the 1950s, there was not really any crossover between illustration and design, between fine art and design.”
Show all 12 chapters

The Challenge of Original Artwork

19:16 to 21:10

Explore the challenges faced in sourcing original artwork for the album covers.

“It's just a source of continual inspiration to us, even at this point after having worked on it so long.”

Typography in Album Design

21:11 to 23:12

Understand the critical role of typography in the design of jazz album covers.

“And you also got access to some of the original artwork that was rejected, like the Lester Young, the purple cover that I showed.”
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Transcript

Automatic transcript. May contain errors.

0:00Mark Havens:With so many things at designers' fingertips now, it's almost difficult to place limits upon a project. That the limits that you put on yourself by choice or by virtue of the project that you've taken on and the realities of that, those limitations often make the difference. Embracing that whole, what can I do with the minimum amount was something that every single prestige designer was great at it.

0:30Chris Entwisle:Years ago, two friends in Philadelphia, both designers, both obsessed with jazz, kept noticing the same notation on the back of their favorite records. It said, recorded by Van Gelder in Hackensack. So one Saturday, they drove out to find it. They tracked down the address in a 1955 phone book. They pulled up and found a parking lot. No sign, no plaque, nothing to mark that Rudy Van Gelder had once turned his parents' living room into a recording studio right there, capturing some of the most important American music of the century. The quiet drive home planted the seed for a 20-year project. Mark Havens and Chris Entwistle are the authors of Whale, the visual language of prestige records.

1:20Chris Entwisle:The first real look at the design history of a label that, unlike Blue Note, never got its design mythology despite cover art that's just as striking and definitely as durable. They tracked down original pressings, interviewed the designers before that history disappeared for good, and uncovered how a label run in one historian's words, like a mom and pop store, No budget, no briefs, no marketing department produced a visual identity coherent enough to still echo through design today. What we love about this conversation is how much of it comes down to constraints driving creativity. Reed Miles couldn't afford imagery, so he made typography of the art.

2:01Chris Entwisle:Tom Hannon had no budget for stock photography, so he shot the musicians himself. Designers got an album title and nothing else. No brief, no comp, no client approval, and turned that absence of direction into creative freedom because Bob Weinstock simply viewed it all as art, the music and covers alike. This is a conversation about jazz, but it's also about what happens to creative work when nobody's watching too closely and why limitations so often produce things that last. This is Design Better, where we explore creativity at the intersection of design and technology. I'm Eli Woolery. And I'm Aaron Walter.

2:33Chris Entwisle:If you're hearing this, you're not currently on our premium subscriber feed. Design Better premium subscribers enjoy weekly episodes. That's four episodes per month rather than just two, and all of them are ad-free. Plus, you'll get an invitation to our monthly AMAs with the smartest folks in design and tech. And if you subscribe at the annual level, you'll also get our toolkit, a collection of our favorite design and productivity tools like Perplexity, Miro, Read AI, and more. You'll hear a preview of this episode, but if you'd like to hear the full conversation, please consider becoming a premium subscriber at designbetterpodcast.com slash subscribe.

3:15Chris Entwisle:The podcast is available to everyone through our scholarship program. So if you can't afford a subscription, just shoot us an email at subscriptions at the curiositydepartment.com. We'll help you out. We'll return to the conversation after this quick break.

3:36Chris Entwisle:Hey, before we start the show, I wanted to give you a heads up that there is a video version of our episodes on YouTube. Head over to dbtr.co.uk. That'll take you right to our YouTube channel where you're going to find not only video versions of episodes, which are fun to watch and kind of see the behind the scenes, but also some bonus content that you can't get in the podcast feed. That's dbtr.co slash YouTube, or just go to YouTube and search for Design Better Podcast. Okay, on with the show.

4:12And now, back to the show.

4:19Chris Entwisle:Mark Havens and Chris Entwistle, welcome to Design Better. Thanks for having us. Thank you. It's great to be here. Yeah, we are big record fans and jazz fans and graphic design book fans. So you fit in the Venn diagram of all the things that we like. Lots of overlapping circles. You've published recently a wonderful book called Whale, The Visual Language of Prestige Records. And I want to know more about why this book and how you got into this project. But before we jump into that, I just want to say how important books like this are at this moment in design history. We hear from our design community, Design Better listeners and readers, that they are frustrated and feel stifled, a lot of anxiety around AI and things becoming less in their control.

5:14Chris Entwisle:And they want to find inspiration and new ways, fresh eyes to look at design. I often find that looking at design history, it's a rich way to reconnect with your passion and your craft. And this book is just full of it. So can't recommend it enough to listeners. Definitely check this book out. But why don't you take us into the origin story of the book and why you wrote this?

5:39Mark Havens:Well, Chris and I have been friends for years. He was into the music earlier than me, definitely. but we had always sort of enjoyed not only the music together, but the graphics together. And that was sort of from the start. The way I met him was I was working at a design firm and I had always heard about musicians like John Coltrane, Arthuronius Monk, Sonny Rollins. And I decided one day, this is in the sort of crossover period between cassettes and CDs going way back. I bought a couple of jazz CDs and I had them on my desk at this design firm and the business manager who happened to be Chris's wife walked by and said what do you got there and I said well these are just a couple of CDs that I just got and on top was an Art Blakey seating and she said you got to meet my husband and when somebody says that you're sort of like well okay and that was Friday And I come in on Monday and on my desk is a stack of four cassettes, each of which has a handmade four panel foldout piece of art with it, half photocopied, half hand done.

6:49Mark Havens:It looked like the paper was ripped out of some accounting ledger somewhere. It was just extraordinary. It's a matching set of four cassettes. And Chris's wife comes back and she says, I told my husband about you. And he said that if you're listening to Art Blakey, you need to hear Jackie McLean. And this was a set of four cassettes of Jackie McLean's music. And I thought, okay, this is a guy I definitely need to meet. And it went from there. And so we would go to shows together and just enjoy the music and the graphics together because we both had backgrounds in design. It was always something that we liked just as much as the music was the graphics.

7:29Mark Havens:And so one day we were sitting around listening to some albums. And on the back of many of the albums, I'm sure you guys know, there's lots of small notations. And one of the notations that we would always see on the back of these albums that we love so much was recorded by Van Gelder in Hackensack. And so we started talking. We were like, you know what? We're both in Philadelphia. And so we said, why don't we go to Hackensack? Wouldn't that be cool if we could actually find where this stuff was recorded? And where it turned out to be recorded was in Rudy Van Gelder's parents' living room. He had convinced his parents to allow him to turn their living room into a recording studio in Hackensack.

8:10Mark Havens:And that was where a number of the albums that we enjoyed together were recorded. So one Saturday we went up, a lot of driving around Hackensack, a stop at the Hackensack Public Library. And in a 1955 phone book, we found the address. We drive up to the address and get out of the car. And the only thing there is the parking lot for Hackensack Sports Medicine. I remember it like it was yesterday. We were just kind of standing in the middle of the parking lot, kind of dumbstruck that there was nothing there. Not a sign or a plaque that so much of what had happened there, so much seminal American music that was recorded there.

8:49Mark Havens:You'd never know. You'd absolutely never know. So it was a very, as you might imagine, a quiet ride back down the turnpike. and we started talking about all the things that are kind of swept under and all of the things that are worthy of exploration and worthy of being shown to a larger audience. And that's where the idea for the book came from. Up until that point, there had never been anything written about the graphic design of Prestige Records and plenty written about Blue Note. They always seem to have had a better handle on the marketing than Prestige did. I mean, it stopped being a label in the early 1970s, and there wasn't much there.

9:28So that's what sort of set us off down the road of the book.

9:32Mark Havens:When we initially had conceived of the book, it was just a bunch of albums. And so we started looking for the albums, but one thing led to another, and it turned into what it is today, gradually.

9:44Chris Entwisle:You did a fair bit of research for this, from our understanding, almost 20 years, tracking down all these copies of every Prestige release. and as you're doing that and going through that process, obviously you probably both had a bit of a design lens as well as appreciation for the music. What do you think maybe some other designers miss as we're flipping through album covers or looking at this type of graphic design? I think Mark and I both feel the same way. We always came to this with a feeling that the design was almost inseparable from the music. Some of the people we've spoken to since we published the book were deeply into the music and enjoyed talking about the music, but they had very little feeling for the design or they felt as though that isn't something that influenced what they listened to for me from the minute I was listening to jazz when I was first seeing this was in the 70s I was looking at I remember seeing the congregation by Johnny Griffin which is another Reed Miles Andy Warhol cover I remember the cooker with Lee Morgan and just being kind of mesmerized not that it looked dated I mean it looked very much of its time but I just felt like this is the kind of design that sort of sustains over the years and it wasn't nostalgic for me.

10:54Chris Entwisle:And, you know, this was in an era just on the cusp of Memphis design and things like that, that I think is really dated badly over the years. But somehow the stuff from this year, the prestige stuff, the Blue Note stuff, I'll even say some of the things at Riverside, I think has a kind of timelessness to it. It's influenced by European design movements and other things, but I always kind of felt, and Mark did too, that this stuff would really stand the test of time and it should exist apart from the music. You should be able to look at it the same way people would publish a book on Alvin Lustig book covers or Paul Rand design or something.

11:31Chris Entwisle:You know, we just kind of felt like, let's really try to concentrate on the design. We love talking about the music. We didn't feel fully equipped to write about it, but we felt like let's really concentrate on what these covers actually are. Yeah, I was remarking to Eli as we were preparing to chat with you, There are a number of these that feel like they could be in a gallery, like they could just be a painting. I'm going to share one here for our YouTube folks, but this is Prez. It's all it says on the cover, which is just a beautiful, simple, curious composition that is not overly descriptive and yet piques your curiosity.

12:13Chris Entwisle:Take us behind the scenes. who are the characters that are creating these covers? Who are they? What's their background? And what do we know about them?

12:22Mark Havens:Well, when we started out, we didn't know much of anything about anyone. Like I said, it was initially a book just of the album covers. But as we began to get deeper and deeper into the album covers, you see little credits in the corners or hiding in an image somewhere, you know, Hannon or Young. You know, you sit around long enough and look at something, you ask yourself just about every question about it. And so we were like, well, who was Hannon and who was Young? And so we started to do a little bit of research and try and figure out who these people were. And it became apparent that in order to really understand the art, what would be best would be to hear from the artists and the designers in their own words.

13:09Mark Havens:And so that sort of opened up a new facet for the project of us going, well, you know, maybe it's not just a catalog of album covers. Maybe we can get a little bit about the creators of these covers, the photographers, the artists, the graphic designers. And that sort of expanded into what it is today, which is sort of a compendium of nine different creative processes as lenses to see the work of prestige. But to get back to your original question, these designers were young artists. They were photographers. They were graphic designers. They were painters. They were creatives in 1950s New York.

13:53Mark Havens:Prestige was run by Bob Weinstock, founded by Bob Weinstock, who was a record store owner. He began recording. He didn't have any employees at first. And we ended up getting an interview with his first employee, who was Ira Gittler, who ended up being one of the world's preeminent jazz historians and ended up, due to his journalism degree that he'd just finished, writing the album liner notes for all of the recordings of prestige in the 1950s. 50s. He was the first employee. He talks about packing boxes of records for shipping and sweeping the floors and writing promo copy and delivering records to DJs, just about everything.

14:39Mark Havens:And prestige was kind of run on a shoestring. It was a very sort of hand-to-mouth operation. One of the people who was really instrumental in this book, Dan Morgenstern, he was the director of the Rutgers University Institute for Jazz Studies and was a huge help to us for this book. He was the editor of Downbeat. And so he had a unique insight into prestige. And he said, we've got the quote in the book. He said, you know, they were recording these world-class musicians, but it was run like a mom and pop store. And so these designers, it was work for hire. They were freelancers, walked in off the street.

15:16Mark Havens:Bob Weinstock, when we spoke with him, sharp as a tack, remembered absolutely everything and every person that he ever hired or ever worked with. But there wasn't really anything deeper than this guy walked in with a portfolio off the street. I took a look at his work. I liked it. I gave him a couple of albums to do and it went from there.

15:36Chris Entwisle:Wow, that's cool. It doesn't read that way. Yeah. The timelessness that you mentioned, Chris and Aaron, you mentioned that kind of painterliness. And in some cases, there were actual paintings that went into like this Reed Miles cover. And there's this great like sort of interdisciplinary approach there. It feels like where he was a designer, but it looks like he was also a painter and photographer. These days, we maybe within different roles tend to overly silo ourselves. Maybe we think like, well, I'm a UI designer, UX designer, and I'm not really a painter. I'm not a graphic designer. And, you know, to some degree, we'll talk more maybe about the negative side of AI, but the positive side is that maybe it lets us kind of branch out and explore and experiment in different ways.

16:16Chris Entwisle:But what do you all feel about this, that sort of multidisciplinary approach that made some of these so special? What played into that? I think you're onto something with Reed Miles, especially because I think he was sort of an omnivore. Of all the designers at Prestige, he was the most comfortable, I think, with the idea of commercial art or graphic design. I mean, he saw what was going on in painting. He immediately hooked up with Andy Warhol and that crowd, along with Ed Wallowich and other photographers. But except for Reed Miles, all the other designers at Prestige had their origins in fine art.

16:50And if you talk about silos, when you think about the art world of the 1950s, there was

16:56Chris Entwisle:not really any crossover between illustration and design, between fine art and design. And there was a prejudice toward commercial work or illustration. So people like David Young, even Tom Hannon, I think were very opinionated about where they would do commercial art. It was only with this music and it was only to be involved with this music that they were doing that. When you read David X. Young's, it's not a memoir, but when he talks about it, you can kind of get that feeling from these abstract expressionists that were condemnatory of anything but the purity of doing expressionist paintings, which is why they had a lot of antipathy toward pop art.

17:33Chris Entwisle:when it's ironic, it's a guy like Warhol that emerged in the 60s. Jasper Johns, Robert Rauschenberg had been window dressers and commercial artists. And I think David Young and Hannan felt completely adrift in the 1960s because they felt the stuff that they had been doing and that they were committed to doing was just kind of, the rug was pulled out from underneath them. So they stopped doing any kind of work at that point. And all of these guys, and I think it's all men as far as I could tell. Is that correct? Actually, a couple women that didn't do sustained work. That's almost unique, too. There was Carol Reif, who was a great photographer, did some early stuff on the 12-inch LPs.

18:12Chris Entwisle:And Fran Scott, who did the first LP cover, first 12-inch LP cover. And they're all based in the New York, New Jersey area. Is that right? Entirely New York, you know. Entirely New York. So they're seeing all of this art change. So for anyone who did not take art history, there's a lot happening in the 50s, the late 40s and 50s in New York, the New York scene. So many artists who have come from Europe have come over. And then also there's just these cultural change that's taking place. Folk music, Bob Dylan goes to New York. You mentioned Rauschenberg and Johns and all these other folks. There's just a cross-pollination of a lot of creative ideas.

18:57Chris Entwisle:is I feel like these covers capture some of that cross-pollination. Absolutely, I feel that way. I feel it's almost like a panorama of those things. These guys were so clearly part of that world. And the painting that you just showed of Reed Miles looks so much like, when I think of some of the work that was being done then, even though he'd never dabbled much. Robert Motherwell or something. Exactly, exactly. It's just a source of continual inspiration to us, even at this point after having worked on it so long. I don't think we ever lost the sense of a kind of wonderment or we'd look at some of these covers as we'd be working on it.

19:31And we would just still feel like this stuff is just, it's remarkable.

19:35Chris Entwisle:And what we talked about a little bit when we first started talking was we shot all these album covers. I mean, these were individually pursued and shot. They're all original issue. And when you look at it, I'm not sure of the David Young that you have behind you. Is that an original issue of a like a 10 inch back there? Yeah, that's an original. So that's an original. So some of those 10 inches are a little different, but when you see some of the 12-inch covers that came out, they almost look like serographs. The printing is so sophisticated and the feel of it. When we first thought, well, maybe we'll be able to do just to save us some legwork, we could maybe shoot some of these reissues or something.

20:10Chris Entwisle:Mark bought, I don't know how many, 100 from a DJ of these original jazz classic reissues. It was as though you were looking at a different thing. It was like looking at something was stepped on 50 times. So we realized we were going to have to find all original issues for this.

20:25Mark Havens:We thought we had the project licked at the beginning. Buying one load of stuff out of some guy's trunk, we could get a lot of what we were after. But it became obvious to us, especially when we tried to photograph the stuff, was nearly unintelligible because it had been obviously made from a copy of a copy of a copy. Just like the records themselves. Exactly. And so we saw a couple of original issues. And like Chris said, they were completely different, completely different visuals. And so we thought, wow, if we really want to do justice to these artists' original vision, which was another thing that we wanted to do, because a lot of these albums were printed in very, very small numbers and haven't been seen since.

21:09Mark Havens:If we wanted to do justice to that work, we were going to have to go back all the way to the first printings of these albums, which is what we were able to do with all of them, which is one of the reasons the project took as long as it did.

21:21Chris Entwisle:And you also got access to some of the original artwork that was rejected, like the Lester Young, the purple cover that I showed. I think that one was rejected, right? You photographed the original. Right.

21:34Mark Havens:That was an album design that David X. Young had done when he was trying to break into the album cover design area. He was a fine art painter as he started out as in Boston and then came to New York City. An album cover design for Prestige was pretty much the only creative work that he ever ended up doing. I believe that's a rejected cover for Clef Records. The corresponding article or letters in Downbeat that are across the page on that spread really shed light on what he was thinking when he was at that stage in his career, sort of seeing these other designers and other artists visualize jazz and what his really distinctive viewpoints were about their work and about what visualizing jazz can and should be.

Read the full transcript

22:22Mark Havens:One critical component of most of these albums is the typography. And Mark, you teach industrial design, is that right? It's industrial design. My practice kind of exists at a number of disciplines at kind of a crossroads, industrial design, graphic design, and art. So I have a degree in graphic design and industrial design and end up doing art and projects like this a lot of the time. So it's a nice mix.

22:47Chris Entwisle:I was curious because I also teach in the product design world. And I think a lot of our students don't necessarily get that grounding in typography and graphic design. And even though it's applicable, obviously, to a lot of product design and physical product design, digital product design. So I'm curious, what's your perspective about what students or somebody earlier in their career or somebody who's just curious about becoming more grounded in typography might take away from a book like this?

23:12Mark Havens:The thing that stands out to me about each of those albums is the deep attention that was paid.

23:19Chris Entwisle:If you'd like to continue listening to this conversation, you'll need to subscribe at designbetterpodcast.com slash subscribe. Once you do, you'll get access to every full-length episode, all ad-free, monthly AMAs with inspiring people in design and tech, and recordings of all our past AMAs. The podcast is available to everyone through our scholarship program. If you can't afford a subscription, just email us at subscriptions at the curiosity department.com and we'll help you out. Your support makes design better possible. Invest in yourself and the design community by subscribing at designbetterpodcast.com.

From the publisher

Years ago, two friends in Philadelphia — both designers, both obsessed with jazz — kept noticing the same notation on the back of their favorite records: “recorded by Van Gelder in Hackensack.” So one Saturday they drove out to find it. They tracked down the address in a 1955 phone book, pulled up — and found a parking lot. No sign, no plaque, nothing to mark that Rudy Van Gelder had once turned his parents’ living room into a recording studio there, capturing some of the most important American music of the century.

This is a preview of a premium episode. To hear the whole thing, head over to our Substack:⁠https://designbetterpodcast.com/p/chris-entwisle-and-mark-havens⁠

That quiet drive home planted the seed for a twenty-year project. Mark Havens and Chris Entwisle are the authors of WAIL: The Visual Language of Prestige Records — the first real look at the design history of a label that, unlike Blue Note, never got its design mythology, despite cover art that’s just as striking and durable. They tracked down original pressings, interviewed the designers before that history disappeared for good, and uncovered how a label run, in one historian’s words, “like a mom and pop store” — no budget, no briefs, no marketing department — produced a visual identity coherent enough to still echo through design today.

Buy the book

What we love about this conversation is how much of it comes down to constraints driving creativity. Reid Miles couldn’t afford imagery, so he made typography the art. Tom Hannon had no budget for stock photography, so he shot the musicians himself. Designers got an album title and nothing else — no brief, no comp, no client approval — and turned that absence of direction into creative freedom, because Bob Weinstock simply “viewed it all as art,” the music and the covers alike. This is a conversation about jazz, but it’s also about what happens to creative work when nobody’s watching too closely, and why limitations so often produce things that last.

Bios

Chris Entwisle is an artist and illustrator. For over thirty years, he has used his passion for both jazz and postwar graphic design in his illustration work. Entwisle has a BA in graphic design from Rutgers University. He and his wife live in the Philadelphia area.

Mark Havens is an artist and educator with a dual background in graphic and industrial design. His work has been exhibited internationally and is held in both public and private collections. Out of Season, his first major monograph, was described by the New York Times as “a decade-long elegy.” Havens is a professor of industrial design at Thomas Jefferson University.

***

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