In Part One of our interview (Issue 221), David and I talked about the beginning of Chesky Records and his career in the audio industry, and his thoughts about recording and listening. We continue our talk with a look at his musical career, thoughts on the future of high-end audio, and more.
FD: You have such a reputation as an audiophile label that people forget how good a musician and composer you are. How did you become so good? I know your mother had you start piano lessons at a young age.
DC: I got into audio as a musician. Look, I'm a musician first. I made my living when I was young as a conductor and a studio arranger. I had a jazz group. At the end of the day, I'm a musician first. I play every day. I write music every day. I've [composed ] ballets, operas, symphonies, piano concertos. But the kind of music I do is not popular like rock and rap and all that. So, it's a little hidden, because most people just can't get into it. But it's what I do. You don't pick the type of music you play. It picks you.
DC: My ears are attracted to a certain thing, just like rockers are attracted to a certain chord, or the sound of an amplifier. I like my music [to be] a little complex. I like it very rhythmic, because it's just what I like in the morning. I live in the middle of New York City. I'm not on some beautiful lake in the mountains where I want to chill out. I get in the subway and it's like, “yo, get out of my face.” New York is in your face. You hear drums and rhythms and cars honking, and it's this thing. I like it. You know what, if I go to the country and I have the window open and it's too quiet, I can't sleep. I need to have the window open. I need to hear someone say, “yo, get out of here!” I need to hear a siren. Every hour on the hour, I need to hear somebody honking and saying, “move that car!” Move it. F*cking move it, bro.
But this is my home and I love it. I travel all over the world, and I love to be in the Caribbean or in the mountains and all that for a few weeks, but [ultimately] I like to be back on the Upper West Side of New York.
FD: You also have a background in Latin music. It really comes across in your music through the rhythms and use of congas and the like, and that might be a musical side of you that people aren’t so aware of.
DC: I have two trios right now. I have my classical trio where we play the music of Beethoven, Bach, Chopin, and we do really elegant, elegant jazz, and it's a little heady. It's a nice evening [wearing] tuxedos. And then I have my Latin trio with Giovanni [Hildago], who's the greatest conga player in the world. And John Benitez, who's one of the greatest Latin bass players in the world. We did this new record called New York Descargas, and whoa, it’s like a groove machine.
FD: People think of Chesky as a niche audiophile label, but you've had some major artists and hits. Why did they go with you instead of Atlantic or Warner's or…
DC: Whoever? Because they wanted to try something new. We've done some big artists; we’ve done Macy Gray, we've done Peggy Lee, we did Chuck Mangione. I mean, a lot of people. McCoy Tyner, Joe Henderson, Phil Woods. Clark Terry.
FD: I loved (violinist) Johnny Frigo.
DC: That was the first real recording we made (Debut of a Legend).
FD: You've got such a body of work – more than 30 albums if I counted right. How long does it take you to compose a piece?
DC: I can write fast. I can write a piano concerto in a few weeks, easy, and I can do an opera in two, three months. I write fast. I mean, opera is long. It's two hours. Yeah. Ballet is an hour. Most works are concertos, around 15, 20 minutes. So you can knock those out.
FD: Some people, as we know, take forever.
DC: I don't say it's good, but I can write. Maybe it's better to take your time for five years and write one [piece].
If Paul McGowan wants to underwrite at the PS Audio Foundation for the Arts, I'll have the New York City Opera give him a call!
FD: A sure way to guarantee ticket sales. Hey, you never know.
There's so many times when I've thought I've made so many wrong decisions. I could have done this; I could have done that. But then look at where we are. We're doing what we love to do. And somehow I don't think we stumbled on this path.
DC: Yeah, yeah, totally. I wouldn't change it for the world. I dig what I'm doing, even with all the aggravation and politics and stuff. I like music. That's what I want to do.
I like the fact that my kid [Lucca Chesky, designer of the Chesky Audio LC1 loudspeaker – Ed.] is doing it and he's going to get young people into [audio]. Because you know what? High-end audio is an art form. Instead of making art with a paintbrush, it’s creating art with soldering irons, and like classical music and jazz, I don't want to see it go away. I look and I see the people [into high-end audio] getting older and older.
Look, any young kid would want a Ferrari, a Maserati. A Rolex, Gucci. There has to be a [similar] demand for high-end audio where kids say, “dad, I want that PS Audio rack. I want that Wilson speaker. I want that Magico. There's a demand, because it's a great art form. But I get very nervous because I don't see young people gravitating towards it, and I think it's because they don't even know it exists.
When Lucca brings his friends over to the house and they hear it, they say, “what the hell is this?” But if you walk down the street now, there are no high-end stores. They don't know about the magazines. So what Lucca's planning to do is to go on TikTok and try to turn all these young kids onto it, because it's a great hobby. It's a cultural hobby, and it supports musicians. But if the tree falls in the forest…if a musician plays alone without the audience, what good is it? We need audiophiles. We need people in the future who appreciate good recordings, that appreciate good music, that want to go to concerts. It's a symbiotic relationship.

That is the most important thing right now, to nurture the youth and get 'em into the hi-fi shows. And it would be great if there was some truck that would go to all the universities, set up in the student union, and [ask students to] play their music on great speakers. And kids would say, “wow, what is this?” But they need to be hip to it.
FD: The high-end audio community has been wringing our hands for 50 years over it, but maybe social media – aside from all the negativity of people on audio forums who are quick to tear things down without really knowing what they're talking about – will be a positive thing. It'll be an enabler. And that's something that our generation didn't have.
I’ve said this over and over again but I refuse to believe that people don't care about good sound anymore, and that we’re looking at the end of an era. I mean, we're living in an age of technological innovation.
DC: I think people want high-end, they just don't know it exists. That's the problem. How are they going to know about it? It doesn't leak over to the mainstream press.
FD: I wonder if it's a question of ad budgets. I don’t know. There are a lot of smart people in the business, but…
DC: Look, it will take someone like Jay-Z or Beyoncé or the Rolling Stones to say, “hey, I listened to this. I dig it.”
It needs [to have] young people talking to young people. What if Bob Dylan got on a stage and started playing for a bunch of 18-year-olds? But if you took an 18-year-old kid playing the same music, they might think it’s all right. It needs to be young people telling young people, “this is cool.”
FD: Another big issue, and I'm certainly not the first one to talk about this: when you go to an audio show or dealer and they won't let you play what you want to hear. Sure, they're afraid that playing a crappy recording or music other people won't like might drive people out of the room. But on the other hand, if you're going to play stuff that younger people can't relate to, you're going to lose them.
It's a gamble. Maybe for an hour you demo your audiophile music to show off what your system can do. Then for the next hour it’s listener's choice. Even the worst recording in the world is going to demolish anything you’re going to hear on a Bluetooth speaker or in a car or whatever. I loved the fact that at the last AXPONA, Cardas hosted their heavy metal listening party.
Maybe you’ve hit upon it – that the high-end industry needs young people talking to young people.
DC: How does the [high-end audio industry] as a group, a coalition, consortium, get young people in it? It almost means like [starting] a club where everybody puts in 50, a hundred dollars, all the audio companies, and then somebody takes out an ad saying, “check this out, take this [QR code] and check out all these cool audio companies. You need to know about it.”
FD: Well, I don't know if you were actually part of it, but remember AAHEA, the Academy for the Advancement of High-End Audio from the late 1980s and 1990s? It looked like it had some momentum for a few years, and then it just kind of devolved. So how do you bring together an industry of strong personalities who will disagree, or people who will have meetings about “action items” and what to do at the next meeting, and get nowhere?
DC: Well, for the next HIGH END show, which will be in Vienna [Editor’s Note: the HIGH END show has formerly been in Munich and will move to Vienna in 2026] they're going to have Lucca and another young kid be the face of it, and go on TikTok and try to get young people into it. They [realize] they need to get young people into the place.
FD: Maybe our generation…a friend of mine used to say, “we're dinosaurs. Let's just face it, we're dinosaurs.” Maybe our generation is of a mindset that can't relate to what’s happening today. I see people watching TikTok videos and they're laughing and cracking up, and I look at the videos and think it’s a dumb waste of time. Like you say, maybe we need people who are teenagers and in their 20s to figure this out.
DC: It's music. Look, music ain't going anywhere.
FD: That's the encouraging part. Music is going to evolve, it's going to change, but it's never going to go away. It's a fundamental human need. And I have a lot of faith in technology becoming better. So maybe better sound will happen in ways that we can't even conceive of now, but I think it will happen. Maybe high-end as we know it today will become more and more of a niche market, but “high-end” sound will be available in ways we can’t imagine today.
DC: This is the danger, though. As our technology gets better, we're going in the inverse [direction]. Now people are listening to Alexa in mono. Whoa, what's going on here? We [as an industry] can make amazing sound. And then nobody's interested. It's called “good enough.” You know what I call it? Reliable mediocrity.
FD: On the other hand…a friend of mine has one of those $150 Bose SoundLink little Bluetooth speakers, and he played it outdoors, and I couldn’t believe how good the thing sounded. Sure, it’s not what we’d listen to, and you can’t get the sonic perspective of a true high-end system, but the sound quality was honestly good. And it’s not realistic to expect people to have to pay insane amounts of money for good sound.
DC: You can get Lucca’s speaker, a Schitt amp and a Schitt DAC for $2,200 and it sounds really good. It’s stupid [to think] that you have to be a hedge fund owner to have a hi-fi system. Look at the Chi-fi stuff.
FD: And I've heard some of it, and some of it sounds really good.
The one takeaway you've given me is that for high-end audio to continue to remain relevant, you need to have young people talking to young people.
DC: If you went to Woodstock, you didn’t want to hear somebody like Bing Crosby telling you, “hey, this is really cool.” People would say, “hey, get me out of here, bro.”
FD: So, you need young people to reach their peers. Plant the seed, and get acolytes to spread the word, which is: if you heard good audio, it would make you very happy.
Header image courtesy of Patricia Dinely.