David Chesky needs little introduction to dyed-in-the-wool audiophiles. He’s been championing audiophile recordings since he and his brother, Norman, founded seminal record labels Chesky Records in 1978 then HDTracks in 2008. Recently, David founded The Audiophile Society, a label that pushes the envelope in recording technology to recreate the most convincing 3D-like concert environments people can experience through their stereos and headphones.

Before carving out a name for himself in the hi-fi industry, David began his career as a professional jazz musician and composer of contemporary classical music. With more than 50 jazz and classical compositions and three Grammy nominations to his credit, David returns to Montreal in a trio setting accompanied by double bassist Walter A. Stinson and drummer Jim Doxas. Together, they’ll perform selections from his latest album, The Great European Songbook—a stunning reimagining of classical pieces through a jazz lens, reflecting what Gramophone aptly praised as David’s ability to blend diverse influences “into a musical language all his own.”

During our recent Zoom chat, David opened up about his life in music and audio, and about where it all began.

“I was always an audiophile, I just dig it,” he told me when I asked when the audio bug bit him. “I grew up in recording studios as a conductor and orchestrator for movies and TVs, so I kind of lived there. And when we did these movies and TV shows, there’d be 50 people in the orchestra with 50 mics and it never sounded good to me. When I’m on the podium conducting, the sound is naturally balanced. So I always wanted to start a record company with the idea of a single-point perspective—two ears, two microphones—and that was my recipe for Chesky Records. I wanted to create a virtual reality of the performance.

“But I’ve been making these single-point records for a billion years,” he continued. “With my Audiophile Society label, I wanted to do something new that used DSP (Digital Signal Processing). Because of crosstalk, most of the music we hear during playback is confined to a 60-degree triangle. I wanted to see if I could get the sound outside that triangle and in front of the listener by manipulating things but keeping them very natural-sounding. I wanted to be able to offer a more immersive experience and I figured out a way to do that with DSP so that when you’re in the 60-degree triangle, instead of the sound coming from a narrow place, it will open up.

“You know, we didn’t have DSP 30 years ago,” he said. “Now we can understand and manipulate it. It’s another form of creativity. We still do things in the studio live, with just a stereo pair of mics over the conductor’s head, but I also wanted the freedom to try other things to push the boundaries with the technology that’s around today. It’s the same stereo we’ve been listening to since 1954. We haven’t done a thing to change it, and this is a conscious effort to see if we can kick it up a notch and do something a little more enveloping.”

I asked what he thought of the state of the audio hobby now—was he a hopeful audiophile?

“My 17-year-old son Lucca just started a speaker company. His goal is to get young people into high-end audio, because they’ve never been exposed to it. When we grew up, we could pick up any magazine and there were always speaker ads—JBL, Panasonic, Pioneer. It was in your face. But teenagers today, where are they going to go online to find this? It’ll be by accident if they do. It’s not like they’ll be walking down the street and see it in a store. Every kid knows what a Ferrari or Maserati is. They can’t afford to buy one but they want it. The thing with high-end audio is young people have to be exposed to it to get it. So my son brought his company on Tik-Tok. And he invites people at the house and when they hear what great gear can do they’re blown away. It’s the X-percentage principle; X percent of the population will always be happy with the plastic speaker in the dining room or on their phone. But today, X percent of these young people are doing technology, computer science, and engineering—those kids are predisposed to being audiophiles, but they don’t have a clue what it is. Those that come to my house and see my equipment say, ‘What is this stuff?’ They think we live on the moon. They need to be exposed to it!

“If you took Bob Dylan and put him on a stage in front of 100 thousand kids,” he continued. “They’re going to say it’s music for old people. But if a barefoot 18-year-old with ripped jeans played the exact same songs, they’d say it’s hip. It’s how you present it. I think you need to have young people presenting it to young people, like how Beats let young people know about headphones. I think there’s a great future for the audiophile world if we can expose the young generation to it.”

He added: “I dig audio more than live music. I write contemporary classical music. The music I want to hear, I can’t walk into a concert hall and hear it. What I want to hear I can only hear online or at my house. And then I want the best experience. I want the best sound. And if I dig it I can play it over again. The thing about audio is it’s there when you’re ready for it.”

Some people maintain that musicians tend to not be audiophiles because they can already hear—reconstruct by memory—“the real thing” in their minds. They don’t need a system to fill in the spaces for them. Did he believe that?

“No,” he said. “You know what the deciding factor is for musicians not having an audiophile system? The money. Most musicians can’t make their rent and buy food. It’s a tough business, especially with Spotify streaming. Any jazz cat I know, if you told him, ‘Here’s a $40,000 system I’ll put in your house,’ they’re going to say,”—he lifts two thumbs-up at the computer screen—“’Yeah!’ It’s just money. They can’t afford it and it’s getting out of line.

“Being a musician today is tough,” he said. “It’s impossible for musicians to make money with streaming. But the guys I play with (in New York), (drummer) Billy Drummond and (bassist) Peter Washington, they are so into (quality audio), it’s crazy. Lots of guys I know are into it.”

Was hearing the soundstage in a live recording important to him?

“It is, because when you go to a concert you don’t listen to a concert,” he said. “You watch a concert. You could be in the third row on the side and there’s the violin. You see it. But when you’re home listening to a concert, there’s no visual medium. Suddenly everyone’s blind. So I create the visuals. I’ll put the trumpet in the back, place this here and that here, so you’ll have the illusion that you’re at the concert.

“The other thing that’s super important is tonality,” he continued. “I don’t care if you’re a rock musician, or tube rolling, or a tenor saxophonist, concert violinist, all your life you practice to get a tone. Jimi Hendrix must have rolled tubes to get that sound. A great saxophone player plays eight hours a day to get the right tone. So, the most important things for me in audio is capturing the tone correctly and getting a soundstage so that when you sit there in a 60-degree triangle, you say, ‘wow man, I’m in the club. Turn the lights off and I am there.’ I want to do virtual reality. A lot of audio doesn’t sound real. It’s like an artificial esthetic. It’s the hyped top end, and the sizzle thing, and that sound doesn’t exist in real life. Real life is very pastel.”

Were there events in his life that stand out as peak moments in his career? “Man,” he said reflectively. “I can’t really pull one out, but some cool things in my life stand out. I studied piano with John Lewis of the Modern Jazz Quartet. At the time, did I think it was the coolest thing? No. Now looking back at it, it was cool because he taught me something that at 18 years old I didn’t know. I was very friendly with Antônio Carlos Jobim. He taught me a lot. At the time, did I know how cool that was? No, but now I realize it. Sometimes it takes a while when you’re young for these things to sink in. But I’ve been exposed to a lot of great people, and I think those are the coolest things to look back on. My regret is I didn’t live close to Oscar Peterson.”

Maybe not, but he was soon going to be performing in Oscar’s hometown of Montreal.

“In The Great European Songbook, I take music of Bach, Chopin, Beethoven, and we do it in a jazz way, which is cool because it crosses over, and it lets you see this music in a different light. It’s kind of hip. At the end of the day, I dig playing it and people dig listening to it. It’s what it’s about.”

Any final words to readers? “If you come,” he said. “I encourage you not to bring tomatoes and don’t throw beer cans at us because that hurts. But you should come because it’ll be a nice evening of audiophiles and live music, and maybe if they let me I can answer some questions from the crowd in a Q&A before the show.”

The David Chesky Trio will be performing Thursday, January 23, 2025, at 6 p.m. at Bourgie Hall, Montreal Museum of Fine Arts, 1339 Sherbrooke Street West, Montreal, Quebec, H3G 2C6. Tickets are available now, for $19 – $38.

For more information, click here.