Miles Meets Monk

Jazz guitarist interprets Thelonious songbook for solo guitar

November 3, 2026November 3, 2026 Ron Hart 0 Comments Cygnus Recordings, Miles Okazaki, New York City, The Jazz Gallery, The Monkathon, Thelonious Monk, Work

One of the most unique and ambitious projects in jazz in recent memory has been American jazz guitarist Miles Okazaki’s 2018 interpretation of the entire Thelonious Monk songbook for solo guitar on a six-disc collection entitled Work.

“It began as a private study, then it snowballed and became a completist project,” the Washington-born musician tells Rock & Roll Globe.

For a pianist as intricate as Monk, one might believe the task of translating all 66 of Monk’s tunes from piano to guitar would be a mountainous one to endure, but Okazaki tackled the challenge with confidence.

“It’s not difficult, if you think of the guitar as a kind of filter,” he explains. “You pass the music through it, and some things are not possible. What remains is what you have.”

And what kind of guitar did Miles utilize to channel Monk?

“I play it on an archtop electric, a Gibson ES 150 from 1940,” he admits. “His style is an expression of his personality, and I suppose that my interpretations are versions of my personality interacting with his.”

Miles Okazaki *Work: The Complete Compositions of Thelonious Monk Volume 1-6*, Cygnus Recordings 2018/2026

The recordings featured on Work stem from a series of performances Okazaki had booked at The Jazz Gallery in New York City, where his history runs deep.

“I’ve played there for 25 years, so it’s a place where I’m comfortable,” he explains. “I know they are going to have respect for the project, and not be stressing about selling a bunch of drinks and food and such. The director there is an old friend, and I like to work with folks who I’ve known for a while, especially for such a high-stakes project.”

In 2024, guitarist Miles Okazaki undertook an extraordinary feat. Over five hours in one evening at The Jazz Gallery, Okazaki played the 66 compositions of the complete works of Thelonious Monk, from memory, on solo guitar. Two days later, he did it again. Filmmaker Frank Heath was there to capture this unique performance, resulting in The Monkathon, which premiered at Roulette in Brooklyn in September.

“It was the idea of a producer that I had been working with,” Okazaki explains about the film. “It was a lot of work, and an intimidating project, but we got it over the finish line. I’ve been getting wonderful feedback from musicians and all kinds of folks.”

Miles Okazaki’s transcription of “Monk’s Mood.” (Image: Miles Okazaki)

Meanwhile, Work was reissued in October on the Cygnus Recordings imprint, marking its first pressing since its original limited edition run in 2018. The Monkathon, meanwhile, is freely available for public viewing at monkathon.com. There, it’s broken down by links to each of the four sets for either the fully unedited performance or a track-by-track breakdown, giving the viewer options to jump around at their leisure. Also available on the site is a “Behind the Monkathon” featurette as well as screenshots of each page from Okazaki’s notebook he used to transcribe Monk’s music.

Thanks to the film, Okazaki became an observer of his own performance. “I can see that I’m making certain decisions,” he says, “but on stage I felt like more of a conduit for the music than an active participant. The music and audience had given me at least as much energy as I had used. I had scoured the limits of my abilities to pay tribute to the miraculous body of work of Thelonious Monk. And that was all I wanted to do, really.”

When asked about his favorite Monk album, Miles didn’t hesitate.

“Probably Misterioso, a live album with Monk and Johnny Griffin,” he proclaimed. “It’s just one that I had when I was younger and listened to a million times. I like the live albums — the 5 spot in 1958, Town Hall, Carnegie Hall, etc. In general, I like live albums in all kinds of music, to imagine the performers really being in a certain moment.”

As he sets his sights for 2027, Okazaki has no shortage of projects and activities to keep him busy in the new year.

“I’m practicing music for sideman gigs, which I really enjoy,” he said. “I know some outstanding musicians who are always challenging me. I’m teaching and documenting the things that I know about guitar, and reach people globally on my Patreon that puts out about three videos a week. I’m getting back into studying classical guitar and a big pile of scores and books that have been piling up. I’m writing stuff for a new album, but that’s a secret.”

For more information on Miles, visit milesokazaki.com.