Miles Okazaki came to the attention of the wider world last year, when he released Work, a 70-track, almost five-hour-long collection of Thelonious Monk’s music, arranged for solo guitar. (An undeniable tour de force—and an invaluable library of sonic ideas for guitar players, jazz or otherwise—the collection was initially an online-only effort, but will be released on CD later this year.) The fact is, though, that Okazaki has been a respected part of the New York underground for two decades, making several records with pioneering saxophonist and composer Steve Coleman, and four more with his own quartet, Trickster.

Which, as it happens, is the group he’s bringing to Vancouver this weekend, although it’s not exactly the band you’ll hear on record. Filling in for the remarkable pianist Craig Taborn is the equally astonishing Matt Mitchell, Okazaki’s neighbour in Brooklyn and a very suitable replacement.

“When you think, ‘Who can I call to do this music?’ you have certain people that work in a similar area that you know will have the skill set,” the guitarist explains. “Matt and Craig have a similar background, musically; they both have a huge amount of knowledge about piano repertoire—classical piano, rock, heavy metal, whatever.

“And for this music, it’s not just about playing parts,” he adds. “A lot of it is about how you interact with the group.”

Fair enough. A key part of Trickster’s music is its conversational quality; even when the four players seem to be creating parallel planes of sound, those strata interact in unpredictable ways. Trying to define Okazaki’s tunes in terms of conflict between “the intellectual and the abstract versus the conversational and the soulful” is a nonstarter, however.

“Basically, we have a rhythmic feel which, given what Tidd and Sean [bassist Anthony Tidd and drummer Sean Rickman] do, is going to be funky, most likely,” the bandleader explains. “And then there’s other things happening. But even when I play standards and stuff like that, I’m not so much into the ‘one person in front and everybody else accompanying’ type of sound. I like the sound of everyone playing, everyone listening, everyone collectively involved.”

That approach, he adds, can give rise to unexpected connections between players—which, borrowing a phrase from jazz critic Whitney Balliett, he calls “the sound of surprise”.

“There’s a lot of that happening in Monk—the feeling of getting turned around, trying to keep your place, and trying to keep your balance,” he says, clarifying the link between Work’s inspiration and his own Trickster tunes. “I don’t know why, but I’ve always been interested in that feeling of just being surprised, where you think it’s going to be this and then it’s that, like a magic trick.”

So will Trickster work its magic on some Monk during its local debut?

“We might sneak some in,” Okazaki allows, laughing. “We probably won’t be playing anything that straight, ’cause that’s not what this band does so much, but I definitely sneak stuff in here and there. It’s certainly possible—so keep that in mind, Vancouver!”

Miles Okazaki’s Trickster plays Frankie’s Jazz Club on Sunday (April 14).