He has played with some of the most forward-thinking jazz musicians and worked hard to produce music that was beyond category, surrounding himself with a string quartet in one instance, appearing frequently with Phil Lesh & friends and Gov't Mule at other times. Like Miles Davis before him, Osby has worked to eliminate the barriers between jazz and popular music.
"My duty," he says, "is to follow in the footsteps of the masters by stepping outside the arena."
Osby's latest release, "Inner Circle," is a good illustration of his searching creative instincts. Originally recorded in 1999, Osby decided not to release it at the time because he felt it was slightly ahead of the curve his music was taking.
Davis also shuffled the release dates of some of his most challenging work in order to maximize its impact on his audience. "Inner Circle" was recorded with members of Osby's working band, New Directions, shortly after completing an extensive North American tour. Osby's quintet on this session -- pianist Jason Moran, vibraphonist Stefon Harris, bassist Tarus Mateen and drummer Eric Harland -- performs a series of challenging Osby originals and covers of Bjork's "All Neon Like" and Charles Mingus' "Self Portrait in Three Colors."
"This is a player's record," Osby explains. "There's a lot of dialogue and a great deal of exchange. We recorded this soon after we did the tour with New Directions, which also included tenor saxophonist Mark Shim and drummer Nasheet Watts. So most of us had played together a lot. In addition to the dates, we spent a lot of time on long bus rides and in late night one-on-ones. That led to a higher level of respect and a desire to dig deeper."
That higher level is in evidence throughout the album, particularly at moments like "Fragmatic Decoding," with piano, vibes and saxophone combining for a collective melodic statement that recalls Thelonious Monk's brilliantly elliptical compositions.
"You become adept at having these wonderful dialogues," Osby points out, "sharing encoded messages that only a tight-knit group can understand. You develop an otherworldly telepathy, hence the title of the CD."
"The Inner Circle Principle" provides a key to that vision, a contemplative, spiritual track that floats on a gorgeous bass figure from Mateen. The music is so special to Osby that he held off releasing it until he was sure it would be appreciated for what it is.
"I made a hard left compositionally when I recorded this album," he explains. "There are some wild ideas and approaches here that I felt might have thrown everybody for a loop. I feel that after my most recent projects -- "The Invisible Hand" and "Symbols of Light (A Solution)" -- people might not be as mystified by what I am doing here."
Born in 1960, Osby made his professional debut at age 15 and went on to attend the Berklee College of Music before moving to New York to join Jon Faddis' group. He formed the M-Base (Macro Basic Array of Structured Extemporization) collective in Brooklyn in the mid-80s with saxophonist Steve Coleman.
Also working as a sideman with Jack DeJohnette's Special Edition and pianist Andrew Hill, Osby proved himself to be a forward-thinking jazz musician and released his first album as a leader in 1987.
Signing with Blue Note in 1990, Osby became a major force in jazz in the late '90s, first with the funky "Zero" in 1998, then even more so with the smoking live set "Banned in New York."
"Invisible Hand," released in 2000, features appearances by Andrew Hill and guitarist Jim Hall, who perform together for the first time. On "Symbols of Light (A Solution)" Osby plays with the string quartet, at the same time he was showing up at the Beacon theater to jam with Phil Lesh.
"Genre differences don't matter," Osby insists. "This is the jazz way. This is what Duke Ellington did, Miles Davis, Charles Mingus, Charlie Parker and Dizzy Gillespie, they dealt with Afro-Cuban rhythms and West African rhythms; this is the jazz way and somewhere along the line it became blasphemous to do that and that's why the interest waned because the music never changes.
"These are the great precedents, but it would be trivial and shortsighted to merely emulate them."
Osby finds his inspiration in a variety of sources, from books and films to geometry and numerology.
"I'm a math freak," he says. "I'm trying to find new ways of composing and improvising based on those resources. A lot of what is on this album represents those bursts of light that have triggered the new directions in my music."
"Entruption," for example, uses the numerological interpretation of Osby's name as the basis for the tune's chord structure.
"I didn't even bother naming the chords," says Osby. "I had to teach the band during rehearsal sessions how to decipher the piece."
It was just as Miles Davis had done in his groundbreaking "Kind of Blue." Osby also talks about playing "in between the cracks," which has long been a useful way to describe Monk's innovative piano technique.
"I'm a work in progress," Osby concludes. "I don't like being bound by the stage that has been set. I like the challenge of straddling the fence stylistically. Otherwise you run the risk of walking around in blinders. The way I see jazz is that it's progressive, that it's fed from a variety of sources, not something that's fixated on living up to other people's expectations."