Born in St. Louis, Osby is a musician who grew up in that city's blues tradition. He studied in Washington D.C. and at Berklee College of Music in Boston, during which he developed into a determinedly modern-jazz player, and an accomplished composer.
Arriving in New York in the early 1980s, he worked with Dizzy Gillespie and John Faddis, but his first major exposure came as a member of Jack DeJohnette's Special Edition from 1985-91. During that time, Osby hooked up with Steve Coleman and members of the M-Base collective, experimenting in creating an angular, abrasive style of jazz that included rap and hip-hop components.
He is firmly committed to finding methods of improvisation that are contemporary in context and style. In 1990, he signed with Blue Note, and began making a series of discs that incorporated his edgy, urban style of playing, with titles such as Man Talk For Moderns, Vol X. Osby also worked with some of the most experimental figures in jazz, such as the pianist Andrew Hill (who later played on some of Osby's discs).
In the late 1990s, Osby became a central figure in Blue Note's group of young signings, and worked regularly on disc and on tour with pianist Jason Moran and vibes player Stefon Harris. With this coterie of players, Osby worked in a more conventional acoustic jazz environment, and his playing blossomed. Some of his finest, most inspired soloing unites the angular lines and edgy rhythms of his earlier days with the flowing swing of bebop, and his informal 'Banned in New York' disc catches him in top form in a club setting.