Born in St. Louis, Missouri, Osby studied at Howard University, where he majored in Jazz Studies, and then at the Berklee College of Music, with Andy McGhee. He played on Jack DeJohnette's Special Edition, and has recorded with Steve Coleman, Jim Hall and Andrew Hill (setting the stage for Hill and Hall's later appearance on Osby's The Invisible Hand).
He began recording albums under his own name for JMT Records in the 1980s, but his most celebrated work has been a run of records for Blue Note. Like Coleman, Osby likes to discover fresh talent and give players a chance to grow within his own band: he was responsible for giving exposure to the young pianist Jason Moran, who appeared on most of Osby's 1990s albums (including the live album Banned in New York and an experiment with adding a string quartet to the band, Symbols of Light).
Osby has contributed to the homages to Miles Davis's 1970s electric jazz performed by Henry Kaiser and Wadada Leo Smith's "Yo Miles" group. The Village Voice critic Francis Davis wrote of his contribution to their double album Upriver, "Greg Osby superimposes his own brand of rhythmic complexity (one fully worthy of Wayne Shorter) on the rhythm section's static vamps every time he steps forward."
Since 2007, Greg has been an active endorser of P. Mauriat Saxophones, playing a 67R DK alto  and a System 76 DK soprano . He was featured in a series of magazine ads in Down Beat , JazzTimes and Saxophone Journal in early 2009. He is currently on faculty in the Ensemble Department at Berklee College of Music.
|Greg Osby and Sound Theatre||05-06/1987 (*)||1987||JMT|
|Season of Renewal||07/1989||1989||JMT|
|Man-Talk For Moderns Vol. X||10-11/1990||1991||Blue Note|
|3-D Lifestyles||1993||Blue Note|
|Black Book||1995||Blue Note|
|Art Forum||1996||Blue Note|
|Further Ado||1997||Blue Note|
|Banned in New York||1998||Blue Note||Live|
|Friendly Fire||12/1998||1999||Blue Note||with Joe Lovano|
|New Directions||05/1999||2000||Blue Note||with Stefon Harris, Jason Moran, Mark Shim|
|The Invisible Hand||09/1999||2000||Blue Note||With Gary Thomas, Andrew Hill, Jim Hall, Scott Colley, Terri Lyne Carrington|
|Symbols Of Light (A Solution)||01/2001||2001||Blue Note|
|Inner Circle||04/1999||2002||Blue Note|
|St. Louis Shoes||01/2003||2003||Blue Note|
|Channel Three||02/2005||2005||Blue Note|
|9 Levels||08/2008||2008||Inner Circle Music|
With Steve Coleman
- Drop Kick (Novus, 1992)
With Robin Eubanks
- Karma (JMT, 1991)
With Gary Thomas
- By Any Means Necessary (JMT, 1989)
- Greg Osby – official site
- Greg Osby discography at Discogs
- Greg Osby discography at JazzDiscography.com
- Greg Osby at Blue Note Records
- Greg Osby interview with Ted Panken at Jazz.com