Osborne artfully blends blues, funk, soul, and classic R&B to create his own distinctive synthesis of styles. Osborne's most widely available early album is 1995's Which Way to Here, recorded for OKeh/Sony; two other independent label releases from the late '90s and early 2000s may still be around for those willing to search: Live at Tipitina's appeared on Shanachie in 1998, followed by Living Room the next year. The introspective Ash Wednesday Blues was issued in early 2001. In 2002, Osborne cut his final two albums for Shanachie, the wonderfully raucous, enigmatic collaboration Bury the Hatchet with Big Chief Monk Boudreaux of the Mardi Gras Indian Tribe the Golden Eagles, and the blues- and Americana-drenched Break the Chain.
He didn't record again until 2006, when he released the larger band session Osborne Orchestra. Osborne was playing nonstop in New Orleans and occasionally in Europe during this period. His 2007 recording, Coming Down, issued on the M.C. imprint, was the most intimate collection of songs he released to date, and walked the line between the nakedly confessional and his observations about living in N.O. after Hurricane Katrina. Live at Jazz Fest 2008, featuring Osborne's killer road band, appeared that year.
In 2009 he signed with Chicago's Alligator label. His first offering for the imprint was the driving, boisterous American Patchwork, issued in 2010. Osborne toured nearly nonstop after the album and produced recordings for Johnny Sansone, Tab Benoit, and Mike Zito. He released Black Eye Galaxy in the spring of 2012; he co-produced the album with Galactic's Stanton Moore and Warren Riker. During relentless touring to celebrate what was his most critically acclaimed album, Osborne took a break late in the year to record the uncharacteristically casual Three Free Amigos, a semi-acoustic, six-track EP, which was released in Feburary of the following year. Later that fall he returned with the full-length Peace. ~ Richard Skelly, Rovi