Osborne was born in Uddevalla, Sweden in 1966. His father was a professional drummer and a jazz fan whose early-'60s combo played clubs across Europe. At a young age, he became fascinated with the singer/songwriters of the '60s and '70s (especially Joni Mitchell's Blue album, whose predominant use of open D guitar tuning became the basis for his own early playing) before tracing their individual roots back to blues and folk. At age 16 he left home and began traveling the world literally playing for his supper, all before he was 20. In 1985 he landed in New York City with only five dollars in his pocket. Making contact with a friend in New Orleans, he hitchhiked to connect. After arriving and taking in the collision of sounds, musics, lifestyles and culture of the Crescent City, he was overwhelmed, but also knew he was home. With the exception of a stint in Nashville working as a staff songwriter, he has lived and worked there since. In 1989, he cut Doin' Fine, his debut, for the independent Rabadash. Break the Chain followed in 1993. Its reception was buoyed by his touring, and sparked interest from Sony's OKeh label. They signed him for 1995's Which Way to Here; the set netted two Top Five singles in "Favorite Son" and "Pleasin' You." 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.
His 2007 recording, Coming Down, issued on the M.C. imprint, was the most intimate collection of songs he'd released yet, and walked the line between the nakedly confessional and his observations about living in New Orleans after Hurricane Katrina. Live at Jazz Fest 2008, featuring Osborne's killer road band, appeared that year.
In 2009, Osborne, who had struggled with substance abuse since he was 13 and a subsequent bipolar diagnosis, eventually got sober after more than a decade of trying. He signed with Chicago's Alligator label and delivered 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 February of the following year. Osborne played gigs with Phil Lesh's Terrapin Crossroads, Tedeschi Trucks Band, Karl Denson's Tiny Universe, and others. Later that fall he returned with the full-length Peace in 2013. Two years later he teamed with the North Mississippi Allstars (Luther Dickinson is a frequent collaborator and old friend) for Freedom Dreams, issued by the band's NMO label. Osborne decided he was done recording for others and created his own Back on Dumaine label to issue his future recordings, and kicked it off with Spacedust Oceanviews, an intimate, laid-back contrast to his Alligator offerings. The set included appearances from Johnny Vidacovich, Ivan Neville, Brady Blade, and Rickie Lee Jones. Osborne also founded the Send Me a Friend organization that year. The group assists musicians in recovery who are at home or on the road. It is an all-volunteer network of sober people who watch over musicians as they travel, helping them avoid temptation.
Osborne had been writing songs at home in New Orleans that contemplated the Southern California singer-songwriter vibe. Wanting to seamlessly fuse two traditions, he teamed with longtime friend and associate, drummer and producer Chad Cromwell. They booked sessions at Brethren Studio in Ojai, California with engineer Niko Bolas. They assembled a team of crack L.A. players: guitarist Waddy Wachtel, keyboardist Benmont Tench, bassist Bob Glaub, Cromwell, and vocalist Windy Wagner-Cromwell. The band tracked a number of songs live and ended up with ten, handling a few overdubs in Malibu, and at Osborne's home studio in Louisiana. The finished offering, Buddha and the Blues, was issued in the spring of 2019. ~ Richard Skelly, Rovi