During his first decade in New Orleans, Anders lived in the French Quarter and played regularly in local clubs. After gaining a following, Anders received an independent record deal with Rabadash Records out of New Orleans, and released "Doin’ Fine" in 1989.
Anders and his band toured the U.S. during these years and in 1995, he was signed to Okeh Records. He released "Which Way to Here", and album that dealt with spirituality and tolerance. The record became Osborne’s first commercial break with two top-five singles “Favorite Son” and “Pleasin’ You.” Both were featured in several Hollywood movies, and the latter was later recorded by Jonny Lang.
Shanachie Entertainment signed Osborne in 1998 and in 1999 released his fourth album, "Living Room", a very personal record that signified some new directions in Anders’ music after the breakup with his longtime partner Theresa Andersson, drug use, and a family death. This album also features guest appearances by Keb Mo, Kirk Joseph and Tommy Malone.
Keb' Mo's 1999 Grammy award winning album "Slow Down", featured two songs co-written with Osborne.
Since 1994, Anders has been working as a professional songwriter in Nashville, first for Polygram and now for Universal where he writes and produces for other artists.