In the early 1980s, he formed the band The X-Rays, which recorded two albums for Rounder Records. The group appeared on Austin City Limits, opened for major acts, including Elvis Costello, and broke up in 1985.
Over the following decades, Olney performed as a solo singer-songwriter, releasing more than 20 albums including six live recordings. He collaborated with artists such as John Hadley and Sergio Webb. His songs were covered by and co-written with Emmylou Harris, Steve Earle, Linda Ronstadt, Steve Young, Del McCoury, and Laurie Lewis, among many others.
Olney was a key member of Nashville’s music community. The Rhode Island native was a compelling and enigmatic presence in Music City. He wrote sonnets and starred at the Nashville Shakespeare Festival, and his live concerts blended tenderness and ferocity, theatre and sincerity, agitation and embrace.