He moved to Nashville in 1973, attempted to sell his songs to record labels, and then formed the band The X-Rays, who recorded two albums for Rounder Records, appeared on Austin City Limits, opened for Elvis Costello, and broke up in 1985.
Since then, he has performed as a solo singer-songwriter, and released more than 20 albums over four decades, including 6 live recordings. He has collaborated with artists such as John Hadley and Sergio Webb.
His songs have been covered by and co-written with Emmylou Harris, Steve Earle, Johnny Cash, Linda Ronstadt, Steve Young, Del McCoury and Laurie Lewis, and others. Townes Van Zandt, a friend of Olney's (but not family), said "Anytime anyone asks me who my favorite music writers are, I say Mozart, Lightnin' Hopkins, Bob Dylan, and Dave Olney. Dave Olney is one of the best songwriters I've ever heard – and that's true. I mean that from my heart."
2006: Kieran Kane, Kevin Welch, and Fats Kaplin – '"Lost John Dean (Compass – track 5, "Postcard From Mexico" (co-written with John Hadley); track 8, "Mr Bones" (co-written with Claudia Scott, John Hadley, and Kevin Welch)
2007: Mae Robertson – Dream (Lyric Partners) – track 14: "Dream a Dream" co-written with Carol Elliott
2008: Eric Brace and Peter Cooper – You Don't Have to Like Them Both (Red Beet / CoraZong) – track 2, "Omar's Blues #2"
2008: Tim O'Brien – Chameleon (Howdy Skies) – track 3, "The Garden"; track 7, "Chameleon"; track 12, "When In Rome" (all co-written with John Hadley and Tim O'Brien
2009: Del McCoury – By Request (McCoury Music) – track 11, "Queen Anne's Lace"
2009: Kieran Kane – Somewhere Beyond the Roses (Compass / Dead Reckoning) – track 8, "I Took My Power Back" (co-written with Kieran Kane)
