O'Reilly began his musical journey as a blues guitar player, exploring the works of Blind Willie Johnson, Mississippi John Hurt, John Lee Hooker, Charlie Patton, and Leadbelly. Through extensive listening and studying of the early delta greats, O'Reilly developed a unique foundation onto which he would incorporate themes from influences in other musical veins such as John Fahey, Nick Drake, John Vandiver, and Tom Waits. Whether it be his original pieces, or his renditions of old American classics O’Reilly tells his story through an old and soulful voice, propelled by a sense of authentic emotional adrenaline.
When performing with his trio, The Old Soul Orchestra, O'Reilly is backed by Jeff Kissell on the Double Bass and Chris Lynch on the fiddle. Their versatile musicianship, and soulful chemistry help to expand O'Reilly's songs into pieces that drive like a ten pound hammer, or float like feather and flow seamlessly in-between. The trio was formed in late 2012, and has rapidly made a name for itself along the west coast, being featured at many notable venues and festivals, including Outside Lands Festival (2013), Rivertown Revival Festival (2013), Do It Ourselves Festival (2013), Cafe Du Nord (SF), Hotel Cafe (LA), and Empty Sea Studios (Seattle). The Band released a self titled live album in 2013 and their debut studio album "Pray For Rain" in Spring of 2014.