By November of 2016 Whitley was in a rut. Tied to a part-time job and music not paying the bills he was battling homelessness and sleeping in guest bedrooms when he could. Yet he was able to record Lay Me Down In Roses during this period using a single microphone in an old movie theater he had access to. The album was met with favorable reviews with many critics recognizing the influence of John Prine and Tom Waits on Whitley's writing as well as celebrating the feel of the album. The success of Roses allowed Whitley to share the stage with Jason Wilber of John Prine, and make headlines and TV appearances.
Whitley’s newest album Moon Songs is a collaboration with a fellow local artist named Charlie Haskins. Haskins, a painter and illustrator, put paintings to Whitley’s songs, and Whitley in turn put songs to Haskins’s paintings. It too was met with success. With mounting success, Whitley becoming a must see in the Ohio area.