Whitmore built a long-term relationship with Southern Records, releasing three records on the label. The three records on Southern, 2003's Hymns for the Hopeless, 2005's Ashes to Dust, and 2006's Song of the Blackbird, were a trilogy that were focused on death and his experience processing the deaths of those close to him. He recorded the records with Mike Lust at Phantom Manor in Chicago.
