His next recording was issued as an album with Chris Layton and Tommy Shannon, known as being part of Stevie Ray Vaughan's backing team. Serving as record producers, they also arranged a deal to ensure wider distribution. Only Shannon remained as the bassist for Cummings' next album. Two years later, in 2006, Cummings recorded a fourth album with new band members.
In 2008, Cummings released a live album, recorded at the Colonial Theatre in Pittsfield, Massachusetts This album is controversial as some believe it to have clips of a late 1990s recording that took place at the Rum Boogie Cafe in Memphis, Tennessee. This recording included numerous artist from the delta south.