[2] Cummings began playing the five-string banjo at the age of twelve,[3] and developed a love for bluegrass music.

[6] He later worked with Double Trouble and the late Stevie Ray Vaughan's rhythm section.

Bassist Tommy Shannon and drummer Chris Layton voluntarily played on and produced Cummings' solo debut recording, self-released, From the Heart in 2003.

In 2008, Cummings released a live album, Feels So Good, recorded at the Colonial Theater in Pittsfield, Massachusetts.

In 2011, Cummings released an instructional DVD for the Hal Leonard Corporation entitled, Working Man Blues Guitar.