1996 saw his first release with them, Making Light of It, a low-key collection of songs, the majority returning to an introspective demeanor and tone, produced by David Miner (T-Bone Burnett, Elvis Costello), and featuring Derri Daugherty and Steve Hindalong of The Choir.

The music of this record was a delicate and successful blend of a more sparse "roots folk" sound backed by solid bass and percussion and produced by Grammy award-winning artist Gordon Kennedy (best known for co-writing Eric Clapton's "Change the World").

2004's Great Big World record saw Pettis collaborating with a number of other songwriters for the majority of the tracks, with a still-present regional tendency, and similar sound musically to the previous album.

In 2009 That Kind of Love included less of a regional focus with a collection of mostly mid-tempo, personal and contemplative songs, although the three cover tracks on the album, from Mark Heard, Jesse Winchester, and Woody Guthrie, are uptempo blues or bluegrass.

Pettis' songs have been covered by artists like Dar Williams ("Family" on Mortal City), Garth Brooks ("You Move Me" on Sevens), Dion & the Belmonts, Sara Groves, Randy Stonehill, Pat Alger, and others.

These are: "Nod Over Coffee" on Chase the Buffalo; "Satellite Sky" on Making Light of It; "Tip of My Tongue" on Everything Matters, "Rise from the Ruins" on State of Grace, "Another Day in Limbo" on Great Big World; and "Nothing but the Wind" on That Kind of Love.