Two Thousand Miles, a fourth studio project, was produced by Maines and was released on January 22, 2008 on El Paisano Records. A review in Allmusic noted "great lyrics full of insight and plainspoken poetry."
A fifth studio album, Dollars and Dimes, was released June 9, 2009. It is a concept album focused on different regions of North America during hard times. In July 2009, the album was the No. 1 record on the Euro Americana Chart. In August 2009, the album was No. 5 on the Freeform American Roots chart.
A sixth studio album, Mountain Home, was released April 26, 2011, and the songs on the album focus on small Texas towns and the eccentrics inhabiting them.