The album was produced by Earle at his home in Greenwich Village, at Sound Emporium and Room and Board in Nashville, TN and The Nest in Hollywood, CA. The track Lungs, was produced and mixed by the Dust Brothers John King and features Tom Morello of Rage Against the Machine/The Nightwatchman on electric guitar. Earle s wife, the acclaimed singer-songwriter Allison Moorer, is featured on backing vocals on Loretta and To Live Is To Fly. Three songs cut in Nashville, White Freightliner Blues, Delta Momma Blues, and Don t Take It Too Bad feature a bluegrass band consisting of Dennis Crouch, Tim O Brien, Darrel Scott and Shad Cobb.

Earle met Townes Van Zandt in 1972 at one of Earle s performances at The Old Quarter in Houston, TX. Van Zandt was in the audience and playfully heckled Earle throughout the performance to play the song Wabash Cannonball Earle admitted that he didn t know how to play the tune and Van Zandt replied incredibly You call yourself a folksinger and you don t know Wabash Cannonball? Earle then silenced him by playing the Van Zandt song Mr. Mudd and Mr. Gold, not an easy feat due to its quickly-paced mouthful of lyrics squeezed into just over two minutes of song. Their bond was immediately formed. On Townes, Earle and his son, singer-songwriter Justin Townes Earle (named after Van Zandt) trade verses on the tune, a song the two of them have been playing together since Justin was a teenager.

The songs selected for Townes were the ones that meant the most to Earle and the ones he personally connected to (not including selections featured on previous Earle albums). Some of the selections chosen were songs that Earle has played his entire career ( Pancho and Lefty, Lungs, White Freightliner Blues ) and others he had to learn specifically for recording. He learned the song (Quicksilver Daydreams of) Maria directly from Van Zandt, and taught himself Marie and Rake specifically for the album s recording. Once a song he played during his live show, Earle relearned Colorado Girl in the original Open D tuning that Van Zandt played it in. Earle recorded the New York sessions solo and then added the other instruments later on in order to preserve the spirit of Van Zandt s original solo performances to the best of his recollection.