The album was recorded in Tepoztlán, Morelos, Mexico between January and February 2008. A temporary studio was created in a mountain villa called Valle Místico at the outskirts of town. Conor Oberst was produced by Conor Oberst and engineered by long-time associate Andy LeMaster. A new band was assembled for the recording, which came to be known as The Mystic Valley Band. The result is Oberst's fourth solo album, and his first in twelve years, following Water (1993), Here's to Special Treatment (1994) and The Soundtrack to My Movie (1996). In that time he has recorded and performed in many bands and musical projects including Commander Venus, Park Ave., Desaparecidos, and most notably Bright Eyes. The song "Moab" was number 31 on Rolling Stone's list of the 100 Best Songs of 2008.[4]
Entertainment Weekly said that on the album, "Conor sounds like Bright Eyes, only heightened--brighter, if you will: He's emo balladeer, country rocker, and ferocious folkie rolled into one."[15]
The seventh track, "Eagle on a Pole", was inspired by a comment made by Sean Foley who said, "I saw an eagle on a pole. I think it was an eagle." Simon Joyner, friend and mentor of Oberst, said that line would be great for a song, which planted the seed for others in the band to write a song from the line. Oberst's version is on this record. Jason Boesel's version is on the second album released by the Mystic Valley Band, Outer South.