The album was financed by issuing promissory notes in exchange for loans from fans, family and friends of the band.

During these years, Drive-By's principal songwriters Hood, Mike Cooley, and Rob Malone continued to contribute songs to "The Rock Opera", as they had come to call it.

After the release of their live album Alabama Ass Whuppin', Drive-By Truckers began recording what they hoped would be their magnum opus: Southern Rock Opera.

According to Patterson Hood, "(the album) was recorded in Birmingham, upstairs in a uniform shop during an early September heat wave, with no air-conditioning.

The Truckers made a prospectus and solicited investors, with a promise of 15% interest, to pay for the manufacturing and distribution of Southern Rock Opera.

In order to meet demand, Drive-By Truckers signed a large-scale distribution deal with Lost Highway Records.