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Almost all of Isbell's family, except his parents, were musicians, and his father was an avid music listener. After some work as a songwriter, in 2001 Isbell joined the rock band Drive-By Truckers while they toured in support of their album Southern Rock Opera. Isbell recorded and wrote with the Truckers for their next three albums, and for most of this time was married to the band's bassist Shonna Tucker, though the two later divorced.

On April 5, 2007 Isbell announced that he was no longer a member of Drive-By Truckers. The following day, Patterson Hood confirmed the break on the band's official site. In his letter to the fans, Hood described the parting of ways as "amicable" and expressed the hope that fans would continue to support Drive-By Truckers as well as Jason's solo efforts.

Jason Isbell released his first solo album, Sirens of the Ditch, on July 10, 2007.

Jason Isbell and The 400 Unit's eponymous album was released on February 17, 2009 on lightning Rod Records. Jason Isbell and The 400 Unit is Isbell's second solo release and his first release with his band The 400 Unit.

SLANT MAGAZINE - "The result is that, in both content and form, The 400 Unit is an unapologetically Southern album, and the lived-in authenticity of its performances, masterful songwriting, and fierce intelligence also make it one of the finest albums of what has already been a strong year for popular music."

THE ONION - "Sirens is the sound of a freshly liberated songwriter scouring his soul - and coming up full-handed."