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Signed to Universal South Records, Jennings made his debut with the single "4th Of July" of his 2005 album Put the "O" Back in Country, which peaked at No. Jennings has since followed with six more full-length studio albums: Electric Rodeo (2006), The Wolf (2007), Black Ribbons (2009), Family Man (2012), The Other Life (2013) and Countach (For Giorgio) (2016), in addition to a live album, a compilation, and numerous EPs.