Recorded in Chicago's House of Blues during the 10 Days Out: Blues From The Backroads tour, Live in Chicago showcases Kenny and his band, Noah Hunt, Chris Layton, Scott Nelson and Riley Osbourn, along with special guests, Hubert Sumlin, Willie "Big Eyes" Smith, Buddy Flett, Bryan Lee and Tommy Shannon (of Double Trouble).

Though an illness nearly kept Kenny from performing that night, his heartfelt commitment to the music (and quite a lot of adrenaline) ensured that he took the stage, sharing with the audience one of the most spectacular performances of his career, and one that fans can now hear on Live in Chicago.

Kenny has been playing since childhood, when he learned Muddy Waters licks by listening to his father's record collection. By 16, Kenny had a deal with Giant Records, and recorded his first album while still in high school. Since then, Kenny has enjoyed two platinum and one gold albums, six Top 10 singles, and his album Trouble Is holds the distinction of being the longest running album on the Billboard Blues Charts, hitting the 2 year mark. Over the course of his storied career, Kenny has amassed four Grammy nominations, two Billboard Music Awards, two Orville H. Gibson Awards, the Blues Foundation's "Keeping the Blues Alive" award and a Blues Music Award. In 2008, Fender released the Kenny Wayne Shepherd Signature Series Stratocaster. 2007's CD/DVD 10 Days Out: Blues from the Backroads was nominated for two Grammy Awards, aired on PBS television nationwide and has been certified RIAA Gold as a Long Form Video.