At the age of 13, Shepherd was invited to play guitar onstage by blues musician Bryan Lee. He subsequently made demo tapes, and a video was shot at Shepherd’s first performance at the Red River Revel Arts Festival in Shreveport. It was this video performance that impressed Giant Records chief Irving Azoff enough to sign Shepherd to a multiple album record deal.
From 1995 on, Shepherd took seven singles into the Top 10, and holds the record for the longest-running album on the Billboard Blues Charts with Trouble Is…. In 1996, Shepherd began a longtime collaboration with vocalist Noah Hunt, who provided the vocals for Shepherd’s signature song, “Blue on Black“. Shepherd has been nominated for five Grammy Awards, and has received two Billboard Music Awards, two Blues Music Awards, and two Orville H. Gibson Awards.
In 2000, Shepherd played guitar on the End Title theme for the animated feature, Batman Beyond: Return of the Joker.
In September 2008, Fender Musical Instruments Corp. released the Kenny Wayne Shepherd Signature Series Stratocaster, designed exclusively by Shepherd. In 2007, he released a critically acclaimed and two time Grammy nominated DVD–CD project, 10 Days Out: Blues from the Backroads. This documents Shepherd as he travels the country to jam with and interview the last of the authentic blues musicians. As they tour the backroads, Shepherd, with members of the Double Trouble Band, play with a host of blues greats including Clarence “Gatemouth” Brown and Bryan Lee, Buddy Flett (with whom he jams at Lead Belly‘s grave), B. B. King, blues harp master Jerry “Boogie” McCain, Cootie Stark, Neal Pattman, John Dee Holeman, Etta Baker, Henry Townsend with Honeyboy Edwards, and a concert session with the surviving members of Muddy Waters’ and Howlin’ Wolf‘s bands, including luminaries such as Hubert Sumlin, Willie “Big Eyes” Smith, and Pinetop Perkins. In 2010 Shepherd was nominated for a Grammy for Live In Chicago which featured performances with Hubert Sumlin, Willie “Big Eyes” Smith, Buddy Flett and Bryan Lee. In 2011, Shepherd released his seventh CD entitled How I Go on Roadrunner Records. In 2014 he released “Goin Home” on Mascot Label Group in Europe and on Concord Records in the US and the rest of the world. In 2015 Shepherd released “Something From the Road Vol. 1,” a live special release for Record Store Day in the U.S.