Kenny Wayne Shepherd went from tearing through cheap plastic toy guitars bought with his grandmother’s grocery reward stamps to playing the white Stratocaster Jimi Hendrix used at Woodstock on national television. This episode traces the unorthodox musical education of the blues rock guitarist born Kenneth Wayne Brobst in Shreveport, Louisiana in 1977, the son of radio personality and concert promoter Ken Shepherd, and explains how he reached the top of the industry without ever learning to read a note of written music.

We begin with the Labor Day weekend in 1984 when a seven-year-old Shepherd met Stevie Ray Vaughan, the plywood Yamaha knockoff with punishing high action that built his hand strength, and the cassette-rewinding method that wired his ear to the microtonal blue notes sheet music cannot capture. From a video of his first public performance at the Red River Revel that reached Irving Azoff and a multi-album deal, we follow seven top-10 singles, the record-setting run of Trouble Is, the decision to hand lead vocals to Noah Hunt on Blue on Black, and The Rides with Stephen Stills and Barry Goldberg. We also examine 10 Days Out: Blues from the Backroads, the 2021 controversy over the Confederate flag on his General Lee replica, and his return to number one with Dirt on My Diamonds.

• Why a plywood guitar and no tutor may have been a hidden blessing for a blues player
• Getting invited on stage by Bryan Lee at 13 and signed by the chief of Giant Records
• Five Grammy nominations and stadium tours opening for Van Halen, the Rolling Stones, Aerosmith, Bob Dylan and the Eagles
• Jamming with B.B. King, Etta Baker, Hubert Sumlin and Pinetop Perkins on their own turf, and at the grave of Lead Belly with Buddy Flett
• The Blues Foundation’s revoked nomination, Shepherd’s public apology, Trouble Is 25, and the question of whether a machine can ever play the blues