Kenny Wayne Shepherd is a blues-rock guitarist and songwriter with one foot in the future and one foot in the past. Honoring the past is something blues artists do, but Shepherd has revisited his own past by rerecording his second album, Trouble Is… (which includes his biggest hit, “Blue on Black”) 25 years after its release—thus interpreting the same material at ages 20 and 45. Now Shepherd is releasing an all-new album, Dirt on My Diamonds Vol. 1, that has a modern snap along with those big riffs and expressive solos. How have his playing and writing evolved since he launched his career at age 18 with Ledbetter Heights? How do his songwriting collaborations work? How does he keep his solos fresh? And what happened when he dreamt a great song and then woke up? (Photo by Mark Seliger)