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From protege to old pro: Kenny Wayne Shepherd reflects on 30 years of playing the blues

The five-time Grammy-nominated guitarist brings his Backroads Blues Festival to Chateau Ste Michelle this Sunday. #k5evening

WOODINVILLE, Wash. — Kenny Wayne Shepherd has spent the past year revisiting and re-recording Trouble Is, the album that made him a breakout star in 1997 when he was 20.

"It's like so much has happened in the past 30 years basically since my career really got off the ground," he told us on a Zoom call from his home in Louisiana. "There's just been a really tremendous opportunity for reflection."

Trouble Is...was home to four top-10 radio hits including, “Slow Ride”, “Somehow, Somewhere, Someway”, “Everything Is Broken” and, of course, “Blue On Black.” This was his second record to reach No. 1 on the Billboard Blues Charts and for nearly two years stayed in the top 10. 

The album also broke into the Billboard Top 200 as well as the Hot 100.

By then Shepherd has already been on the road for five years, starting off as a 15-year-old bespectacled guitar prodigy who wanted to go on tour like his hero Stevie Ray Vaughan.

"For anyone to take a kid seriously that's that young, first of all,  to play in a band was a big deal," Shepherd said. "And then, at the time, I wasn't even singing lead vocals so it was like 'I'm forming the band. It's gonna be my name. But I'm the guitar player. I don't sing. And I'm doing blues.'"

From the start, Shepherd's dad has been his business manager.

"Kenny Wayne had to be involved in every business decision that was made," said Ken Shepherd in a previous interview. "He had to be in every meeting with the lawyer and record company execs that we did because to me that was important."

"At a young age, sometimes that stuff goes in one ear and out the other, but really it all kind of penetrated to some extent," Kenny Wayne Shepherd said.

On Late Night With Jimmy Fallon, Shepherd once played the same Stratocaster Jimi Hendrix played at Woodstock. Paul Allen lent it to him for the evening.

"It's a unique experience for sure," he said. "The guitar kind of like had this energy about it. I'm just stating facts. Like when the guitar entered the room everybody was like all abuzz.

"It wasn't set up for me and I didn't touch it because I didn't have the audacity to make any modifications to the guitar, so I kind of struggled a little bit in certain moments because it was kind of fighting me. It was set up that way for Jimi Hendrix so that was good enough for the moment for sure."

Kenny Wayne Shepherd is 45 years old now. He has six kids and a garage full of super-charged cars. We asked what he thinks about when he solos, or whether everything coming out of his guitar is instinctual.

"It's a combination of things," he said. "It's really completely dependent on what is happening in the moment. That's a beautiful thing about music for me. It's one of those things that really forces you to be completely in the moment. You're not in the future ,you're not looking back on the past. It's like you have to focus now.

"And then the most magical moments are when there are no distractions and you're just completely 100% in the moment and you're able to just really let go and let the music kind of carry you through."

Kenny Wayne Shepherd brings the Backroads Blues Tour to Chateau Ste. Michelle Sunday. Joe Bonamassa, Bobby Rush and King Solomon Hicks are all part of the lineup.

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