“Shepherd is still standing high atop the blues-rock guitarist heap, blazing his way with a sound and fury rarely heard today. The fact that the self-taught guitar virtuoso has never learned to read music has been a plus, freeing him to create and play his own way.” -- Shepherd Express, August 2011

By his own admission, Kenny Wayne Shepherd hit the jackpot more than 30 years ago when he began playing professionally as a teenager.

While still in high school, the 16-year-old was signed to a record label and made his first album, "Ledbetter Heights." To say he was a child prodigy is probably an understatement. He grew up in household filled with music and a father who was the program manager for a Shreveport, Louisiana, radio station. When he was four, Shepherd’s grandmother redeemed her books of S&H Green Stamps to buy him a plastic guitar with nylon strings. When he wore the guitar out, she got him another one.

“I picked up the guitar because I loved music and I loved playing that instrument," Shepherd said. “Our family listened to B.B. King, Hank Williams, Aretha Franklin, Muddy Waters, you name it. If it wasn’t playing in the house, it was on the car radio.”

Shepherd became more proficient on the guitar by playing his favorite songs over and over on a cassette tape recorder, which allowed him to learn the song one note at a time. His first electric guitar was a cheap Fender Stratocaster copy made by Yamaha. But he doggedly kept at it, and by the age of 13, Shepherd was being invited to join established bluesmen on stage to play. 

“Looking back, I realize that I’ve always been a goal-oriented person,” Shepherd said. “Setting goals and accomplishing them is good for a person’s self-esteem, their feeling of well-being.”

Shepherd’s second album, “Trouble Is,” was released in 1997 and spawned a best-selling single, “Blue on Black.” Over the next two decades, he released nine more albums while building a massive fan base, many of whom remain loyal to this day.  

Back on the concert tour circuit after nearly two years of COVID lockdowns, Kenny Wayne Shepherd returns to Milwaukee on Thursday, April 28. Prior to his Pabst Theater show, Shepherd spoke with OnMilwaukee about his career, major influences, and spending time with his wife and five children.

OnMilwaukee: You’ve been married for 16 years and now have five kids. You travel a great deal, so how do you maintain those critical family relationships? 

Kenny Wayne Shepherd: I really have only two commitments in my life. The first is to my wife and my children, and the second is to my fans. I grew up Christian and was raised to believe in God. I’ve always tried to do what’s right according to my faith. Keeping the proper balance between family and work responsibilities is what matters most, and I don’t neglect either of them. Typically, I’ll do four weeks on the road and then come home for a while. All my band members have families, and there’s a reason we need to spend time at home. The band takes an extended break in December, January and February, so there’s some more quality time to reconnect.

There’s a dark side to being a successful musician. A lot of people were unable to avoid the pitfalls of fame.

I’m no stranger to that lifestyle. Every one of us has some sort of run-in with that. When I got started, I was still young enough to experience the golden age of crazy rock-and-roll and the behavior of the people we looked up to. You know, like Joe Walsh using a chainsaw to cut out the wall in his hotel because they wouldn’t give him an adjoining room. We’re all watching this, and thinking, "Yeah, we’re making it and this is what we’re supposed to do too." I’m grateful that I didn’t spend too much time on that path. I wanted to make music and all the other stuff was just too much for me to handle. I stopped doing chemicals, and I haven’t had a drink in 20 years. 

Young people look up to you now. 

They know my story; they know I first found success as a teenager. I try to be the best example for them that I can.

Are you a great guitar player?

Am I a great guitar player? That’s not for me to answer. Other people can speak to that. I guess my fans think I’m pretty good. Their opinions are very important to me. Winning awards doesn’t matter to me. I don’t care what some committee or block of voters think. It's my fans that matter. I didn’t pick up the guitar when I was young and think, "I sure hope I can win an award someday." I picked up that guitar because I wanted to play music. I think I’ve worked very hard to get where I am, but if you ask a bunch of people who’s the greatest guitar player, you’re going to get a bunch of different answers. It’s subjective. In the end, it’s what the listener enjoys. Personally, I feel responsible to give credit where credit is due, to acknowledge the musicians who came before me and inspired me to do what I do. They created the genre that I play in, they paved the way.

Then let me ask the question another way. Name some people who influenced your progression to where you are now. 

I love listening to musicians who can make me feel something deep inside. That comes from players who can channel their feelings and emotions into their music. To play from your heart matters more than dipping into a bag of guitar tricks. I learned that by listening to B.B. King, Stevie Ray Vaughan, Hendrix, you know? There was nobody like Albert King. He could hit one or two notes and milk that sound just the right way. He could bend those notes and let them hang out there for the perfect length of time. I really appreciate those players who have a far greater vocabulary on guitar than I have. They can do things that I can’t.

You do a lot of great cover songs – stuff from Bessie Smith, Freddie King, Bob Dylan, those are some that come to mind. What made you want to cover The Beatles’ “Yer Blues”?

My mom loved The Beatles and I wanted to do something from them, but their music really wasn’t my style. I heard “Yer Blues” on a radio station while I was in Los Angeles, and I loved the bluesy sound on that one. I love our cover of it. I think we really killed it!

You’ve performed in Milwaukee almost 20 times, but your first show in Wisconsin was in 1995 at the Club Tavern outside of Madison.

That sounds about right. We’ve played so many shows in 30 years that I have trouble remembering them all. But that would have been our first tour outside of the Texas, Louisiana and Arkansas circuit. At that time, we were just starting out and making a name for ourselves. Back then, a band would play places that held maybe 200 or 300 people and be happy for the exposure. Today a band can put themselves in front of fans using their favorite media platforms. It’s the 21st century way to let them know who you are and stream your music to them. We have a huge social media presence to stay in touch with our fans. Personally, I’m an old school guy. I love vinyl.  But it doesn’t matter what I like. You have to go where your industry is going or you’ll be left behind.

A few years later, you played your first show at the Summerfest musical festival.

It was great to see the hard work paying off. Our audiences were getting bigger. But all I recall about that show was that Luther Allison was on the bill with us, and I got to watch him play his set. I was a huge fan of his.

What can the audience expect from the Kenny Wayne Shepherd band on this tour? 

Everybody is fresh and playing well. COVID took us off the road for nearly two years, and I got pretty rusty. I wasn’t about to get up on stage and embarrass myself in front of the audience, and I didn’t want to let the guys in the band down, so I spent a couple of weeks really playing a lot to get back in shape and regaining my speed and dexterity. I feel great. This is the 25th anniversary of “Trouble Is," the second album of ours. We’re going to perform the entire album live, which is something we’ve never done. The second half of the show is a lot of fan favorites and few surprises. It’s fun for us, and it’s going to be fun for the audience.