Kenny Wayne Shepherd: Revisiting His Landmark Blues Album Trouble Is… at 25

Kenny Wayne Shepherd: Revisiting His Landmark Blues Album Trouble Is… at 25

Written by Ray Chelstowski

The most impactful blues artists have always been able to transcend the genre by seamlessly ushering in outside influences that add colors and texture to a foundation that is timeless but also fairly structured. Kenny Wayne Shepherd is among those who have lifted the blues to new heights by combining his seemingly endless sense of musical curiosity with boundless amounts of creativity. Since his onstage debut in the early 1980s at age 13, he has always found a way to pay homage to the past and balance it with an eye toward the future. 2023 is already shaping up to be a year where this mission will be expressed in ways that continue to wow his fans.

It begins with a revisit of his 1997 breakthrough record Trouble Is…, the longest-running album ever on the Billboard Blues charts. To celebrate the album’s 25th anniversary, he reassembled almost everyone involved with the project and re-recorded it track by track. The new edition, Trouble Is…25, presents the music with a fidelity that is nuanced by experience from the road that make the songs’ sonic impact even stronger. It has more punch than the original and even more character.

Shepherd will also return to the road beginning in May with a follow-up to last year’s inaugural Backroads Blues Festival. It’s inspired by B.B. King’s famous annual Blues Festival tours, which ended with his passing back in 2015. Once again, the Backroads Blues Festival will find Shepherd operating as a traveling ambassador for the blues.

As if that wasn’t enough, Shepherd and his band made use of some rare downtime last fall and knocked out two new records worth of material. Copper had the opportunity to speak with Kenny about these projects and what gets his creative juices going. Given the recent passing of David Crosby, we also asked Shepherd what the odds are that he and Stephen Stills might be able to reunite their supergroup, The Rides, for one more spin.


Kenny Wayne Shepherd, Trouble Is…25, album cover.


Ray Chelstowski: How far in advance of the Backroads Blues Festival did you begin work on putting things together?

Kenny Wayne Shepherd: Well obviously it’s a process. As soon as we finished the one last year we were already in discussions about what we could do for this year and who we might want to have involved. The first thing we do is compile a list of where we want to go and who we want to be involved, then we begin to plan out all of the logistics involved in getting it off the ground.

Last year was the inaugural run. It was more about “proof of concept” and we had an amazing lineup with Buddy Guy, Christone “Kingfish” Ingram, and my band. So this year to have Joe Bonamassa with us for a couple of shows and King Solomon Hicks, Eric Gales, and some others that we are talking to makes this about bringing the best people in the genre together.

RC: You’re going to take this on the road, but have you ever considered doing it in a single residency?

KWS: We could do something like that depending upon the market, but I don’t it should be exclusive to one market. I think being stuck for three to six months every night doing the same thing in the same city isn’t for us. If we ended up doing multiple nights at a place like the Beacon or the Ryman that would be fine because it wouldn’t be the beginning and end of the tour. To me, bringing the music to the people through traveling and everything that comes with it is all part of the experience.

Thinking forward, if this becomes something that always happens in the month of June or is peppered through the spring and summer touring experience, it can either help people plan ahead or allow us to have a different line up every night depending on the venue and the location. Either way works for us as long as we give the fans an amazing show.


RC: This festival was inspired by B.B. King. What inspired you to do the 10 Days Out: Blues from the Backroads documentary and what were you hoping to achieve?

KWS: The whole purpose of this was to give the blues community something really amazing that showed my appreciation for the genre and the artists who came before me. It was also a vehicle to get more exposure for some of the featured artists who maybe had never broken out into the mainstream; [but] not for any lack of talent. I also made it a point that every song that we wrote and performed for that project would be owned by the artist so that they would get publishing income from it. We didn’t want them to perform someone else’s music. I wanted these people to financially benefit from this. Lastly, it was an opportunity to play with some [musicians] who I had already known, and some who I were meeting for the first time.

RC: You’ve been able to expand the boundaries of the blues without losing your footing. How do you know how far you can push the music toward any other direction before it loses its connection to the blues?

KWS: That is something that you just know intuitively. But depending upon who you talk to, some hard-core blues fans might say that all of my music is too far in one direction. That’s all completely subjective. I’ve had my moments where I’ve known that the song I’m recording isn’t the blues. In fact, my fourth album (The Place You’re In) is a straight-up rock record. I had no problem doing that or admitting that at the time. I’m a multi-dimensional artist. I don’t think that I am placed in one box, nor do I want to be.

My musical aspirations are pretty wide. Although, the blues is the foundation of everything that I’ve done.

RC: You release new studio albums every two to three years. How do you know when it’s time to record?

KWS: A lot of it is schedule-related, trying to find an opening when we can go into the studio and seize the moment. We actually have almost two albums worth of material already recorded, mixed and ready to go. Back in October we had an opening in the schedule and we decided to do a rock and roll covers album recording “outside of the box” rock songs. When I cover songs I like to pick the ones that aren’t the most obvious. I like when people are surprised to hear that our band covered a certain song and that they think it sounds great. So we did a record of songs like that just for the fun of it. I love the creative process, the touring, and things that are fun. If we are having fun it translates through the music.

RC: Was there something that you have often wanted to revisit with Trouble Is…25 that this 25th Anniversary edition allowed?

KWS: If there was ever an opportunity to go back and change something that’s been bothering you for 25 years this would have been it. When we went into the studio I told everyone that we were going to do two versions of this record. We’re going to do one where we get as close to the sound of the original as we possibly can without breaking it down to a molecular level. Then as soon as that was done I told them we were going to do the same songs but the way that we play them live, which is how they’ve evolved over all these years.


What’s interesting is that as I started listening back to decide which version we would put the finishing touches on, it became glaringly apparent to me that the further we got away from the original album the more we started to lose what was really special about the original record, which was the vibe. So the final version of the record is very close to the original with subtle changes on vocals and guitar, but that sounds like the album that [everyone has] been enjoying for 25 years. As they listen to this version a little more closely they’ll pick up on these adjustments and begin to like the record even more.

RC: Recently you’ve had a steady relationship with producer Marshall Altman. Did you turn to him for this anniversary project or did you reach back out to original producer Jerry Harrison [of the Modern Lovers, Talking Heads, Tom Tom Club and others]?

KWS: No, Jerry Harrison produced this too. We brought everyone back that we could. Tommy Shannon from Double Trouble had retired several years ago so we did didn’t have him on bass. But we had Chris Layton on drums, Reese Wynans on keys, myself, and Noah Hunt on vocals. We even had my old A&R guy come by the studio for a few days. So we kinda had the whole team back together. It was pretty awesome actually.

RC: With the passing of David Crosby, have you had any conversations with Stephen Stills about reuniting The Rides?

KWS: We were talking about making another record right before COVID happened. We just played together at a concert in San Francisco back in December, and we are actually going to be playing together next week in Las Vegas as part of an all-star group for my friend Jim Irsay (owner of the Indianapolis Colts) who puts on these free concerts. He and I love playing together, so who knows?


Header image courtesy of Mark Seliger.

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