Kenny Wayne Shepherd was all of 18 years old when, in September 1995, he released his debut album, Ledbetter Heights. To say it was successful would be an understatement. The 12-track recording, produced by David Z—whose other clients have included such blues heavyweights as Buddy Guy and Etta James—spent 20 weeks at the top of the Billboard blues chart, selling over half a million copies. By 1996, it had been awarded a gold record and, eventually, it attained platinum status. That’s around the time that an interviewer asked the young guitarist and singer if he feared the dreaded sophomore slump.

“What’s that?” Shepherd remembers asking his inquisitor, who explained that many recording artists release a stellar debut album featuring all of the material they’ve had years to perfect, only to discover— when it’s time to make the next one—that they have no good songs left over.

“I had never even considered that for a moment,” Shepherd, now 44, says. “Then, I was like, ‘I don’t know. Do you think we’re going to?’”

He need not have worried. Trouble Is…, the Kenny Wayne Shepherd Band’s 1997 release, outpaced the guitarist’s debut, sailing to No. 1 on the blues chart. The single “Blue on Black,” one of several tunes Shepherd co-wrote, cracked the trade publication’s singles chart and several other songs, notably the album[1]opening “Slow Ride,” became standards of the blues-rock genre. The album, produced by Talking Heads’ Jerry Harrison, not only featured Shepherd’s eponymous band, but also guest appearances by harmonica great James Cotton and Double Trouble’s Tommy Shannon, Chris Layton and Reese Wynans. The LP was certified gold in 1998 and platinum the following year, ultimately selling more than a million copies.

Shepherd has now had a quarter-century to reflect on the impact of Trouble Is…, and he decided a celebration was in order: As of this interview, a 25-year anniversary run is slated to kick off on Feb. 12 in Shreveport, La.; Shepherd plans to livestream his stop in Virginia on Feb. 20.

“Originally, we had talked about just doing one show as an anniversary, and we thought it would be nice to make that available to people that couldn’t get down to Louisiana for the show or weren’t comfortable traveling,” Shepherd says. “But we started getting so many messages from people saying, ‘Hey, please bring this to our town. Please do more of these.’ So we booked a leg of the tour. But there was so much demand that we’re looking into booking an additional leg. But the Shreveport gig is exceptionally special for me because it’s my hometown. We’re playing the same theater where we did the original album-release party for that record. There’s a lot of sentimental value there for me.”

Shepherd well remembers the circumstances that led to Trouble Is… “You make a record and you really never know what the reaction is going to be,” he says. “You can hope that it’s going to be great, but the rubber meets the road once it gets out there and you see what the people’s reactions are. But when Jerry Harrison played back ‘Blue on Black’ in the control room, it was this amazingly euphoric experience. Everybody was dancing around the room, high-fiving. We knew we had something special. “Having success with the first record gave me confidence in the music that I was creating,” he continues. “I was like, ‘Hey, I’m doing something right. This is working.’ I felt liberated to a degree. I’d proven that what I was doing was working. I felt like I had creative freedom. There wasn’t a bunch of doubt.”

That confidence continued as the band recorded album number three, Live On, which became their highest-charting studio release, reaching No. 52. As the new century dawned, with file-sharing and streaming beginning to replace sales of a physical product, the numbers began dwindling, but Shepherd takes it all in stride. “You just have to keep adjusting how you gauge success,” he says. “In today’s world, for our fans, it’s about ticket sales—putting butts in seats and who’s showing up to come see the band play. That’s really what we do best.” Shepherd is optimistic about the future. Among other plans, he hopes to get back into the studio with his pals Stephen Stills and Barry Goldberg, who released LPs as The Rides in 2013 and 2016. Shepherd also has a couple of albums in the can, recorded before the lockdown, waiting to see the light of day. “We’ve been holding onto that stuff,” he says. “I didn’t think it made any sense to put out new albums when we couldn’t tour. And we have a lot of yet-to-be[1]announced stuff for the 25th anniversary of Trouble Is…

Now that Shepherd’s had plenty of time to fill in the blank that follows that ellipsis, one question remains: “Trouble is… what?” He laughs and says, “Well, if you’d asked me that when I was 16 years old, I would’ve said Kenny Wayne Shepherd. But now, it can be any number of things. I don’t go around causing trouble though. I don’t focus on the negative things in my life nowadays. But back in 1997, it was like, trouble is the Kenny Wayne Shepherd Band. We were out, we had our sleeves rolled up, and we were ready to throw down every night, in every town we went into. I feel like I’ve lived such a blessed life.”