Takin' A Walk: Music History with Buzz Knight

Episode: Kenny Wayne Shepherd – Blues, Guitars, and Inside Bob Dylan Stories

Date: January 12, 2026
Guest: Kenny Wayne Shepherd
Host: Buzz Knight

Overview:

This episode of "Takin' A Walk" dives deep with blues guitar virtuoso and songwriter Kenny Wayne Shepherd. From recounting his early inspiration and family influence to sharing behind-the-scenes stories with legends like Bob Dylan and Eddie Van Halen, Shepherd gives an insightful look into a prodigy’s path through the evolving world of music. He also explores the blues, creative process, the balance between innovation and tradition, and advice for the next generation of musicians—all in his candid, passionate style.

Key Discussion Points & Insights

1. Musical Upbringing and Family Influence

• Father’s Role: Kenny credits his father—a disc jockey, program director, and music lover—for immersing him in every genre of music and giving him backstage access to concerts.

  “We had music playing around the house all the time, in the car, everywhere we went, and all different kinds of music too.” (02:22, Kenny)

• Early Exposure: Meeting musicians and the touring side of music business as a kid "contributed to who I would eventually be... but at that age, nobody had a clue at that point." (03:36, Kenny)

2. Key Early Inspirations

• Stevie Ray Vaughan Experience: At age seven, seeing Vaughan perform was "life changing... gave me relentless determination to learn the instrument because I wanted to figure out how to play with that kind of passion and intensity..." (04:01, Kenny)
• Other Influences: Hank Williams Jr., James Brown, and a variety of genres, absorbing "something away from each one of them." (04:55, Kenny)

3. Teen Prodigy and Personal Identity

• 16-Year-Old Breakout:
  • Shepherd recalls the "child prodigy" label and insists the guitar became his "companion... the friend you could always rely on. So it ended up giving me an identity and a purpose... which is not common." (05:34, Kenny)
  • Signed his first record deal at 16 and started recording at 17:

    “I signed my record deal when I was 16… that's very abnormal. But it gave me a lot of things that I think were really important to me as a teenager at the time and certainly have served me well through my adult life.” (06:58, Kenny)

4. Influence of Jimi Hendrix and Innovation

• Creative Permission & Groundbreaking Sound: Hendrix’s use of limited technology and blending of genres taught Shepherd he could “take elements of all the things that I had been exposed to and combine them and try and create something that sounds a little bit different.” (07:48, Kenny)
• Trusting the Artist’s Journey:

  “Each album, I mean, there are certain common themes… but you listen to the songs on my newest albums... you’re hearing things that you haven’t heard from me ever before.” (10:13, Kenny)

5. The Making of 'Dirt on My Diamonds' Volumes 1 & 2

• Studio Magic: Prefers the “old school way of making records,” leaving creative space and building songs live with his band. (13:10, Kenny)
• Companion Albums:
  • Both volumes recorded in the same sessions, released separately to keep fans engaged and to fit listening habits: “Eight-song record…there’s no filler, every song has a legitimate purpose.” (13:10–16:30, Kenny)
  • Comments on the return to tighter albums: “Some of the most iconic albums ever recorded have eight songs on them... It goes back to the days when vinyl albums... you can only put so much music on each side." (15:50, Kenny)

6. Sequencing and Listener Experience

• Curating the Journey:

  “We put a lot of effort in the order that the songs are in… the experience of the listener… what keeps it interesting and doesn’t become boring.” (17:19, Kenny)

7. Road Tripping Soundtracks

• Car Culture: A self-confessed gearhead, Shepherd says sometimes the best music is the “sound of that V8 engine.”
  • Go-to album for road trips: ZZ Top’s Fandango! (18:39, Kenny)

8. Working with Legends

• Bob Dylan:
  • Two tours opening for Dylan who defied all negative rumors:

    “When I met him, he was the exact opposite… every day, I did a sound check, he came out and watched… walked right up to me and he shook my hand... big lesson: you really have to treat every individual encounter as a unique situation.” (19:55, Kenny)

• B.B. King:
  • Observations on King’s unique playing:

    “He never really played rhythm guitar… he always weaved his guitar playing in and out in between him singing, but he always had such a big band backing him up that could fill in…the musical gaps.” (23:45, Kenny)

• Eddie Van Halen:
  • Friendship forged over two tours:

    “Every day, Ed came and found me wherever I was... he always went out of his way to spend time with me and make me feel important, and that was really special.” (33:03, Kenny)

  • Fascinating family connection—Kenny’s dad introduced Valerie Bertinelli to Eddie Van Halen.

9. Embracing Change in Live Shows

• Introducing Horns:
  • “...It was really cool to experiment. And because I had used them on so much of the record [The Traveler], then I decided I needed to bring horns out on the road.” (26:24, Kenny)
  • Continues to use horns for evolving sound and to keep the live experience fresh.

10. Production Philosophy: Realness over Perfection

• Pop Music and Authenticity:

  “Pop music... can become so saturated that, like, you could hear five different songs, and they all sound like they could be the same artist... That’s not striving for perfection. That’s trying to cash in on what’s trending.” (28:45, Kenny)

  • Strives to capture “the essence of a live performance in the studio… sometimes there may be a missed lick here and there... but we got the vibe, and that’s what’s most important.” (29:15–30:40, Kenny)

11. Legacy, Mentorship, and Advice

• On the New Generation:
  • Celebrates up-and-coming blues talent and, now part of the “older generation,” sees the genre’s future in good hands:

    “Crhis Stone 'Kingfish' Ingram, Samantha Fish, Ally Venable… there’s a lot of good young talent out there.” (31:23, Kenny)

• Advice to Young Artists:
  • Don't be obsessed with numbers or instant gratification:

    “If you just play music for the love of playing music, and that’s your reason for doing it, then there won’t be all this disappointment attached to it…” (37:27, Kenny)

  • Emphasizes patience, authenticity, and focusing on the intrinsic joy of music rather than chasing success metrics.

Notable Quotes & Memorable Moments

• On Creative Evolution and Genre Boundaries:

  “By listening to [Hendrix’s] music... he was very blues-based... but he didn't just stop right there. He took it and ran with it... gave me permission to do the same thing.” (08:58, Kenny)

• On Touring with Bob Dylan:

  “He was so nice to me. He was so outgoing... every single day, I did a sound check, he came out and watched my sound check. And then... he walked right up to me and he shook my hand. He would stand there and talk to me every day.” (20:35, Kenny)

• On Perfection vs. Authenticity:

  “If you try to make things perfect, then it also…it can possibly lose the realness in the music, you know, because it’s too perfect. So I embrace some of the flaws.” (29:15, Kenny)

• On Advice to Young Musicians:

  “Play music for the love of playing music... If it works out, then that's fantastic. But if it doesn't work out, that's okay too. Don't let it take away your joy of playing music.” (39:43–40:50, Kenny)

Timestamps for Major Segments

• Early Family and Musical Immersion: 02:14–03:52
• Key Performances & Inspirations: 04:01–05:08
• Teen Prodigy, Identity & First Deal: 05:34–07:30
• Hendrix & Musical Freedom: 07:48–09:50
• Creative Process for New Albums: 13:10–17:19
• Album Sequencing and Listener Experience: 17:19–18:19
• Driving Soundtracks: 18:39–19:31
• Dylan Stories: 19:55–22:25
• BB King Guitar Lessons: 23:45–24:58
• Van Halen Friendship & Shared History: 33:03–35:32
• Advice for Young Musicians: 37:27–41:00

Concluding Themes

Kenny Wayne Shepherd’s journey is rooted in honest love for the guitar and music discovery, never satisfied to stay in one genre or rest on prior achievements. His respect for tradition is matched by a desire to innovate, and his stories—from jamming with legends to reflecting on new voices—offer a generous, hard-won wisdom for anyone passionate about music’s past, present, and future.