On this episode of Circling The Drain, Johnny B, Jay Harper and James Patrick McCarthy sit down with guitarist and broadcaster Dez Dickerson – best known as Prince’s original guitarist from the 1999 and Little Red Corvette era.

Dez takes us from his early days in Midwestern cover bands to his legendary audition with Prince, life on the road, opening for the Rolling Stones, his faith journey, leaving the band just as they were about to headline stadiums, and his unexpected path into conservative talk radio.

Along the way, the guys dive deep into Jimi Hendrix’s legacy, the darker side of the music business, the opioid epidemic and fentanyl, and why modern rock rarely hits as hard as it used to.

What you’ll hear in this episode:

- Dez’s wild origin story, starting professional gigs at 14 without even a driver’s license  

- The real story behind his Prince audition and how “having the vibe” got him the gig  

- Inside the infamous Rolling Stones opening shows and how Hells Angels changed the narrative  

- Why he walked away from Prince’s band at the brink of stadium-headliner status  

- Dez’s conversion to Christianity on the Dirty Mind tour and how it reshaped his choices  

- Moving to Nashville, discovering the Christian music business and landing an A&R role  

- How Phil Valentine pushed him toward talk radio – and why the mic felt like home  

- His unapologetically conservative views, pushback he’s gotten, and “clear thinker” philosophy  

- Guitar talk: Hendrix, Eddie Van Halen, Santana, bikers, death metal, and why no one is truly “original”  

- Dez’s thoughts on today’s rock, podcasts vs radio, and what he wants to do next

Hit play for a fast, funny, honest conversation about music, faith, politics and life from someone who’s actually been there, on stage and on the air.

Listen, subscribe, and join the Drain Gang at: circlingthedrain.net

2:47 Dez’s first days with Prince and the audition at an empty tire shop  

3:36 Growing up in Midwest cover bands and touring before he could drive  

4:47 Inside the Prince audition: playing with the band vs trying to “blow them away”  

6:38 Seeing Prince’s real personality after joining the band  

8:04 Opening for the Rolling Stones, Hells Angels and getting “booed off stage” in the media  

10:49 Dez’s conversion to Christianity on the Dirty Mind tour  

11:17 Moral discomfort on stage and the moment he knew he had to leave  

12:38 Intense years in the band and the image from the 1999 video  

13:07 Little Red Corvette solo and Dez’s guitar legacy  

13:19 Why and how Dez moved to Nashville and into A&R  

15:11 Early days in Nashville and culture shock over a little snow  

16:00 How Phil Valentine pushed Dez toward talk radio  

18:01 Discovering talk radio feels like “home” and plans to blend radio and podcasting  

19:41 The story behind the iconic kamikaze headband  

21:27 Fan art, the faceless cartoon band, and Dez as a visual icon  

22:03 Prince’s pain, opioids, fentanyl and the tragedy of his death  

24:49 The opioid epidemic, fake fentanyl and near-misses with pain meds  

26:17 Personal stories of back surgeries, painkillers and dependency  

27:08 Dez’s first guitar, outgrowing lessons and early school gigs  

29:25 Early career breaks, agents, and being “the kid who plays like Hendrix”  

29:53 Guitar heroes: Clapton, Zeppelin, Grand Funk and growing into Hendrix influence  

30:54 Winning over biker crowds and the Stones show irony  

31:30 How Prince fused Sly Stone, Hendrix and the Stones’ Glimmer Twins  

32:17 Hendrix’s unrealized future and his deep influence on guitar players  

34:05 Being the only one at school mourning Hendrix and the “players’ player”  

35:04 Eddie Van Halen, borrowing from Hendrix and other influences  

37:04 Why “best guitarist” debates miss the point  

37:31 Practice, grind and scaring your parents with your obsession  

38:02 Reading music vs playing by ear and learning the Nashville number system  

39:09 Reconnecting with Prince in Nashville and the “show after the show”  

40:49 Sharing the stage with Larry Graham and surreal “Forrest Gump” moments  

41:54 First Avenue stories, U2 and Minneapolis memories  

42:26 Moving from cold Minnesota to too-hot Nashville  

43:03 Dez’s conservatism, being “just to the right of Attila the Hun” and industry blowback  

45:41 Leaving the Democratic Party and becoming a “clear thinker”  

47:16 The problem with political echo chambers, even in conservative talk radio  

48:12 Label me an American: political parties vs founding ideals  

49:31 Why you cannot recreate Phil Valentine and why listeners still compare  

50:09 Radio vs record labels and the business side of both worlds  

51:00 Why copying Phil can never work and why he was a true radio rock star  

52:32 Inside label culture in Nashville and signing left-of-center artists  

53:47 How a meeting with Jimmy Bowen helped shape modern Christian music  

55:01 How Prince’s band wrote and arranged: endless rehearsals and recorded jams  

56:47 Creating The Time, Vanity 6 and how Morris Day got his band and career  

58:32 Writing “He’s So Dull” and Prince “Prince-ing up” Dez’s ideas  

59:17 Classic MTV videos, shooting 1999 and Little Red Corvette  

1:00:19 Spot the reshot close-up in the 1999 video  

1:01:23 Dez’s take on today’s rock and the bands that still move him  

1:02:29 Guilty pleasures: death metal, screamo and Seven Dust  

1:03:16 Darkness in lyrics, the state of the world and wanting more light  

1:03:47 Wrapping up, future plans, Dez’s socials and the “Dez Dickerson Is Based” brand  

1:05:05 Talk of Dez’s book, possible audiobook and closing thanks

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