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
Follow Johnny B:
Follow Jay Harper:
Follow Jim:
Circling The Drain is produced by It's Your Show dot Co