The Bobby Bones Show #534 – Dierks Bentley

Date: September 3, 2025
Host: Bobby Bones
Guest: Dierks Bentley

Episode Overview

This episode of The Bobby Bones Show features award-winning country artist Dierks Bentley for a candid, humorous, and wide-ranging interview. Dierks discusses everything from the realities of sleep struggles and the logistical quirks of married life to the controversy surrounding his latest single, the impact of social media, manifestation, and the ethos behind his Broken Branches Fund for mental health. The conversation is laid-back but insightful, full of personal stories, behind-the-scenes details, and mutual ribbing between old friends.

Key Discussion Points & Insights

1. Sleep Struggles and Relationship Logistics

Conversation: 02:01 – 07:00, 18:31 – 25:00, 28:11 – 31:00

• Dierks candidly shares his lifelong issues with insomnia—both on the road and at home. He discusses every sleep aid tried, from medication to red light beds, as well as nightly routines and technology designed to capture sleep data.
• A unique marital arrangement: Dierks reveals that he and his wife now sleep in separate beds (and sometimes separate rooms), a setup he describes as "separating church and state" to preserve his precarious sleep (28:22).

  "Years ago, I decided to separate church and state and I got rid of our bed. Got two platform beds and two box springs and two mattresses. ... She can move around all she wants ... lately, she's sleeping on the couch now.”
  — Dierks Bentley [28:22]

• They also discuss Scandinavian comforters and why shared beds are overrated for solid rest, referencing scientific studies on sleep disruption (29:53, 30:03).

2. Musical Origins, Influences, and Family Life

Conversation: 07:02 – 13:32, 11:51 – 14:34

• Dierks recounts the story of falling in love with country music at 17, after hearing Hank Williams Jr., leading to a total musical reorientation.

  “…I heard this… and I remember when I heard That's Country, I like kind of fell down in my… sat down in my chair. …I equate it to like meeting my wife. It was one of those moments.”
  — Dierks Bentley [08:02]

• Reveals early attempts at music (from saxophone to electric guitar) and how playing was about changing one’s mood rather than impressing anyone (10:27).
• Family updates: Dierks’ children are involved in theater, hockey, and singing—reflecting a wide spectrum of talents and interests.

3. Touring, Injury Stories & Aging in Entertainment

Conversation: 15:56 – 18:29

• The realities of being an “old guy” on tour are discussed with relatable banter: injuries from pickleball, refusing to warm up before games, and the universal experience of lingering aches as you get older.

  “Those band guys are even younger… we’ll go find a court… I hate warming up. I don’t want to do the dink, dink, dink… And yeah, it's just a small tweak. …You go, ooh, that might hurt a little bit tomorrow.”
  — Dierks Bentley [16:12]

4. Mental Health, Therapy, and Sleep Anxiety

Conversation: 19:44 – 25:00

• Both host and guest open up about sleep-related anxiety, managing mental health, and strategies for coping with negative thoughts—including journaling and gratitude practices.

  "I talk about it a lot. I'm sure everyone the road. I know, they get sick of me talking about it because… don’t sleep.”
  — Dierks Bentley [24:34]

• Bobby describes nightly existential fears and the impact of PTSD from past traumas (23:18).

  “Every night I wonder, that's a lot. Or not wake up at all. ...Odds are we're in a simulation anyway.”
  — Bobby Bones [23:30]

5. Controversy: "She Hates Me" and Single Selection

Conversation: 35:20 – 39:13

• The hosts probe the controversy involving Dierks’ recent single “She Hates Me" — specifically, its similarity to Puddle of Mudd’s song. Dierks admits they proactively credited/added Puddle of Mudd writers after the similarities were noticed.

  “…Nobody in the room goes, oh, this sounds like Puddle of Mud wrote the song. Obviously it was in somebody's subconscious. ...Let’s just put them on the song, who cares?”
  — Dierks Bentley [37:22]

• Dierks expresses the frustration of investing years in albums only for singles to get limited airplay before moving on.

  “You put the song out first ... and you kind of back it up with these other songs, and you give your fans ... a Cliff Notes version of the bigger record in general. But you only get to get the introduction.”
  — Dierks Bentley [36:15]

6. Relevance, Fame, and Media Saturation

Conversation: 39:30 – 45:16

• The group discusses the changing landscape of fame and relevance, agreeing everyone is “a little less relevant now because so many people have relevance.”

  “Everybody's a little less relevant now because so many people have relevance now. And I just wondered if you felt that at all.”
  — Bobby Bones [41:26]

• Dierks is comfortable with the idea, referencing Arthur Brooks' “Second Mountain” philosophy about focusing on new pursuits after one’s peak career.

7. Notable Gifts & Anecdotes

Conversation: 49:24 – 50:44

• Tim McGraw once sent Dierks a box of intimidatingly dense and esoteric books — the “ultimate one-up.” Unclear if prank or real gesture, but very on-brand for McGraw.

8. Manifestation, Passwords, and Life Philosophy

Conversation: 53:13 – 58:15

• Dierks describes how he manifests wishes by literally making them his computer passwords (like “Signature” for private jet travel, “Pete Fisher” before becoming an Opry member).

  “…it hit me like, wow. Like, it did happen in a totally different way than I wanted it to, which is the way the universe works. …I really believe like the power of putting it out there, it will come back to you.”
  — Dierks Bentley [54:43 – 58:15]

• Journaling and gratitude: Dierks endorses the 5-minute gratitude journal, finding it useful for setting intentions and counterbalancing negativity (59:29).

  “It's a place to kind of like set some intentions for the following day or have an attitude of gratitude for the day that’s around you.”
  — Dierks Bentley [60:24]

9. Broken Branches Fund & Mental Health in Music

Conversation: 65:56 – 68:32

• Discussion on Dierks’ Broken Branches Fund, supporting mental health for musicians and touring professionals in partnership with the Music Health Alliance.

  “Everyone in Nashville is a little bit of a broken branch… we kind of create our own family, make our own tree here. So it tied in well…”
  — Dierks Bentley [66:13]

Notable Quotes

• On sleep and marriage:

  "Years ago, I decided to separate church and state and I got rid of our bed. ...And I got two platform beds and two box springs and two mattresses."
  — Dierks Bentley [02:01 and 28:22]

• On musical epiphany:

  “It was a real… I equate it to like meeting my wife. ...It was a very like, thing, like right away at that exact moment. Hard to describe.”
  — Dierks Bentley [08:02]

• On relevance:

  “Everybody's a little less relevant now because so many people have relevance now.”
  — Bobby Bones [41:26]

• On manifesting via passwords:

  "So I made that my password on all my computers and devices... Long story short, I achieved it, but in a completely different way..."
  — Dierks Bentley [54:43]

• On gratitude journaling:

  “It's just a place to kind of set some intentions for the following day or have an attitude of gratitude for the day that’s around you.”
  — Dierks Bentley [60:24]

• On the Broken Branches Fund:

  “Everyone in Nashville is a little bit of a broken branch. We all came here from somewhere else, and we're, you know, we don't, we kind of create our, make our own family.”
  — Dierks Bentley [66:13]

Memorable and Lighthearted Moments

• The Tim McGraw book prank:

  “He sent me a box full of books... every book was this thick… about Russian philosophy, painters... I still can't tell if it's a joke.” — Dierks Bentley [49:24]

• Debate over favorite “old” Dierks song to play live:
  • Dierks teases Bobby for grilling him over not naming a single favorite, saying with mock exasperation:

    “My hand sore from the ruler. Like the ruler kept smashing my wrist about. Wrong answer. Wrong answer.”
    — Dierks Bentley [70:19]

• Existential sleep fears and simulation theory banter.
  • Bobby confesses he sometimes fears going to sleep because he won’t wake up in the same “simulation world.” (23:30)
• Swordplay over reading lists (and accidental flexes):
  • Dierks quips, “Tell me the books you read because I probably read them” — which Bobby and the team highlight as the episode’s “most aggressive” book flex. (49:33)
• Light-hearted pokes at podcast culture:

  "Now someone does a podcast...they'll cut it up in five second snippets... and that's not really the point of the podcast."
  — Dierks Bentley [62:17]

Timestamps for Key Segments

• Dierks on sleeping in separate beds: 02:01, 28:22
• Musical awakening and country music conversion: 07:29 – 08:31
• Pickleball/back pain and aging talk: 15:56 – 18:29
• Dealing with sleep/anxiety/therapy: 19:44 – 25:00
• Controversy over "She Hates Me": 35:20 – 39:13
• Manifestation and passwords: 53:13 – 58:15
• Broken Branches Fund (mental health initiative): 65:56 – 68:32
• Fan-favorite live songs/reflections: 68:49 – 71:00

Conclusion

This episode is as much a relaxed reunion between friends as a deep-dive into the complexities of marriage, artistry, and mental health in the public eye. Dierks Bentley oscillates between humorous stories of daily life and honest discussions of anxieties, aging, and the evolving nature of fame. Fans get a behind-the-scenes look at the making of his latest album, his personal philosophies, and the creative (and logistical) oddities of a life in country music. The exchange is both endearing and thought-provoking—a must-listen for longtime fans of Dierks or anyone navigating similar life (and sleep) challenges.