The HoneyDew with Ryan Sickler – Episode 353: Josh Wolf - Taking My Son to Rehab

Release Date: September 29, 2025
Guest: Josh Wolf
Theme: Stories from life’s lowlights, specifically Josh Wolf’s candid, difficult journey as a father taking his son to drug rehab.

Episode Overview

This episode of The HoneyDew goes deep into family, addiction, recovery, guilt, and personal growth as comedian Josh Wolf returns to discuss the painful chapter of taking his son, Jacob, to rehab. Employing the show’s signature humor and vulnerability, Wolf and host Ryan Sickler explore the complexities of parenting through addiction, personal regret, boundaries, and the many shades of parental love. The conversation unpacks not just the act of intervention, but the introspection and aftermath that follow.

Key Discussion Points & Insights

1. Opening Catch-Up & Wolf’s Recent Work

• Josh and Ryan start with some banter, shoutouts to Patreon stories, and plug their current projects.
  • Notable: Josh’s "Campfire Special" (YouTube, [06:46]), the relaunch of his podcast with his son as "Generation Wolf", and his tour with Jacob.

2. Touring with Jacob: The Decision and Dynamics ([10:34]–[13:14])

• Josh describes the pros and cons of touring with his son. Despite many “cons,” the main “pro”—time together—always wins.

  • “I could have listed 100 cons and only had one pro. And as long as that pro was I get to spend time with Jacob, it didn’t matter what the cons were.” — Josh Wolf ([11:20])

• Wolf explains how their genuine on-stage chemistry and shorthand developed, their close relationship, and their “one room, two beds” set-up to keep boundaries clear.

3. Parenting, Drugs, and Generational Change ([13:14]–[17:52])

• Josh opens up about his own attitudes towards weed and psychedelics, describing his transparency with Jacob but strict boundaries about hard drugs.
  • “I have zero tolerance for cocaine. I have zero tolerance for meth... when I was trying it, you weren’t dying from a bump.” — Josh Wolf ([20:08])
• Discussion on the shifting culture around weed and how it affected his parenting and perspectives—with both hosts admitting their thoughts changed as society did.

4. The Discovery: Jacob’s Addiction ([23:55]–[25:32])

• The heartbreaking moment: Josh and his partner Beth receive a text from Jacob overseas, admitting he is a drug addict and feels helpless.
  • “It did say in the text, I’m an addict. I’m a drug addict.” — Josh Wolf ([23:50])
• Jacob reveals it’s cocaine; Wolf is blindsided — prior warning signs were chalked up to Jacob’s constant congestion.

5. Guilt, Blind Spots, and Parental Responsibility ([25:55]–[31:13])

• Grieving over missed signs and grappling with parental guilt: Was his own openness about drugs partly to blame for Jacob’s addiction?
  • “I felt such enormous guilt about being so open about drugs... and what was my responsibility in his addiction, which was really brutal for me.” — Josh Wolf ([26:27])
  • Reflecting that being a parent is central to his identity, Wolf wonders if he failed at “the one thing I thought I was good at.”
  • “I’ve always considered myself to be a good parent and shook the core of who I thought I was.” — Josh Wolf ([27:26])

6. Rehab, Boundaries, and Tough Love ([31:13]–[34:48])

• Josh and Beth trick Jacob into coming home and immediately bring him to a sober living house, not a cushy facility, to experience proper withdrawal and recovery.

  • Clear boundaries: “You leave, dude, but you’re not coming home to a job. You’re not coming home to me and you on the road.” — Josh Wolf ([31:23])

• Jacob feels anger at this intervention and for not getting a say—a dynamic they’ll “disagree about until the day he dies” ([49:53])—but Wolf stands by the choice.

7. The Road, Temptations, and Comic Life ([22:48]–[25:06]; [35:04]–[38:01])

• Ryan highlights the unique temptations of the road, especially for young comics: substances, party culture, the risk of being taken advantage of.
• The “one room, two beds” rule is both an expression of protectiveness and a practical boundary.

8. Post-Rehab: Recovery, Relapse Risk, and New Normal ([40:41]–[55:40])

• Jacob leaves sober living early but stays clean from cocaine and alcohol, though he still smokes weed (“more than I'm comfortable with, but way better than doing coke” — [33:59]).
• He cuts ties with old party circles in Vegas and focuses on work and comedy.
• Both Josh and Beth wrestle with ongoing guilt, but outside advice from sober friends (notably Steven Randolph) helps reframe accountability.
  • “An addict is going to find what they want to find.” — Steven Randolph via Josh Wolf ([32:10])

9. Personal Transformation: Sobriety, Therapy, and Self-Work ([61:01]–[68:10])

• The ordeal changes Josh’s relationship with drugs, his self-perception, and his artistry.
  • He quits weed for 90 days, transforms his creative habits, and sees a therapist (“doing some real work on little Josh” — [64:41]).
  • “For seven nights in a row in my dreams, I woke up weeping… 20 years of emotions just pouring out of me in my dreams.” — Josh Wolf ([63:37])
  • He stops hiding (e.g., not dying his beard, going without hats) and embraces vulnerability in his comedy and life.

10. Rebuilding Family, Acceptance, and Moving Forward ([68:10]–[71:26])

• The family emerges stronger, with more honest communication. Jacob is now a valued stage partner (“back to him… compassion and empathy, all that had kind of gone off… now it’s back” — [56:30]).
• Wolf expresses gratitude for the growth that came from pain: “It was one of the most challenging things that I’ve ever… as a parent. But it really has led to… me waking up emotionally and in life.” — Josh Wolf ([71:06])

Notable Quotes & Memorable Moments

• On Fatherhood and Sacrifice

  • “As long as that pro was I get to spend time with Jacob, it didn’t matter what the cons were.” — Josh Wolf ([11:20])

• On Addiction and Parental Guilt

  • “I felt such enormous guilt about being so open about drugs and how I was okay with it and what was my responsibility in his addiction, which was really brutal for me.” — Josh Wolf ([26:27])
  • “I’ve always considered myself to be a good parent and shook the core of who I thought I was.” — Josh Wolf ([27:26])

• On Hidden Struggles

  • “I was so blinded by it, man… It was right in my face.” — Josh Wolf ([38:01])

• On Recovery and Honesty

  • “He said, ‘all the lies I had to keep up with… it was killing me. That has lifted me more than not doing the coke.’” — Josh Wolf ([35:04])

• On Letting Go of Masks

  • “To slowly be able to take off the mask… has felt amazing.” — Josh Wolf ([71:01])

• On Growth through Pain

  • “It really has led to… me waking up emotionally and in life.” — Josh Wolf ([71:06])

Important Segments with Timestamps

• Josh plugs his upcoming special and podcast — [06:12] to [08:55]
• Touring with Jacob & ‘One Room, Two Beds’ Philosophy — [10:34] to [13:14]
• Drug Policy with Jacob & Generational Shifts — [13:14] to [17:52]
• Jacob’s Addiction Confession — [23:55] to [25:32]
• Dealing with Guilt & Parental Identity Crisis — [25:55] to [31:13]
• Intervention & Setting Boundaries — [31:13] to [34:48]
• Post-Rehab Struggles and Progress — [40:41] to [55:40]
• Josh’s Own Sober Experiences and Therapy — [61:01] to [68:10]
• Acceptance; Letting Go of Vanity/Mask — [68:10] to [71:26]

Closing Reflections

• Ryan thanks Josh for his honesty:
  • “Thank you for doing this. I know that wasn’t easy to come on and talk about.” — Ryan Sickler ([71:01])
• Josh credits the experience with inspiring deep positive changes, and they end with laughter and a reminder to check out Josh’s new “Campfire Special” and the “Generation Wolf” podcast.

Episode Takeaways

• Addiction can blindside even the most engaged, loving parents.
• Honest, difficult conversations—and boundaries—are essential to support and recovery.
• Guilt and self-questioning are natural but must be processed and not left to fester.
• Therapy, sober friendships, and vulnerability help parents and children heal.
• Letting go of one's "mask" and being truly authentic can be transformative.

Where to Find More

• Josh Wolf’s “Campfire Special”: [YouTube, released Aug 12]
• Podcast: “Generation Wolf” (formerly “Hey Man”), with Jacob Wolf
• Tour Info: ComedianJoshWolf.com
• Ryan Sickler’s Stand Up Special: Coming October 24 on YouTube

This episode is a vulnerable, at times harrowing, look at parenting-scarred by addiction, but full of love, humor, and hope. Whether you’re a parent, child, or simply human, there’s something meaningful in Josh and Ryan’s unflinching honesty and laughter through the hard stuff.