Podcast Summary: This Past Weekend w/ Theo Von

Episode 630: Stephen Wilson Jr.

Release Date: December 23, 2025
Host: Theo Von
Guest: Stephen Wilson Jr.

Overview

In this heartful and often humorous episode, Theo Von sits down with rising songwriter and musician Stephen Wilson Jr. The conversation traverses Stephen’s Southern Indiana upbringing, the deep legacy of his father, the complex journey of grief after his father's passing, authenticity in art, “relay races” through generations, and the healing magic of songwriting. The episode is rich with vulnerable reflections on masculinity, loss, and family, punctuated with stories about childhood, small-town quirks, and the music that shaped a generation.

The session concludes with Stephen performing emotional live renditions of his songs "Gary" and "Grief Is Only Love That’s Got No Place To Go".

Main Themes & Discussion Points

1. Stephen’s Upbringing and Family Life

• Growing up Country: Stephen shares about his childhood in Southern Indiana hunting for food, growing up in a single-parent family where his father, a promising boxer, put his dreams aside to raise Stephen and his siblings.
  • “We just grew up very country. Wasn't trendy at all either. It was like, just a means of survival.” (03:28)
• Father’s Influence: Stephen’s father, also Stephen Wilson, was a single parent who doubled as a bus driver and body shop worker while pursuing boxing. His sacrifices left a deep impression on Stephen, with his father having to fill both parental roles.
  • “A lot of my dreams, I live kind of, you know, for him and myself, but because he put a lot of his dreams on the back burner to raise me.” (05:53)
  • “About a year from that picture, he would have been curling my little sister’s hair … even though his eyes were swollen shut from sparring the night before.” (06:41)
• Anecdotes from Childhood: Stories range from sibling rivalry and boxing, to attending church in rural Indiana, and feasting on local foods. Theo and Stephen reminisce about the customs and comfort of Midwestern family gatherings.

2. Faith, the Bible, and Personal Identity

• Religious Upbringing: Both discuss how formative church was. Stephen talks about seeing exorcisms, revivals, and “slain in the spirit” episodes in Pentecostal churches, balancing faith with skepticism from his scientific background.
  • “I believe God did show up in those places ... but there was a lot of it that was 100% not [real].” (16:56)
  • Theo: “A pop tarts and exorcism. I'm there, dude.” (17:59)
• Namesakes and Identity: Stephen unpacks the biblical story of St. Stephen and reflects on how being named after a Christian martyr wove into his identity and familial expectations.

3. Art, Songwriting, and Authenticity

• The Relay Race of Generations: Theo and Stephen dive into how aspirations and trauma are passed down like a baton, and the responsibility/pressure felt as a son to carry on or diverge from those dreams.
  • “When you see a relay race, the runners before you dictate your position in the race... the baton becomes something bigger than just this thing you’re holding in your hand.“ (28:56)
• Songwriting as Survival and Science: Stephen shares his transition from scientist and food R&D specialist to songwriter, utilizing scientific methodologies to process grief.
  • “I joke around calling myself a song scientist. But that's essentially what it is.” (78:38)
• On Authenticity: Both explore the rarity and necessity of authenticity in the arts today.
  • “It's hard to find out what is real ... I tend to authenticate things with emotions and experience.” (67:59)

4. Grief, Loss, and Healing

• Father’s Death: In a moving segment, Stephen recalls the sudden passing of his father and the last phone call they shared.
  • “He said, ‘everything’s gonna be okay.' ... 'Write a good song for me, Stephen.' And he said, ‘I love you’ four times.” (34:57)
• Music as Grieving: Stephen credits his career (and particularly his record "Son of Dad") as being catalyzed by grief and the urge to keep his father alive through song. He discusses the shared humanity in expressing—and giving others the space to process—grief.
  • “That conversation is what catalyzed my whole career, really... Write a good song for me, Stephen.” (37:03)
  • “Grief is only love that's got no place to go.” (86:09+ singing)

5. Storytelling, Masculinity & Small Town Living

• The pair reflect on the lost tradition of oral storytelling and the crucial role of feelers and creators—songwriters and comedians—in helping people, especially men, process emotion.
  • Theo: “There's a lot of feeling and processing that we've missed somehow ... there are a lot of guys that are trying to feel.” (87:10)

6. The Role of Science and User Bias

• The discussion turns to user bias and the intersection of scientific thinking with creative work—with references to ongoing lawsuits about social media’s effect on mental health.

7. Personal Growth and Step-Parenting

• Stephen, now a stepfather, discusses how his experience as a stepchild informs his approach and the challenges and rewards of loving children not biologically his own.
  • “His faith was led by his works, not his words.” (125:44)

Notable Quotes & Memorable Moments

• On the “catalyst” of loss:
  • “With any great chemical reaction, there is a catalyst. Everything... is because of that conversation.” (36:30)
• On grief:
  • “Grief is only love that's got no place to go.” (86:09, echoed in performance)
• Theo, on learning from others' lives:
  • “Let me be the leader. Instead of saying, you should have led me... How many times am I gonna miss the grow up bus?” (55:07)
• On masculinity and emotion:
  • “If you have. If you can find the tears, find them, like, right now... When my dad died, I swear, all I did was cry. For two years. I. Like, it's all I did.” (42:31)
• On storytelling:
  • “Great comedians are great storytellers and great songwriters are great storytellers... it's kind of a lost art.” (65:48)
• On being "different":
  • “I was called different a lot as a kid. It was not a compliment most of the time.” (70:07)
• On step-parenting:
  • “My dad just loved his stepchildren like us. There was never, like, I feel like a lot of step parents... But he never said that. He just did that.” (126:28)

Timestamps of Key Segments

• [03:28] — Stephen’s upbringing and hunting for food as survival.
• [05:53] — Father’s sacrifices and single parenthood.
• [16:56] — Exorcisms, religion, and faith vs. science.
• [28:56] — Generational relay race: inheriting and passing down dreams.
• [34:57] — The last phone call with Stephen’s father.
• [37:03] — The impact of his father's last words; “write a good song for me”.
• [78:38] — Songwriting and "song scientist" philosophy.
• [86:09]/[148:19] — “Grief is only love that's got no place to go” (discussed and later performed).
• [141:33], [148:19] — Live performances of "Gary" and "Grief is Only Love That’s Got No Place To Go".
• [67:59] — Discussion on authenticity in the arts.
• [125:44] — On step-parenting and learning by action.

Notable Musical Moments

• [141:33] — Live performance: "Gary"
• [148:19] — Live performance: "Grief Is Only Love That’s Got No Place To Go"

Tone & Style

The episode is deeply sincere and personal, punctuated by Theo’s trademark wit and capacity for absurd, poignant tangents. The conversation oscillates between humor, nostalgia, and profound vulnerability, with both Theo and Stephen comfortable navigating uncomfortable truths about grief, family, and masculine expectations in the modern world.

Conclusion

This episode stands out as a powerful meditation on fatherhood, grief, legacy, and the role of honest art in giving people space to feel and heal. Stephen Wilson Jr.’s openness offers a template for emotional vulnerability, particularly for men, while Theo’s curiosity and warmth help ground the conversation in everyman experience.

Recommended for: Anyone interested in songwriting, processing grief, familial bonds, or lovers of authentic, story-driven podcasts.

End of summary.