Staying Alive with Jon Gabrus & Adam Pally
Episode: “Matching Tatts” (w/ Henbo Henning)
Release Date: October 9, 2025
Guest: Matthew “Henbo” Henning – Tattoo artist, musician, multidisciplinary creative
Overview
In this episode, hosts Jon Gabrus and Adam Pally recount a weekend packed with life milestones, culminating in matching tattoos from their guest and friend, tattoo artist Matthew “Henbo” Henning. The episode explores ideas of adulthood, health, art as impermanence, the working-class roots of creativity, and the rituals of male friendship. The conversation is raucous, self-deprecating, and deeply human—at times both rowdy and moving. Henbo offers insight into the life of an artist straddling cultures and disciplines, while Jon and Adam reveal the ways they’re (reluctantly) embracing healthier lifestyles.
Key Discussion Points and Insights
1. Milestones, Growing Up, and Parental Perspective
- Bar/Bat Mitzvah Reflections: Adam describes the emotional experience of his children celebrating their bar and bat mitzvahs, which led to contemplation about aging and parenting.
- "It's a reminder of your own age mortality every day with children." (Adam, 03:10)
- The Emotional Weight: Jon and Adam reflect on generational shifts and the bittersweetness of seeing your kids step into adulthood.
2. Friendships and Living Life to the Fullest
- Wild Weekend Recap: Jon and Adam detail their “Saturday/Sunday/Monday” of partying, meaningful family time, and spontaneous tattoo sessions.
- "That's life to the fullest... I'd trade that 10 times out of 10 for just rest and nothing else." (Adam, 04:21)
- Matching Tattoos: They decide to commemorate their friendship and this period of change by getting matching tattoos from Henbo.
3. Introducing Matthew Henbo Henning
- Multidisciplinary Life: Adam praises Henbo’s status as a “quadruple threat”—tattooing, music, fashion design, and art—a major theme throughout the episode.
- "You literally can do everything. It's wild." (Adam, 10:41)
- Tattooing as a Calling: Henbo shares how he came from a working-class background in northern England, gravitated toward art as a kid, and found tattooing as a vehicle for self-expression.
4. Working-Class Roots and Finding Art
- Early Jobs: All three share hilarious and sometimes harrowing stories about bad jobs—dishwashing, landscaping with ex-cons, call centers, and more.
- "You’re like the lowest of everyone, you know?... I used to do it in between. So I used to work the morning shift... And then I’d go back home, play on my N64." (Henbo, 06:08)
- School as Survival: The group bonds over school memories, likening them to prison—“schools are, I mean, they are… something very prison-like about them.” (Adam, 19:49)
5. Entering the Tattoo World
- Finding His Style: Henbo traces his unique artistic signature (“your style is kind of unmistakable”) back to doodling and hustling in the back of class as a kid.
- “It’s just, I’ve always done that... I’d actually charge people to draw as well, so I’d make a bit of money on the side.” (Henbo, 18:55)
- Apprenticeships and DIY Spirit: He discusses the rare tradition of apprenticeships in tattooing, learning from mentors, and the nerve-wracking reality of “scarring up 99 people” before being trusted with clients (51:01).
6. Culture, Humor, and National Identity
- Northern England vs. Long Island: The banter highlights the similarities between their upbringings, with both locales being “anti-culture,” stubborn, and full of characters.
- British Drinking & Malaise: Henbo gives a comedic but sharp analysis of British social life—cocaine, “nose beers,” drinking as escapism, and the “get on with it” mentality.
- “English people love drugs in general because they’re just like, this is shit. And it’s off my fucking mind, right, for three days—and then I can go back to work, you know?” (Henbo, 30:11)
- Rituals of Pub Culture: They riff on flat cask ales, parkas, sausage rolls, and the collective impulse to seize rare sunny days.
7. Health, Fitness, and Body Image
- Staying Active—Reluctantly: The group talks working out, running, ginger shots, and maintaining their “chubby but functional” physiques.
- “Inside of me, there’s a much fatter man dying to get out all the time.” (Henbo, 35:07)
- Body Image & Acceptance: Gabrus and Pally joke about running shirtless, the realities of being big dudes, and the value of honesty (“I’d rather be open about it…” – Adam, 36:44).
- Fitness Habits: Henbo trains thanks to his wife Jen ("jacked," into weights), likes F45 classes, the “bro split,” and runs marathons—often disbelieved by others because of his build.
- Endurance and Perspective: Henbo describes getting through marathon pain and tattoo pain by mentally going “to dark places” and drawing inspiration from seeing others who have bigger challenges (47:25).
8. Art as Impermanence & Tattoo Philosophy
- On Permanence: Henbo presents the philosophy that tattoo art “dies with the canvas”—tattoos are uniquely impermanent, living and dying with the person.
- “It’s the art that dies with the canvas.” (Henbo, 26:26)
- Shock Value: The trio swap stories about tattoo pain, embarrassing tattoo locations, and bodily mishaps during sessions—Henbo’s “full butt cheek” tattoo is highlighted for its agony (46:55).
- Matching Tattoos & Friendship Rituals: Jon and Adam get matching “hard 10”/dice tattoos, commemorating their decades-old friendship and their love of Vegas and “rolling hard.”
9. Henbo’s Broader Creative Life
- Goodluck NYC: Henbo describes his tattoo shop as inclusive, calm, and elevated, with a rooftop that encourages community.
- Music and Collabs: He’s in a band called Night Sports, collaborating with members of Long Island legends the Movie Life and others, and is working with Dave’s New York clothing on design projects.
- Community Engagement: Next up is teaching art and tattooing to kids for Philadelphia’s outdoor mural project (64:25).
Memorable Quotes & Moments
-
On art and mortality:
“People are like, tattoos are so permanent…But it’s the art that dies with the canvas.”
— Henbo, [26:26] -
On tattoo pain:
"No, it hurts the most — anus."
— Henbo, [46:55] -
On running shirtless:
“It looks like someone’s throwing a trash bag of butter down the road.”
— Henbo, [44:18] -
On British resilience:
“They’re just really real about the human condition—‘This is shit, but everyone’s gotta do it, so just get on with it.’”
— Henbo, [30:32] -
On body image:
“If I didn’t exercise, God only knows what I’d look like. This is what I look like with constant exercise.”
— Jon, [35:17] -
On male friendship & rituals:
“Now I just can’t wait to go to Vegas and bust it out.”
— Jon, about their matching tattoo, [55:58]
Timestamps for Major Segments
- [00:12] – Weekend recap: bar/bat mitzvahs, milestones, friendship
- [10:10] – Introduction of guest Matthew Henbo Henning
- [11:41] – Henbo’s roots: Growing up in northern England, work, art
- [18:55] – Developing his distinctive style; art as school survival
- [26:26] – Art that “dies with the canvas,” impermanence of tattoos
- [33:44] – Fitness routines, “bro splits,” running marathons
- [39:00] – Rugby, agility for big bodies, athleticism as identity
- [44:18] – On running shirtless and public vulnerability
- [46:55] – Tattoo pain stories; most sensitive body parts
- [51:01] – Early tattoo apprenticeship, first tattoos, building skills
- [54:24] – Branching into fashion, music, and creative projects
- [55:42] – Matching tattoos ritual; meaning in shared symbols
- [60:22] – Plugs: Goodluck NYC, Night Sports band, Dave’s NY project
- [64:25] – Art education and community projects in Philadelphia
Conclusion
This energetic and heartfelt episode blends comedy, vulnerability, and creative insight. Gabrus and Pally, ever the self-mocking “professional partiers,” reflect seriously—even as they joke—on what it means to age, support friends, stay healthy, and keep your inner artist (or child) alive. Henbo Henning, their guest, offers a window into the working-class roots of artistry, the rarefied world of tattooing, and the possibilities that open when you say yes to life’s messy, vibrant impermanence.
Further Info & Plugs
- Tattoo Shop: Goodluck NYC (Greenpoint, Brooklyn, second floor)
- Band: Night Sports (with members of the Movie Life, Incendiary, Angel Dust, etc.)
- Instagram: @henbohenning
- Upcoming: Collaborating with Dave’s New York fashion, art teaching for Philadelphia mural project
“That’s life to the fullest...I’d trade that 10 times out of 10.”
— Adam Pally, [04:21]