Son of a Boy Dad #358: "Stuy Town" — Detailed Episode Summary

Release Date: December 9, 2025
Hosts: Harry Shuttleworth (Lil Sasquatch), Roan Shuttleworth (Rone), Francis Ellis
Podcast: Son of a Boy Dad by Barstool Sports

Episode Overview

In this episode, "Stuy Town," the hosts dive into an offbeat and deeply personal journey through everyday struggles, recent achievements, and philosophical riffs about adulthood. The topic lens ranges from Lil Sasquatch’s troubling eye sty (“Stuyvesant” pun intended) to eSports victories, absurd home hygiene confessions, the state of insurance in America, and building a healthy worldview post-college. The trio's comedic, irreverent tone persists throughout as they trade stories, self-roast, and support each other, offering an authentic peek into what it means to be finding your way as a young adult.

Key Discussion Points and Insights

1. Lil Sasquatch’s Eye Sty Fiasco (01:19—13:00)

• Complaint: Harry is suffering from a painful sty on his right eye, cracking, “The Mayor of Stuy town, Stuyvesant.”

• Riffing on Causes: Hilarious speculation on the cause (e.g., “from eating ass in Boston” - 01:36) morphs into a riff on culinary hygiene and regional stereotypes.

• Medical Confusion: The group debates the difference between styes, pink eye, and folliculitis.

  “I feel like pink eye’s much more shameful than a sty.” — Francis (03:28)

• Suggested Remedies: Roan suggests lid scrubs and warm compresses; jokes about “just touching my eyes” causing further spread (45:12).

2. Gift-Giving and Glass Art (05:03—10:32)

• Harry surprises Roan with a hand-blown glass fish bong, courtesy of Blue Lobster Cannabis Company.

  “It’s a stunning, stunning piece of art.” — Harry (07:46) “500 on my neck and it’s a fucking fish bong, dude.” — Francis (08:03)

• Conversation drifts into glassblowing as an underappreciated art, with Netflix show references, and usage beyond bongs (lightbulbs, stemware).

3. Boston Recap and Ivy League Reflections (15:04—19:52)

• Boston’s Transformation: Harry praises Boston’s surprising cleanliness and elegance, the “Beacon Hill butthole” riff turning heartfelt:

  “From the apartment buildings to... Beacon Hill… the most charming, stunning neighborhood I’ve ever seen in any city in the world.” — Harry (15:05)

• Homelessness Commentary: America vs. Europe, and how harsh winters drive the homeless south.

• Speaking at Harvard: Francis shares experience giving informal career advice to Harvard men’s lacrosse team, encouraging non-traditional (beyond finance) careers:

  “...there’s options out there for them professionally other than finance… I have a really cool life and a really cool job.” — Francis (19:51)

4. Video Games and The Rise of “Bush” (21:12—36:32)

• Bush eSports Team: Rone breaks down the team’s big victory, outlasting 450+ competitors — massive commitment for their amateur squad.

  “We won the whole thing… for us obviously, we were fucking psyched.” — Roan (24:19)

• Marathon Gaming: Two days; first day was “a total joke,” second day was 14+ hours with technical delays and “torching” (delaying) tactics by other teams.

• Jerry as Content King: Both Harry and Roan praise co-worker Jersey Jerry’s comedic brilliance, despite fan grumbling about work ethic:

  “Jerry is one of the... funniest people that works at Barstool. Easily.” — Roan (27:53)

5. eSports Business—Content vs. Competition (36:06—39:58)

• Debate: Should the Bush team aim for pro status (CDL) or focus on content?

  “Once you get into the top league... it becomes more of like a business. Salaries, coach, merch…” — Roan (36:37) “You’ll make money off the content no matter what. Like, Jerry could be yelling at the commissioner of this tiny league, or... the big league and it’s still funny.” — Francis (39:03)

• Promotion/Relegation in CDL: Discussion on structural barriers and the financial hazards of eSports orgs.

6. Apartment Hygiene & Living in NYC (41:13—44:43)

• Dirty Apartment Antics: Roan reminisces about a time when his floors “were like walking down a gravel driveway.” Now—thanks to a vacuum and a helpful friend—standards have improved.
• Neighborhood Gossip: Murray Hill, Bushwick, and the shifting scenes for young professionals and the LGBTQ+ community:

  “There was a time where it was like that. Luckily, that’s not an issue anymore. Or keep it tidy.” — Roan (41:49)

7. NFL Talk & Quick Sports Hit (62:16—65:52)

• NFL Playoff Scenarios: Eagles optimism, Chiefs struggles, and the Bills as Super Bowl dark horses.

  “I think the Bills are going to win the Super Bowl. Mark it.” — Harry (64:34)

• Casual Picks and Banter: Patriots, Rams, Seahawks odds; debate over who’s truly a contender or a dud.

8. Insurance Nightmares & Medication Realities (66:32—74:39)

• Francis’ Battle: Insurance stops covering his necessary (and effective) Wellbutrin prescription, with Kafkaesque bureaucracy:

  “They’re just throwing as much red tape… as they possibly can to quite simply avoid having to pay for an expensive drug.” — Francis (68:45) “Insurance makes its money betting that you’re not going to get sick.” — Harry (69:46)

• Real Anxiety: The group offers ironic “just pay $2,000” advice and jokes about GoFundMe, but highlight real systemic issues.

  “If… I start reverting to my rather disconsolate self, don’t blame it on me… It is the fault of Anthem, Blue Cross, Blue Shield.” — Harry (73:26)

Notable Quotes & Memorable Moments

• “The Mayor of Stuy town, Stuyvesant. Yeah, I got a sty that is truly aids.” — Harry (01:19)
• “You came out of a storage bin. No, you came out of like a hidden door, secondary compartment.” — Roan (05:41)
• “The team is only going to go as well as the team is.” — Roan (37:38) (Gibberish as high comedy)
• “If you could talk to Harry’s balls, they would sound like this…” — Harry, then launches into fake Japanese/Yoda voice. (62:43)
• “Insurance makes its money betting that you’re not going to get sick.” — Harry (69:46)
• “I hope something good happens with your fucking… with your insurance.” — Francis (73:19)

Useful Timestamps for Segments

• Eye Sty Debacle: 01:19–13:00
• Gift Unwrapping (Fish Bong): 05:03–10:32
• Boston and Harvard Visit: 15:04–19:52
• Bush Esports Victory: 23:53–39:58
• Apartment Hygiene: 41:13–44:43
• NFL Playoff Chat: 62:16–65:52
• Insurance Hell: 66:32–74:39

Tone & Episode Vibe

The trio maintains a brutally honest, self-deprecating, and quick-witted rapport. They oscillate between legitimate life advice (“there’s more to life than finance”), to deeply unserious bits (glass bongs shaped like trout, grainy debates about ball shaving), to airing frustrations about adulthood (insurance problems, hygiene struggles, blurry self-worth after dropping out of college). This mix of absurd humor and cathartic real talk is what makes the episode so inviting for fans and newcomers alike.

Conclusion

Episode #358 of Son of a Boy Dad combines sharp, wild humor with slices of modern young adult struggle—emphasizing friendship, self-doubt, hustle, and moments of unexpected wisdom. Whether dissecting the nuances of pink eye vs. styes, celebrating gaming triumphs, or bemoaning the broken health care system, the show stays relatable and hilarious.

For more episodes and content from Son of a Boy Dad, visit Barstool Sports podcast page.