The full episode features another lively and unfiltered roundtable with Garrett Morris, Harold Sylvester, Earl Billings, Willie C Carpenter, Jim B, and Tucker Smallwood. The group moves from hilarious stories about aging and purging possessions, to honest confessions about dental work, Vietnam-era military draft memories, New Orleans family roots, economic advancement, and generational perspectives on Black life in America.
By the end, these old heads are acknowledging that even though they like to joke around, this stuff matters for their kids and grandkids who are gonna have to figure out how to navigate this mess.
A few clips from the latest two hour episode of Old Black Men Sittin on the Porch Talkin Shit.
We have a lot of lessons about how to get rich. But we have zero lessons on how to be rich. Harold Sylvester
In The Full Episode
Systemic vs. Individual Solutions: Balancing acknowledgment of systemic barriers with individual responsibility
Generational Humor & Aging: Laughs about getting older, cleaning out the closet, three sizes of clothes, and the insurance company runaround.
Black Family, Roots, and Passing: Tall tales about who can “pass” for different races, hilarious stories about over-tipping and New Orleans ancestors, and ICE jokes about racial profiling.
Military Draft and Black Service: Vivid tales of draft-era tricks, whether they served (and why), and the meaning of military service for Black men in America.
Family Skeletons & Royal Cousins: Jokes about Adam, Eve, and Black genealogy (“Whoa, man!”), cousin marriages, “keeping money in the family,” and Toni Morrison’s novels as historical reminders.
Black Management, Nostalgia, and Modernity: Reflections on how Black executives rose and fell in Hollywood and academia, the promises and pitfalls of social mobility, HBCUs, and navigating the world as Black professionals.
Vanity, Health, and Dental Implants: Open discussion on age, health, the pain and price of dental work, and the real reasons for “getting teeth done.”
Blues, Music Clubs & Black Community: Plans for launching a new blues night at Harold’s club, supporting Black musicians, and elders as cultural stewards.
Economic Mobility & Black Media Myths: Debate over the realities behind “million-a-year” Black professionals compared to widely held media tropes. The struggle, the hustle, and the exceptions.
Wealth, Inheritance & The Next Generation: What it means to leave something behind for children and grandchildren, worries about “crabs in a barrel,” and the punchline: “He’s an heir!”
Closing Thoughts – Wisdom & Community: Camaraderie, grandkids, passing on values, and making each weekly gathering meaningful for the culture and for each other.
Sneak peek - The complete conversation releases soon for premium members and supporters and can be found at tribalconnections.substack.com
These aren’t your typical podcast conversations. Picture cultural archaeology performed through razor-sharp humor, lived experience, and the kind of wisdom that only comes from veteran storytellers who’ve seen it all. Every episode challenges what you think you know about history, culture, and truth.
As always, expect humor, honesty, and the kind of unfiltered perspectives that only come from decades of lived experience.
