Heavyweight: Live from New York (November 13, 2025)

Podcast: Heavyweight (Pushkin Industries)
Host: Jonathan Goldstein
Location: Live at Caveat, Lower East Side, NYC

Overview

This special live episode of Heavyweight brings together host Jonathan Goldstein, producers Stevie Lane and Kahlilah Holt, and CEO of Pushkin Industries, Greta Cohen, for a night of storytelling, reminiscence, and audience engagement. Recorded at Caveat in NYC, the episode features a signature Goldstein retelling of the biblical story of Cain and Abel, heartfelt confessions at the Wall of Regrets, and an in-depth Q&A with the creative team. The show explores regrets, difficult conversations, and the nuanced process behind the beloved podcast, all served with Heavyweight’s characteristic self-deprecating wit and warmth.

Main Segments & Timestamps

• [02:11] Setting the Scene – Welcome & Regret Wall
• [03:11] Greta’s Introduction – Launching the New Season
• [05:24] Cain & Abel: A Heavyweight Parable (live reading by Jonathan Goldstein)
• [17:36] Wall of Regrets – Sharing Personal Regrets (with audience & producers)
• [21:04] Q&A with Producers Stevie Lane & Kahlilah Holt – Behind the Scenes of Heavyweight
• [35:20] Heavyweight Story Phone – Audience Stories
• [38:55] Live Audience Q&A
• [45:25] Closing Thanks

Key Discussion Points & Insights

Setting the Scene & Regret Wall ([02:11])

• Description: The team describes the festive, regret-themed atmosphere at the live show, including a wall where attendees wrote their regrets and a meet-and-greet with Jonathan.
  • “There was a wall to write down your regrets and a meet and greet where you could take a picture with yours truly.” – Jonathan Goldstein (02:11)
• Tone: Warm, irreverent, and welcoming, inviting both nostalgia and introspection.

Greta’s Introduction: Heavyweight as Modern Parable ([03:11])

• Greta Cohen introduces the evening and sets up Jonathan's live reading, contextualizing the show's focus on confronting the past:
  • “Cain and Abel… were the sons of Adam and Eve. Adam and Eve lived in a beautiful garden called Eden, where they frolicked in the nude all day. But relax, back then, nudity was less a Rio de Janeiro, HBO after Dark thing and more a Nordic health spa thing filled with good, clean living and fruit platters.” – Greta Cohen (03:11)
• Tone: Light, humorous, and explanatory.

Jonathan Goldstein’s Retelling: Cain and Abel as the First Heavyweight ([05:24–17:36])

Summary

Jonathan’s witty, poignant retelling of the biblical story frames Cain and Abel as Heavyweight’s earliest “beefing brothers.” The parable is explored as an origin story for the kinds of difficult, emotional reckonings the podcast pursues: sibling rivalry, existential angst, regret, jealousy, and the ambiguous search for closure.

Notable Quotes

• “Abel just toppled over. He toppled over the way he did everything. With an easygoing acceptance… I must fall, so I will fall. I am falling. I have fallen here.” – Jonathan Goldstein (16:25)
• “In life, Cain had been jealous of his brother, but it was in death that he became more jealous than he ever thought possible.” – Jonathan Goldstein (16:58)
• On facing immortality and fading memory:
  “After 700 years, when he told the story to himself or heard it told by others, he felt nothing. He was too old to feel guilt or remorse or anything. He didn’t even miss his brother anymore… And in this way, he finally got his wish to be just like Abel. And then God let him die.” – Jonathan Goldstein (17:29)

Insight

This well-crafted retelling captures the show’s ethos: confronting uncomfortable truths of human relationships with vulnerability and dry humor.

Wall of Regrets — Audience & Producer Confessions ([17:36])

• The team reads audience-shared regrets from the wall, sparking candid revelations.

  • “Not finding a therapist, saying no to a freezum, not being more patient with my mother's cognitive decline, lacking patience with my brother's behavior then he died. How I said goodbye to my best friend before he died.” (18:01–18:08)
  • “I wish I joined a band.” – Jonathan Goldstein (18:18)

• Tone: Raw, introspective, sometimes darkly funny; this is signature Heavyweight content, both meaningful and relatable.

Behind-the-Scenes Q&A ([21:04–33:22])

Jonathan and Jackie, On- and Off-Air ([21:53])

• Q: What’s the real relationship between Jonathan and Jackie?
  • “She likes to laugh at me and hang up… I just bring out the worst in her.… I did a story about our relationship on This American Life called ‘The Allure of the Mean Friend.’” – Jonathan Goldstein (21:53–22:59)

Hardest & Most Memorable Calls ([23:24])

• Kahlilah: Nervous about calling sorority girls for a story—worried about being perceived as a scam.
• Stevie: Called the “two or three fingered man” (Carl), who threatened to find and kill her—“a rite of passage” for the show. (24:16)
• Jonathan: Most awkward was calling a former psychiatrist’s other patient after 30+ years.

Dream Celebrity Episodes ([25:22])

• Stevie: Sarah Jessica Parker & Kim Cattrall reunion dream
• Jonathan: Joking that celebrities "don't have problems"
• Kahlilah: Augie (Jonathan’s son) wants to reconcile Kendrick Lamar and Drake.
  • “Why can’t you fellas just…” – Jonathan Goldstein (26:38)

Maintaining Morale for Long, Unresolved Stories ([27:08])

• Kahlilah: “I think I am discouraged most of the time. I think I don’t maintain the morale would be my answer.”
• Stevie: “I just believe it actually will always work out… It’s blind optimism.”
• Jonathan: “For me it’s desperation… That’s what passes for hope.”

If an Episode Became a Series ([28:01])

• The team jokingly describes a multi-day “descent into madness” trying to create the Heavyweight equivalent of S-Town.
• Series idea: "The Ehrlichs," following the stories of Gregor and Dimitri Ehrlich.

Getting People to Spill on Tape ([29:28])

• Kahlilah: More skepticism, suspicion of scam; people answer unknown numbers less than in past years.
• Jonathan: “What kind of scam would it be? Not a very good one. Like a real long con.”
• Stevie & Jonathan: Sometimes, persistence and a sense of empathy break through. Example of a subject who ultimately agreed to be interviewed to set a good example for her daughter.

Who Would Play You in a Heavyweight Movie? ([32:20])

• Kahlilah: Aubrey Plaza.
• Jonathan: Jokes about his self-image: “In my mind I’m like a very lanky, tall, sort of like Johnny Knoxville type… but I know it would end up being like Wallace Shawn… maybe a Paul Giamatti.” (33:00)
• Stevie (later): “Tilda Swinton.” (33:06)

Heavyweight Story Phone ([35:20])

• Audience members share their own regret stories via a staged “answering machine,” including stories of being ghosted by classmates, family secrets, and coincidences around loss and dreams.
• Memorable Call:
  • “I was ghosted by every single male member of my high school class. And I don’t know if I did something. I thought all these people liked me.”
  • Story of learning about a family divorce’s impact on community.
  • Dream of grandmother’s death coinciding with her actual passing.
  • Dimitri Ehrlich jokingly asks if Jonathan has considered theatrical acting due to his over-the-top massage parlor performance at a bachelor party.

Live Audience Q&A ([38:55])

On Sobriety and Performing Sober ([39:05])

• Audience member references Jonathan’s past about drinking before performing.
  • “Yeah, I haven’t had anything to drink and… Yeah, it was definitely in my thoughts because I used to really like to do that, to have a drink or two or three before talking and a couple afterwards. So, yeah, I’m just… I’m free balling it. I don’t know. Yeah.” – Jonathan Goldstein (39:28)

On Addiction and Impactful Episodes ([40:47])

• Listener shares that Jonathan’s honest episode about alcohol opened up important conversations for their friend group.
  • “Thank you for being honest and open.” – Audience member (41:08)
  • “That’s really… That’s encouraging to hear. Thank you.” – Jonathan Goldstein (41:11)

Stories “In the Vault” ([41:16])

• Producers cautiously allude to ongoing stories that have stalled but may still “come back to life.”
• Example: “The Messenger” was thought dead but revived unexpectedly after networking and serendipity.

Self-Awareness & Audio Editing ([42:32])

• Kahlilah notices she laughs out of nervousness and tries to curtail it; Jonathan wishes he laughed more freely; Stevie pitches her voice up on calls, which she’s working on.

Vulnerability & Embracing Mistakes ([43:41])

• Kahlilah credits Jonathan for putting embarrassing moments “front and center in the story… for art.”
• Jonathan: “You’re embarrassing yourself for a holiday. Most people go through their lives just embarrassing themselves willy nilly for nothing.” (43:56)

Advice on Friendship Longevity ([44:22])

• Jonathan: “I think it helps to be amused… If you get a kick out of that, then you’re unstoppable. I mean, what’s gonna happen, you know, what’s gonna destroy you? Nothing.”
• Kahlilah: “I do have some long friendships… but I don’t know why, I don’t know why they’re still my friends, but I’m grateful for it.”
• Jonathan: “You’re a good person is why.” (45:12)

Notable Quotes & Moments

• “Let’s play something else. But God would only laugh.” – Jonathan Goldstein (paraphrasing the Cain & Abel game) (07:26)
• “My hardest call was… calling a professor I’d seen in the waiting room of my psychiatrist 30 odd years ago… Even for me, that felt very weird.” – Jonathan Goldstein (24:36)
• “I just have the feeling that he actually wants to talk about this.” – Jonathan Goldstein, on producing emotional interviews (32:08)
• “Thank you for being honest and open.” – Audience member (41:11)

Episode Tone & Style

• Signature Heavyweight: Blends humor and existential angst, candid admissions, and group banter.
• Audience Engagement: Playful and conspiratorially warm with live participation, audience Q&A, and regret-sharing.
• Behind the Curtain: The creative team discusses the show’s mechanics, failures, frustrations, and joys with honesty and self-mockery.
• Theme of Regret & Redemption: Both in storytelling (Cain & Abel) and the lived moments shared by guests, producers, and the audience.

Conclusion & Closing Thanks ([45:25])

Jonathan and the team thank everyone in attendance and behind the scenes, close with appreciation, and tease a return to “regular” episodes next week.

For New Listeners

This episode is a funny, vulnerable, and illuminating window into why Heavyweight resonates with fans: It’s about regrets, reconciliation, persistence, and the gallows humor necessary to face painful memories. The live setting deepens the show’s trademark warmth and approachability, and the creative team’s candor underscores the real human effort behind the podcast’s production.

[End of Summary]