This Past Weekend w/ Theo Von — Episode #609: Chris Distefano

Aired: September 10, 2025

Episode Overview

In this episode of "This Past Weekend," Theo Von welcomes back New York City stand-up comedian Chris Distefano (recently engaged, host of the returned "History Hyenas" podcast) for a wide-ranging, irreverent, and laughter-packed conversation. The comedians touch on topics from modern-day racism, family dynamics, and the evolving landscape of comedy, to the pressures of show business, the importance of presence, and what love looks like over the years. The episode mixes candid insight and outrageous humor, providing fans of both comics with plenty of memorable moments and quote-worthy exchanges.

Key Discussion Points & Insights

1. Comedy as a Tool to Address Race and Social Change

• Racism in Today’s America:
  • Chris jokes about how modern racism feels "confusing" due to intermixing of races, joking about "fractional racism" and the impossibility of being prejudiced against just part of someone ([03:12]).
  • Both comics riff on their mixed families, jokingly turning family dynamics into parody (“My ten-year-old’s chosen to be more Latina, my four-year-old’s chosen to be more white” [03:16]).
  • Discussion on the trend of race-baiting in the media and how profit is often made off stirring racial division ([13:10]–[15:02]).
• On Comedy Crossing Racial Lines:
  • Watching and critiquing Drewski's viral skit, Theo and Chris debate if these depictions perpetuate stereotypes or are valuable social commentary ([12:01]–[14:16]).
  • “In the name of comedy, I say, give it a try... Give it a try. Any white person that's offended by that is just, you know, they're kind of Guantanamo Bay, in a way.” — Chris ([14:54])
  • They discuss how humor can expose or alleviate racial tension, comparing “funny” versus “racist and hateful” comedy ([16:09]).

2. Parenting, Family, and the Absurdities of Raising Kids

• Raising Children in a Diverse Household:
  • Chris' comedic take on his daughters’ self-identification and “calling ICE on each other” ([03:34]).
  • Parodying over-the-top discipline, he describes the “Guantanamo Bay” timeout room in his basement ([04:16]).
• Safety and Social Media:
  • Chris talks about letting his kids loose on social media while he stays off for sanity ([06:17]). Theo contrasts the "online world" drama to real life.
• Preparation for the Modern World:
  • Riffing on true crime and TikTok “predator busting,” they debate the strange psychological space of vigilante justice ([07:04]–[09:14]).

3. Comedy as Salvation and Social Commentary

• Lessons from Old-School Comics:
  • Both comedians praise the sharpness of New York comics like Jim Norton, Colin Quinn, and the late Patrice O'Neal ([54:22]–[55:07]), differentiating between authentic comedy and content manufactured for the internet.
• The Need for Selective Attention:
  • Chris stresses the importance of focusing on one's immediate family and friends rather than being consumed by the anonymous internet fray ([15:02], [67:33]).
  • “If I don't know you personally, you don't affect me at all, positive or negative.” — Chris ([15:02])
• Comedy and Regulation:
  • Reflections on Nazi jokes, the restrictions in Germany, and the evolution of what's permissible in comedy ([18:00]–[19:32]).

4. Personal and Career Growth

• Showbiz Highs and Lows:
  • Chris opens up about moving his Madison Square Garden show from the arena to the theater after slow ticket sales and learning to accept losses as learning opportunities ([27:40]–[32:12]).
  • “In this life, there's no losses, just learning.” — Chris’ daughter (via Giannis Pappas, [32:12])
• Priorities Shifting with Family:
  • Explains not chasing perpetual stand-up tours anymore: “Time has literally become more valuable than money to me right now because of my... kids” ([34:27]).

5. Current Events and New York City Politics

• NYC’s Political Future:
  • Discussion on Zoran Mamdani’s mayoral campaign and "millionaires’ tax," with skepticism about taxing the wealthy too hard ([41:06]–[42:40]).
  • Debate on whether media exaggerates certain issues, and the complex opinions within ethnic communities ([42:20]–[43:13]).
• Tribality vs. Racism:
  • “Everybody's kind of racist, man... People are tribal, too." — Chris ([43:04]–[43:16])

6. Reflections on Love, Relationships, and Presence

• Love as Action, Not Feeling:
  • Chris shares candidly how real love emerged from loyalty, imperfection, and action rather than infatuation ([69:59]–[73:36]).
  • “Love is an action. All these years later... the real love was her and I coming back together after a big fight. Her showing me so much loyalty, me showing her loyalty.” — Chris ([71:15])
• Power of Being Present:
  • “I'm where my feet are. I'm fully with you right now.” — Chris on prioritizing presence over distraction ([76:05])
  • The joys of time with family, and ongoing effort to “make your life a little smaller” and focus on what matters ([88:48]–[89:16]).

Notable Quotes & Memorable Moments

On Race, Family, and Social Dynamics

• “You almost need a calculator...you know what? I'm only gonna be racist against a half of this person or a quarter of them. It's like, it's just too confusing now, right?” — Theo ([02:58])
• “My 4-year-old has been fully on FaceTime with ICE agents trying to get my 10-year-old locked up.” — Chris ([03:34])
• “If I don't know you personally, you don't affect me at all, positive or negative.” — Chris ([15:02])

On Comedy as Reflection

• “In the name of comedy, I say, give it a try. Any white person that's offended by that is just... they're kind of Guantanamo Bay, in a way.” — Chris ([14:54])
• “Undeniably to me, you can't be racist and funny. It's one or the other.” — Chris ([16:09])

On Career Ups and Downs

• “In this life, there's no losses, just learning.” — Chris’s daughter/Giannis ([32:12])
• [Regarding Madison Square Garden] “And now the theater is all but sold out. And I haven't stressed about it in six months.”* ([28:47])

On Love and Presence

• “Love is an action....She's taking me in for my imperfections. So for me, that makes her perfect to me.” — Chris ([71:15])
• “I'm where my feet are. I'm fully with you right now.” — Chris ([76:05])

Important Timestamps

| Timestamp | Segment/Topic | | ---------- | ------------------------------------------------------------------------------- | | 00:30 | Theo intros Chris Distefano with playful banter and joking on race | | 03:12 | Mixed families & confusion in "modern racism" | | 03:34 | Chris's joke about kids FaceTiming ICE | | 14:08 | Drewski skit breakdown, commentary on comedy and racism | | 15:02 | Chris on not letting online strangers affect his mood or life | | 27:40 | MSG show story — moving from arena to theater, humility, learning | | 32:12 | “No losses, just learning” — lesson from daughter (Giannis Pappas) | | 34:27 | Prioritizing family over showbiz, the value of time | | 42:15 | NYC mayoral politics, Zoran Mamdani, skepticism about progressive tax hikes | | 53:07 | Jim Norton impression & “comedy for audiences vs. for comics” | | 69:59 | Chris's philosophy on love evolving from feeling to action | | 76:05 | “Be where your feet are” — on practicing presence, learning from Giannis Pappas | | 88:48 | “Make your life a little smaller” — closing reflections by Chris |

Episode Highlights

• Hilariously Honest Family Talk:
  Chris and Theo’s banter about their kids, raising mixed families, and comedic exaggerations of discipline and tribal loyalty.
• Nuanced Discussion of Comedy:
  The line between offensive and funny, shifting media landscapes, and the difference between comedy for laughs, change, or shock.
• Candid Professional Vulnerability:
  Chris’s honesty about ticket sales, recalibrating dreams, and learning that “there's no losses, just learning.”
• Powerful Reflections on Love:
  Chris’s clear-eyed view of long-term love as action and acceptance, delivered with both warmth and humor.
• Real Talk about Focus & Presence:
  Theo and Chris’s shared belief in the value of keeping attention on what really matters—family, friends, and the present moment.

Final Takeaway

This episode is both laugh-out-loud funny and rich in perspective, blending the raw honesty of two friends with varied experiences in comedy and life. Listeners get a behind-the-scenes look at stand-up's psychological challenges, New York City’s ongoing transformation, and modern family life—all delivered with the unique, offbeat rhythms that make “This Past Weekend” a standout in the comedy podcast world.

For more:

• Chris Distefano’s tour dates and new episodes of History Hyenas are discussed and promoted.
• Theo teases his own upcoming special at the Beacon Theatre in New York.

If you missed it, these moments embody the episode’s soul:

“Love is an action... the real love was her and I coming back together after a big fight. Her showing me so much loyalty, me showing her loyalty. That’s the love.” — Chris ([71:15])

“Make your life a little smaller. That’s what I try to tell my kids, man. There’s so many things going on in the world...but you could sweep up in front of your crib.” — Chris ([88:48])