Podcast Summary: You Made It Weird with Pete Holmes
Episode: Bert Kreischer #3
Release Date: February 25, 2026
Host: Pete Holmes
Guest: Bert Kreischer
Episode Overview
This rich, hilarious, and personal conversation marks Bert Kreischer's third appearance on the show. With Pete Holmes digging into comedians’ secret weirdness, Bert brings vulnerability, nostalgia, stories about his family and career, and plenty of punchlines. They discuss Bert’s new Netflix show “Free Bert,” dig into memories of the stand-up grind, and reflect on life, ambition, identity, advice culture, and what it means to stay grounded amidst success. Much of the episode is about honoring your true self, resisting showbiz pressure, and cherishing ordinary joys over hollow status.
Key Discussion Points & Insights
1. Family, Nostalgia & What Matters Most
- Bert opens up about family life, especially the intense nostalgia for when his daughters were young:
- [03:02] Bert: “I got really emotional in the bathroom, I saw those little stools with their names on it... I’d give it all for this house and my girls to be 2 and 4.”
- The humility of “starter homes,” raising kids, and the quiet joy found in small moments, contrasted with chasing status or wealth.
2. Comedians Influencing Comedians
- An extended, affectionate discussion on who today’s comics idolize (Brian Regan, Bill Burr, Jim Gaffigan), and how bits echo each other.
- [06:19] Bert: “You got the big house, and next thing you know, you’re screaming for someone to go to dinner with you... You should really appreciate right now.”
- Stand-up as oral tradition: swapping voices, favorite jokes, stories of the comedy grind.
3. Soda, Slippers, & Everyday Weirdness
- Deep dives into the tastes of Mountain Dew ([09:09] Bert: “Tastes like dreams.”), the sociology of soda preference, and generational habits.
- The evolution of “house shoes,” slippers, ratty sweatshirts, and everyday attire—how these mundane things say a lot about comfort, identity, and getting older.
4. The Power and Peril of Real Names in Stories
- Bert lays out the emotional and ethical risk of using real names and stories in comedy, including stories about his daughters and neighbors.
- [75:19] Tom: “I want to mention I tell the story now when I do it live, I go, I’m gonna tell you the person’s real name because it makes it better.”
- [78:21] Bert: Tells the story of a parent saying, “I’m assuming this is my son you’re talking about” after a bit aired, highlighting the real world impacts of stand-up.
5. On Being Outsiders & Finding Your Place
- Both reflect on never quite fitting into the New York comic scene, and the pressure to conform to others’ paths:
- [56:00] Bert: “When I’m around my friends from college, I don’t talk much... I’m not the life of the party.”
- How what makes you feel weird or out of place can be your secret strength in life and comedy.
6. ‘Hutch’: The Archetype of Contentment
- Bert’s friend Hutch is invoked throughout as a “guru” of keeping life simple and meaningful. Hutch is the antidote to showbiz stress, representing the value of authentic joy and presence.
- [45:05] Bert: “Hutch had a problem as a child with throwing sticks in the air and them sticking in his throat...”
- [49:41] Bert: “A-list” stories—buying group groceries for all the roommates, visualizing the future you want.
7. Ambition, Advice, and Fame
- A running tension: The push to be bigger, busier, more famous—vs. carving out space for peace and real priorities.
- How chasing more (“make hay while the sun shines”) can be a trap, and each person needs to prune their own tree.
- [100:09] Bert: “Life becomes complicated when your dreams and your life are tethered.”
8. Creativity, Overthinking, and Jumping In
- Stories about writing, acting, and whether it’s better to plan or to leap:
- [94:38] Bert: “I just was like, let’s just jump in feet first...I don’t overthink things...I think just do it, and then deal with the consequences.”
- Contrast with comics who agonize over making each bit perfect.
9. Parenting, Boundaries, and Public Vulnerability
- Candid conversations about telling stories that involve real kids and family moments—period parties, playground burns, and “oversharing.”
- [88:36] Bert: Tells Conan the story of his daughter’s period party: “She named her period Jason. She got it last Friday. Friday the 13th.”
- How these bits can unexpectedly resonate for others, giving comfort even as they create awkwardness at home or school.
10. Getting Grounded & Moving Forward
- Pete and Bert wrestle with advice-giving, pruning commitments, and when to listen to your gut. The importance of not recommending your way to other people’s happiness.
- [111:15] Tom: “I like how I’ve pruned my tree. Maybe I should learn that lesson.”
- Bert reflects on his shift from relentless podcasting and touring toward a healthier, more intentional workflow.
Memorable Quotes & Moments (with Timestamps)
- [03:02] Bert: “I got really emotional in the bathroom, I saw those little stools with their names on it... I’d give it all for this house and my girls to be 2 and 4.”
- [09:09] Bert: (On Mountain Dew) “Oh, like dreams.”
- [17:40] Bert: “I refuse to wear T-shirts with a logo or anything on them. Zero.”
- [75:47] Tom: “I want to mention I tell the story now when I do it live, I go, I’m gonna tell you the person’s real name because it makes it better.”
- [100:09] Bert: “Life becomes very complicated when your dreams and your life are tethered.”
- [111:15] Tom: “I like how I’ve pruned my tree. Maybe I should learn that lesson.”
- [94:38] Bert: “I don’t overthink things, I think just do it, and then deal with the consequences.”
- [88:36] Bert: (about his daughter’s period party) “She named her period Jason. She got it last Friday. Friday the 13th.”
- [45:05] Bert: “Hutch had a problem as a child with throwing sticks in the air and them sticking in his throat because he would look up with his mouth open.”
- [128:17] Tom: “Bert Haymaker Kreischer. The show is Free Bert. I mean, I just have the softest spot for you.”
- [129:19] Bert: “Keep it crispy.”
Important Segments & Timestamps
- 03:02–06:19: Nostalgia for early family life, importance of appreciating the present.
- 07:03–09:50: Comedy influences, mimicking favorite stand-ups, comedic oral tradition.
- 09:11–15:01: Deep dive on soda favorites, Black culture and drinks, passing down weird family habits.
- 17:16–21:46: Monopolies, fashion, the symbolism of T-shirts, slippers, everyday comfort.
- 25:00–28:31: Parenting habits, ritual, the role of slippers and house shoes.
- 45:05–54:47: Extended “Hutch” stories—life lessons from the man who saw through showbiz.
- 83:41–90:08: The ethics and impact of using true stories, names, and family life in comedy.
- 100:09–104:18: Reflections on ambition, slowing down, staying sane in showbiz, inner peace.
- 111:02–114:59: Accepting others’ paths, letting go of advice addiction, learning to prune.
- 121:11–123:02: Comedy writing philosophies—storytelling vs. pithy jokes.
- 126:04–128:17: “Juicy Fruit” table read story—the importance of odd connections and curiosity.
Final Thoughts
This episode is a masterclass in comedy heart, self-reflection, and the art of living well. It’s as much about fatherhood, friendship, and self-acceptance as it is about making people laugh. Wonderfully weird, unguarded, and wise, it’s a must-listen for comedy fans, creatives, or anyone wondering how to stay themselves even as life gets louder.
Keep it crispy.