Transcript

Bert Kreischer (0:02)

Lemonade.

Tom Segura (0:18)

You made it weird with Pete Holmes. What's happening, weirdos? This is the return return. The third time. The incredible, the hilarious, the funny, the fun. Bert Kreischer is back on the show and I'm so glad he is. His new show, Free Bert, is available on Netflix now. We talk all about that. I watched it. I love it. He's so good in it. Check, check, check it out. Yeah, check, check, check it out. Free Bert on Netflix. In the meantime, enjoy this chat. I don't have much to plug up top other than my tour dates. I'm gonna be in Los Angeles on March 7th. Yep, March 7th. Then I'm going to be in Royal Oaks, Michigan, Tallahassee, Irving, Texas, Madison, Wisconsin, Denver, North Carolina, South Carolina, Vancouver, and then Portland. Tickets to all of Those are on PeteHomes.com Also be sure to subscribe to my YouTube channel because my new special, Silly Silly Fun Boy is dropping in March. It's also going to be available for pre order, meaning you can watch it early on 800 pound gorillas one website. So check that out. Silly Silly Fun Boy. So excited about that new special and I really hope you enjoy it. And of course we'll be posting and blabbing and boring quite a bit about it in the month coming up. In the meantime, enjoy my chat with my friend Bert Kreischer. He's so fun. He's so good. I'm so glad he's here. Enjoy. Get into it.

Julia Louis Dreyfus (1:46)

Hey there, it's Julia Louis Dreyfus. I'm back with a new season of Wiser Than Me. The show where I sit down with remarkable older women and soak up their stories, their humor and their hard earned wisdom. Every conversation leaves me a little smarter and definitely more inspired. And yes, I'm still calling my 91 year old mom Judy to get her take on it. All Wiser Than Me from Lemonada Media is out now. Wherever you get your podcasts,

Bert Kreischer (2:23)

It's morning in New York. Hey everybody, I'm Mandy Patinkin.

Tom Segura (2:32)

And I'm Kathryn Grody.

Bert Kreischer (2:33)

And we have a new podcast.

Tom Segura (2:35)

It's called don't listen to us.

Bert Kreischer (2:37)

Many of you have asked for our advice. Tell me, what is wrong with you people? Don't listen to us.

Tom Segura (2:43)

Our take it or leave it advice show every Wednesday.

Bert Kreischer (2:47)

Out now. A Lemonada Media original. I'd give it all for this house for this house and my girls to be 2 and 4. I would give it all. I got really emotional in the bathroom. Are we rolling?

Summary

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.