Transcript

A (0:00)

You made it with. You made it with. You made it with. Oh yeah, you made it weird.

B (0:08)

Yes, you made it weird with Pete Holmes. What's happening, weirdos? This is Annie Letterman, who is such a funny, funny person and a wonderful and hilarious stand up comedian. She has her own podcast which is called the Annie Wood Podcast. Check that out for sure. She's also on the touring. You gotta go to Annie Letterman.com and check that out. She's also in Grand Theft Auto 5, which I think is incredibly cool. But most importantly, she's just a very dynamic and hilarious talent that I'm so excited has joined us on the show today and I'm so glad you guys are here. Not much to plug up top. Go to Pete Holmes.com for my tour dates. May 24th at Largo. I'm happy to say sold out. Thank you everybody for that. That's so exciting. The next date on the calendar is Nashville. So excited. That's May 30 through June 1 for Nashville, followed by Irvine, California, San Jose, California, Houston, Texas, Royal Oak, Michigan, Washington, D.C. boston, Massachusetts, Portsmouth, New Hampshire. New Hampshire. I could say Portsmouth, but not New Hampshire. That's weird. Spokane, Washington, St. Louis, Missouri, Cleveland, Homestead, Pennsylvania and Atlantic City, New Jersey. And as I've been saying every single week, New York City will be around there as well. And that will all be on peteholmes.com take us to all of those. I'm. I'm saying with no hyperbole. This is my favorite hour I think that I've ever written. It's called the Pete Here now tour. I really, really hope you can be there and that you enjoy it if you do make it out. And in the meantime, enjoy this wonderful chat with the incomparable Annie Letterman. Get into it. You and me is like the way that.

A (1:53)

Oh my God.

B (1:54)

Oh no. What I did.

A (1:55)

Are you kidding me? You ruined the whole gu.

B (1:59)

I did.

A (2:00)

But I think your magic mind is.

B (2:01)

Like under the mine's empty.

A (2:03)

Oh, you already drank it.

B (2:04)

I already drank it.

A (2:06)

I know. I have a sleep too.

B (2:09)

They make sleep ones.

A (2:10)

Summary

You Made It Weird with Pete Holmes

Guest: Annie Lederman
Date: May 21, 2025

Episode Overview

In this lively and revealing episode, comedian Annie Lederman joins Pete Holmes for a classic "You Made It Weird" deep dive. True to the show's format—focused on uncovering "secret weirdness"—they roam through Annie's upbringing, family dynamics, comedy journey, psychedelic adventures, and philosophy on life, all interspersed with laughter, earnest storytelling, and sharp, self-aware humor. The tone is playful, candid, and occasionally profound, with both hosts riffing, oversharing, and peeling back layers of vulnerability.

Key Discussion Points and Insights

1. Family, Upbringing, and Comedy Roots

Quaker Background & Early Education:
Annie and Pete discover their shared Quaker roots, and swap stories of Quaker schools and silent meetings. Both attribute some of their comedic instincts to the enforced silent reflection and open community structure.
Quote (Annie, 20:41):
“Being a Quaker made me a comedian. Just because of Quaker meeting — you’re supposed to stand up if you’re moved. I spoke every meeting.”
Parental Dynamics and Sibling Rivalry:
Annie describes her "team fun" relationship with her dad (relatable, mischievous, supportive) and a more competitive one with her mother, including a wild anecdote about her mom joining her childhood swim team, and familial in-jokes about "team responsibility."
Quote (Annie, 40:15):
“My dad and I call ourselves team fun. And my mom and my brother are team responsibility… and my twin brother’s a floater.”
Rebel High School Years:
Lederman recounts her rebellious teenage phase—getting her nipples pierced at 14, fighting school dress codes, and dodging parental concern with boundary-pushing behavior.
Quote (Annie, 11:45):
“I would wear shirts without a… and they changed the dress code at my school because of you—‘You can’t have a visible nipple.’”

2. Stand-Up Comedy: Approach and Process

Natural Crowd Work:
Pete gushes over Annie’s stand-up special, noting her uniquely "effortless," hyper-receptive style that blurs the line between crowd work and crafted material. Annie emphasizes her ADD-driven need to interact with the room.
Quote (Annie, 26:40):
“I have ADD so I can’t, like, not… if something falls, it’s like, I can’t [ignore it].”
On Writing & Performance Rituals:
Both discuss the mechanics of writing—Pete’s detailed transcription and refinement process versus Annie’s more spontaneous connection-seeking. Annie shares her "Parrot App" pre-show affirmation practice.
Quote (Annie, 64:49):
“It records you giving yourself subliminal messages... So I’ll just be like, ‘Shine your light on the audience.’”
Comedy Industry Reflections:
The evolving pressure from the "algorithm economy," anxiety about burning material online, and the tension between crowd work trends and more traditional joke writing.

3. Psychedelics, Spirituality, and Therapy

Ayahuasca, Mushrooms, Breathwork:
Annie discusses her experiences with ayahuasca starting in 2019, the supportive presence of her gay shaman, and how plant medicine guided her through family trauma and provided insights into forgiveness and self-acceptance. Pete compares with his own recent mushroom trip, describing merging with the "creator God."
Quote (Annie, 69:21):
“I’ve done a lot of ayahuasca, and I always… also love her [my mom] and I need her… want to release anger… but it’s not—I don’t need to punish them.”
Self-Work and Inner Transformation:
Extensive discussion on therapy mindsets, self-hypnosis, setting boundaries, and the balance between acceptance and change. Annie details working with a hypnotist and the journey from self-loathing and addiction to genuine self-love.
Quote (Annie, 99:33):
“I just did so much work on myself. I just always... try to take my own inventory, see what I can do… I know I can’t control the outside world.”
Comedic Shadow Work:
They riff on embracing the "shadow" side, compassion for one’s own weirdness, and channeling darkness into laughter.
Quote (Pete, 17:22):
“The closer someone is to a… light, like a candle, the bigger their shadow. This is what happens when somebody falls… [they’re] not trying to look like they’re all together. And as a result, they have a very short shadow.”

4. Relationships, Gender, and Literal “Weirdness”

Marriage, Engagement, and Comedy Couples:
Annie talks about her engagement to Todd ("Steady Eddie"), why she avoids wedding planning, and lessons learned from dating comedians.
Quote (Annie, 32:11):
“Can we just call each other husband and wife and just be that—so I don’t have to deal with that? I’m not like, feminine like that.”
Sexuality and Wild Meet & Greets:
Much laughter about signing fans’ "bat-winged" balls at meet and greets, the strange energy at places like Skank Fest, and the "pierced hole" subculture.
Quote (Annie, 74:59):
“My diddle boys—come to me. My diddle boys! …I do sign their balls. Let me sign—yeah. I’ve signed so many.”
Body Image, Ozempic, and Aging:
They talk weight, hormones, Ozempic trends, navigating aging in comedy ("I have to be on the road... there’s no me taking like nine months"), and how society pressures women about fertility timelines.

5. Philosophy, Meaning of Life, and “Weird” Wisdom

Life’s Purpose, Death, and the Afterlife:
In the closing stretch, Annie offers her spiritual worldview shaped by psychedelic insight—life as an exercise in surrender, trusting everything’s as it should be, and the belief in a loving, continuous consciousness.
Quote (Annie, 106:43):
“I think it’s an exercise in learning to surrender… just trust that everything will be fine… in the end, it’s dick jokes.”
Ultimate Reality and Ego:
They meditate on the nature of self, quoting non-dual teachers, and joke about the paradox of being everything/nothing.
Quote (Pete, 108:49):
“Wisdom tells me I am nothing. Love tells me I am everything. In between the two, my life flows.”

Notable Quotes & Memorable Moments

On Annie’s Comedy Persona:
Pete (06:12): “There’s a calm, effortless talent about you… that's what I’m picking up on.”
Sharp Family Humor:
Annie (35:43): “It’s me on stage, my dad’s in the front row cracking up. No one else is laughing. Everyone else is, like, bored. And my dad’s like [losing it]—and it’s the best.”
Ayahuasca Parental Forgiveness:
Annie (69:21): “I always try to see it from her perspective… wanting to get even with them, or let them, like, feel and understand—I don’t think they have the capacity to truly feel that… I just love her and I need her.”
On Signing Fans’ Bodies:
Annie (75:05): “I do sign their balls… the wives are usually the ones pushing them to do it. It’s usually like a woman being like, do it.”
On “Team Fun” and Family Camping:
Annie (40:15): “Team fun! And my twin brother’s a floater. He can be both.”
On Psychedelic Sex with Zeus (yes, this episode goes there):
Annie (82:09): “It was Zeus… there was lightning bolts shooting everywhere… And I knew he was everyone… with Zeus, you know you’re pregnant.”
On Letting Go:
Annie (107:08): “Everything’s happening exactly how it’s supposed to happen at the perfect time… just telling dick jokes—in the end, it’s dick jokes.”

Timestamps for Key Segments

[06:04] – Pete compliments Annie’s "effortless" comedic coolness.
[11:04] – Annie’s rebellious adolescence and nipple-piercing/dress code battle.
[20:41] – Quaker upbringing and speaking in silent meetings.
[26:40] – How ADD shapes Annie’s standup and crowd work.
[40:15] – "Team Fun" vs. "Team Responsibility" in Annie’s family.
[54:01] – Family resemblance to Busy Phillips's Freaks and Geeks character.
[69:21] – Ayahuasca journeys and forgiveness around parental trauma.
[74:59] – Signing fans’ balls at meet and greets ("bat wingers").
[82:09] – Breathwork, visions of having sex with Zeus, and cosmic pregnancy.
[99:33] – Annie describes moving from self-hatred/addiction to self-love.
[106:43] – Closing "meaning of life" reflections.
[108:49] – The duality of everything and nothing.
[115:05] – Afterlife beliefs: Consciousness cycles, loving light.
[117:12] – Malcolm Gladwell, beef-tallow fries, and the power of nostalgia.

Final Thoughts

This episode is a testament to the "weirdness" that Pete Holmes’s show celebrates. Annie Lederman proves endlessly game for both confessional storytelling and raw riffing, effortlessly swapping between childhood trauma, comedy shop talk, wild anecdotes (from Quaker school to ayahuasca ceremonies in Costa Rica), and an oddly comforting cosmic optimism. The episode is peppered with irreverent wisdom, sharp commentary on gender and comedy, and genuine warmth—offering listeners both laughs and plenty to ponder.

Where to Find Annie Lederman

Instagram: @annielederman
Podcast: AnnieWood (drops Thursdays on YouTube)
Tour Dates: annielederman.com

“Keep it crispy.”

— Annie Lederman ([123:44])