Men Can’t Handle Jokes Michelle Wolf - CHIT CHAT WEDNESDAY

Summary

Podcast Summary: The JTrain Podcast

Episode: Men Can’t Handle Jokes Michelle Wolf – CHIT CHAT WEDNESDAY
Date: October 22, 2025
Host: Jared Freid
Guest: Michelle Wolf
Theme: Comedy worlds, the realities of being a standup comic, online algorithms, parental judgments, hotel breakfasts, corporate gigs gone wrong, and why men can’t handle jokes.

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Episode Overview

This Chit Chat Wednesday episode features comedian and friend Michelle Wolf, whose new special, The Well, is streaming on Netflix. Jared and Michelle riff on the promotional hustle demanded by the streaming world “algorithm,” the pitfalls and pathos of life on the road as a comic, parental culture wars on social media, and the wild misadventures of performing for tough crowds. The episode is light, honest, and deeply funny, filled with break-neck banter, memorable road stories, and meta-commentary on comedy and modern life. They close with a riff game, spinning breaking news into comedy bits.

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Key Discussion Points & Insights

The Netflix Promotion & The Tyranny of the Algorithm

[00:55–04:00]

• Jared goes meta, opening the show with a plea to watch Michelle’s The Well on Netflix:

  “Go turn it on right now. It’s hilarious. It’s spectacular. You’re going to love it.” (Jared, 01:34)

• Both joke about pleading with fans just to boost the almighty “algorithm”—not even caring if it’s muted or only for dog-viewing.
• Michelle reflects on the absurdity:

  “When are we going to admit the algorithm isn’t real?... you made the algorithm, like, you just changed a couple zeros and ones in there…” (Michelle, 02:30–03:01)

Social Media Parenting Judgment

[03:16–06:14]

• Jared refers to Michelle as an “expert mom,” sparking a tangent about online mom-shaming.
• Michelle describes moms on social media as “riddled with anxiety,” always warning about unsubstantiated dangers.
• Jared sees mom-group drama as a metaphor for all internet fights:

  “If you do it differently, then you’re somehow saying that...You must inherently think anyone who does it differently than you is a mother murderer, idiot.” (Jared, 04:51)

• Michelle’s advice: “Just relax. Just do what works for you. Take a breath and take a nap.” (05:07)

Standup Comedy: “Policies” and Relatable Material

[06:17–08:25]

• Jared and Michelle bash hacky airplane and Starbucks jokes, calling them “cheap tricks” for easy audience connection.
• Michelle quips:

  “If you’re talking about airplanes, you’re not doing enough…you need to do stuff other than standup.” (Michelle, 07:07)

• Jared’s “policy”: Save mundane “airplane jokes” for online, not the stage.

Comic Life on the Road: Hotels, Buffets, and the Sad Extended Stay

[10:19–16:17]

• They lampoon comedian Todd Barry’s infamous preference for sitting in the middle seat on flights.
• The comic’s relationship to hotel breakfast buffets:

  “If they have a Greek yogurt…maybe I’ll take that. But I’m never sitting down and getting, like, a waffle…that’s not my jam.” (Michelle, 11:01)

• Both discuss “tier badges” for comedians based on what hotels they endure.
• Michelle shares her “Red flag” for rooms with kitchens, recalling a night in an extended stay that stank of “a combination of everyone’s food—apple cinnamon and everyone else’s food…so gross.” (15:01–15:27)
• Jared distills the comic’s emotional extremes:

  “The happiest is sold out show, fun show. The saddest is way sadder than the happiest could ever be.” (Jared, 16:17)

Google Searches & Awkward Gigs

[17:03–21:59]

• Both trade stories about the dumbest things they’ve Googled (“doctor who does butts”).
• Michelle: A comic’s life is full of ridiculous searches and stranger gigs.
• Jared recounts a traumatizing gig presenting at a urologists’ event—“I got hired by a pharmaceutical company…couldn’t even pronounce the words on the PowerPoint…all I was thinking was, ‘Don’t lose the money!’” (20:10–21:10)
• “The problem is you…” Michelle: "I remember when you went to this gig…” (20:05–20:10)

Corporate & Odd Comedy Gigs

[21:34–27:05]

• Michelle recounts performing at a corporate dinner with a “fish on ice” theme:

  “So I was like, you can’t escape it. It’s either me talking about periods or the fish behind you smelling like them.” (Michelle, 22:53)

• On men who can’t handle period jokes:

  “[He was] like, I can’t even… How can you not hear the word? What gilded cage do you live in?” (Michelle, 23:27)

• Saddest gig: The birthday of a billionaire’s ex-wife, who’s "too rich to laugh," with a crowd rendered inert after a mentalist’s act:

  “Everyone was very aware that…we have to make sure she has a good time. This is the first birthday that’s right. Without her husband.” (Michelle, 27:38)

Audience Dynamics & Comedy’s Emotional Highs and Lows

[27:38–29:45]

• Jared recounts a bachelorette party “destroyed” because the bride cried, leading to mass walkout.

  “At one point, I was like, you guys are taking forever…Their description of the bachelorette party is, like, forever horrific.” (Jared, 28:29–29:29)

• Both riff on how disaster becomes legend—for both comics and audience.

“The Well” Comedy Special—Content & Artistic Intent

[30:16–34:39]

• Michelle admits she hasn’t fully watched her own special since 2024:

  “I know it’s ready, and I know it’s good. But… I just can’t. I can’t watch it again.” (Michelle, 30:48)

• Special covers “everything—gay men, Democrats, Republicans, first-time mom stuff” and takes risks.
• Michelle:

  “The first joke, you may hear it and go, I’m out… but if you’re in after the first joke, you’re in for the whole thing.” (31:19–31:47)

• On material: “I’m never actually thinking about the audience. I’m doing the jokes I want to do, and I hope they like them.” (31:47–32:04)

The Old Hairy Back Baby Gift Story

[34:03–36:26]

• Jared recounts gifting Michelle’s baby a monogrammed towel (“Old Hairy Back”) after Michelle joked her newborn looked like a “little old man…with hair on his back.”
• On being a comic in real life:

  “If they believe you’re a comedian…then you’re in this weird valley where you can literally do anything you want.” (Jared, 36:26)

“What’s the Bit?” News Spin Game

[37:45–44:34]

• Michelle and Jared take outrageous news headlines and riff on how they’d turn them into stand-up bits.

Example 1:

Headline: Kevin Federline accuses Britney Spears of wishing her kids dead.
Michelle’s take:

“This guy [the son] is not a guy who has to feel guilty about missing holidays…he’s free.” (38:31–39:08)

• Jared: Kevin Federline’s life has been the extreme highs and lows—"he’s seen the Four Seasons Hotel and he’s also seen the Hyatt house in the parking lot." (39:37–39:56)

Example 2:

Headline: Why Tom Cruise and Ana De Armas relationship fizzled out
Michelle:

“For me, I would fizzle out because he probably didn’t jump on Oprah’s couch celebrating his love for me…For Katie Holmes you jumped on Oprah’s couch. Her white couch. With your shoes on.” (42:49–43:26)

• Jared: “That’s the most female way to look at dating Tom Cruise.” (43:05–43:18)

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Notable Quotes & Memorable Moments

• On standup comedy:

  “Would I tell a room full of people, sit down, shut the fuck up, I got something to say? ...I don’t think a lot of people do that anymore.” (Jared, 08:08)

• On the emotional range of a comic’s life:

  “The happiest is sold out show, fun show. The saddest is way sadder than the happiest could ever be.” (Jared, 16:17)

• On audience discomfort:

  “You’re a grown man living in the world. How can you not hear the word [period]?” (Michelle, 23:27)

• On post-conservatorship Britney:

  “No one…was like, hey, my bad. Like, no one…was like, okay, maybe free wasn’t the right word.” (Jared & Michelle, 41:40–41:54)

• On promoting comedy specials:

  “Just put it on in the background. Let your dog watch it. You don’t have to watch it.” (Michelle, 01:55; repeated at 44:36)

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Segment Timestamps

• [00:00–04:00] – Cold open, promoting The Well, and Netflix algorithm jokes
• [04:01–07:07] – Social media parenting wars
• [07:08–08:25] – Jokes and “policies” in standup
• [10:19–16:17] – Road life, hotel buffets, and sad extended stay hotels
• [17:03–21:10] – Weirdest gigs and awkward Google searches
• [21:34–29:45] – Corporate, private, and crowd disaster stories
• [30:16–34:39] – Comedy special content and artistic authenticity
• [34:03–36:26] – The “Old Hairy Back” baby gift story
• [37:45–44:34] – “What’s the Bit?”—improvised news riffing

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Conclusion

A lively, sharp, and revealing conversation about comedy on and off stage. Jared and Michelle’s chemistry covers the real tensions of making people laugh in 2025: algorithm anxiety, getting shamed by strangers, and the constant search for stories worth telling. If you’re a fan of unfiltered comedy, you’ll love both this episode and Michelle’s special, The Well.

Key takeaways:

• Watch The Well—or just play it (for yourself, your dog, anyone)—on Netflix
• Embrace your own way of doing things; ignore internet morale
• Standup comedy is still brutally honest work, and the best jokes are the riskiest
• Bad gigs and hotel breakfasts are comedy gold
• Men (sometimes) really, really can’t handle jokes about periods

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Listen to the full episode for even more punchlines and storytelling.

Transcript

[A]

Chit Chat Wednesday for you to listen to. I have a guess who will be your new boo. You're gonna love them, too. Chit Chat Wednesday. I hope you're having a good day today. I hope it's gonna be a perfect week, too. I hope you have a nice poo. It's a ch. Chitchat Wednesday, too. Hello and welcome to the J Train Podcast. Is J Train Jared Freed coming to you live from Richmond, Virginia? That's right, every Wednesday is a Chit Chat Wednesday where I talk with a comedian, a friend, an expert. Today we have all three. We have a comedian, we have a friend, we have an expert. I would call them an expert moment. An expert in Mom. Also expert comedian Michelle Wolf. How are you? Good to see you. And also in my intro, the one time I fuck up an intro, the special, it is called the well, it is on Netflix today. Look it, they're crying in the streets for how great this special is. It's called the well, it is out on Netflix right now. I want you to pause this and I want you to put on your Netflix and add it to your queue. Actually put it on. Play it on mute. Just play it. I. Listen. I know, I know. I got to tell the baby that we're. We're promoting the special. I did it wrong. I should have promoted it first and then introduced their name. Listen, the. Well, it's on Netflix. Go turn it on right now. It's hilarious. It's spectacular. Going to love it. Michelle Wolf, thank you for coming on. How are you?

[B]

Thank you for having me. I would say just even put it.

[A]

On for your dog, right? Just let it.

[B]

Run it on. Put it on in the background. You don't need to watch it.

[A]

This is.

[B]

That's what I. I would say.

[A]

This is like the sad part about the whole thing. Like, we're telling people to just, like, we want them to watch it, enjoy it, but we're also like, do it now. So it helps me. You know, like, you gotta watch it early and often and you gotta, like. Because we're like, this is the new God algorithm. You know, Father algorithm has to look kindly upon us so that more people can see it and be on more front pages. You know, this is annoying, right?

[B]

Well, it's also. It's like. It's like, when are we going to admit the algorithm isn't real? You know, like, when are we going to admit that, like, the wizard behind the curtain, you know, I'm not funny.

[A]

It's the algorithm.

[B]

That Netflix doesn't have complete Control over all of this.

[A]

Yeah. They get. They're not, like, perfect excuse. It's the algorithm.

[B]

Yeah. They. Anytime they need to get out of a situation, like, I love it.

[A]

I love it.

[B]

I thought it was so funny. The algorithm hates it. Just didn't like that you made it. You made the algorithm, like, you just change a couple zeros and ones in there, and then now he likes it, so.

[A]

Right. I like that you made the algorithm a he. Look at you. This is.

[B]

Yeah, Yeah.

[A]

I called you an expert mom. Is that scarier than telling, like, getting called an expert mom? Is that scarier than telling a joke that's about a tough subject?

[B]

I mean, the funniest thing, and it's. I mean, maybe they've always been this judgy, but, like, social media moms are like, just like. First of all, they're people that are, like, riddled with anxiety, and they're like, you can't hold your baby like that because sometimes they can't breathe. And you're like, that's. What are you talking about?

[A]

Right?

[B]

Who scared you?

[A]

You know, like, well, that's why they're commenting on the Internet. No one will listen to them anymore.

[B]

Baby might die.

[A]

Right. Everything leads to death. Everything you do is, like, one step, you're on the doorstep. I see that. Like, just like, anytime I've seen a comment page that involves mothering, like, as an outside, I'm just like, whoa, I think I walked into the wrong room in the house. And I'm like, everyone here is being mean to one another, and there's, like, a lot of morality play. Like, if. If you do it differently, then you're somehow saying that. I like the mom commentary is really a very, like, transparent metaphor for how we, you know, how all Internet fights happen.

[B]

Oh, yeah. I mean, it's a perfect. Because it's like, well, you're not doing it the way that, like, I would do it, or you're not doing it the way it's supposed to be done. So I have to tell you that that's the wrong way.

[A]

Right.

[B]

And because you must feel better. I have to feel better about the way I'm doing it by telling you.

[A]

Right. And the way you're doing it wrong. Because you're doing it differently. You must inherently think anyone who does it differently than you is a mother murderer, idiot. Like, that's, like, the only thing.

[B]

They're putting everything at risk. Like, it's just like, just relax. Just do what works for you. Take a breath and take a nap.

[A]

I can't Imagine? Yeah. Like, I can't imagine. I guess I have to have kids to know I can't speak on it because I don't have kids. Like, I do feel like anyone can say, well, you don't have kids. And listen, I agree. I hope I don't. But I just can't imagine being, like, having to say something to a stranger about how if they fuck up their kids, not my problem, I don't give a fuck. Go ahead.

[B]

Right. Like, I don't know. Everyone's got such strong opinions about everything in mothering. Like, especially, like, when it comes to baby sleep and stuff like that. And everyone's like, I'm not sleeping at all. And I'm like, I mean, the secret is just sleep with your baby. But everyone is gonna, if you say that out loud, then everyone's like, it's so dangerous. You're not this. And this, and this will happen. And it's like, or not.

[A]

Or, or not. Right?

[B]

Or, or not.

[A]

Or, you know, I ride a bike without a helmet. Oh, you got. I know. And they always reference one person they know who, Like, I saw it happen. And you're like, okay, I, I, I just, I just, I just put out a thing about, like, travel. Like, I, you know, I, I, I reserve any travel commentary now. Like, I've kind of had this. Do you have policies with your standup? Is there a policy you have the. Well out on Netflix right now? I don't know. I've started to develop policies. Like, I'm like, if, if I'm gonna talk about air travel in any way to be funny. Like, when I have air travel thoughts, I'm like, that's an online thing to me. That's not, that's an Internet tweet. Like, I'm not gonna do that in my standup. Would you ever.

[B]

I, I read once, or someone said something once where they're like, if you're talking about airplanes, you're not doing enough. Like, you're not, like, you need to do stuff other than stand up.

[A]

Well, you're right. The, the, like, when I see a, When I see an airplane joke, I'm like, Or like a reference to something that happened while flying, I'm like, I guess that's the only variable in your life. But it's also a cheap trick because you're relating to people in the easiest way. Because everyone's been to an airport. Like, everyone. It's not, everyone doesn't know your mom. Everyone has been to an airport, you know, like, so the difference between those two Stories and difficulty are different.

[B]

I also think it's like, it's. I don't know, it's one of those things that's like, can you believe what they put on my Starbucks cup? You know?

[A]

Like, it's like I can believe it.

[B]

Unless it's an absolutely insane story, you know, Like, I'm like, I don't, I don't know, I'm not invested.

[A]

That's the. I, I'm with you. I. That's why I put it online. I'm like, let me just put this thing that I think is funny, but it's not something I'm like, like I wouldn't, I always think of it like, would I get on stage to tell this story? Like, I'm trying to. Like, that's kind of like what I get on stage.

[B]

Like, give it to the content monsters, right?

[A]

Give it to the. Like, I know it's going to do well. I'm not going to think better of myself because it does well. I'm just going to go, this is something funny and. But I guess when I think of like what I'm going to do as my stand up, I'm like, would I tell a room full of people, sit down, shut the fuck up, I got something to say. And I don't think a lot of people do that anymore. Like, I think they're just like, I'm me, I got something to say. I don't know, I, maybe I wish I was that confident to just be like, it's me and I'm going to talk about middle seat comfort. Plus, your gut has a massive impact on how you feel each and every day. Bioma keeps things in tip top shape so you can feel your best no matter what life throws your way. Bioma's blend of prebiotics, probiotics and postbiotics helps restore a healthy microbiome. You're gonna want to give bioma a try and get things sorted down there. I'm telling you right now, I'm taking it and it's been awesome. It like, it is weirdly a flush out. Like I started taking Bioma health and I take it every morning. I have it with my coffee in the morning and it's been great and I feel like a lot less bloated, which is nice. So I'm really enjoying it. If your gut is full of the wrong bacteria, get byoma and get it together. It's not just about smooth and regular digestion. Your gut can mess with your hormone levels, energy, weight management and even lifespan. Take 15% off your bioma order. To get started, just click the link in our show notes and press in code J train. That's code J train for 15% off your order. When you click the link in our show notes.

[B]

Don't Todd Barry us here.

[A]

Todd Barry, middle Todd Barry, hilarious comic who claims he. Well, he says he flies middle seat sometimes as a comedian. And we made fun of him for about an hour, and I was gonna ask you about this, and then he.

[B]

Left, and then he came back and we made fun of him again, again.

[A]

For sitting middle seat. I think it was international or something. And I was just at the Hyatt House here. World of Hyatt. I'm looking at the coffee cup. Do you eat the breakfast given to you by the hotel? Have you ever. Would you ever. What's your policy there?

[B]

No, almost never. I'm not a huge breakfast person. I'll get the coffee for sure.

[A]

Yeah.

[B]

If they have a Greek yogurt or something, maybe I'll take that. But I'm never sitting down and getting, like, a waffle and, you know, some. Some cereal that you. You get out of a trough.

[A]

Yes.

[B]

Or some, like, I don't know, like, eggs that came out of a. A carton and are, like, lukewarm. That's not my jam.

[A]

Listen, I am with you. I. But I always give the hotel buffet a look. Here's the problem. Here's the thing. Like, I'm gonna. I'm gonna browse. And here's the thing about. I was. When I was bringing you on, I'm saying, Michelle's an expert comedian, and you need to go watch a special. It's called the. Well, it's out on Netflix. But, like, you and I get annoyed at people who go on stage, and we're like, this isn't a comedian. Like, I think people, comedians should be given badges for, like, their level. Like, because I'm at a hotel right now that I could go on and on about. I am. And you know this hotel intimately. It is a hotel in a mall that's far from downtown and fun and kind of far from the mall stuff. So I have to walk to mall things through a parking lot if I want to do anything or.

[B]

I saw your story. I saw where the hotel. You got a big parking lot, huge.

[A]

Parking lot, and you know it. That's the thing. You've done this. This is part of the job in a certain way. But for some people, they're not doing this. Like, you go. You have to go to Richmond to make sure the joke Works like, you have to do it. And then I'm sitting downstairs and I go to the. Like, the hotel breakfast. I'm like, michelle would know this breakfast in two seconds. And you just said it. And then I was like, I saw that they had eggs, and they had egg whites, and then they had regular sausage and chicken sausage. And I was like, whoa, this is, like, a good one.

[B]

So let me guess. You did the egg whites and the chicken sausage.

[A]

How'd you know? And they had onions and peppers alone on its own that you could put on top of the eggs. I was like, this is my perfect breakfast. Like, I was like, the amount of happiness I got from them having egg. Like, the things I needed to build a house. Like, I was, like, so happy. And I'm like, only a comedian who has to stay in these places has to go to these places. Like, and, like, the whole lobby is, like. It's like. It's like 17 weddings and, like, all these, like, husbands and wives and a business conference and. Right. All the things that are, like, annoying going on around you, and you're this, like, weirdo alone looking at the. You know, the breakfast buffet going, this is pretty good. Like, Like, I was like, oh, look at you, Hyatt House. Like, I was, like, super impressed.

[B]

I saw. I saw that you had a kitchen in your room.

[A]

I do have.

[B]

Always a red flag for me.

[A]

It's. It's something that tells you you're not doing well. You're not. You're not doing, like, kitchen in the room is either you're doing really well or not really well at all. Like, it can go.

[B]

That's true. It could be really, really. It could be because you're in, like, a really penthouse. Like, oh, yeah. And then there's the kitchen that someone will come in and make food for you.

[A]

Right.

[B]

I think I just have a terrible. I think because the one time I played that. That club that's outside Kansas City that I don't know if it exists anymore, it had the guy who, like, it's.

[A]

The comedy club of Kansas City. I just did the. The Funny Bone, which is on the other side of town. I know where you're talking about.

[B]

Yeah. And so this one, I just. They put me in an extended stay that had a kitchen.

[A]

Yeah.

[B]

And it was before I could, like, get buyouts and stuff like that. And it just smelled like. The whole place smelled like an. Like. Like a combination of everyone's food. And I, Like, I was. It was one of those things where it was like, it was a Thursday and you know, I was like, there's a CVS nearby. I'm gon buy candles. And so I bought like apple cinnamon candles or something like that, like whatever they had at cvs. Because I was like, I gotta change the smell of this place.

[A]

Right.

[B]

But then it ended up just smelling like apple cinnamon and everyone else's food. Like, it was so gross. And then, I mean, the owner of that club, I believe he. I think he died, but he.

[A]

Or maybe this is a different club. The one I'm thinking of, he's alive and well.

[B]

It's outside Kansas City. It's not in Kansas City. It's. The guy, he had like a. A terrible hairpiece. And that's.

[A]

This is. We're thinking of two different clubs. Yeah.

[B]

And so I got to look it up because it's. It's really. But he. Yeah, it was just a terrible. And ever so, ever since then, I see a kitchen in a hotel room and I'm like, no, it's going to smell like everyone's food. Well, can't do it.

[A]

That it is. When you get into these rooms with the kitchen, it is very. Like, you do think of the saddest divorce dad. Like, you do think of like the dad whose life went the wrong way. Like, it's very much Mickey Rourke from the Wrestler. Like every time you're in these sad comedian spaces. Like, I've like. The happiest is sold out show, fun show. The saddest is way sadder than the happiest could ever be.

[B]

Oh, yeah. The saddest is like. I mean, this place was. Gotta look it up. This is gonna drive me crazy. I'm just. This is what I'm gonna Google because this is. This is a fun game I like to play.

[A]

Yeah.

[B]

The least amount of like, like the. What you Google. Okay. So this is what I'm googling for this terrible Kansas City comedy club.

[A]

I did this last. I actually thought I googled something and I was like, this is the dumbest thing someone has ever googled.

[B]

And.

[A]

Here'S my most dumb Google recently. Ready?

[B]

Stanford and Sons.

[A]

I've never done that club and I've heard of it, so I don't think that one had a reputation.

[B]

I don't think it's open anymore.

[A]

I don't think so either. That one had a reputation that it was like, notoriously bad. It was called Stamford and Sons, not Samford. Like, it was like a play on the TV show.

[B]

Yeah, well, maybe it was just Stanford's Comedy club. Whatever it was, it was.

[A]

Do you want to hear my Google.

[B]

Terrible Kansas City Comedy Club? And they came right up, right up.

[A]

I was trying to tell a story about how I did a show for 11 urologists. I was telling a friend about how I did a show for 11 urologists. And it's a crazy story about how I had to like present someone's business. Like they hired me to like present their business in Big Sky Montana. Like it's this whole story. So I was telling the story, but I couldn't remember that they were urologists. So I was like, what's a urologist? You know, like. And I, and I, for some reason, a urologist. To me it's a penis doctor. But they have to check your prostate. Like, that's the doctor who checks your prostate, right?

[B]

Uh huh.

[A]

I think I should know more better than you. So I googled doctor who does butts.

[B]

Did you give plastic surgery doctors?

[A]

No, I got like, I don't even know what would come up. Well, the AI overview that Google does, a doctor who specializes in butts is a proctologist, also known as a colon and reckless surgeon. And, and I was like, that's not it.

[B]

Yeah, urologist deals with like pee.

[A]

Right.

[B]

And kidneys.

[A]

Well, but they have to give you a, like a rectal exam. Don't they have to give you like the finger in your butt? I just was, I was like, this is the dumbest.

[B]

Not me. Maybe for guys, but for women, they just.

[A]

Or maybe the doctor was just into me and this is, you know, he was just.

[B]

Is that how you got paid? You got a free urology exam?

[A]

That was.

[B]

And they were like, it's a free exam. And they just.

[A]

I opened the show by saying, I go, hey guys, we're gonna have a great time tonight. By the end of it, it'll be just like the end of an appointment. We'll have our finger up each other's butts and we'll be laughing like nothing ever happened. And they were like, what the fuck is this? Like, they, they, they like were like, that's not what we came for. Like, this is stupid. What are you talking about? They didn't know I was a comedian. It's a whole story. I mean, like, we get. The problem is you.

[B]

I remember when you went to this gig. I remember you talking about it.

[A]

They literally. I got, so I got hired by a pharmaceutical company and they're like, they had like the, they were like, we need to do a zoom before you go to Big Sky. And they were paying me all this money and I got on the zoom. And they're like, do you have the PowerPoint? And I'm like, no, not yet, because you don't want to, like, lose the money. And then I'm like. So I'm like, just going along. And they're like, oh, we'll send it to you now. And then they email me this PowerPoint, and I'm on zoom with, like, the president of the company. And they're like, okay, so slide one. And it's, like, information about their company that I'm supposed to, like, present. And I'm sitting there just like, yeah, yeah, yeah, looks good. Like, I'm just like, get to the end of the meeting. I'll talk to my manager, and then I'll. We'll figure this out. Like. But, like, don't lose the money is, like, the whole thing. So, like, they're like, okay, so we do this and we do that, and you're okay presenting this. And I'm like, I can't even pronounce the words on the PowerPoint. And I remember getting to the end, and I go. And they go, so you're cool? And I'm like, good to go. And then I hang up with them immediately call my manager. I'm like, hey, we got a problem here. Like, I couldn't have been more opposite. What is the. Do corporate gigs? Do you get them? Do you have one that you remember that was, like, horrific?

[B]

I have only done a couple. I think people tend to find that I'm maybe not built for corporate, Although, I don't know.

[A]

That's, like, a crazy assumption of you. But I. I guess I get, like, if they hear you talk about, like, so abortion and, like, making jokes about that, they're like, we're not bringing her to HR you know, Like, I don't know, but that's stupid.

[B]

You're right. I did one. I did one that was terrible. But it was at this beautiful resort in Santa Barbara, and I was like, well, that's worth it. You know? Like, it was like. I mean, also, the money was good, but I was like, yeah, I'll do, like, 30 minutes on stage to stay at this place. Like, sure, yeah, yeah. The one that I did, that was hilarious. I was in L. A. And it was first. I don't even remember what the company was, but it was at, like, some restaurant that had, like. You know those restaurants that have, like, fish on ice.

[A]

Yes.

[B]

You know, like. Like, display.

[A]

Yeah.

[B]

And so I. I was. You know, the crowd was like, mostly men, but there were some women that were Having a really good time. So I was like, you know what? I'm going to do some of my periods. Because I was like, I'm just playing for these women, you know, like. Cause you gotta find, like, the one or two people that are not having a terrible time.

[A]

Absolutely.

[B]

And I said something about periods and this guy, like, this, like, typical, like, can't hear about. Can't even hear the word guy. Like, he was like, oh. And he turned around, but the fish were right behind him. And I was like, you can't escape it. It's either me talking about periods or the fish behind you smelling like them.

[A]

Nothing worse than angry at a joke guy.

[B]

Yeah. Like. Like, I can't even. Like, I was like, I'm like, you're a grown man. You're a grown man living in the world. Like, how can you not hear the word? You know? Like, how can you. How is it so offensive? What. What gilded cage do you live in?

[A]

The only thing funnier would be if he stood up, tripped, and fell into his wife's pussy face first. He's like, and she has her period, and he's just, like, wiping period blood off of his face.

[B]

He gets a bloody nose and some guy's like, just put a tampon in. And this guy is a shell of a human by the end of it.

[A]

Yeah.

[B]

He's like, oh, my whole world.

[A]

This is why the world needs stupid movies. Like, that should be in a movie.

[B]

Yeah.

[A]

Like, that's a scene.

[B]

The worst one, though.

[A]

Yeah.

[B]

The absolute worst one I had was some, like, the ex wife of a billionaire. So it was like. It was in the. Like, the private room at 11 in Madison Park.

[A]

Ex wife of a billionaire. You should be living the way we would all live. Like, to me, you are like, you have unlimited funds. You're on your own. Like, I would if I. Ex wife of a billionaire. Like, that's heaven on earth. You should be living.

[B]

So, like, they have. They have, like, two adult kids together, like, in their 20s, you know, like, she's older, I think, and I think it was her first birthday since the divorce. And I'm like, lady won, you know? Like, you have, like, however much of his money, you know, like, you. So they have this beautiful. I mean, like, the dining room is, like. The walls are, like, covered in roses. And so I'm like, oh, wow, is this a dinner or an Eyes Wide Shut party? And, like, I mean, not a tinkle of laughter.

[A]

Not even. Not even a. Not even a Nothing.

[B]

Absolutely nothing. And, like, to be fair, I was up Against a challenge. Because before dinner, like, during. Like, the cocktail hour or whatever, they had a mentalist.

[A]

And people love a mentalist.

[B]

If you could have seen the reactions of this guy remembering their names.

[A]

Yeah.

[B]

You would have been like, I'm gonna die. I'm gonna die on stage. And.

[A]

They love the mentalist.

[B]

They love the mentalist. And after me. And after dinner, they wanted me to do this while they were eating. So I'm also up against that. The tables are circular.

[A]

You know, like, everything's bad.

[B]

Everything is working against me. The only thing that's good is the wait staff is on my side, and they're just, like, shoveling me Manhattans, you know, like. And it's like a really good. With one of those really good cherries, you know?

[A]

Yes.

[B]

And luckily, the woman's son is, like, a gay man in his 20s. And I was like, that's my guy.

[A]

Right? That's.

[B]

I'm gonna do all my jokes right to you.

[A]

Right?

[B]

Zone in on the material from 38 minutes.

[A]

That's what happens. You start. You get in a chatterbox. You're like, I just gotta go faster. Maybe faster will help. And you're like, that's the worst thing you could do.

[B]

I was just like, I just want to get paid and get out of here. I can't. Like, these were. They're too rich to laugh. Like, that was like. That was like, the overall takeaway.

[A]

It's like, look to your right, look to your left. If you feel that, like, especially at, like, a fancy birthday, you feel you're on stage too. You got dressed or people talking about my outfit. So it's like, there's too much going on in people's heads to, like, sit back and let their, you know, their button undone and, like, enjoy the comedian. Like, it's just not gonna happen that way.

[B]

Yeah, no one wants to. And also, I think everyone was very aware that they were like, well, we have to make sure she has a good time. This is the first birthday that's right. Without her husband. And so it was like, well, if.

[A]

And if you lose the birthday girl, you lose the party. Like, and if she's not having fun, oh, my God, none of us can have fun. I had that with a bachelorette party. They came to my show in Kansas City, and the woman getting married, the bachelorette, she started crying because the club asked her to, like, pipe down a little bit. And the whole party was done. 13 people. It felt like I was, like, performing for a room where, like, a meteor hit a section of it and killed everyone in its way. Like, it was like. I'm like, why is this section good? And then I'm, like, looking over in the bachelorette party. They're all just whispering. They're like, I think we should go. We should get out of here. And they ended up leaving. And it took them legit 7 minutes to leave the room. And I. And I. At one point, I was like, you guys are taking forever. Like, I was like, in a funny way, you're taking forever. And this one woman goes, oh, God. Like, we can't even get out of here. She said something like that. And I. She said, oh, God. And I go, well, there can't be any. I said something along the lines of, there can't be any God, because that voice just made me never want to fuck again or something like that. Like, I had, like, she broke me. And then I was like, I just started calling them the unfuckables. And I can't imagine being at your bachelorette party and just some guys calling your whole group a bunch of unfuckable people. Like, I like. Their description of the bachelorette party is, like, forever horrific. Like, I like.

[B]

Well, I would love to hear how they tell the story, too, because they'd probably be like, we were at the comedy club, and we were having a great time. We were having a great time, and then he just asked us to leave.

[A]

Right?

[B]

We didn't even leave.

[A]

And then called us unfuckable, then said, no one should ever want to fuck us.

[B]

Yeah.

[A]

Like, that's the funniest story, them retelling it. I would be laughing so hard, I'd be like, and then he told you. He told the bachelorette party that there's someone no one would want to have sex with. Like, that's crazy to happen at your bachelorette. I want to play a game with you. The special is called the. Well, what are the subjects you're talking about? Everything I saw. You're talking. I. I've seen the special, right? Like, I. I. Yeah.

[B]

Well, I mean, here's the thing. I taped this in 2023, so it's perfect. It's not. It's not brand new, you know, so. And as someone who hates watching myself.

[A]

You don't know what to.

[B]

I haven't watched it the full way through since, like, 2024, which I understand completely.

[A]

Like. Like, listen, I. We are. We are so alike. Because I would do the same thing. I'd be like, just get it out there. I don't know. It's. It's done. I, like.

[B]

I know. I know it's ready, and I know it's good. But, like, I was like, I just can't. I can't watch it again. I've seen some clips. I've picked some clips. You know, like, all that stuff. But, like, I. There's. I mean, I talk about. I talk about everything. There's a real fun bit about gay men in the beginning. I talk about, you know, Democrats, Republicans.

[A]

It's like giving the book report. You're like, the beginning. You have the first 10 minutes. You're like, the beginning joke, right?

[B]

Yeah, the beginning and then it ends.

[A]

It's the last joke.

[B]

Yeah. I will say I start. The show starts off on a joke that I think might lose. People immediately love it. I will say that the first joke.

[A]

That's a great way to promote it.

[B]

Yeah, the first joke, you may hear it and go, I'm out.

[A]

Which is, listen, if you're in after the first joke, you're in for the whole thing. That's a good thing.

[B]

Yeah, it's one of those things where it's like, listen, if you. Cause this is the thing. Someone asked me this the other day. They're like, well, do you try to do jokes that your audience likes? And I'm like, I'm never actually thinking about the audience. I'm doing the jokes I want to do, and I hope they like them.

[A]

That's a good. That's the sign of a good comedian. If you were doing the jokes that you knew the audience would like, you'd be talking about spirit airlines.

[B]

Right?

[A]

You know, that's the difference.

[B]

Yeah. And so I'm like, so the first joke is. It's, you know, you're either gonna like it or not.

[A]

I'm trying to think of what the joke is. Cause I've seen this. I. I definitely saw this whole special and.

[B]

Oh, yeah, you have. I mean, I honestly forgot what the first joke was, too. And then I was like, oh, right.

[A]

That's the thing about your watching your own work. If you get away from it enough, you go, wow, this is pretty good. You're like. You, like, feel like a weirdo. You're like, oh, okay. That's funny because you forget about it. Like, once it's done, it's done. Like, I mean, like, someone asked me. I just. The book is done. And they're like, so how is it? I go, I hope it's good. They're like, you don't know? I go, well, I've read it in parts. Like, I never Read it together, right? I wrote it.

[B]

And you're also like. I mean, my opinion about it doesn't really matter.

[A]

No, not at all. Right. That's true. I think everything I do is great. And I can't believe I'm staying at a Hyatt house in a parking lot of a Dillard's. Like, like, I can't believe this.

[B]

What a southern reference. Dillard's.

[A]

I'm looking out the window. I haven't seen A Dillard's in 7,000 years. It must be the most northern Dillards.

[B]

I think it went out of business.

[A]

Maybe it is out of business. Maybe I'm dead and this is just hell and I'm just.

[B]

Some sort of, what's it?

[A]

Limbo. Right.

[B]

The other thing. But, you know, this was. This is a special I did after I had my first kid. So it's like, it's. It's some, like, societal stuff, but then it's also like, first time mom stuff, which is kind of weird because now I have another kid. But I think a lot of people still don't know I have one kid. So this will be like a lot.

[A]

Of shock and awe. Wait a minute. We were gonna talk about this when we started. I got your kid a gift. The new. The new kid, but I didn't know the name yet. Yeah, so. So you got the. You got the gift. So I go to Bliss Monogram. Bliss is in Boca. It's my mom's baby gift spot. And for the first time, I usually call Diane. And I'm like, diane, I got another one for you. And this time I was in the store and I saw it. It's a beautiful store. And I talked to her and I'm like, you know, my friend just had a kid and I got to send it. You know, she lives abroad. I'm like, it's a whole thing. She's like, well, what do you want to put on it? I go, oh, I don't know the kid's name, but like, let's have some fun here. What did I put on it?

[B]

You put old hairy back.

[A]

Yes. Cause you said the baby had a hairy back.

[B]

Well, first of all, it's like a little old man.

[A]

Yes.

[B]

And then there's like, hair on his back. And I was like, he even has hair on his back. And so Jared gets a towel that says old Harry back, which is great. It's a great towel to have.

[A]

Here's old Harry back.

[B]

But what I wanted to know was what these lovely, I assume, lovely older women, right. Said when you said, I want this monogrammed on a towel for a baby.

[A]

Well, this is like the fun part about being a comedian. Like, there's horri. You know, once people, there's like a weird mountain of telling people you're a comedian. It's like, at first it sucks because you're like, they're like, if they don't know you, they're like, is that what you do for work? For real? Like, do you make any money? They ask a lot of like hyper specific consulting questions. But then if they believe you're a comedian, if they are somewhat just accepting that that is your career and your. What you do and you make a living from it and other people know you and like you and you and you're doing okay, then you're in this weird valley where you can literally do anything you want. So when I went to the ladies and I'm like, I want old Harry back on the towel, they're like, oh, Jared, like you would like. It's all fun and games.

[B]

Yeah. And they're. I bet they're like, this guy, he must be the life of the party.

[A]

Every party, right?

[B]

Friends must just have a ball.

[A]

Little do they know I'm just quietly in the corner of the room eating egg whites with onions and peppers on it.

[B]

I just had a vision of you, like at a party and they're passing around deviled eggs and you just scoop out the middle and eat just the shell part of it.

[A]

The most I'm on Weight Watchers move that's ever been moved. Okay. I wanted to play a quick game before we go. Okay. It's called what's the bit? I have some news articles and you tell me based on the title. What would be your bit from it? I think this is a fun. Okay, you ready? Kevin Federline accuses Britney Spears of wishing her kids dead punching son. What? No, that's not the way they shorten the title to the worst hyperlink. I was like, I won't click on wishing her kids dead. Oh, she did. Kevin Federline accuses Britney Spears of wishing her kids dead Punching son. Sean Preston. That's an actual title.

[B]

Well, that's funny because I was gonna do a story later today about how she. He said that she like, did cocaine while breastfeeding.

[A]

I think. Well, I think it's a big Kevin Federline is trying to get the public on his side day because there's a few Britney Spears stories. I think he's like trying to get more money out of her.

[B]

Yeah, I Think he. I think she doesn't pay him anymore. I think she doesn't give him money anymore. And now he needs the book to make money, so he's kind of like teasing out some of the big stories. But what's my bit from Kevin Fairline.

[A]

Accusing Britney Spears of things?

[B]

Well, I would say for the son, I mean, now it's like, this guy is not a guy who has to feel guilty about missing holidays. You know, this is a guy who can just be like, you know what? I'm not gonna go home for Christmas.

[A]

Right. The son has full immunity. No one would tell him to go home. They'd be like, oh, yeah, come to our house.

[B]

Yeah. They'd be like, he's getting invitations to go other places. Like, he's a guy who is like. You know, on one hand, it probably seems really tragic if your mom doesn't want you to live, but on the other hand, you're free.

[A]

You're free. You can do whatever you want. The tattoo you wanted that mom wouldn't like. Who even cares anymore? No one can say, what does your mom think? You know, at this point, you're. I, I think I like that direction. My direction initially was like, man, Kevin Federline, that guy, like, would you take his life? Like, would you like, it sounds like he lived in the highest and most luxurious. He's seen the Four Seasons Hotel and he's also seen the Hyatt house in the parking lot. Like, this guy has gotten all versions of wealth and fame and, and lifestyles. Like, is he. Is.

[B]

This is a guy who. Sorry.

[A]

No, go ahead, go ahead, please.

[B]

He was. He went from background dancer to whirlwind Britney Spears husband to father Britney Spears kids, to soul caretaker of said children. So he just spent the last, like, I don't know, 18 plus years. Cause the kids have to be older now, right? Like they're 20 or. And so, like, he was just dad, but he was dad with like alimony, I would presume, or child support. Either one.

[A]

The kid is 19, 20 and 19. They've got two kids.

[B]

Oh, yeah. They're out of child support. Like, she didn't have to pay him anything anymore and she doesn't have to give them any money. But you know what I always think about. And this is because I think this is so funny. And it's your bit. It's how Britney Spears, like, someone's gotta be your conservator, right?

[A]

Remember when it was for a long time and I couldn't get people beyond the sadness of it and like, there's people that, like, it was. It was just weird that, like, we. No one took that back. Like, that Britney, like, Britney was like, released from her conservatorship. Like, like Britney's like, free. This whole campaign was to free Britney. And then she got freed and we were all just like, watching this person, like, online have these weird moments. And no one was like, hey, my bad. Like, no one. Like, yeah, right. And like some.

[B]

No one was like, that's okay. Maybe free wasn't the right word.

[A]

Right? Is there something between free and. And can we get an eye on her? Like, like, like it felt like she needed an eye.

[B]

It's like, it's like you. She at least needs someone to be like, Britney, there's eyeliner. You just wipe it. Okay, Right? She need for the video starts. Let's just wipe it.

[A]

Right? But then the bit was always like, who know? None of us would do that job. None of us after seeing what Britney's like, right? None of us would ever be like her guardian. Like, we'd be like, no, no, no, I'm too exhausted. Like, it would be. It looks like the most exhausting job.

[B]

In the world is taking care of a child.

[A]

Right?

[B]

That has a lot of money and is your boss.

[A]

Okay, I got one more for us and then we'll be done. This is okay. Why Tom Cruise and Anna De Armas relationship fizzled out report. I can't even believe we're reporting on Tom Cruise relationships at this point.

[B]

I mean, I would be mad if he. For me, I would fizzle out because he probably didn't jump on Oprah's couch celebrating his love for me.

[A]

Right? That's the boss.

[B]

Wow. I never saw you got quite that excited about us.

[A]

Right? That's the most female way to look at dating Tom Cruise. It's like, you're either on that couch or you don't love me at all.

[B]

This is like, like you for Katie Holmes. You jumped on Oprah's couch. Her white couch with your shoes on.

[A]

Right?

[B]

Okay.

[A]

In front of.

[B]

And I don't care if you're Tom Cruise or not. She's Oprah.

[A]

Right?

[B]

Okay.

[A]

You don't just jump on Oprah's couch.

[B]

So you either need to do. You need to do something bigger than that so that I know you love me.

[A]

What would be bigger than jumping on Oprah's couch for someone in this 2025.

[B]

Age, setting Oprah's house on fire.

[A]

Going on Joe Rogan and being like, I just love my wife. Like, having to deal with the amount.

[B]

Going on Joe Rogan and pulling, like, a deer head off the wall and being like.

[A]

And humping it like, this is how much I love my wife. As Joe Rogan's going, but careful, you'd have to. No, that's my favorite deer head.

[B]

You have to be careful because I don't listen to Rogan. So you'd have to go back and see if, like, I don't know, Theo Vaughan's already done that or something.

[A]

Michelle Wolf, everyone go. Go follow Michelle. But more importantly, go watch the well on Netflix. It is hilarious.

[B]

Or don't watch it. Just put it on in the background. Yeah, just don't have to watch it.

[A]

Here's the thing. If you're this Let it podcast, you are, like, you're into what we've been doing, so I can trust that you can understand. The messaging here is like, we want you to watch it, enjoy it, but we also want other people, more people to watch and enjoy it so that Michelle can tour the world and do stand up and keep writing more jokes. That's, like, the whole point. I make it sound like Michelle's gonna be fine with or without you. I'm just saying, like, this is what we want, is to just do standup. So go watch. Go enjoy.

[B]

Just want to do more of this.

[A]

Yes. I want to stay more panthouses.

[B]

I know you watch terrible television. Whoever's listening. I know you watch at least four shows that you're ashamed of.

[A]

Right?

[B]

So just put it on in the background.

[A]

Add a fifth one to that. You could be ashamed of this first joke that you laughed at that made other people angry. Michelle Wolf, the well, it's on Netflix. I'm Jared Freed. Chitchat Wednesday. Back next week. Boom.