Moshe Kasher and Mike E. Winfield

Summary

Podcast Summary: Wrong Turns with Jameela Jamil – Episode Featuring Moshe Kasher and Mike E. Winfield

Release Date: July 17, 2025
Hosts: Jameela Jamil
Guests: Moshe Kasher and Mike E. Winfield

---

Introduction

In this episode of Wrong Turns with Jameela Jamil, host Jameela Jamil welcomes two esteemed guests from the comedy world: Moshe Kasher and Mike E. Winfield. Both comedians bring their unique experiences of life's missteps, sharing stories that are raw, hilarious, and utterly relatable.

---

Mispronunciations and Allergic Reactions ([02:05] - [04:10])

The episode kicks off with a humorous exchange where Jameela struggles to pronounce Moshe Kasher's name correctly, leading to light-hearted banter about her peanut allergy. Jameela humorously describes her predicament:

Jameela Jamil ([02:19]): "Right now my tongue is swelling because... he's given me a nut bar that's got peanuts in it, knowing I am allergic to peanuts."

Moshe forgives her with grace, showcasing the camaraderie between the trio.

Exploring Public Persona vs. Inner Emotions ([03:35] - [05:11])

Mike E. Winfield delves into the dichotomy of maintaining a positive public persona while grappling with inner rage. He reflects on the importance of channeling anger into creative expression:

Mike E. Winfield ([04:10]): "I need anger... the comedians and artists I love, they have such great spins because it comes from rage."

Jameela draws parallels to high-profile incidents, contemplating the fine line between humor and emotion.

Moshe Kasher’s Middle School Mayhem ([20:42] - [28:44])

Moshe shares an intense and formative story from his eighth-grade years. Aspiring to be a "straight-up gangster" with his friends, Moshe recounts a fateful encounter with a younger student that escalates into a physical altercation. The narrative reaches its peak when Moshe describes the aftermath:

Moshe Kasher ([27:02]): "That was the end of my middle school career. That was my dropout moment."

He humorously yet poignantly discusses the embarrassment and long-term impact of this event, highlighting themes of identity and vulnerability.

Mike E. Winfield’s Cruise Catastrophe ([33:20] - [44:12])

Mike recounts his misadventures while performing on Carnival cruises. A pivotal moment unfolds when he accidentally takes Cialis instead of aspirin, leading to an uncontrollable erection during his comedy set. The hilarity and discomfort escalate as Mike describes:

Mike E. Winfield ([36:37]): "It's a 70-year-old's birthday party for the cruise. Her ass was so soft and it was warm. It was like a cinnamon roll."

The story culminates with Mike navigating an awkward dance line while managing his unexpected predicament, blending humor with human awkwardness.

Moshe Kasher’s Early Drug Use and Tunnel Incident ([44:12] - [51:56])

Moshe opens up about his tumultuous youth, detailing early drug use and a near-death experience involving a train in the Caldecott Tunnel. His vivid storytelling brings listeners into the chaos of his adolescence:

Moshe Kasher ([47:21]): "We feel there's a shift in the air... The train is so close. I remember... it was so scary."

This gripping account underscores the unpredictability of youth and the thin line between reckless adventures and life-altering moments.

Micro Humiliations and Personal Reflections ([44:12] - [54:19])

Both Moshe and Mike share additional stories of minor but memorable embarrassments, weaving in reflections on personal growth and resilience. Their anecdotes serve as a testament to the show's theme: embracing and laughing at life's wrong turns without seeking morals or silver linings.

Conclusion and Promotions ([53:29] - [54:19])

As the episode wraps up, Moshe and Mike promote their respective projects. Moshe highlights his upcoming tour and books, while Mike shares his comedy specials and podcasts. Jameela appreciates their candidness, reinforcing the show's mission to celebrate misfortunes with humor and camaraderie.

---

Key Takeaways

• Embracing Vulnerability: Both guests illustrate the importance of sharing embarrassing and challenging moments to foster connection and laughter.

• Humor as Coping Mechanism: Turning personal disasters into comedic material not only entertains but also aids in personal healing.

• Authenticity in Storytelling: Genuine recounting of misadventures creates relatable and engaging content for listeners.

---

Notable Quotes

• Jameela Jamil ([02:19]): "Right now my tongue is swelling because... he's given me a nut bar that's got peanuts in it."

• Mike E. Winfield ([04:10]): "I need anger... the comedians and artists I love, they have such great spins because it comes from rage."

• Moshe Kasher ([27:02]): "That was the end of my middle school career. That was my dropout moment."

• Mike E. Winfield ([36:37]): "It's a 70-year-old's birthday party for the cruise. Her ass was so soft and it was warm. It was like a cinnamon roll."

• Moshe Kasher ([47:21]): "We feel there's a shift in the air... The train is so close. I remember... it was so scary."

---

Listeners who enjoy candid and humorous tales of life's mishaps will find this episode both entertaining and relatable. Moshe Kasher and Mike E. Winfield bring their unique perspectives, making "Wrong Turns" a must-listen for anyone who appreciates comedy rooted in real-life experiences.

Transcript

[Oregon Lottery Representative]

In the summer, all of Oregon is our playground thanks to our incredible park system. That's why it's so cool that Oregon Lottery gameplay like video lottery or cash pop helps support tons of parks projects statewide like accessible trails at Silver Falls State park or upgrades to your favorite dog park in Newburgh. It's just one way a little lottery play for many Oregonians can add up to a lot of good the Oregon Lottery Together we do good things. Lottery games are based on chance and should be played for entertainment only. Must be 18 or older to play.

[Will]

This podcast is sponsored by IQ Bar.

I've got good news and bad news. Here's the bad news. Most protein bars are packed with sugar and unpronounceable ingredients. The good news? There's a better option. I'm Will and I created IQ Bar Plant protein bars to empower doers like you with clean, delicious, low sugar, brain and body fuel. IQ bars are packed with 12 grams of protein, brain nutrients like magnesium and Lion's Mane and Zero Weird Stuff. And right now you can get 20% off all IQ Bar products plus free shipping. Try our delicious IQ Bar Sampler Pack with seven plant protein bars, four hydration mixes and four enhanced coffee sticks. Clean ingredients, amazing taste and you'll love how you feel. Refuel smarter, hydrate harder, Caffeinate larger with IQ Bar.

Go to eatiqbar.com and enter code BAR20. To get 20% off all IQ Bar products plus free shipping. Again, go to eatiqbar.com and Enter code BAR20.

[Moshe Kasher]

Foreign.

[Jameela Jamil]

Welcome to wrong Turns. This is a podcast where misery just loves company and where dignity goes to die. I bring on my favorite funny people. They tell me tales of their woes and disasters. And joining me today we have a comedian, writer and actor. You can see him perform on Honeymoon special on Netflix or listen to his podcast, Endless Honeymoon with his wife, Natasha Leggero. I've been on it. It was very fun. It was one of my favorite times on someone's podcast. It's the fantastic mush. Like I always do this.

[Moshe Kasher]

It's the peanut allergy swelling eaters.

[Jameela Jamil]

Moshe Kasha.

[Moshe Kasher]

Sorry.

[Mikey Winfield]

Hello. Hey, Moshe in the building.

[Jameela Jamil]

I fuck up the first name of every single time I'm reading one of these. It's a nightmare.

[Moshe Kasher]

Anyway, Moshe does not roll off the tongue. It does only in certain neighborhoods in Brooklyn. It rolls off the tongue.

[Jameela Jamil]

So not my tongue. Cause right now my tongue is swelling because for about the fourth or fifth time, my beloved producer Stuart on this show, and I don't know if you're doing this for content. At this point, no. He's saying no. Has given me a nut bar that's got peanuts in it, knowing I am allergic to peanuts. So as we speak, my body temperature is heating up and my tongue is swelling, and I don't know what I'm gonna sound like by the end of this. I've taken a Benadryl, so I'm either gonna die or sound super drunk, but it's gonna be very on brand for this wonderful podcast.

[Mikey Winfield]

Well, that's exciting.

[Moshe Kasher]

I've had my name mangled many times over the years, and I've never had somebody have an excuse that was so biological, medical, and irrefutable. So I forgive you. I forgive you. I forgive you.

[Jameela Jamil]

Moja. I've known. I know your name. I apologize.

[Mikey Winfield]

No.

[Jameela Jamil]

And we welcome comedian, writer, and actor who has appeared on America's Got Talent, Netflix, and Amazon. He hosts the podcast Stefan's and Chill. It's Mikey Winfield.

[Mikey Winfield]

Thank you very much. What a time.

[Jameela Jamil]

What a time.

[Mikey Winfield]

Yes, yes, yes.

[Jameela Jamil]

How are you doing?

[Mikey Winfield]

I'm in a good energy and excited about your tongue growing out of your mouth during the course of this.

[Moshe Kasher]

Thank you.

[Jameela Jamil]

And if anyone just tuned in. That sounds really filthy.

[Mikey Winfield]

Absolutely.

[Jameela Jamil]

Why are you in such a good fucking mood? What's your problem?

[Mikey Winfield]

You know what? I think that's just what happens. I see it through the bright lenses, you know, I see it all.

[Moshe Kasher]

You're hot.

[Mikey Winfield]

Yeah, okay.

[Moshe Kasher]

I got you.

[Mikey Winfield]

I see it all. I see. No, no, no, no. Just life. I see it all.

[Moshe Kasher]

He's high on the spot. I've known Mikey, what, 20 years?

[Mikey Winfield]

At least. Yeah.

[Moshe Kasher]

I never seen you in a bad mood. Now, I'm sure you've been in a bad mood. Yeah.

[Mikey Winfield]

Cause behind closed doors, I'm violent.

[Moshe Kasher]

Yeah. But he's always a happy guy.

[Jameela Jamil]

So it is just publicly. Do you have private rage?

[Mikey Winfield]

Yeah, I do. And now I'm growing more rage, and I'm excited about that.

[Moshe Kasher]

Through the bright lens, there's rage within.

[Mikey Winfield]

No, it's necessary. It's happening in real time, just from just growing and aging and watching things happen. And I think that's necessary for me to turn the corner. I need to in life. I need anger to. Like, the comedians and artists I love, they have such great spins because it comes from rage. And if you're seeing everything so positive and you just making funny stuff. Positive, ha ha. No, you want anger, Darkness. Yeah. And darkness.

[Jameela Jamil]

Isn't that what happened to Will Smith, though? Wasn't he all, like, ha, ha, Funny, funny. And then the rage Caught up with him too fast and then he hit someone in front of the entire world.

[Mikey Winfield]

Not so much too fast, though.

[Jameela Jamil]

No, too late. You're afraid of it popping up and surprising you. Too late.

[Mikey Winfield]

Yes, I see.

[Moshe Kasher]

I think what happened to Will Smith is that his wife fucked a bunch of guys.

[Jameela Jamil]

No, I think.

[Moshe Kasher]

Isn't that what happened to Will? I thought that was what happened to Will Smith.

[Mikey Winfield]

That was part of it, yeah.

[Moshe Kasher]

Yeah, I think it was that one.

[Jameela Jamil]

I DM'd him and I was like.

[Moshe Kasher]

I believe you did.

[Jameela Jamil]

I DM'd him recently.

[Mikey Winfield]

And I was like, and guess who read the DM first?

[Jameela Jamil]

No.

[Moshe Kasher]

If you want something to keep in.

[Jameela Jamil]

Your fucking mouth, I DM'd him. Just being like, hi, Will. We don't really know each other. I was on the Red Table Talk once, but I've got this new podcast called Wrong Turns, and it's about, like, bad decisions that we've made. I was like, obviously we don't have to talk about the slap, but I'd love it if you come on the podcast. And obviously he's not responded, but why did I do that? And then once you've sent it, you can't unsend it. If you're not in a conversation with them, you only get one shot at a message and then once it's gone, it's gone. You can't undo it.

[Mikey Winfield]

Yeah. Steal his phone.

[Moshe Kasher]

Well, what was the message you wish you had sent?

[Jameela Jamil]

Not mentioning the slap, just casually. I said, obviously, we don't have to mention. And I called it the slap.

[Moshe Kasher]

Like, he knows which slap you mean.

[Mikey Winfield]

Yeah, yeah, yeah.

[Moshe Kasher]

He's gotta know. He's gotta know.

[Mikey Winfield]

Imagine him being here, though, and not mentioning that.

[Moshe Kasher]

I know.

[Mikey Winfield]

With us all wanting to hear that.

[Jameela Jamil]

I think that would be comedy genius.

[Moshe Kasher]

Yeah. Jamila keeps trying to seed it. Like, have you ever done anything on, like, a kind of very large scale that you kind of regret or just like an embarrassing situation that might happen in front of others? Is there anything you could think of at all? He's like, nah, nah, not really. Oh, yeah, yeah. There was a time there was a concert where I flubbed the lyrics a bit. Is that what you mean? No, Will, no. No, Will.

[Jameela Jamil]

It's a nightmare.

[Moshe Kasher]

And then he tosses you out of the front door like Joffrey.

[Jameela Jamil]

When it comes to the world of disaster, is it a world that is familiar to you?

[Moshe Kasher]

Well, the world is a disaster. I've been thinking about it. What do you mean?

[Jameela Jamil]

Everything's great.

[Moshe Kasher]

Come now. Come now. There are Marines down the street from your house. I was thinking this is keeping us safe.

[Jameela Jamil]

They're here to protect us.

[Moshe Kasher]

Uh huh.

[Jameela Jamil]

Yeah. From the brown people.

[Moshe Kasher]

They're here to protect you from the brown people?

[Jameela Jamil]

Yeah, yeah.

[Moshe Kasher]

Protect me from myself, technically, if anybody on this panel, they're here to protect me from the brown people. Oh my God. I've been thinking lately that how are you doing? Has become a loaded question. Yeah, it's like everyone's lying. Everyone's like, oh, yeah, pretty good, pretty good. But no one's doing well.

[Jameela Jamil]

No, no.

[Mikey Winfield]

Should we all scale back then to just high?

[Moshe Kasher]

Yeah, high. I know shit's fucked up high.

[Jameela Jamil]

Yeah, hi.

[Moshe Kasher]

I could get into that.

[Jameela Jamil]

We're moving on. Tell me what micro humiliations you have experienced, Mikey.

[Mikey Winfield]

Oh, well, this is recent. Actually as recent as almost last week, I'd say. I had the pleasure of opening up for Latoya Jackson.

[Moshe Kasher]

A dream gig.

[Jameela Jamil]

Wait, what?

[Mikey Winfield]

Yes, yes. And I'm excited about it. This is like at a room, the Catalina Jazz Club, you know, so I know I'm a fancy it up and just get real sexy for him, you know, It's a big opportunity. About to meet Latoya Jackson, you know, and I'm ready.

[Jameela Jamil]

So what's she doing at the moment?

[Mikey Winfield]

That's a great question. Cause I didn't know, you know, so now I'm looking for what she does, you know, and it's just videos and it's just reels of her just walking and looking out of windows and things.

[Moshe Kasher]

She's old, right? Oh, yeah, she's like 70, 80.

[Mikey Winfield]

Well, it depends on what you think is old, right? You know, she's 69.

[Moshe Kasher]

69, nice.

[Mikey Winfield]

Yeah, yeah, yeah. So I show up and I'm wearing that stuff, you know, Like I got on the. The gear, you know, so I'm doing it and you know, a mature crowd, they're like, hey, man, even her friend, she had a friend there and she was like, you know, I'd like that you do your own thing, you know. I'm like, thank you very much. She's like, I can tell, you know, you just don't care. And I'm like, well, I care. You know I do, you know.

[Moshe Kasher]

Is this after your set?

[Mikey Winfield]

No, this is before it, you know.

[Moshe Kasher]

They already knew. You didn't know?

[Mikey Winfield]

They already. They just knew. So now I'm in this room, packed room. And anytime you're an artist, you see a packed room, you're like, oh, I'm about to slaughter, you know, like I'm opening up. What a great opportunity. These Are my people. I like the mature crowd, you know? So, boom, I'm ready. I go up. I meet latoya before.

[Jameela Jamil]

How is she?

[Mikey Winfield]

She's so sweet. Just so fragile. Like, I didn't want to, like, tap her. I might knock her over or something, you know, she even gave me.

[Jameela Jamil]

That is a way to describe someone.

[Mikey Winfield]

Oh, yes. Yes, she was. She was very.

[Jameela Jamil]

Just a walking osteoporosis.

[Mikey Winfield]

Ye giving me that look too.

[Jameela Jamil]

Or did she?

[Mikey Winfield]

You know that look. The one I don't know.

[Jameela Jamil]

The look. Do the look.

[Mikey Winfield]

Let me show you the look.

[Jameela Jamil]

She was suspicious of you, and she didn't think it smelled very good. What's the.

[Mikey Winfield]

Can I trust him?

[Moshe Kasher]

Yeah. She gave.

[Jameela Jamil]

Show him the look.

[Moshe Kasher]

Why don't you give me the look? This could be a really fun improv game, so I'll see if I can. I wanna fuck. I wanna fuck you. Yeah. Okay. That's the look you just did. Did I do that? That was a different look. That didn't feel like. I think I did that.

[Mikey Winfield]

Or maybe that's what latoya said and I read him wrong.

[Moshe Kasher]

Now, that Mike would be a story if you were like. So anyway, the set went great. I fucked Latoya Jackson.

[Mikey Winfield]

Yeah.

[Moshe Kasher]

The God among us.

[Mikey Winfield]

That's way better than what I'm about to say right now.

[Moshe Kasher]

I have a feeling. I know.

[Mikey Winfield]

I'm okay.

[Jameela Jamil]

So she gave you this sort of look of, are you gonna fuck up my show?

[Mikey Winfield]

Right? And I gave her the look back of, I got you.

[Jameela Jamil]

Okay, show me what that looks like.

[Mikey Winfield]

That look is like, okay, Can I see? Yeah. I'm that.

[Moshe Kasher]

Oh, I'm a man who wants to fuck you.

[Mikey Winfield]

I'm that guy, right? So now I'm like, in the zone. I know it. I'm like, I'm gonna give them all old stuff. You know. I'm gonna go up there and hammer this crowd down. So apparently no one was told that a comedian was at the show or even opening up the show. And during the intro. Cause I'm the first face they see. A loud noise happened during the PA announcement. So he's like, jordan, you know, you guys from agt. And then clap, clap, clap, Winfield. And so I walk to the stage, and at that point, no one even knows.

[Moshe Kasher]

They don't know you're even a comedian.

[Mikey Winfield]

Yeah. And then while I'm up there is when I find out that they could even care less that I existed. You know, they just didn't. They weren't there for me. Which is. You know, that happens as an opener. But this particular time, I even made it worse. And I go up and I know my mistake. I shouldn't have told jokes. I should have just spoke to the people. But nah, I. I just go straight to the bag. And I hit him with a first one. I'm like, I'm gonna kill him with this one. And I'm like, y' all just staring at me. What? Is it weird seeing a microphone, holding a microphone?

[Jameela Jamil]

Nothing.

[Mikey Winfield]

Man. I'm sweating. I'm sweating. It's hot. And I'm like, oh, man. Maybe they didn't hear me.

[Moshe Kasher]

My hair looks slightly microphone like. I'm saying, it's I assemble.

[Mikey Winfield]

And now I'm looking around, and I'm like, all right, just go to the next one. Cause there's always two voices in your head as an artist. It's the one that's, like, on autopilot, doing the content, and it's the other one navigating you, saying, okay, that didn't go like you wanted it to go.

[Jameela Jamil]

It's like finally having the nerve to pull the trigger, and then it fucking. The bullet doesn't come out. This is a fucking nightmare.

[Mikey Winfield]

In a packed room, you look around, there's pockets of, like, six or seven people dying. But, you know, they're not laughing at your material. They're laughing at your live dying.

[Moshe Kasher]

They're laughing at your situation.

[Mikey Winfield]

And they're like, oh, oh. And it's these three older ladies, man, in the front. And I'm like. I can tell they, like, they want me to win. They want me to survive. And they're just like, come on, you can.

[Jameela Jamil]

Tyra Banks were like, we were rooting for you, right?

[Mikey Winfield]

And so they're there, and I'm like, oh, man. So I'm sweating now. I'm stuttering. And when you're stuttering, you just know. It's. So I grab my water, right? And so I take a sip of water, right? And I'm good. And then I'm like, oh, you mind if I grab your napkin? These are to my three ladies.

[Moshe Kasher]

The three.

[Mikey Winfield]

Yeah. Right? And so she's like, sure. She puts the napkin up, and I reach down to grab it.

[Jameela Jamil]

No, you accidentally spill the water all over.

[Mikey Winfield]

The water spills. And she's like, ah.

[Moshe Kasher]

And I'm like, ah.

[Mikey Winfield]

And I still have, like, 12 minutes, and I can't bail. Like, I can't.

[Jameela Jamil]

Right, well, you don't get paid if you bail.

[Mikey Winfield]

Yeah, you have to do the time.

[Moshe Kasher]

I describe it as you're on stage, you start physically picturing the check like, you leave your body a little bit, and the only thing that's left is like, a physical. You can see the picture of the check. Like, my children will eat. I just must suffer for 12 more minutes.

[Mikey Winfield]

Yeah. And I know. I know Latoya's in the back. Oh, yeah. I know. She can hear this, you know, and it's just. It's just this suffering. And it was pretty much. I gave a speech. I just gave a very long speech.

[Jameela Jamil]

What was your speech about?

[Mikey Winfield]

No, it was my material.

[Moshe Kasher]

Oh, no. But it felt like a lecture.

[Mikey Winfield]

Yeah.

[Jameela Jamil]

Oh, God, your TED Talk. That's such a fucking nightmare. Weirdly, it reminds me of my boyfriend went on tour with Kendrick Lamar, who everyone's a big fan of, and he was a huge fan of everyone.

[Moshe Kasher]

There's one guy I know that's really not.

[Jameela Jamil]

Was he in the audience of that show?

[Moshe Kasher]

No, he's a Canadian fella, and he's not a huge fan of Kendrick Lamar. I wouldn't say he's the biggest Kendrick Lamar.

[Jameela Jamil]

Not anymore, anyway. Yeah. So anyway, so my boyfriend was on tour with Kendrick. This is like, maybe eight years ago. Kendrick was, like, peak, like, fame, everything. Everything going amazingly. And so it's a big arena tour. My boyfriend's never played arenas, so he's like, this is a huge opportunity. Now he's playing for Kendrick fans. There are no James fans in the audience. It's just Kendrick fans who are up front. And the light of the stage only reflects on the first few rows of the audience. So the only people he can see are people who are standing there with crossed arms looking up at him like, when the fuck is Kendrick coming? Who the fuck are you? And there's this song he's got called don't miss it that's got so many lyrics that he can't remember the song. So he always keeps his phone up to look at the lyrics. And he's forgotten to put it on airplane mode. And so the whole time he's trying to sing this song, people are tweeting him and he's, like, getting all of the tweets and the notifications live. Being like, this fucking sucks. Get off the fucking stage.

[Moshe Kasher]

Bring Kendrick on. And he's just sitting there, and I.

[Jameela Jamil]

Don'T know how he got through. And I was like, God, this is the saddest rendition of this song I've ever seen him perform. And I had no idea what he was going through, but he was having, like, a live panic attack that he was having to sing through. Looking at truly some of the meanest tweets I've ever seen anyone receive.

[Moshe Kasher]

I have. I have to say I would. If you told me, like, who would you rather open for, Kendrick Lamar or Latoya Jackson? Like, I could have. I would have said no to the gig because I would have felt like I would have known I was gonna bomb you. I. I could see. I could see that you. You thought you could get through that. But Latoya Jackson, that just feels like that was a bomb waiting to happen.

[Mikey Winfield]

I just saw them as people and I was very arrogant.

[Jameela Jamil]

And that was your wrong turn.

[Moshe Kasher]

I have a grown and sexy black audience story from early in comedy.

[Jameela Jamil]

Oh, yeah.

[Moshe Kasher]

It just reminded me I was Bruce. Bruce was performing at Pepper, you know, Pepper Bellies. Pepper Bellies, one of the two comedy clubs in America where someone was. Has been murdered.

[Jameela Jamil]

Cool.

[Mikey Winfield]

And it burned down.

[Moshe Kasher]

And it burned down. Bruce. Bruce wanted a white opener. They said, okay. And I was excited. I said, that sounds amazing. I went. And he had a middle. Well, so that his crowd is very church, very sort of conservative black audience.

[Mikey Winfield]

Absolutely.

[Moshe Kasher]

And, like, dressed up for church, basically.

[Jameela Jamil]

Right.

[Moshe Kasher]

And I would go out and I did. I think I did it twice, actually, two different weekends. It was eight shows total. And they never. It was like. It would go from, like, sort of quiet acceptance to open hatred. Their response to me.

[Jameela Jamil]

Right.

[Moshe Kasher]

But so. But I would just put my head down, try to get through the set. But the. The middle act, his middle act was a guy named Black Boy. And I had to, every night after sort of bombing, say, okay, well, that's all the time from me. Put your hands together, ladies and gentlemen, for your feature performer tonight. Black Boy had no information about this man or me or all they knew was that they barely wanted see me. And at the end, I'm saying those two words to introduce the person. And so there was this. There was this 32nd period between him taking the stage and him saying, hey, everybody, my name's Black Boy. Where you could feel this audience being like, what the fuck did that white motherfucker just say? And then he would let me off the hook. And every night, if I did well, he would go, give it up for that white boy. He was funny. Or who the fuck was that? If I bombed and I would be in the back like, you know who the fuck I am. We've met over the course of a weekend.

[Jameela Jamil]

It's such a traumatizing. Such a traumatizing industry. I wish he'd gotten up and been like, that's not my name.

[Moshe Kasher]

I know.

[Jameela Jamil]

That would be the.

[Moshe Kasher]

I would have gotten in my car and driven back home.

[Jameela Jamil]

I would be like, sorry, my name's Steve.

[Mikey Winfield]

What a great joke to play on just for his entire career. What an inconsiderate name.

[Moshe Kasher]

Would be funny if that was the reason they wanted a wide opener, was for that, just for that, for that moment.

[Jameela Jamil]

All right, we're gonna go to a quick break, and then we're gonna come back and hear everyone's wrong turns.

[Will]

This podcast is sponsored by IQ Bar.

I've got good news and bad news. Here's the bad news. Most protein bars are packed with sugar and unpronounceable ingredients. The good news? There's a better option. I'm Will and I created IQ Bar Plant protein bars to empower doers like you with clean, delicious, low sugar, brain and body fuel. IQ bars are packed with 12 grams of protein, brain nutrients like magnesium and Lion's Mane, and Zero Weird Stuff. And right now, you can get 20% off all IQ Bar products, plus free shipping. Try our delicious IQ Bar Sampler Pack with seven plant protein bars, four hydration mixes, and four enhanced coffee sticks. Clean ingredients, amazing taste, and you'll love how you feel. Refuel smarter, hydrate harder. Caffeinate larger with IQ Bar.

Go to eatiqbar.com and enter code BAR20. To get 20% off all IQ Bar products plus free shipping. Again, go to eatiqbar.com and Enter code BAR20.

[Coop Sleep Goods Representative]

Did you know that you can live longer without food than sleep? Ready to learn more? Go back to school early with Coop by learning how to achieve an A in getting better sleep. They're here to teach you how to get your best sleep ever. With their back to school sale and 20% off your first order. Sleep and school go hand in hand. In a Carnegie Mellon study, every lost hour of sleep meant a 0.07 dip in GPA. It's time to sleep smarter. Shop. Coop's back to School sale today. Hand picked for parents, students, and anyone who's failing in the sleep department. Coop's curated collection has everything you need to solve your biggest sleep problems. Summer school is in session with Coop sleep goods. Visit coopsleepgoods.com sleep 101 to get 20% off your first order. That's copsleepgoods.com sleep 101.

[Jameela Jamil]

So welcome back. All right, Moshe, what was your big wrong turn? Give me a big wrong turn.

[Moshe Kasher]

Big wrong turn. One of the biggest wrong turns that I ever made was in eighth grade. I mean, this was actually a true wrong turn in my life. Yeah, I Was in eighth grade and I was like a. I guess a. I guess you'd call it like a straight gangster. Like a straight up gangster. Like a straight up.

[Mikey Winfield]

You were.

[Moshe Kasher]

I was like, yeah, yeah, yeah, yeah. Like a straight up real.

[Mikey Winfield]

Are we talking Oakland, California?Oakland, California.

[Moshe Kasher]

8Th grade, 14 year old white boy. Like, you know, like a real gangster. Like a real scary kind of gangster is what I. Yeah, I see it like the genuine article and well I.

[Jameela Jamil]

Comes through very clearly now.

[Moshe Kasher]

I really do appreciate that 100%. My friends and I all were in this phase. It was like the. You know, this would be like 91. So it was like we really thought like we were in a gang called the Pure Adrenaline Gangsters. I don't know if you know this about gangs. Pag Pag. Yeah, we were gonna call it the pure Hardcore Adrenaline Gangsters. But there was a. Yeah, there was a problem, so. But the thing about gangs is like there's no, no one can stop you from being a gang. You can just be a gang. You can just be like, we're a gang and then you're a gang.

[Jameela Jamil]

Well, one thing could stop you, which is that I didn't have any friends.

[Moshe Kasher]

Yeah, an actual gang. You're not a gang. And we'll show you how.

[Jameela Jamil]

Yeah, you have to at least have some friends to then be called a gang. I was solo, so I couldn't ever. I'm the only person I know who.

[Mikey Winfield]

Couldn'T have a gang of one. Army of one.

[Moshe Kasher]

The gang of one.

[Jameela Jamil]

Yeah.

[Moshe Kasher]

I mean, I hope I'm painting a vivid enough picture. We were a bunch of like straight up wann deep identity crises.

[Jameela Jamil]

I was giving 8 mile the whole thing.

[Moshe Kasher]

It's way below 8 mile. Okay, it's way below way. But Eminem had some street cred and had black friends. Like, this was just a group of white boys that thought that they were not the fuckers. Okay? So just pathetic loser energy. Right? And we're in eighth grade and we. I thought everyone's scared. Well, I thought every other white person is scared of us.

[Mikey Winfield]

Right.

[Moshe Kasher]

That's what I thought. And there was this seventh grader and I was in a lot of trouble. Like already I'd been in and out of rehab. I'd been locked up in a mental hospital at this point I was like.

[Jameela Jamil]

Wait, are you serious?

[Moshe Kasher]

Yes. Serious? Yes.

[Jameela Jamil]

Before eighth grade?

[Moshe Kasher]

Yeah, in eighth grade is when things really.

[Jameela Jamil]

Do you think it's quite fair for you to think you're a gangster?

[Moshe Kasher]

Well, gangsters don't go to mental hospitals. Gangsters don't get medicated. That's the problem.

[Mikey Winfield]

Yeah, you live life at that point.

[Moshe Kasher]

Don't have a psychiatric intervention. Are you kidding?

[Jameela Jamil]

Gangsters aren't on Klonopin.

[Moshe Kasher]

Yeah, I wish I was on Klonopin. So I was just. I was already in a lot of trouble, but I was in this deep identity crisis, and I just, like, thought I was something I wasn't. And anyway, this seventh grader came up to me and he started talking shit, and I was like, man, fuck this little seventh grade bitch. So I just, like, slapped him in the face. Like, pimp slapped him, you know? And I was like, that's the end of that. Like, he just got slapped by the eighth grade. Pure adrenaline. Gangster. Yeah.

[Jameela Jamil]

Nothing like just picking on a smaller boy to show how big and tough you are.

[Moshe Kasher]

Yeah, he's out. No, he was not out. He was in. He was. He was dedicated and committed and he wanted to fight. He wanted to fight me. And I was like, wait, no, no, no. See, I kind of had. I ended it a little bit earlier when I, you know, it was kind of like I gave you a message like, ah, we're done. Like, go back to class.

[Mikey Winfield]

That was the closer?

[Moshe Kasher]

Yeah, that was the closer.

[Mikey Winfield]

I thought it was the closer.

[Moshe Kasher]

He was, in fact, the opener, and he squared up and I was like, oh, no. Like, okay, so we. So I was like, all right, so let's do this.

[Mikey Winfield]

Where are the rest of your gangsters at this point?

[Moshe Kasher]

That's a great question. That is a great question.

[Mikey Winfield]

Where are my friends?

[Moshe Kasher]

They are not there. They are not. Or maybe they're there and they're not. I don't really remember the. I don't know. But he was there and he squared up and I was like, all right, let's do this. So I swung on him and he would do this. He had this very tricky technique where he would. I would swing and he would dodge the punch so I wouldn't hit him already. But then he would punch me in the face and I would go, okay, that's not. This is not ideal. Okay, let me. I'll try again. So I would swing again. Once again. He would go to this. Go to. Dodged a punch, punch me in the other side of the face. This went on and on and on. I mean, he hit me.

[Jameela Jamil]

He spattered you.

[Moshe Kasher]

I never. Oh, I did touch him. I touched him once for the opener, and then he just punched me in each side of the face at least eight times until finally the school administration came, broke the fight up, pulled me away. That's when. And that's when the gangster instinct really kicked in.

[Mikey Winfield]

Oh, yeah.

[Moshe Kasher]

You know, once the principal and the vice principal was pulling us apart, that was the time for me to remind him what could have happened. You know, I was like, oh, now it's over. But it could have been a whole different situation. Pure adrenaline. Gangster.

[Mikey Winfield]

Hold me back.

[Moshe Kasher]

Yeah, yeah, you are. You are holding me back. Lucky you, motherfucker. And we were both in a fight. We both got suspended.

[Jameela Jamil]

Yeah, right.

[Moshe Kasher]

And he. I mean, I'm not. I am not exaggerating. I did not hit him one time. He did hit me so many times that when I got home, I had a weak suspension. And I think he did, too. I had two black eyes. Full. Two full black eyes. And it was the seventh day, and I still had the full black eyes. And I was like, I'm not going back to school. Like, I'm not gonna do this. I'm too embarrassed. This is humiliating. And my mommy was like, what if I put some makeup on the black eyes? Cool. And cover them up and then the. The kids won't see them? And I was like, that sounds wonderful, Mommy. Yes. And so my mommy said I should definitely do this. Yeah. Like a little gangster geisha. I sat down and my mom just began to put foundation and, you know, a blush maybe. I don't know what the process is, but by the end of the makeup session, I was like, okay, I think this will do. And I got dressed, and she dropped me off at school.

[Mikey Winfield]

Wait, so you still had the black eyes after the suspension?

[Moshe Kasher]

Oh, I went through the full seven day suspension.

[Jameela Jamil]

He's only just recovered recently.

[Moshe Kasher]

Like, I got the shit beaten out of me. Like, I was. He. He beat my ass. Like, there's no way to. There's no way to say it differently. He beat me up thoroughly, and I never hurt him. Yeah. Zero. So I go back to school, Claremont Middle School, and I walk into the halls and everybody's. I mean, they're having a party, you know. I mean, they're just like, doing back flips, going like, ha, ha, you got your ass beat. And I was like, yeah, yeah, I did. Like, I knew there'd be some embarrassment. Yeah, you know, I did. I got the shit beat out of me by a seventh grader. And I was like, yeah, yeah, I got my ass beat. Yeah, that's true. And then another kid would come by. You got whooped by a seventh grader. And be like, yeah, I guess I did. And then this kid named Corn Nuts came up to me and he's like, haha, you got your ass.

[Jameela Jamil]

Oh, no, no.

[Moshe Kasher]

Is that. And it time slowed.

[Mikey Winfield]

Oh, no.

[Moshe Kasher]

Like the universe bent. He goes, you got your ass beat? Is that makeup? And then he called to the throngs, he goes, this motherfucker's wearing makeup. It felt like the whole student body of Claremont Middle School was like, makeup. And I am not exaggerating. That was it. I walked out of school. I never went back to middle school. I dropped out of eighth grade that day.

[Jameela Jamil]

No way.

[Moshe Kasher]

Never returned. That was the end of my middle school career. That was my dropout moment.

[Jameela Jamil]

Oh, that is fucking excellent.

[Moshe Kasher]

Brutal.

[Jameela Jamil]

What a fucking crazy story. I love an Irish exit like that. I think that's very inspirational. There was a Hollywood executive. That's what I know, but I'm gonna just call it that.

[Moshe Kasher]

Where you get beaten up by a smaller child and then drop out of middle school.

[Jameela Jamil]

Listen, it's a smaller part of Ireland that you just don't know about. All right? It's Southern, okay. But I enjoy just bouncing, just leaving and never looking behind you. There's a Hollywood executive who released a photograph of her wedding ring. This was about 10 years ago, like high, high up. Everyone who she was, she was working at one of the biggest studios in the world. And she sent out the picture of her engagement ring to everyone. And it was like a huge fucking diamond. And it was a very braggy sort of like, look how valuable I am, kind of message send it out to a bunch of people. This was just at the beginning of live photos. And so she didn't know that she'd sent out a live photo. And you know, live photos can be embarrassing at the best of times. Even watching someone like, watch you settle into a pose is humiliating. But the problem is, is that her brand new fiance saw her taking the picture, thought it would be a hilarious time to pull down his underpants and quickly get his cock out in the. And so what you see in the video is it starts on just her hand with her ring, and then you suddenly see this, like, swinging cock come into the photo and shake itself around.

[Moshe Kasher]

Now that's what I call an Irish accent.

[Mikey Winfield]

There it is.

[Jameela Jamil]

And she sent it around accidentally. And then obviously it traveled. Like I don't know her. And I have this picture in my phone. Ten years later, it's in my forever folder of my phone.

[Moshe Kasher]

That's so brutal.

[Jameela Jamil]

I know, it's pretty good. I'm gonna show it to you later. It's unbelievable. But she, the next day, quit her job, moved country, left the industry was never seen ever again.

[Moshe Kasher]

Oh, my God.

[Jameela Jamil]

I support this. I think sometimes you just have to. That's what.

[Moshe Kasher]

You just have to leave. That must be the thing. Yeah, I guess it's nice to. Cause you can heal. Black eyes do eventually heal. I know this acutely. But emotional wounds can be forever.

[Jameela Jamil]

You said black eyes. Cause you pointed at him and it sounded like you said, black guys do eventually heal.

[Mikey Winfield]

You say healing black guys too. I was like, yeah, we do. Black guys heal. I accepted it. It. I was like, yeah, we got overwhelmed. We're like Wolverine.

[Moshe Kasher]

I'm panicking a little bit. Ladies and gentlemen, your next performer, Black Boy.

[Jameela Jamil]

We're going to a break.

[Mikey Winfield]

Trip Planner by Expedia. You were made to have strong opinions about sand. We were made to help you and your friends find a place on the beach with a pool and a marina and a waterfall and a soaking tub.

[Moshe Kasher]

Expedia Made to travel.

[Will]

This podcast is sponsored by IQ Bar.

I've got good news and bad news. Here's the bad news. Most protein bars are packed with sugar and unpronounceable ingredients. The good news? There's a better option. I'm Will and I created IQ Bar Plant protein bars to empower doers like you with clean, delicious, low sugar, brain and body fuel. IQ bars are packed with 12 grams of protein, brain nutrients like magnesium and Lion's Mane and Zero Weird Stuff. And right now, you can get 20% off all IQ Bar products plus free shipping. Try our delicious IQ Bar Sampler Pack with seven plant protein bars, four hydration mixes and four enhanced coffee sticks. Clean ingredients, amazing taste and you'll love how you feel. Refuel smarter, hydrate harder, Caffeinate larger with IQ Bar.

Go to eatiqbar.com and enter code BAR20 to get 20% off all IQ Bar products plus free shipping. Again, go to eatiqbar.com and Enter code BAR20.

[Coop Sleep Goods Representative]

Did you know that you can live longer without food than sleep? Ready to learn more? Go back to school early with Coop by learning how to achieve an A in getting better sleep. They're here to teach you how to get your best sleep ever. With their back to school sale and 20% off your first order. Sleep and school go hand in hand. In a Carnegie Mellon study, every lost hour of sleep meant a 0.07 dip in GPA. It's time to sleep smarter Shop Coop's back to School sale today. Hand picked for parents, students and anyone who's failing in the sleep department. Coop's curated collection has everything you need to solve your biggest Sleep problems. Summer school is in session with coop sleepgoods. Visit coopsleepgoods.com sleep101 to get 20% off your first order. That's C-O-O-P sleepgoods.com sleep101.

[Jameela Jamil]

All right, Mikey, tell me what was your wrong turn?

[Mikey Winfield]

All right, it's even weird to say this. So it started off with. I started doing standup on Carnival cruises in about 2018, right? And what they do, I since stopped, but I was doing. They pair you up with someone so you can learn the ropes. And I learned the ropes with this guy who's been doing cruises for 35 plus years, right? And then I tell people I'm working with and they're like, oh, he's the man. Like, you're gonna learn a lot. But he's the man. He has quite the reputation. And by that they mean he is knocking em down on the cruises. I'm like, really? They're like, yeah.

[Jameela Jamil]

Does that mean. Is that a set thing?

[Moshe Kasher]

He fucks passengers.

[Jameela Jamil]

Thank you for knowing. I wouldn't know what that meant to translate that to my like innocent, pathetic English self, right?

[Mikey Winfield]

So I. Knocking them down, knocking them down. And I guess we're like yin and yang, you know? Cause he's like the man. I'm just like naive. Learning the ropes, getting on there. Yeah. Just popping on, you know. And so we do it. First night, it's a great night. And then the second night, I never get headaches. I'm not one of those guys, right?

[Jameela Jamil]

So one of what guys?

[Moshe Kasher]

A headache guy. You don't know about headache guys.

[Mikey Winfield]

Yeah, yeah.

[Moshe Kasher]

You know, like a weakling.

[Jameela Jamil]

Those weak dehydrated men never.

[Mikey Winfield]

I never get headaches.

[Moshe Kasher]

Sorry.

[Jameela Jamil]

Okay.

[Mikey Winfield]

And so him and I are bonding and I'm like, man, I got a headache. He's like, hey man, I got some bear. Bear aspirin in my backpack. Just go grab it. I'm like, okay, cool. Where? He's like, the second pocket. I'm like, okay, cool. So I go to his backpack, I take the second pocket and I take out the yellow canister of the bear and I take a couple, you know. And he's like, hey, bring it to me when you're done, right? And I'm like, all right, cool. And I go hand it to him. And he's like, hey man, did you take this? I'm like, yeah, you told me to take the bear. It says it takes four hours and you know, I could take more. He's like, did you take this? I'm like, yeah, it was Cialis.

[Jameela Jamil]

Wait, I don't know what that is. I don't know what that is.

[Mikey Winfield]

Dick pills.

[Jameela Jamil]

Viagra.

[Mikey Winfield]

Yes. Ish. But it has a different effect than Viagra. This just Sialisa.

[Jameela Jamil]

Dick's soft for Alice.

[Mikey Winfield]

Yes, just soft. Just spongy. No, it goes in your bloodline. So whenever you need to recall it, it's there. It's not like instant.

[Moshe Kasher]

Oh, so Viagra. And I ask this as a person who's never needed it. Viagra gives you an instant boner. Cialis gives you the power of boners.

[Mikey Winfield]

Yeah. It gives you, like, when you need it, I'll be there.

[Moshe Kasher]

Just call. Wait, but why would anyone take.

[Jameela Jamil]

Why would anyone take Viagra? Yeah. Yeah.

[Mikey Winfield]

Oh. Cause you're about to knock it out right now.

[Moshe Kasher]

But is it a better boner?

[Jameela Jamil]

So it's a slower. It goes into your system Slower.

[Mikey Winfield]

It's in your system, and you can use it all.

[Moshe Kasher]

Viagra. You shoot. You know that you mainline Viagra.

[Mikey Winfield]

You put it under your tongue. Under your tongue as well, too.

[Jameela Jamil]

No, but wait, wait, wait, wait, wait, wait. Okay, sorry. So maybe it's that Cialis is like, it can get you erect, but it won't make you keep going for hours. You just have a Viagra. You just pop a little Viagra. No. Okay, so sorry. So maybe. But you don't keep going. Cause Viagra, you can, like, keep going for hours. Right? Of shaggin. Maybe it just gives you a normal amount of penis time.

[Moshe Kasher]

Which one? Viagra?

[Jameela Jamil]

Cialis. I don't know why I'm pointing at you. Let me kill you.

[Moshe Kasher]

Let me continue. He literally got roofied with Cialis, and we're like, tell us everything about the biochemical compound makeup of all the boner pills.

[Mikey Winfield]

But it does make sense that he would have it, because on the course of a cruise, maybe he only needs to take it once.

[Jameela Jamil]

Yeah, yeah, yeah.

[Mikey Winfield]

And then he has the power of boners when he needs them.

[Jameela Jamil]

Amazing.

[Moshe Kasher]

Okay, so what happened?

[Jameela Jamil]

This has turned into an infomercial for Sialis.

[Mikey Winfield]

Absolutely.

[Moshe Kasher]

I mean, straight up, if I needed a pill, I would take Cialis and Al. Viagra. I feel convinced by this.

[Jameela Jamil]

I don't have a tick. I'm text him later.

[Mikey Winfield]

Something will happen.

[Moshe Kasher]

Yeah. What would happen?

[Jameela Jamil]

I don't know.

[Mikey Winfield]

I want to know, too.

[Jameela Jamil]

So what's your reaction when you find out you've taken Cialis?

[Mikey Winfield]

So I'm like, oh, no, that was it, you know? And I forget about it. I just kind of forget about it. And I'm like, hey, man, do you have any real aspirin? And he's like, oh, yeah. And so I take an actual bear.

[Jameela Jamil]

Okay, right.

[Mikey Winfield]

And so boom. It's a 70 year old's birthday party for the cruise. That's what the Cruise is, like 70 plus, man. It's just all like, like older people, you know. And you know, I've said this publicly, you know, that's my jam. I like the mature, you know, I'm into that romantically. Yeah, Romantically, like, yeah. You know, it moves me. So we're doing the. I do a show, this is probably four or five hours later, and I'm knocking them out. I'm. No, well, I'm performing. Well, I'm performing on stage. I'm telling jokes.

[Moshe Kasher]

It was a subtle difference.

[Mikey Winfield]

Yeah, yeah, yeah.

[Moshe Kasher]

That's when he translated.

[Mikey Winfield]

Yeah, yeah.

[Moshe Kasher]

Like knocking them out comedically. But thinking about.

[Mikey Winfield]

I'm not thinking. I'm trying to get through this week to, you know, make sure I still have a job on the cruise line. And they are loving me. They like, they recognize me from like the guy, the black guy that went to their high school. Like, it's like I'm vibing, have a great set, get off so much. So everyone in the room wants photos. So I'm like, yeah, all right, let's do this. So now I'm taking photos. I'm doing we posing. It's wild, right? But I've taken so many pictures. I've already been on stage for so long. I just need to sit down. I'm gonna continue taking pictures, but I'm gonna just sit down, right? So a woman comes up next to me to take a photo, and she's standing next to me. And as the person goes to take the photo, as it happens, she just plunges right on my lap and I'm like, aw. You know? And for the record, her ass was so soft and it was warm. It was like a cinnamon roll.

[Moshe Kasher]

Did you enter that into the record? That was for the record. Did you enter that into the record swinging.

[Mikey Winfield]

That was for the record. Like, she smelled like pastries, you know? And she's just sitting there and I'm.

[Jameela Jamil]

Like, I don't think I'd want to be described as any of these things.

[Moshe Kasher]

Listen, you gotta get into the delightful world of Mikey Winfield, right?

[Mikey Winfield]

And everything about it smells creepy ass.

[Jameela Jamil]

The smells of pastries.

[Moshe Kasher]

Kind of a French bakery aroma coming through of a freshly cooked macaron.

[Mikey Winfield]

So good. It was like, yeah, it was like a cushion. It was warm. And, you know, she's moving you know, the pose. And I think that was the trigger. I think that there was the trigger. And the photographer's like, hey, Mike, come on, stand up. Let's grab another one. I can't.

[Jameela Jamil]

Oh, Donna.

[Moshe Kasher]

Mike will not be standing for a while.

[Mikey Winfield]

So now I'm there, and I'm like, this is weird. This is weird.

[Moshe Kasher]

And it's not gonna go away. You can feel that it won't go away.

[Mikey Winfield]

It's nothing. I'm, like, counting. I'm thinking of cartoons, you know, Dead relatives, like, nothing will not see this.

[Moshe Kasher]

Is where we would have diverged. Cause for me, dead relatives are my cinnamon roll, right? That's what gets me going. You know what I mean?

[Mikey Winfield]

So now this is happening right now. There's still a line of people to take photos. And then the cruise director pops in. The cruise director is. Let me see. How to explain. His name's Jeff, but he goes by J. Jeffy. And see how you say this. He's. He has a lot of energy. Charismatic.

[Moshe Kasher]

He's like the guy that comments on your Facebook. He's a Trump voter.

[Mikey Winfield]

We get it, right? He's like, Mike, you know, and what he's doing, he's running a dance line through the show into every room. So he has all these people lined up and their hands on the shoulders, dancing like a. I don't know. Is it a toga line? Whatever.

[Jameela Jamil]

This is the captain of the ship.

[Mikey Winfield]

No, no, not the captain. It's called the cruise director.

[Moshe Kasher]

5, 5, 5, 6, 6.

[Mikey Winfield]

Captain is somewhere who. I hope he's behind the steering wheel. But this is the director, right? And he's just the life of the party.

[Jameela Jamil]

Yeah, yeah.

[Mikey Winfield]

And he's like, mikey, come on, get in the dance line. I'm like. He's like, no, come on. To get in the dance line. Cause the line's getting longer, and I know exactly how I'm feeling right now. And I'm like, oh, but I don't want to mess up the opportunity now. Blow it. Where, for whatever reason, I think if I don't do this, I might not be able to work cruises. I might, you know, send off a bad vibe. And that's not what I'm there to do. I'm there to continue working. I need to work.

[Moshe Kasher]

There's nothing to Jeffy. There is nothing that is a better vibe than a man with an uncontrollable erection in the conga line. I feel like he would have responded really well to that. Been like, mikey, is that a Cialis boner? Come on in the Conga line.

[Mikey Winfield]

So I go, right. And now I'm behind Jeffy. Hands on shoulders, and the line is behind me. And they have me by the hips. And we're just dancing and I'm doing. I'm just. It's just so uncomfortable. Embarrassing. Who knows? And I'm just there and it doesn't. It doesn't go away. We're dancing from four rooms.

[Moshe Kasher]

Four rooms.

[Mikey Winfield]

At least four rooms worth of dancing.

[Jameela Jamil]

Thank Christ it wasn't Viagra. It would have been four days.

[Moshe Kasher]

I'm curious, was it a different quality of erection? Was it more erect?

[Mikey Winfield]

Absolutely. It was potent. It was strong.

[Jameela Jamil]

How did no one notice it was high?

[Mikey Winfield]

Well, I held it. I held my. I propped my. And I had on slacks. Cause I was trying to dress for the older people, you know, And I threw on my slacks and. I don't know, I didn't notice.

[Moshe Kasher]

Maybe that's why you're wearing the fanny pack right now.

[Mikey Winfield]

That's why I put a fanny pack over it. I mean, this is what. I believe someone noticed. But what are you gonna say, right?

[Jameela Jamil]

Yeah, they're probably just jealous at that age, aren't they? They're like, oh, good for him. Youth, Yo.

[Moshe Kasher]

He's still got it. You killed so hard. If anybody noticed, you could have been like, yeah. Yep. This is killer instinct right here. This is what happens when a. When a master at work really goes to town and knocks him down. This is what. This is what you get.

[Mikey Winfield]

This what happens.

[Moshe Kasher]

What happened? Did you go. Did you go manually? Manually.

[Mikey Winfield]

Take.

[Moshe Kasher]

Take it away.

[Mikey Winfield]

Yeah. Later on, you knocked it.

[Moshe Kasher]

You knocked him down alone. Knocked me down.

[Jameela Jamil]

Did you. Did you find. Did you find the buttery woman? Or did you.

[Mikey Winfield]

Oh, no.

[Jameela Jamil]

Had a quick cheeky wank.

[Mikey Winfield]

I wasn't trying to do. I was like. I was there for business, 100%. But I'm with the man. You know, the other guy, he's like the ladies guy, you know? And I'm just like, right.

[Jameela Jamil]

What a fucking nightmare.

[Moshe Kasher]

But you didn't get a reputation as, like, the boner King of the Caribbean or anything?

[Mikey Winfield]

No, no, no.

[Moshe Kasher]

It's a happy ending, I think, actually.

[Jameela Jamil]

Yeah. Very happy ending indeed. Well said. We'll be right back after the break. All right, we're back. Moshe, tell me, what is your micro humiliation?

[Moshe Kasher]

Well, the podcast is called Wrong Turns. This is actually about a physical wrong turn.

[Jameela Jamil]

Okay.

[Moshe Kasher]

When I was a youth, I was like, you know, I was like a drug boy.

[Jameela Jamil]

As in you were delivering drugs to other people.

[Moshe Kasher]

A bicycle. And I would go to the elders of the community. And I would throw their medication into their front yard and say, drug boy. Actually sort of Willy Wonka esque, you know, drug boy's here. No, I was a drug addict. I was a child drug addict, I guess.

[Jameela Jamil]

How old were you when you started taking drugs?

[Moshe Kasher]

Like 12.

[Jameela Jamil]

Lovely.

[Moshe Kasher]

Yeah. Pretty nice. Pretty cool. And me and my friends, that was all we ever wanted to do. All because we still had the spirit of boy in us. You know, it's like we were still children, but we. But we also had this like, bad, terrible habit. But we still had the spirit of like a Huckleberry Finn. So like, what we would do is we would be constantly like, scanning the neighborhood for like a. A place to go smoke weed. That would be like our mission in life. Like, the spot. Let's find a spot, you know, like, you know, like now a grown person. The spot is their living room.

[Jameela Jamil]

Yes.

[Moshe Kasher]

You know, but our living rooms are off limits because our parents lived there.

[Mikey Winfield]

Where do you get drugs at 12?

[Moshe Kasher]

A drug dealer. Oh, yeah, yeah, yeah.

[Mikey Winfield]

Was he 13?

[Moshe Kasher]

Like, actually, it's funny you mentioned that, because one of our main, like, pot connections was 13 because his mother was a. Was a big grower and he, he would sell to and he was like one of our friends.

[Jameela Jamil]

Fucking insane.

[Moshe Kasher]

Well, yeah, but it was also pre legalization. It was, you know, it was the 90s, so we had some. Some real shit. And somewhat we lived in this neighborhood in Oakland that was between. That was near the Caldecott Tunnel. It's a place called the Caldecott Tunnel, which separates Oakland from the suburbs of Contra Costa County. This won't mean very much to you, but it's like, it's a tunnel through a mountain. Mountain. And one of my friends was like, I heard there's a little room in the tunnel and there's a room in there. It's like an antechamber. And if we go in there, we could be in a room and we could get high in the room. And that was like on some Uncle Berry Finn shit. That was enough. That's what enough that we needed.

[Jameela Jamil]

And which pedophile told him about this room under the tunnel?

[Moshe Kasher]

So we were like, let's do it. Room it is.

[Jameela Jamil]

Okay.

[Moshe Kasher]

So we get there, we had to like throw a rug over a cyclone fence and climb a fence and then jump on the rug and then jump over the rug, and then we're on the other side of the fence and we get to the tunnel and it's like a subway tunnel. It's a BART tunnel. And we're like. We get onto. We see that the walkway is A1. It's a single file.

[Jameela Jamil]

Yeah, yeah.

[Moshe Kasher]

It's for when the train stops and you have to do an emergency evacuation. So it's one man, one position, single file. And I start to walk onto the platform, and my friend Jay is like, nah, not you, Pork Chop. They used to call me Pork Chop, which. I was chubby when I was a teen.

[Jameela Jamil]

At this time, children are so mean.

[Moshe Kasher]

So mean. And I'm Jewish. You call me Pork Chop.

[Mikey Winfield]

Wow.

[Moshe Kasher]

Call me matzo ball. You know, if you got it, you gotta do a food relay. You know what I mean? Call me boiled chicken, Something, anything. A pork chop chop. But he go, nah, pork chop. Back of the line. You'll slow us down. So I was like. It was humiliating. My friends were the worst. That same friend.

[Mikey Winfield]

Friend.

[Moshe Kasher]

That same friend. One time, he was. There was a kid that came that was hanging out with us, and that guy Jay. We were all drunk, and he punched the guy in the face. He beat. He beat the guy up. And I ran over. I go, jay, no, leave him alone. He's cool. And I grabbed Jay. And Jay turns to me, who. I'm his friend, and he punches me in the face. And then I run off crying. I'm like, oh. I go into an alley and I'm all mad. Jay comes over. Just to give you a picture of who he is. He comes over and he's crying. He's like, I'm sorry. I should. I don't know why I hit you. I just do that sometimes. I'm so sorry. And I go, you should be sorry, Jay. Fuck you, man. That was really fucked up. And he punched me in the face again during the apology.

[Mikey Winfield]

Jay's unstoppable.

[Moshe Kasher]

He was apologizing for punching me in the face, and he punched me in the face. Face. That's Jay.

[Mikey Winfield]

Jay really couldn't help it.

[Moshe Kasher]

He could not help himself. Not a nice guy.

[Jameela Jamil]

I really hope Jay gets hit by a train in the story.

[Moshe Kasher]

A nice guy now, but. But at the time had some striking issues. So he goes back of the line. Pork Chop. And I took my position at the back of the line because I understood he was right. Pork Chop should not be at the front of the line. So we're single, filing up this, like, safety sidewalk to get to the. To the room where we're going to smoke weed. I don't even know why we wanted to be in a room. I mean, there are rooms everywhere. There are rooms on land. And then all of A sudden, like, as we get a bit in, we feel there's a shift in the air. We feel this, like, sort of like kind of like, oh, the temperature changes. It either drops or. I don't really remember viscerally, but it was like something was different. And then we start to hear this, like, and we see a light coming towards us. We go, oh, my God, the fucking train is here. And the train is. I mean, it comes. There's no time to do anything but stop and, and lean up against the. The wall. And the train is so close. It feel. I don't know, it could be further. But if in my memory it's this close, like I. I remember. I. Like, I was like watching people on their commute, like reading the newspaper and they were like looking back at me. I don't know if they could see us or not, but that's how it felt in my mind. And then it was so scary. It was like an inch away. And then the train stopped. The conductor must have seen that there were people in the tunnel or something. And the train stopped. And we're all like, oh. And the train stops. And somebody from the front line, probably Jay, probably emotionally damaged Jay, goes, run. So do you see the problem that's about to occur? Yeah, Pork Chop is batting clean Pork chops in the back of the line. But we all turn in this single file line, flip around and begin to run out of the tunnel. And guess who's in the pole position? Good old PC. Good old Porkchop is at the front of the line. Not only that, there's wind. There's now a wind resistance coming from the train that just burst into this aperture. And I'm running. It's like I'm running with all that I can. Pork Chops trying. I'm sweating. It's like, stand by me. I'm just like.

[Jameela Jamil]

This honestly feels like a movie.

[Moshe Kasher]

Well, unfortunately, Showtime didn't see it that way, but they're no longer a network, so I feel like I won in the long run. But I'm running with all that I can. Like all my pork choppy and shame. I'm like, running. And I can hear Jay from the back of the line, run. Run, you fat motherfucker, run. And I'm like, I'm running as fast as I can and I want to turn around and scream back, Jay, the positioning of this line was actually your idea in the first place, but we didn't have time for that. And finally we left, like, see the light? I burst out. And the train takes Off. And my. Another friend of mine, Donnie, realizes as we're, like, heaving at the site, we're safe now. And he goes, I dropped the weed. No, I dropped the weed. And, like, we just almost died. And we're like, we gotta go back in there.

[Mikey Winfield]

So we go back in there and he literally.

[Moshe Kasher]

I'm not kidding, he leaps down onto the train track. He. He can see it. I remember it was this little, like, fake walnut that. I don't know why, but he jumps onto the tracks, grabs a little fake walnut, we go back over the rug, we go to this place called Chabot School to a little play structure.

[Jameela Jamil]

We never found the pedophile room.

[Moshe Kasher]

We never went to the room.

[Jameela Jamil]

No, no, no.

[Moshe Kasher]

But we did jump. We did find the weed, which was much more important than the room. And I remember, like, shaking as we, like, sat in this little play structure getting high one more time. And we lived to get high another day.

[Jameela Jamil]

Wow, that is fucking unbelievable. When I was that age, I was in my room alone, listening to Bohemian Rhapsody on repeat while doing, like, my trigonometry, you know, just like, sitting there, just like. Just like, just trying to see, like, how can I get 100% on my maths test, not 97%? How do I get 100 and then I'll be cool.

[Moshe Kasher]

Were where you were sitting? In what?

[Jameela Jamil]

My bedroom.

[Moshe Kasher]

Your what?

[Jameela Jamil]

A bedroom.

[Moshe Kasher]

A room. A room. I gotta call some friends.

[Mikey Winfield]

Give me a second. I wanted. I wanted Jay to punch one more guy.

[Moshe Kasher]

He definitely did. He definitely did. He punched me many, many other times. Although Jay, to be fair.

[Jameela Jamil]

Really, let's be fair to Jay.

[Moshe Kasher]

No. A decent dude. When I wrote my book Cashier in the Ride, my first book, which that story is in the best next, I wrote him and I said, listen, I wrote this book about our childhoods. And, like, I just, like, want to give you some warning that there, you know, there's some embarrassing stuff and in there about you. Because some of my friends got mad when they knew I was writing this book. And he was like, you know what? Whatever you said in there, didn't even read it. He goes, whatever you said, I deserved it. You know, I'm a grown man now. I like my life. I'm sorry. And I was like, to me, that was like, he's got a lot of integrity. Everybody grows up eventually.

[Jameela Jamil]

Yeah, apart from that school bully of mine who's still changing my Wikipedia every day. Little fucking cunt. Oh, my God, thank you so much for these fucking enthralling stories. That is mad. I adore you. Both. And before you go, will you tell everyone where they can find you and what they can watch and look at and read?

[Mikey Winfield]

Ooh, ooh, I'll start. Ooh. I have some specials on YouTube. I have my social media, which you can find under. You can go to bigass teeth.com that'll get you everywhere. Or go to Mikey Winfield across the board on the Instagrams and the Facebooks and all of that jazz. New special coming out on Dry Bar very soon. And step fans and chill. Find me in podcast land.

[Moshe Kasher]

Can I say that Mikey is one of the funniest? Just 100% a super pro, a super funny. I'm just very kind. 20 years in the game. I'm just. I'm glad to still know you.

[Mikey Winfield]

Look at that the same.

[Moshe Kasher]

Thank you.

[Mikey Winfield]

You're incredible. And it's great to meet up again.

[Moshe Kasher]

Yeah, same here. And it's because of you.

[Jameela Jamil]

Oh, sure.

[Moshe Kasher]

You can find [e-mail]. no, I will be going on a big tour the whole month of July. I am doing a Endless Honeymoon podcast tour with my wife, Natasha Leggero. And you can find [e-mail] for all my Upcomin Stand updates. Listen to the Endless Honeymoon podcast. Buy my first book, Casher in the Rye. Buy my second book, Subculture Vulture. I think that's everything.

[Jameela Jamil]

I mean, it's a lot.

[Moshe Kasher]

It's a lot.

[Jameela Jamil]

It's a lot. You both have a lot going on. Thank you so much for coming and telling me your tales of woe and misery and adventure. I have never felt more like I had a really uneventful childhood than I have today.

[Moshe Kasher]

Trigonometry is very eventful.

[Jameela Jamil]

Oh, fuck you, Moshe. Goodbye. Wrong Turns was created and produced by me, Jameela Jamil and Stuart Bailey. And thank you to our launch producer, Eve Bishop, our editor, Shannon Joy Rogers, and consulting producer, Colin Anderson. And you can email us a voice memo of your own wrong turns that we will read out on the show. Just email personal disaster storiesmail.com and if you are also enjoying me as a person, I have a substack. It's called a low desire to please. And that's enough of me. I'm gonna fuck off now. Bye.

[Will]

This podcast is sponsored by IQ Bar.

I've got good news and bad news. Here's the bad news. Most protein bars are packed with sugar and unpronounceable ingredients. The good news? There's a better option. I'm Will and I created IQ Bar Plant protein bars to empower doers like you with clean, delicious, low sugar brain and body fuel. IQ bars are packed with 12 grams of protein, brain nutrients like magnesium and Lion's Mane and Zero Weird Stuff. And right now you can get 20% off all IQ Bar products plus free shipping. Try our delicious IQ Bar Sampler Pack with seven plant protein bars, four hydration mixes and four enhanced coffee sticks. Clean ingredients, amazing taste and you'll love how you feel. Refuel smarter, hydrate harder, Caffeinate larger with.

IQ Bar go to eatiqbar.com and enter code BAR20. To get 20% off all IQ Bar products plus free shipping. Again, go to eatiqbar.comand enter code BAR20.

[Coop Sleep Goods Representative]

Did you know that you can live longer without food than sleep?

[Moshe Kasher]

Ready to learn more?

[Coop Sleep Goods Representative]

Go back to school early with Coop by learning how to achieve an A in getting better sleep. They're here to teach you how to get your best sleep ever. With their Back to school sale and 20% off your first order, sleep and school go hand in hand. In a Carnegie Mellon study, every lost hour of sleep meant a 0.07 dip in GPA. It's time to sleep smarter Shop Coop's back to school sale today. Hand picked for parents, students and anyone who's failing in the sleep department, Coop's curated collection has everything you need to solve your biggest sleep problems. Summer school is in session with Coop sleep goods. Visit coopsleepgoods.com sleep 101 to get 20% off your first order. That's copsleepgoods. Com sleep 101.