2 Bears, 1 Cave with Tom Segura & Bert Kreischer
Tom Shows Harland Williams His Chocolate Starfish | 2 Bears, 1 Cave
Mon, 26 May 2025
Check out the newest podcast from YMH Studios "Not A Damn Chance"! Hosted by pro skateboarder Neen Williams and Michelin-starred chef Phillip Frankland Lee SPONSORS: - Get started at https://factormeals.com/bears50off and use code bears50off to get 50% off plus FREE shipping on your first box. - Make friends and grab some merch at https://www.drinkporosos.com/ This week on 2 Bears 1 Cave, Bert is on a retreat in Istanbul so Tom Segura is joined by the brilliantly bizarre Harland Williams for an unhinged episode packed with supposedly true stories, bootyholes, and too many farts. Harland kicks things off by reminiscing about fingering calamari and the first time someone touched his arse—with a thermometer. Tom shares the traumatic moment he had to show a friend his infamously hairy sphincter... and yes, he ends up showing Harland too. Surprisingly, the conversation spirals into absurd territory with erotic drawings, smut searches, fart-catching attempts, a Dominican dick flash, and a deep dive into Enny’s alleged fondness for buttholes. Harland doesn’t disappoint either—he reacts to fart videos, tells a story about dating Madonna, and looks forward to tanning with Tom. The two also talk about creativity, recreational drugs, Harland's distrust of nicotine pouches, the anthems of both Canada and Texas, plus playing doctor, and horseshoes with neck pillows. Oh, and Harland names his favorite dictator. Stick around to find out if Harland ends up eating Tom. 2 Bears, 1 Cave Ep. 290 https://tomsegura.com/tour https://www.bertbertbert.com/tour https://store.ymhstudios.com Chapters 00:00:00 - Intro 00:02:55 - Arses & Calamari Rings 00:14:34 - So Much Hair 00:26:10 - What's Going On With Canada? 00:31:24 - Measurements, Buzzes, & Vices 00:41:37 - Favorite Dictator 00:51:49 - Dating Madonna 00:55:46 - Clip: Baddie Farts 00:56:49 - Play Back The Tape 00:58:13 - Clip: Fart In One 00:59:29 - Tanning & Tour Dates 01:05:45 - Gas, Gashes, & Gruesome Videos 01:11:48 - Harland Wants To Eat Tom Learn more about your ad choices. Visit megaphone.fm/adchoices
Chapter 1: What are the craziest stories shared in this episode?
I love that I started the Not a Damn Chance podcast with just the nastiest story I have.
Part of the idea of this podcast is how you can become successful as living as just a regular human. I went to culinary school and I only went for a few months and I dropped out.
Chapter 2: What happened with the calamari ring?
Look at that, kids. You can drop out of culinary school and get two Michelin stars.
I do what I can do so I can come back and do it all over again.
Not a damn chance. Not a damn chance.
If you see yourself somewhere, take all the necessary steps to get there.
I just don't know how to quit. That might be my superpower. You can all try and stop me. I hope you do.
Consistency was exactly what life was all about. Don't be genius here and wild there.
There's a beautiful moment where obstacles become opportunities. Messes become messages.
I got shot in the face.
Jail was the best thing that ever happened to me. And I did put my head in a noose.
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Chapter 3: What are the challenges of showing your hairy sphincter?
That's insane, dude. That's how you drink? Yeah. That's insane. I love it. He's loud, he's fat, and he's not here. Bert is on hiatus. He's in Istanbul doing a bit of a retreat, and sitting in for him is an absolutely hilarious comedian. You can see him on the road. You can get tickets right now at harlanwilliams.com. It's Harlan Williams, everybody. Buddy. It's good to see you, man.
You did it down here. I did it here. You went like this. You did like a breast salute.
Yeah, people have different... This is cultural.
I know, but dude, I was up here. I'm like, is that an insult? That's like putting the flag at half mass. It does feel almost like. You gave me a halfie, guy.
Sorry, man. I'll do it again.
And I can't do this because I don't have a chin. You can still do it. You can do it. Well, it kind of slides off and goes right up my face. Ow. Ow, did that hurt? Ow. Shit, okay. Like, I want to fangula you real bad. Do it. Like, to start the show, but all I'm going to do is hurt myself. Yeah. Oh, careful. Let's try this hand. Okay. Oh, shit. Are you okay? Dude, when's it my turn to fungula?
You can do it whenever you want. I know, but I don't want to hurt my face. Just do the finger. One finger? Oh, one of these.
Yeah, the middle. Wow. Nobody really gets that from Harlan Williams, I bet.
Well, I don't like this because really the implication is it's like I'm supposed to be getting the better of this exchange, right? I'm the tough guy, but what am I really saying? Hey, you, I want to put my finger in your anus.
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Chapter 4: What does Harland think about dating Madonna?
Well... Good Lord. Do you remember the first time your butthole got touched in a way that you weren't ready for? Can you just say arse for me?
Your arse? arse hole yeah okay what's the question you remember the first time somebody just kind of jimmied the lock a little bit and you weren't ready how do you mean like just by accident or sexually or well i guess in either way i think it would have to be in all honesty when my mama when i was a little boy i was sick yeah she put a thermometer in there oh yeah is that locked into your memory
Now it is, thanks to you. Was it traumatic? I didn't want to ever remember it. But now, honestly, my legs are shaking, my heart's having a palpitation, and I'm picturing my mother behind bars. Because when I was a kid, I thought it was just natural. I didn't even have a cold.
I just woke up and it was sticking out of me arse. She thought maybe you didn't seem well, so she wanted to check on you.
Well, what really sucks is the week before... I had a real cold, and it was in my mouth. Yeah. I was like, dude.
Well, that's the right order.
I had a lot of kids in my family. Yeah.
How many brothers and sisters? Four sisters, guy. Four sisters. Four, yeah. Jesus. That's a lot of arseholes. That's a lot of feminine energy in the house. Yeah.
But yeah, I think that was the only time I remember diddling.
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Chapter 5: How does Harland want to eat Tom?
Chapter 6: What are the differences between Canada and Texas?
No, but I fingered a calamari ring. It was at a Greek restaurant, Mr. Greek, down on Melrose the other night. Yeah. And they brought these delicious fried calamari rings. I thought they were deep fried assholes. Yeah, yeah. And I just grabbed on and it looked like the perfect fit and I put it on and it screamed. Yeah. I don't know if you ever had your food scream. No, so it was still alive.
I don't know.
I don't know what an asshole does, but when you deep fry it... But you're not a big asshole guy in regular life?
What do you mean? That's a big question. Put it in context.
If you're going to throw the asshole at me, like a life ring... Their whole life revolves around their asshole and other people's. That's where their pleasure source is. Are you one of those guys?
Oh, you're talking pleasure.
Yeah, like fun.
i'm more like i like to go behind like a grassy knoll on a busy road and throw raw potatoes at old ladies driving by in cars they have to be raw like a like a picked potato i just love to throw it and hit like the side window while they're driving and they don't throw them off yeah what's your porn search like what do you like to look for i don't do that ever no how come that's for losers jesus you can't use your imagination
I mean, we can think of anything. Do you ever do like... We got people to Mars. We got people to the moon. I don't need to... I can imagine someone having squishy, squishy time. How about erotic drawings? Do you like those? It depends if I have a box of crayons. Because then... Because then it gets hot. Yeah. When you're drawing, they melt. No, erotic. I like erotic art. Yeah. Yeah. I do too.
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Chapter 7: What are the funny moments involving arseholes?
Chapter 8: What is the significance of the anthems in Canada and Texas?
You can watch it, but I'll block it. Okay. Because I don't want to watch it. You don't want to see any of it? No. Last time I was here, you tried to make me watch a guy pee in his own mouth. Like, I'm not going to. Nice try, Captain Crunch.
god what side of the waffle iron are you on god okay that's bananas um but what about you with arseholes they're called arseholes by the way that's how the english say it that's how this the the squid fishermen say it down off the coast of newfoundland which is where you're from Let me kick you in the arsehole thereby. Yeah. Let's go out jigging for squid, you dirty old arsehole, yeah.
Did you... Let me sniff your arsehole in the sun there, friend. Don't you feel like a girl can have just too gamey of an asshole some days? Like there's a Monopoly hotel sticking out of it? Yes. Yeah. I've had that happen. Yeah. Or the little car, the boot. Yeah. Yeah, sometimes they get... I don't know. I guess...
look dude it's an arsehole of course it's gonna smell gamey what do you what do you think it smells like like potpourri in there i think it smells like a like a thanksgiving dinner with stuffing no it's an arsehole it's gonna smell beyond gamey well it's gonna smell like skanky it's gonna smell like carrion you know what carrion is you don't i think you do Well, I used to work on a farm.
Okay, rack your brain. Let's go. Let's go. Let's find out what carrion is. I think you know what carrion is.
We didn't have that on the farm.
Dude, you're sitting here as a 41-year-old man telling me you don't know what carrion is? Is it a? Suggs. Suggs? Segura. Tommy. Yeah. What's carrion? Carrion? Yeah. That's decomposed flesh, like from a dead carcass. Oh, I guess. That's what vultures eat, carrion.
Well, we were a sheep farm, and so that's where I learned to make cashmere and stuff when I was in college.
How do we go from talking about the stank on an arse? Yeah. To you wearing a sweater, party boy. Making sweaters. Okay, God. Those two things don't jive. They should. Does someone need to go to dialogue school over here? Yeah, maybe. Dude, that's like the Titanic hitting the Edmund Fitzgerald. And, you know, come on. I know, you're totally right.
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