Digital Social Hour
The Wildest Jail Story You’ll Ever Hear – Che Durena Tells All | DSH #1230
Mon, 10 Mar 2025
🔥 Che Durena on Stand-Up Comedy, Viral Fame & Hustling His Way to the Top 🚀 In this hilarious and raw episode, we sit down with Che Durena, comedian and viral content creator, to talk about his journey from struggling in Mexico to selling out comedy shows worldwide. Che shares his wildest stories, how he built his massive social media following, and the hard truths about making it in stand-up. We dive into: ✅ How he went from broke in Mexico to a full-time comedian ✅ His wildest travel and jail stories (including Mexico!) ✅ The rise of social media comedy & how he blew up on TikTok ✅ What makes a great stand-up comedian & his writing process ✅ Why comedy podcasts are taking over entertainment This episode is packed with laughs, unfiltered advice, and inside stories from one of the fastest-rising comedians today! 📲 Follow Che Durena & Get Tickets: 🔗 Website & Tour Dates: CheDurena.com 🔗 Instagram: @CheDurena 🔗 TikTok: @CheDurena 🔗 Podcast: Dark Souls with Che Durena ⏱ CHAPTERS 📌 00:00 – The Wildest Jail Story You’ll Ever Hear 📌 04:10 – How Che Durena Became a Stand-Up Comedian 📌 09:20 – From Living in Mexico to Performing in New York 📌 14:50 – The Struggles of Being a Broke Comedian 📌 20:15 – How He Blew Up on TikTok & Social Media 📌 25:30 – What Makes a Great Stand-Up Comedian 📌 30:45 – The Truth About The Comedy Grind & Open Mics 📌 36:15 – Why Comedians Need to Adapt to Social Media 📌 41:10 – Comedy Podcasts vs. Traditional Late-Night Shows 📌 46:30 – The Future of Stand-Up & Where Comedy is Headed SPONSORS: SPECIALIZED RECRUITING GROUP: https://www.srgpros.com/ 🔥 Apply to Be on the Podcast & Business Inquiries: 🎙 APPLY TO BE ON THE PODCAST: https://www.digitalsocialhour.com/application 📩 BUSINESS INQUIRIES/SPONSORS: [email protected]
Chapter 1: What is Che Durena's wildest jail story?
Security guard sees me and he calls the police. But he's like, this guy's like scaling the walls. I get to the floor. The cops are there. But what had happened when I left and I was like on the balcony, I took off my condom, which I was wearing, and I didn't want to just throw it on the balcony. So I shoved it in my pocket.
So when I get to the ground floor, the cops come and they're asking me all these questions like, where were you? And I was like, I was in there. They're like, what room? And I'm like, I don't know. I'm like still pretty drunk from the night before. They're like, they're like, where are your shoes? I'm like, they're in the room. Like I had flip flops on or I left my flip flops in the room.
Yeah.
And I remember the guy pulling him out and being like, and then all the other cops dying laughing. And then, yeah, then they took me to jail.
All right, guys, we got Che here. My man, best afro I've ever seen. Thank you, dude. Yeah, I've been rocking this for a long time.
For real? How much work goes into that? Not a lot. It's honestly the easiest of all the hairstyles I've had. I had cornrows when I was younger. I had a mohawk when I was younger. I had dreads for a long time. Afro is the easiest. How tough was the mohawk? The mohawk was kind of a pain just because of my hair texture. To make it really good, it took a lot of work.
I would literally like, obviously, you have to keep the sides maintained. But then I would blow dry it. Then I would put hard gel in it. Then I would comb the hard gel out. And then I would wax it. But it was like a Spartan helmet. It was like feathered almost. Yeah, it looked sick, but I was like, I don't know, I was like 17 or something like that.
Which hairstyle had the most success with the ladies? Oh, probably just Afro because I've had Afro the longest. Afro has been the best for me. It gives me, it distinguishes me a little bit more. Like I've always found like success with ladies, it's better to go niche. Like you, like, I don't know, I guess if you're like the most handsome dude ever, you can just be like a generically hot guy.
But if you, if you're, if I, I need to angle a little bit more. So I'm like, if I get like a mustache, the Afro, I have more of a specific look. Say like 80% of women aren't really into it, but 20% are really into it. And that's, you just want to work on your niche. Smart, you're like a sniper with it. Yeah, yeah. Just play to your strengths. I love it though.
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Chapter 2: How did Che Durena start his stand-up comedy career?
And the whole time I was staying at the youth shelter, I told them, I was like, yeah, I just moved here from Mexico, blah, blah, blah, the whole story. And I was like, I moved here to do comedy. And they trusted me and let me stay out and break curfew and go do open mics and then come back later. And I never drank, no substance use, nothing like that.
And then, yeah, stayed there for six months, stayed in their intermediate housing that had no curfew or anything like that. But it was a place you could stay and have your room and buy your own stuff and get a little bit more of like, I'm living on my own kind of thing. And then after that, I moved into my first comic house. This is a very common thing in different comedy scenes.
It'll be a house of four or five comics all just living in some shitty apartment, all sharing rent. And so there was four of us in there. And it was three comics and one musician. And the rent was dirt cheap. It was like $400 a month, maybe $450. Total or each? Total. Wow. Oh, no, no, each, each. Sorry, sorry, sorry. Each. Still cheap. Yeah, cheap. And this was downed. And this is Canadian, too.
So that's like $300,000. American. And this was downtown Toronto. It was like prime location Toronto, but it was a shit hole. It was owned by this dude. His name was Armando. Armando was this like Portuguese dude who was like half deaf and he owned several properties in the area. And he didn't give a shit about ever raising the rent. He just wanted his rent money.
He made wine in his basement and he just he was like, just give me your money and I want to be left the fuck alone. He just made some good investments when he was younger and just is living his life. And so yeah, I lived there for probably six months then moved into another comic house and then just like kind of bounced into like, I lived in four different places living in Toronto.
I lived in Toronto for about eight, I think eight years, maybe eight and change. And then in the last few years, when COVID hit, I started doing all the social media content. Because you couldn't do stand-up. Toronto had the strictest lockdowns in all of North America. Damn. Our lockdown was a year longer than in the States. Holy crow. And you couldn't sit in a restaurant and stuff.
The summer was a little bit better because of the patios, but the winter is freezing. And so there was like barely any standup going on. So I was like, the first few months felt very nice because I'm very much of a grinding comic. Like the way I grow and my like work system has always been like do as many, get on stage as much as possible, try and write every day.
and just be on that consistently. Not everyone grows like that. There's just different comics who have different workout patterns. Some people only write on stage. Some people, everyone has their own system. The system that works for me is very like the ones and twos. Like I go on stage, I do my jokes. I look over the stuff I did. I write my jokes out and like, it's very structured.
It works for me. And so I had been doing 12 to 20 sets a week for, I don't know how long was, yes, for the, up until that point, probably like seven years. Holy crap. That's like two a day. Yeah, yeah, yeah. So you would, I mean, a lot of that was open mics.
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