
🔥 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...
Loading summary
Chad
From taco night in Tulum to sushi.
Che
In Tokyo, make every bite rewarding with gold from Amex. Wherever you dine, four times. Membership rewards points at restaurants worldwide are piling up. Learn more@americanexpress.com Explore Gold terms and points cap apply. 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, wear your shoes. I'm like, they're in the room. Like, I had flip flops on. Or I. I left my flip flops in the room. And then they're like, okay, we gotta search you. And. And then the guy searches me and pulls out the used condom out of my pocket. Dude, 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.
Chad
All right, guys, we got Che here, my man. Best afro I've ever seen.
Che
Thank you, dude. Yeah, I've been rocking this for a long time.
Chad
For real, how much work goes into that?
Che
Not a lot. It's honestly the easiest of all the hairstyles I've had. I 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.
Chad
How tough was the mohawk?
Che
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 like, keep the sides maintained. But then I would. I would like blow dry it. Then I would put like a 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. Like, it had like, it was like feathered almost. Yeah, it. It looked sick. But I was like, I don't know, I was like 17 or something.
Chad
Which hairstyle had the most success with the ladies?
Che
Oh, probably just Afro. Cuz 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, 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, but if you, if you're, if I, 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.
Chad
You're like a sniper with it.
Che
Yeah, yeah. Just play to your strengths.
Chad
I love it, though. A lot of people try to attract everyone, but.
Che
Yeah.
Chad
You're like, nah, screw that.
Che
No, I've never been like that. I've never been attracted to everyone either.
Chad
You.
Che
Yeah, right.
Chad
You're picky.
Che
What's that?
Chad
Are you picky with.
Che
I'm not super picky. I just like, I like, I like chicks who are specific, who have like a look. Like my. I think my least thing I'm the least attracted to is like, for lack of a better word, like a bimbo. Like a, like a Barbie. Like a, like if you see a girl, blonde hair, like, skinny black dress, sorority girl style. That's never been my, my go to. I've never, I've never had success. I don't think they like me either. To be fair. I've never had success with them. But I've also never been like, that's what I'm looking for. Yeah.
Chad
Yeah.
Che
I like, if it's like, she's got, like, I don't know, a bunch of tattoos or like a specific look. She's got a look going.
Chad
She's like an intellectual with a bit of a dark side.
Che
I guess so, Yeah. I mean, any. You can't. It's hard to be in a relationship with someone who doesn't have, like, some brains. You want to be able to hang out and have a good time. You're looking for, like, your best friend. Right? Like, realistically. But a bit of a dark side. She's got to have a little grime on her. She can't be completely squeaky clean. There's no. That just won't work for me. Like, I'm. I'm definitely got some mud on my hands for sure. So I do need a little bit of grime. Yeah.
Chad
We were just talking about the grime. You Grimy cities, man.
Che
I do. I love. Yeah, we're talking about Spokane, Washington, which is a sleeper hit. I mean, I don't think it works for all comics, but definitely for my brand of comedy. Spokane, Washington is. I've been there. I've done six shows there so far. They. They've all been incredible. They've all been super fun crowds. Awesome. Like, one dude at a show was like, he was like kind of floating around the. The merch table. And I was like, hey, man, do you like, want a picture or something or you want some merch? And he was like, yeah, I'd love a T shirt. And I was like, oh yeah, what size? And he was like, can I just give you a bag of weed for it? I was like, yeah. And he just pulls a bag of weed out of his pocket and hands it to me. There was another one where this lady. I was crow. I would. Every time I go to Spokane, I like, sometimes I'll like prep certain questions to ask the audience. I always ask, has anyone here been to prison? Because like, the crowd lights up. Dude with people have been to prison. This one lady, she had like crazy neck tattoos and she was like, yeah, I've been to prison. And I was like, oh, I bet you were like running. You had like chicks you were running because you were topping them. And she was like, no, no, I was a pillow princess. Girls were banging me. And I was like, for real? She's like, yeah. They would give me snacks and I was like. And she goes, I was like, oh, well, they like use their hands and stuff. And she's like, no, we would make dildos. And I was like, out of what? And she said, jolly Ranchers. Yeah, they would like craft them out of Jolly ranchers. People get very handy in prison. Very creative. Yeah. Yeah.
Chad
All right. Shout out to today's sponsor specialized recruiting group. Navigating the professional job search is hard. You know the perfect job is out there. You're just not sure how to find it. The good news is you don't have to go at it alone. You need specialized recruiting group connect@srgpros.com srgpros.com they're here to guide you and help you find a role that fits all without costing a dime. Meet specialized recruiting group offering a tailored approach. To find your next role, go to srgpros.com srgpros.com and get on the right course. Your local specialized recruiting group team knows which businesses are hiring and can offer you a path to contract and full time roles. If you don't See the role you're looking for on the website. Specialized recruiting group also recruits for confidential roles. So give an office near you a call to learn more. Take the next step in your career by starting@srgpros.com SRGpros.com is nuts. That doesn't sound pleasant.
Che
I mean, I don't. Jail isn't pleasant. So, like. Yeah. So have you been? No, I have, actually. No. I was in jail once for, like, a day. I got arrested for being wasted in Mexico.
Chad
Yeah, Scary Mexican prison.
Che
I was living out there, so it wasn't too spooky. They kind of wanted a bribe. Oh, my God. This was so, like, what happened was I was hooking up with this girl, and she was. She was there with, like, a university program that basically sent people to Mexico to study in Mexico. And, uh, and I was hooking up with her. But you weren't supposed to have guests in your room. So her roommates got home, and she's like, you have to, like, sneak out through the window. So I snug out through the window. I'm like, on a balcony, and I start, like, climbing down balconies to get down to the. To the ground floor. Security guard sees me, and he calls the police because 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. And then they're like, okay, we got to search you. And then the guy searches me and pulls the used condom out of my pocket. Yeah. And I remember the guy pulling him out, out and being like. And then all the other cops dying, laughing. And then, yeah, then they took me to jail, and they just, like. I had to, like, call a friend. And then my friend came and picked me up. And then they lied about what I did. They said I was like, banging on all the doors and trying to break into places but they weren't even there to see.
Chad
It sounds like Mexico.
Che
Yeah, they. They wanted a bribe and I had no cash on me. It was basically.
Chad
You were broke at the time?
Che
Yeah, well, I, I just, I. I would. Oh, yeah, I was kind of broke. Yeah. I was like, living like paycheck to paycheck at that point in my life, for sure.
Chad
That was pre comedy career.
Che
Yeah, yeah, yeah. I think maybe I had just started comedy because I started comedy in Mexico. Wow. My first, like, year, year and a half of comedy was in Mexico. So I. My. The way I kind of got into it, like, early on, like grade four, I did public speaking and I did a speech about my family, and it was funny. And so I kind of got a taste of. For something like that. Never touched anything like that again. Then in high school, public speaking came back in English class and I was like, oh, I remember grade four. I made a speech and it was funny. I should, like, try and do that again. And I had success with it. I did really good. And then what ended up happening was I. I didn't touch it ever again. And then. Or not. Not for a little while. Then my brother started doing stand up. And this is when I was living in Mexico, and that kind of opened the door for me because prior to that, I had. Was like, consuming stand up like crazy, watching stand up all the time. I was. I loved it. It was like one of my favorite forms of entertainment. But I thought you had to be famous in order to do stand up.
Chad
Yeah.
Che
And so when my brother was like, oh, I'm doing standup, I was like, what do you mean you're doing standup? Like, I thought it was like, you're famous, so people come see you. And it was a byproduct of fame where it's the other way around. And he was like, I'm just going to open mics. And I was like, there's like open mics for comedy. What is this? And so I just started writing jokes with the intention of sending him these jokes. And then I wrote enough jokes to be like, well, if I wrote enough, I can probably just do it myself. And then I found an open mic in Mexico and Plato Carmen. It was like five dudes. It was like four Canadians and one American that ran this show. And I, I, like, called and was like, hey, can I do the show? And they were like, yeah. And I came and I did whatever, seven minutes. And it went well enough. And I was like, oh, I think if I. I could keep doing this, that maybe I could Be good at it. And I just started, like, really focusing on that. It felt like the first time I ever had, like, a purpose and a goal and something to, like, dedicate myself to.
Chad
That's cool.
Che
Yeah.
Chad
Mexico. So did you have to do it in Spanish?
Che
No, we did in English. It was all for tourists. Sometimes the tourists spoke English, sometimes they didn't. Got it. But that was. Yeah, that was. That was the start. And I did that for about. Yeah, a year, year and a half. And then I moved to Toronto. And when I moved to Toronto, so I was. I was working as a scuba diving instructor in Mexico. Then I started bartending and diving at the same time. Then I was making, like, okay money. I had, like. I kind of had throw around a little bit. Then I stopped doing both of those, started working at a call center, and that was, like, more scraping by kind of thing. Like, I wasn't hurting, but I wasn't making a lot of money. Call center got shut down. They didn't renew my visa. So then I was, like, working illegally in Mexico, selling tours on the street. And then I was really broke. I had, like, no cash. Wow. Then I tried to renew my visa. They didn't want to through, like, the. The system that you go to renew it. They didn't want to renew my visa. And then I got, like, a letter of, like, deportation. Like, they were basically like, you have 20 days to get out of the country, or we're going to deport you. Yeah. And so I was like, okay, I want to do this standup thing. I'm really dedicated to this. I was like, I have no cash. And there was this guy who I worked with at the call centers. This guy Dave. Dave, I will remember forever. He was this older dude. He made a bunch of money selling timeshares. He kind of had some demons. Like, he drank a little bit too much. He had, like, a drinking problem he got over and stuff. But he was a very, like, wise person. He was, like, the closest thing I ever had to, like, a mentor. Like, we would stay late at the call center and, like, shoot the. And he introd me to, like, health in a way that I hadn't never experienced before. Like, do you know. Have you ever heard of Rob Wolf?
Chad
Rob Wolf.
Che
He's, like, an early health guru guy who is big on, like, micronutrients, like, spirulina. And that was the first time I'd, like, ever heard of spirulina. Dave, are we allowed to swear?
Chad
Yeah.
Che
Oh, sorry. Okay, cool. Dave introd me to, like, coconut oil. He was like, yeah, I put coconut oil in my hair, and it took my gray hair away. And I was like. So then I started eating, like, maca root, and you could get cacao, like, fresh cacao by the kilo in Mexico for, like, nothing. You could buy two kilos for, like, five bucks. And so I started putting that in smoothies and stuff. And then I got really into health. And then when this, like, the comedy thing started coming in, I would stay late and watch comedy on the computers at the call center. And I remember one day, me and Dave were just, like, shooting it, and he was like. He was like, oh, you want to do this comedy thing? You should go chase it. And I was like, yeah, you know, I think I'll go. I'll go to Toronto. I'll move to Toronto, and I'll try it for, like, three years. And if it works out, it works out. If it doesn't, it doesn't. And then he went home and he watched comedy, a bunch of comedy. And then he. And then the next day, we were, same thing. We're shooting the shit. And he was like, yeah, I remember you saying you were gonna go for a few years. He's like, that's not gonna work. He's like, these people either are or are not comedians. And I didn't understand that at the time, but I get that now. Like, it's like being a comic is, like, your perspective on the world and how you communicate with people. Hanging out with the comics is a different experience. How you open yourself up to people and your willingness to be raw, like, and exposed, it's like. It's a whole. I think anyone who, like, dedicates their life to something will understand. Like, if you're a fitness person, it's how you eat and how you sleep, and you're thinking about it all the time, and your decision making all changes because of this thing you are passionate about. And comedy is the same way. He saw it right away. I didn't understand this, but after the call center got shut down, we were both looking for jobs, so we were both working the tour thing. And we used to have a coffee before we would go to the tour thing. And this was what, Like, I got the letter of deportation. I was like, kind of. I had no time to get out of the country. And he was like, you should just go. Like, if I was you, I would sell everything I owned and just go. And I was like, I don't own anything. Like, I have a blender. Like, what am I going to sell, dude? And I was. And then I remember walking home from work. It was. Or was it late at night? I remember it being night time, so it must have been late at night. Maybe I was walking to get food and it, like, clicked in my head. I was like, oh, I have all this scuba diving gear still. I'm going to sell all my scuba gear. And so I just sold all my scuba diving gear. And I remember looking up the sky and saying, thank you. Like, I was like, I have the answer to how I'm gonna chase this dream. And so I sold all my scuba diving gear. I got like 450 bucks. I got totally ripped off, but I didn't give a shit. And then I bought a plane ticket to Toronto. I knew no one in Toronto, but I knew Toronto had the biggest comedy scene in Canada. And I could have gone back home to Vancouver and, like, stayed with my dad and, like. But I knew it. I knew that I was too lazy and that if I went home, I would have just, like, it would take me forever to do it, and I just had to jump into it. So I flew to Toronto, knew no one. By the time I got to downtown Toronto, I'd like 25 bucks down. And I went to a Starbucks. I took out my laptop and I Googled Toronto homeless shelters. And then I found a youth shelter close by. And I went there and they were like, oh, we. We don't have any beds left. And so they're like, we can feed you, but we got to, like, we'll give you, like, an address for a men's shelter. And a men's shelter is, like, a much rougher environment, like the youth shelter. Honestly, like, it could have been the best situation possible. It was basically a hotel. Like, its social services in Canada are really good. That was one of the reasons why I wasn't afraid of just going and chasing it, because I was like, I'm. I barely have any money in Mexico and I'm surviving. I'm going to be fine in Canada. Like, I just knew it was going to work out. And so I was sitting there eating, and then one of the kids who was staying there showed up, but he was drunk. And they were like, hey, we have a zero tolerance policy on any substance use while you're here. So he. They're like, he can't stay here tonight so you can get a bed. And so then I was able to stay there. And then I stayed there for, like, six months. I never had to sleep on the streets or anything like that. Like, I was technically homeless, but I did Bobby Kelly's podcast. I told him that, and he was like, you weren't fucking homeless. Because Bobby was actually homeless, like, sleeping on benches and there's love levels to homelessness. Oh, yeah, yeah. And so this was the best case scenario. Like, you got fed, you got three meals every day. You got a bed to your. You. I was sharing a room, and then I got a room to myself. They, like, there was laundry services and everything. It was for, like, homeless youth to, like, get up on their feet. Like, and some kids there had, like. It really opened my eyes to how people end up homeless and on drugs and these different things. Like, some of these kids, they were like, yeah, I've been homeless since I was, like, 12. Or, like, one girl was like, she was so smart. I know she's doing well because I saw her working somewhere later, but she's so smart going to school. But her mom was super abusive, and so she had just. She had to, like, run away.
Chad
Wow.
Che
And so I was like, man, it really starts for a lot of these people super young before they ever have a chance to get up on their feet, that things fall apart for them. And so I was so grateful for that place. So I stayed there for about six months, and then I went to this intermediate housing thing where there was, like, no curfew or anything like that. And the whole time I was staying at the youth shelter, I told them, like. Like, 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. I never. No substance use, nothing like that. And then, yeah, stay there for six months. Stay in the intermediate housing that had no curfew or anything like that. But as a place you could stay and, like, have your room and, like, buy your own stuff and, like, 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, like, comic house. There's, like, very. This is a very common thing in different comedy scenes. It'll be a house of, like, four or five comics, all just living in, like, 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 bucks a month, maybe. 450 and total or each? Total? Oh, no, no. Each. Each. Sorry, sorry. Each.
Chad
Still cheap?
Che
Yeah. Cheap. And this was down. And this is Canadian too, so that's like like 300American. 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 re. 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 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 that 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 in I think eight years, maybe eight and change. And then in that, like in the last few years, like when Covid hit I. I started doing all the social media content because like I couldn't. You couldn't do stand up. Toronto had the strictest lockdowns in like all of North America. Like our lockdown was like a year longer than, than in the States.
Chad
Holy crap.
Che
And you couldn't like, you couldn't like sit in a restaurant and stuff. Like the summer was a little bit better because the patios, but the winter's freezing and so there was like barely any stand up going on. So I was like, what? 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, and just be on that consistently. That's 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, it's very structured. It works for me. And so I hadn't, 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.
Chad
Holy crap. And that's like two a day.
Che
Yeah, yeah, yeah. So you would, I mean a lot of that was open mics, so you would go get your five minutes and then like the, when you first go. When I first got to the Comedy scene. It was like, go to a show, show up like two hours early, wait out in the cold, then sign up on the list. And I just would bounce around and do that every single night over and over and over and over again. I would take a night off like once every two weeks. That was once every two weeks, take a night off.
Chad
And you don't get paid for that, right? No, no, that's the grind.
Che
Yeah. I didn't start getting paid in comedy, like, and we get like a 20 bucks on a show here or there. But I didn't start like living off of comedy until like year eight or nine.
Chad
Holy.
Che
Yeah.
Chad
There is a ten year rule in comedy.
Che
I've heard there. It can be. Some people get really lucky, some people blow up way sooner. Like Gerard Carmichael had his first special like six years in. Some people go and pop way earlier. Most of the people who I idolize in comedy were like into their 40s before they really cemented themselves. Like they were living off of comedy before. But before they were cemented themselves as who we understand them as now. They were like 20 years into their careers. So it is very much a grind. But same as like if you go to school to be a doctor or something. I'm not saying it's as valuable, but it is, it's like go. It is going to school and so you have to do your time and you're not getting paid before. But it was, it was a, it was a long road of that. And because of COVID I. Yeah, I took like two months where I was just like enjoying the time off. I was like, it was guilt free. I didn't, I was like, I can't do comedy. And then after a little bit, there was some cities around Toronto that were having comedy shows, but with like, you had to be like behind plexiglass and tables could only have this many people. And they all did like all the COVID rules. And there was one place we went to in Kingston, Ontario, it was me and two of my buddies were doing a, like a weekend there or two or three shows or something like that. And my buddy was making Tiktoks and I'd never. I wasn't on Tick Tock. I think I'd only been on Tick Tock because I knew it came from musically and I was like, it's lame and cringy and blah blah, blah. And he was making Tick Tocks and he wasn't getting crazy views, but he was getting like 3, 000 views. And I was like, damn, this show. This, that room that we're in. Sold out would be 150 people. I'd have to do 20 sold out shows for the same amount of people to see me that just saw him on this little tick tock. And so I was like, all right, well, I should start doing this. Even if I'm only getting 100 views. It's. That's a show every time, right? So at this point I was working for this YouTube channel called Most Amazing Top 10. And so I was actually working through all of COVID because we could, we could work off our computers and be a little bit more whatever, what was like separated or sectioned or whatever the term was. And I had built up a little bit of following from working for this big YouTube channel, about 50k followers on Instagram. And I was like, okay, I can kind of co op this little bit of popularity into something else. And a lot of the people that work there were younger. And I was like, tell me about TikTok. What should I do? How do I do this? And one girl there was like, you want to be doing mirror rants, stitches and duets. That's what you got to focus on. That's like. Because you just want to focus on your comedy and like your strength is your joke telling. So just, that's your strength. And so I just started hammering those out. I would do six a day, six a day, six a day consistently. And I would, I would probably spend like an hour, an hour and a half making content. And then I would spend an hour, an hour and a half watching YouTube videos about how to be successful on the platform. And then just started grinding it, grinding and grinding, grinding, grinding, grinding it. And then it just started blowing up and blowing up and blowing up. And then I started really posting consistently in like December of 2020. And then by February of 2021, I had a manager reach out, being like, I want to represent you.
Chad
Holy crap.
Che
And at this point I was like, at about 900k followers. And then that my manager, who's incredible, shout out Rachel Helix, she is absolutely goaded. She helped me get my visa, helped me get all the paperwork and everything so I could get my visa to come to the States. She was. She's a titan.
Chad
That's a great manager.
Che
Oh, she's so good, dude. So good.
Chad
I've never heard of a manager doing that.
Che
Oh, my manager. My manager is locked in and fucking works her ass off. Yeah, if it wasn't for her, I wouldn't be able to do what I'm doing now. And helped Me a ton. And then that opened the door to me moving to the states, which was always the goal. It was just, how do you do it? And now I finally had like the finances. I was like making like a little more cash and stuff. And then my first tour, I made like really nice money. And then it was like, okay, this is like real now and I'm living in the States. And then so it's been about two and a half years I've been living in New York and just grinding the New York comedy scene and then also shifting my presentation on social media as well. Because when I started posting on social, I didn't have a backlog of stand up clips. So I was just making all those duets and mirror rants. So a lot of people think I'm a tick tocker who started doing stand up, but it's way the other way around. I own. The only reason I ever started making TikToks was because I. I'm doing standup. I knew it would help the career. So now I'm shifting all of my social to being like, podcast. Here's my podcast here, my standup clips and reducing the amount of like stitches and duets and stuff I do. They're still in the mix, but not. But I don't, don't want them to be as important. And even if I have to take it, take a hit on views and take a hit on the algo, it'll take time to shift, to teach people. Like, this is the primary thing you should be paying attention to.
Chad
I have noticed you take a step back on content.
Che
Yeah, yeah. For sure.
Chad
Yeah. Did anyone other than Dave from Mexico believe in you those first few years?
Che
Everyone was super supportive. Like, I've never had trouble with people, like, doubting me, my fam. Like, I was, I've always been a very, like, lone wolf. Like, I'm gonna kind of do whatever I'm gonna do. So my family just supported me because I think they knew that if they were like, hey, you shouldn't do this, I would have been like, okay, I don't give a fuck. Talk to me. Like, I would have just, I'm gonna go do whatever I want to do. Like, I literally flew to a city I'd never been to before and risked living on the streets to do what I wanted to do. So I think everyone was very supportive. Everyone was, which is great. I've always had a very positive outlook on life. Even if stuff gets shitty, there's someone who's life is much shittier than mine.
Chad
Yeah.
Che
And I Think it's hard to hold on to that, especially as you grow, like you've grown a big platform and you know how the baseline changes, which is good. You want to keep trying to achieve bigger and better, but you also need to sometimes step back and have gratitude for, like, if I look back three years from now, and sometimes, like, if I have a weekend that didn't sell as much as I wanted, I go like, oh. And I go, man, three years ago, I would have killed to sell this many tickets, dude. Yeah.
Chad
Yeah. When I have an episode flop, I'm like, wait a second. Three years ago, two years ago I would have been like, damn, 10,000 views, you know?
Che
Exactly, exactly, dude. So it's like that stuff I. To be really grateful for and understanding that it's like, it's up and down. Entertainment goes like this constantly.
Chad
Yeah. Yeah. Sometimes I'm so hard on myself, dude. It's nuts.
Che
It, it's, it's. I think it is a good, it's good, but you have to have the balance. You can't let it consume you to the point where it's negatively impacting you, where you feel down on yourself for like days or weeks at a time. But you do need that, like, little bit of doubt to double check everything, to dot your eyes and cross your T's to make sure that the product is, is tight as it is.
Chad
Right.
Che
Like, I just recorded my special and after the first night, we really got incredible footage. And I was like, yeah, you know, well, I was talking to the crew and I was like, okay, we're gonna work on this. And he and the guy running it was like, I thought you'd be more excited. Like, we just got two really good shows of the bank recorded four shows. And so. And I was like, yeah, no, I just want to get it perfect. And the next night was even better than the first night. But having that, I wasn't like broken about it. But the next night I made sure that I double rehearsed everything. I did little things. Like I went to the sauna and went did cardio to like focus my mind.
Chad
I love it.
Che
Yeah. And hey, those look like if you were, if I was too lax, I wouldn't have done those things. And then maybe there would have been a couple moments that were a little sloppier. Like there was a couple tags I made in the weekend that made the special a little tighter and a little nicer and I would have missed those if I didn't, if I didn't have that little bit of doubt.
Chad
Yeah, yeah. I think you really adapted well to social media, man.
Che
Yeah, yeah, yeah.
Chad
Because that really changed the comedy scene. Yeah, for sure, like, hugely now. Comedian podcasts are, like, the biggest in the world.
Che
Yeah. It is, like. That is, like, a big focus of mine now. Dark Holes with Chad Rainer. Check it out. Yeah, my. I'm. I've got my podcast now, and I'm pushing that because I think it is one of the best. For one. It is some. It's a product I truly believe in. Like, I've made a ton of shit. I've done sketches. I've been in, like, commercials and movies and different things, and you can tell when something is like, this is fine, and when this is, like, really good. And my podcast, I'm like, this is a really good product. I will put in the time and the love to grow this. And I know it's a labor of love, and it takes a lot of time to build the audience for something like this, but it will be great. And it already is. The product's already so good. But part of the motivation for that is the conversion for, like, comedy fan to ticket buyer on a podcast is, like, one of the highest of any medium you can do as a comic. Yeah.
Chad
I see Theo Von selling out every show.
Che
Oh, yeah, dude. Theo Vaughan. Theo Vaughan. I won't say who told me this, but someone who's a big comic told me, like, he does theaters, and they're like, he could be a stadium guy if he wanted. He just chooses not to be. Wow.
Chad
That's.
Che
Yeah.
Chad
That's respect.
Che
Yeah.
Chad
At the same time, you're turning down a lot of money, so I don't know how I feel about it.
Che
I mean, some people just, like the different level of, like, intimacy with their shows. Stadium's a way different vibe. I got to open for a stadium comic, and it's very different. It's cool as hell, dude. It's sick. But it's. It is a very different vibe, and you really need to be a very certain kind of act to perform in front of a stadium. It's a different. You're doing a different thing.
Chad
That's a good point, though, because perfect example. Kendrick Lamar, yesterday, he's getting a lot of hate.
Che
Yeah.
Chad
That performance, I wonder if it's because it was too big of an audience.
Che
I thought it was good.
Chad
You thought it was good?
Che
I thought, okay. I watched. After I watched it, I was like, I think we get so inundated with, like, the online opinion so quickly.
Chad
Yeah.
Che
And so I try to consume. I was Happy. I watched it because I tried to consume stuff before you get that outside opinion. But I thought it was. The critiques I think are accurate. Like, they're like, oh, it wasn't like, you know, Lady Gaga coming down from the ceiling or like people doing a bunch of crazy. He kept it simple, but it was like, kind of creepy. And it reminded me of like a Jordan Peele movie. Like, there was this horror, like, uncomfortableness to it. And people were like, oh, none of these. He wasn't playing any songs that people know because he's not as, like, mainstream. I was like, so many of these songs are like famous tick tock sounds. And that's how I was recognizing them. And I was like, oh, I know that. I. Maybe I don't know the name, but I know this one. I'm not a big music guy at all. I know music's probably the area of media I know the least about. But I thought the performance was good. I thought it had its own personality. I thought it was raw. I thought. Yeah. And I thought it was like, creepy in a cool way. Like, I liked how it felt a little unsettling. And it was supposed to be because it was taking a shot at someone. It was like a disc. It was the. The final pin in the. The whole disc saga.
Chad
Yeah. I thought the expectations were too high just because it's a Super bowl halftime show.
Che
Yeah.
Chad
People do some crazy stuff during those.
Che
People do do crazy stuff.
Chad
Like last year, 50 Cent came out like. I don't know if you remember, his feet were on top of the ceiling and he was singing upside down.
Che
Yeah.
Chad
People just wilding out.
Che
Yeah. And there's been way crazier ones. But if you go back and you watch. I don't like. I'm not saying that Kendrick Lamar is on Prince's level, but if you go back and watch his Prince, now, Prince had the hits to. To get people excited. Kendrick Lamar doesn't have the same catalog, but Prince did a very simple performance. He came out with his guitar and he sung. And there was like the. The. His symbol was like the stage and like, it was. It was a good. It was a good performance without any sort of bells, as many bells and whistles on it. I do like the bells and whistles for the halftime show, but I thought it was good. I thought it was good. I'm gonna say I thought it was good.
Chad
No, that's a good point, though. You brought up the crowds. It must be a little intimidating, the larger the crowd is.
Che
Yeah, yeah.
Chad
It's a Different vibe. You can't get as personal.
Che
Yeah.
Chad
You can't do hecklers. Yeah.
Che
Yeah.
Chad
So that's kind of your vibe. The more intimate crowd.
Che
Yeah, for sure. I'm not on like, like I've. I've sold out a couple theaters, but I'm not at the level where I'm doing theaters consistently. I'm still a club comic doing weekends, which is great. I'm so super happy about that. But yeah, my shows are way more intimate than that.
Chad
I feel like that's the purest form of comedy shows.
Che
It. A lot of people do think that. I think the. I think theaters are still really, really good if you're doing like a thousand seater, which is. That's the biggest I've done. And that still feels incredible and very intimate and very nice. I don't know what it's like to do like 5,000 seats or something. I've only done like a thousand seats or 12,000 seats.
Chad
Didn't Schultz do MSG?
Che
Yeah. Yeah.
Chad
That's like what, 80,000.
Che
I know. Clue. It's something huge. Hit him. And who else is it?
Chad
Tony. Kill Tony.
Che
Kill Tony sold out two shows there which were incredible. I saw both Kill Tony shows and those were some of the, maybe the greatest live shows I've ever seen.
Chad
Was that the Trump Biden one or was.
Che
I saw both. I saw when they did Trump Biden and I saw when they did. What was the other one? The other one was Shane Gillis and Joe Rogan was on the panel and it was like the first show was definitely that the Trump Biden was the second night. The first show I thought was crazier because I didn't know what to expect.
Chad
Yeah.
Che
But I felt for the comics that got pulled out of the bucket. Dude, there was. Because normally Kill Tony, you have like your Kill Tony regulars, then you have the panel, which is like famous.
Chad
Yeah.
Che
It's like you're still stacked up against a lot, but if you come up, that's your competition is going up against the regulars. But there's also a bunch of other like just regular people who've come up before you. This show, what they did was they would have a legends bucket, then the regulars bucket, and then just like regular Joe bucket. So they open the show, they intro Shane Gillis, they intro Joe Rogan, Tony's on stage, then they go, okay, we're gonna do something we've never done before. We have this special bucket. We're going to pull out Legends. And it's like your first comic. He's the first guy to ever sell out msg. Absolute killer and influence to me. Everyone gave it up for Andrew Dice Clay. Andrew Dice Clay opens the show, then you have a regular come out who I think might have been. Fuck, I can't remember who. I think it was Jared Nathan, who actually, we were in the same comedy scene for a long time. Yeah, Jared's Canadian guy. Dude. It was great to see. I was so happy for him to see him come out. So then you have a crowd favorite come out, and then you have some regular guy nobody knows. I couldn't imagine a harder situation. You have to follow a legendary comic then someone everyone loves, and you're. You're just nobody. One dude who did kill it was Jason King. Jason King is a comic from Queens, and he came out, murdered his set. And then after on the panel, they're asking him questions. They're like, hey, so, like, what do you do? And he's like, oh, I'm like, I'm a musician. I produce music. They're like, oh, what can you play? And he's like, I can play anything. Give me the drums, the guitar. He's like, you can play guitar. And they're like, should he play guitar for us? He goes to the band, takes the guitar, starts, like ripping the guitar, and everyone's losing it. It was literally like, if you're watching a movie and they're like, hey, our guitarist isn't here. Can you play guitar? Like, it was nuts, dude. It was like. It was the. I'm like, in front of a sold out msg, you're just like, like, oh. I felt so, like, I was like, I never met him before, but I saw that. I was like, dude, you couldn't ask for anything better. And you're like, this is. That's a story you tell for the rest of your life.
Chad
Legendary. You only have a minute, right on kill, Tony.
Che
Yeah, you only have a minute.
Chad
Yeah, that's hard.
Che
I mean, it's a hard amount of time to kill in for anyone. Even like a very seasoned comic. It's very hard to kill in a minute. Yeah, because you.
Chad
You did seven minutes when you were on the come up, right?
Che
Yeah, yeah, yeah. Like, usually 5 to 7 is like your normal time. You're getting on set sets. Doing one minute is like, you need to be, like, super tight and very focused, and you really need to think about how you have no time. You got to get to your punchline so quick, and you don't have time to, like, build into what's gonna happen. And yeah, like, It's a muscle that no one's really ever working except for when you know you're gonna do Kill Tony.
Chad
Have you been on there before?
Che
No, I would be down to do it 100. Like, kill Tony is, like, basically late night right now. It's like. Like, it's the equivalent of doing late night, like, 20 years ago. Like, doing late night now doesn't really do anything for your career, but if you did late night in, like, the 80s, that could be like. Yeah. So I would say Kill Tony is the version of that. Now. It's the biggest thing you can do for your career as, like, a newer comic or even, like any. Anything below. I would say, like a theater comic. Even like, if you're a weekend guy. Like, I. Like, I'm a weekend guy. It would benefit me hugely.
Chad
Yeah.
Che
So many. My buddy did it. He's got millions of followers. He's a great comic. Andrew Packer, man News, like, destroys it. He. He did Kill Tony Murdered. And then he got instantly got 10,000 more views on his comedy special. Like, it's. It's. It really can help your shit.
Chad
Yeah. I mean, I think it's the number one or two comedy podcast in the world.
Che
Yeah. Yeah. It's huge, Giovann. Yeah.
Chad
And Schultz is also huge.
Che
But.
Chad
Yeah, you're right, though. I used to watch the talk shows. I don't watch them.
Che
No one does anymore.
Chad
It feels inauthentic.
Che
Yeah. And it was. It was a time. It was like. It was. Everything has an era and then things fade out. People aren't watching cable television like they used to, so it's just. It's moving on to a new medium, a new platform, a new system.
Chad
Yeah. I think podcasts are in right now. It'll be interesting to see what's next. After pods.
Che
There's always something new. There's always. As technology changes, the, like, AI will like, undoubtedly open some doors for us to have new platforms and people to experience things in new ways. Like, it's very hard to predict what these things will be, but who would have thought that, like, radio would make a comeback after television? And maybe it will be an older form. Maybe plays are back in after. Who knows? I learned that plays are completely far away, but they're not that big.
Chad
Hey, don't rely on musicals. I just watched Hamilton the other day.
Che
Oh, yeah? Did you like it?
Chad
I liked it.
Che
I've never. I've seen one musical. I saw Book of Mormon because it's the south park guy. So I was like, I'll go Check it out. And I liked it, but I don't know if I'm. Musicals aren't really my.
Chad
Yeah. You're not big on music.
Che
Yeah.
Chad
Do you use AI to brainstorm any ideas for your sets?
Che
No, not brainstorm ideas for sets. I use it for a couple other things. More like, I guess, logistical work or. But yeah, comedy wise, not funny enough yet. It's. It's. Yeah, I don't think it's funny enough yet. It's also restricted. Like, if you go like, hey, write me 10 jokes about analyzing, it just won't. It's like, I can't do that. So it's too restricted. So you can't. You can't explore what you need to. My writing style is I. I always start by looking. I have this folder on Instagram called the Best, and it's all, like, reels that have made me laugh. I'll watch that for maybe five or 10 minutes, and I get into the point where I'm laughing out loud and I'll be like, drinking coffee while I'm doing this. Wow. And then I put my phone on airplane mode, and then I go and just start writing and I'll literally walk around my apartment and talk out loud and, like, do the act outs and get into it. Like, I try to get into it as much as possible. And so. And once I'm working on a bit and I. And I start making myself laugh from the bit, I go, okay, we're cooking. We're cooking. I like this. I like this.
Chad
I love that.
Che
Because part of what I really like about it is that I'm performing it. Like, I. And enjoying performing a bit is my favorite part of the bit. Like, I want. Sometimes you come up with something and I'm like, oh, I can't wait to say this on stage. Like, there's. They do this thing on. Have you ever heard of Good Ones?
Chad
No.
Che
Good Ones is a comedy podcast where he brings on comics or comedy writers, and they talk about one joke and they break down how the joke happened. It's a very interesting comedy podcast. And one thing he'll do is he's like, if you could have someone else's joke, like it's an alternate universe and you came up with this joke, which joke would it be? And that for me, it's like. Like it's not the structure of the joke, it's like the. The chance to perform it would be so good. Like, there's this one comic in Toronto, his name's Monty Scott, and he has, like, one of My most favorite jokes ever. And it's. He's like, who invented the two man luge? Like, what the is that? Sport was the top of a mountain on fire. And they were like, there's one way down and it's gay as. And I just. Every time I hear that, I go, oh, I wish I could do that joke. He's like, it's just a man on. A man on a loose. But that's like, that is. So when I'm riffing in my apartment and just talking, when I'm. When I have fun performing it to no one, I'm like, oh, this is. We're good, we're good. Write this down. Write this down. Yeah.
Chad
That's so cool, man.
Che
Yeah.
Chad
Yeah. That must be a cool feeling to see it come to life too.
Che
Yeah.
Chad
You could think it's funny and then perform it and it flops, right?
Che
Oh, 100%. That's part of the reason why the stage time is so important. Like, I think. I mean, I've never created music, but I'm pretty sure you get a good idea for if a song is good by yourself, right? A joke, you never really know if it's gonna work until you take it on stage. You have to take it on stage and you have to work it like again and again. And sometimes like 30 of it works. And then you're like, okay, what do I change here? How do I take this out? And there's been jokes where the whole, like, beginning and premise doesn't get a hit and then just the punchline hits and it's kind of like a long tail to get there. And then I've. I've taken the punchline out and put it into a different joke where the beats are better and the joke's funnier. And so I've like completely scrapped the premise, but I need the punch line and you can. And it just all fits together. There's all this.
Chad
It's like a puzzle.
Che
Yeah, yeah. It is very much like figuring out a puzzle. And it's. You're trying to get people to do something involuntary as well. Trying to get people to laugh, right. Which is they. It needs to be genuine. It needs to come out of them. Which is fun about the. That the expression is that it's hard for people to lie. Like, if the crowd's not laughing, you're not doing well. Like, if you look at a painting, people have their perception if it's good. And modern art is. There's a lot of it that people say is just trash and a Cash grab. But comedy, it's very hard to fake it.
Chad
Yeah. Yeah, for sure. Have you ever had to kick someone out of one of your shows? They got a little too crazy.
Che
Me, I've never, like, personally been like, get this person out of here. But there's been, like, the security takes care of it.
Chad
I went too much.
Che
Yeah. I, I, I have always sort of prefaced the security and stuff being like, hey, you know, like, my crowds can be a little bit rowdier. So everyone gets a warning. Everyone gets like a hey, you know, don't talk. We're gonna have to kick you out. But I've never had to be like, get this person the hell out of here. And they're usually. The security is like, ninjas, man. We were. I think it was in Chicago. I usually will do meet and greet before and after the show. It gets people kind of excited when they see you before the show. And there was this couple. I was doing meet and greet. I'm selling merch. They just cut to the front of the line, and they're loud and already very drunk. And I was like, oh, they're gonna be a problem. And so the show starts, they're sitting second row and they're yelling stuff out, and I'm like, I tell them to shut the fuck up a couple times, and then they die down, and they pipe up a little bit, and then they die down. And then I just. I don't look at them because I'm like, if you interact with them, that's going to trigger them. I wait about 10 minutes. I'm like, I haven't heard from them. And then I look at their table, and they're gone. And I'm like, wow. The security came in and got them, and I didn't even notice, dude. And there was second row, and I'm like, that's good. They're taking care of business.
Chad
Yeah, they're probably used to it at that.
Che
Oh, yeah, yeah. That's. That's what they're trained to do, that to get people in and out without disturbing the show.
Chad
Yeah. Did you see Kanye deactivated his Twitter last night?
Che
No, I didn't see that, but that's not surprising. I think he's probably, like, he's building. I'm not trying to justify what he's doing right now, because I'm really like, man, like, I, I, like I said, I don't know music. I love Kanye's music. I. I've listened.
Chad
Got some bangers, dude.
Che
He's got an every album, so many bangers. Dude. Like even like, like people. Some people didn't like Donda and stuff. Like Donda has bangers. Yeah, man. But the stuff he's doing now, I think he lives like, I saw that clip yesterday of when he was at TMZ and he said slavery was a choice.
Chad
Yeah.
Che
And the guy just like doing the monologue at him and I was like, yeah. Like, he's like, I live in the real world. And I think Kanye lives in this other space where he can say the. And he's like, oh, it's a joke. It's building up press, whatever. And who knows? He's. He's living amongst the ultra rich and I don't know what's going on over there, but there's definitely trickle down effects that reverberate amongst people. And these things can be dangerous when they're thrown out there. And I think it's. It sucks that he's doing that.
Chad
Yeah. A lot of people look up to him.
Che
Yeah, it's. And it. A lot of people might try to justify their bad behavior, bad, evil behavior because of this. The good thing is though, I think there was. I don't know if you saw this. It was in Ohio. People put up like Nazi flags over like a. It was horrifying. Like, I'm a person of color, so when I see stuff like this, like, I, I get legitimately worried because I'm like, if it did. If that did get out of control and there was hate groups that grew immensely. I can't hide. I'm in legitimate danger.
Chad
Yeah.
Che
So one thing that made me feel good was a very small group of people. But then everyone driving by sort of rallied together and tore all their down. And I think if anything, this stuff, even for how sickening it is, it will bring more people together because I do truly believe most people are good. Most people care about each other. Most people just want regular shit. Most people just want to like, be able to afford a house and have kids and, I don't know, live safe and live in a healthy community. And people get upset and they get cut off in traffic and they say some shit. But I truly believe very few people are actually bad, evil people.
Chad
Agreed.
Che
And so when you see people like tear down something horrible like that, it. I'm like, we're. We're still all on the same side.
Chad
Yeah, that's a good sign. That's why comedy is beautiful though, because it brings people together. I feel like. Does all sorts of people at your shows, I'd imagine, you know.
Che
Yeah, yeah. I Do I get Honestly? Because my stuff is. I'm intentionally non political for one. I. I'm very uneducated on politics. So I don't want to be spouting politics because I don't know what like.
Chad
Just came to the States exactly.
Che
Like and like ask me about video games. I got. I got it, dude. But politics, I don't know. And so I don't want people taking advice from me on anything like that. And also it's never been what I go to comedy for. I don't co to comedy to learn about politics and stuff like that. There are great political comedians and kudos to them, but it's just not my ballpark. But because I. I talk about like relationships, sex, interpersonal things. I'm very observational because of that. I ha. I attract all kinds. So like there'll be people on my shows that are like the most bro y backwards hats, dudes who like drive a truck and then they'll be like a bisexual people with like septum piercings who like peg their boyfriend. Like it's. I get the of most wide spectrum. Like I remember I was in Appleton, Wisconsin. I was doing a weekend there and then I was doing a. Going right after to Madison to do a one nighter. And there was this dude after the show, he's like, oh, where you headed next? I'm like, oh, I'm going to Madison. And he was like, oh, it's real blue over there. And I was like, dude, I don't care. I talk about come. Like I was like, dude, come is universal. Everyone loves it. So I do think it helps like the. For as much as there can be discourse or we're told that there's this insane amount of discourse. I really think people are much more alike than you think.
Chad
Yeah, for sure. We'll end it here because you mentioned video games. What is the greatest video game of all time?
Che
That's such a hard question. The greatest video game of all time.
Chad
What have you spent the most hours on?
Che
What? Oh me personally, what have I spent the most hours on? I've probably spent the most hours on maybe Elden Ring. I'm a huge fan of the Souls series. I love the Souls series. I think Bloodborne, either Bloodborne or Dark Souls 3, whichever came out first. That was my first intro into them and I didn't really get them at first. I didn't level my character correctly. I. I didn't understand the mechanics well enough and I didn't. I enjoy them really deeply right away. It wasn't until Sekiro, I remember Sekiro was coming out, and I had played Dark Souls 3 not too long before that, and I was like, I kind of got the bug. I want to get this game. And I don't know why. And then I. That was the first one I really loved, and the first one I beat, and I was like. Then I, like, went back and played other ones. And since then, I've. I've. I've beat one, I haven't beat two. Two is so fucking hard, and it's a very different game. 3 I haven't beat yet. I'm at the last boss, but I'm trying to get as many of the trophies done before I finish it. Bloodborne I've beat a couple times. I've. Platinum Bloodborne Sakura I've beat a few times. I'm close to platinum on that Elden ring I have beat a couple times. Dark or demon Souls I've beat once. And so I'm trying to get the platinum in as many of them as possible. I really. That series is where I've dedicated the most time. But my sleeper hit for what I truly think is one of the greatest video games of all time is Def Jam Fight for New York. Dude, have you. Have you ever played this game?
Chad
I've never even heard of it.
Che
So Def Jam Fight for New York is basically. They took a wrestling engine that is a very exaggerated, like, one of the finishing moves. You use a guy as a skipping rope. You, like, smack them on the ground and then throw them in the air and, like, tombstone them. It's that engine. But they took wrestler rappers, and every character is a rapper. So, like. And it's from the 2000s. So, like, it's like Sean Paul, Busta Rhymes, Snoop Dogg. Fuck. Who else is in it? Method Man, Redman, Eminem. Eminem's not in it. No, but there's just. It's all rappers, and they have the craziest finishers. And so you start as, like, a street fighter and then, like, work your way up. There's multiple different fighting styles. Your trainer who you go to the gym, who trains you how to, like, learn new moves, is Henry Rollins. Dude, the game is so outlandish, and it's just, at its core, so fun. It's one where, if you did a modern version, it would cost you a fortune. Because to license all these rappers, unless they were being really generous, it would be impossible. But you would be so sick if you had this crazy wrestling game with, like, Drake and Kendrick and eminem and, like, 50 Cent. And all these people. It'd be so sick if they did a modern one. But that is my sleeper hit for one of my personal favorite games of all time.
Chad
What system was that on?
Che
It was on all the ones of the generation. So it was like GameCube, PlayStation 2, and Xbox. It was like across that generation.
Chad
GameCube was one of my favorites.
Che
GameCube reps, dude. Yeah. Slapped. Yeah. Yeah. What was your GameCube game? What was the game either?
Chad
Smash. I was basic, probably Smash.
Che
Smash.
Chad
Melee.
Che
Yeah, yeah. Smash is sick, dude.
Chad
I mean, Kirby.
Che
You're Kirby Maine. It's a little dirty, a little scummy, dude. Fly up. Do the brick. Yeah, you do.
Chad
I was cheesy with it, too.
Che
Yeah, dude.
Chad
I would wait till two people were fighting and then you do it to.
Che
Hit both of them. Yeah. 100.
Chad
Yeah. Those are the days, man. Yeah. Well, man, where can people see your next shows and.
Che
Oh, yeah. Okay, so when's this coming out?
Chad
Probably three weeks.
Che
Three weeks. Okay, so three weeks from now, you can definitely catch me. I'll be in California, so you can catch me in San Jose and Brea. And where am I right after that? Oh, Salt Lake City. Okay, for any other dates, go to chaterina.com. we're adding dates all the time right now. I'm really busy on the road. We got a huge Canada run coming up that will probably be displayed by now. But I'm going all over Canada, so you're going to be able to catch me everywhere. A bunch of cities I've never gone to before. Find my podcast at Dark holes with Cheaterina on all platforms. And, yeah, for tour dates, go to either chaterina.com or punch up.live/cheaterina.
Chad
Boom. Check out the links below. Thanks for coming on, man.
Che
Hey, thanks for having me, man.
Chad
See you guys.
Digital Social Hour Episode Summary: "The Wildest Jail Story You’ll Ever Hear – Che Durena Tells All | DSH #1230"
Host: Sean Kelly
Guest: Che Durena
Release Date: March 10, 2025
Podcast Description:
Digital Social Hour invites listeners into unfiltered conversations with some of the world's most controversial and thought-provoking figures. Host Sean Kelly delves deep into the stories, challenges, and triumphs that define their lives, exploring no topic off-limits.
The episode kicks off with Che Durena recounting his wildest jail story, setting the tone for an honest and raw dialogue.
Che's Arrest Story (00:02 - 08:18):
Che narrates a chaotic night in Mexico, detailing how a flirtatious escapade led to his arrest. He describes attempting to sneak out of his accommodation, only to be caught by a security guard who "calls the police" after witnessing him "scaling the walls." Amidst the confusion, Che humorously recalls hiding a used condom in his pocket to avoid littering, leading to the police discovering it during a search.
“Security guard sees me and he calls the police. But he's like, this guy's like, scaling the walls... And then the guy searches me and pulls out the used condom out of my pocket. Dude, yeah.”
— Che Durena (06:26)
The situation escalates with Che being taken to jail, where he had to navigate through a confusing interrogation while still under the influence from the night before. The experience ends with him being detained until a friend arrives, highlighting the unpredictable nature of his adventure abroad.
Transitioning from his tumultuous arrest, the conversation shifts to personal style and self-expression.
Hairstyle Evolution (01:09 - 03:00):
Chad praises Che's distinctive afro, to which Che modestly responds about the simplicity of maintaining it compared to his previous hairstyles like cornrows, mohawks, and dreadlocks.
“I've been rocking this for a long time.”
— Che Durena (01:13)
Che elaborates on the challenges of maintaining a mohawk during his younger years, describing it as "kind of a pain" but admiring how it "looked sick" despite the effort.
Che delves into his journey into the world of stand-up comedy, highlighting the pivotal moments that shaped his career.
From Mexico to Toronto (06:26 - 12:08):
After his brief stint in jail, Che discusses his initial attempts at stand-up in Mexico, inspired by his brother's foray into comedy. Initially hesitant, he gradually built confidence by writing jokes and performing at local open mics in Playa Carmen, despite the small audience size.
“I just started writing jokes with the intention of sending him these jokes... I did whatever, seven minutes. And it went well enough.”
— Che Durena (09:31)
Che's mentor, Dave, played a crucial role in encouraging him to pursue comedy seriously, even suggesting a move to Toronto to tap into a more vibrant comedy scene.
Che recounts his struggles and triumphs while establishing himself in Toronto's comedy landscape.
Challenges and Homelessness (12:08 - 17:12):
Facing visa issues and financial hardships, Che shares his experience of living in youth shelters and intermediate housing. These periods were formative, exposing him to diverse stories and strengthening his resolve to succeed in comedy.
“I saw that stuff... it will bring more people together because I do truly believe most people are good.”
— Che Durena (48:09)
Che emphasizes the importance of relentless dedication to his craft, comparing the grind of comedy to other demanding professions.
Comedy Routine and COVID-19 Impact (20:47 - 27:43):
Detailing his rigorous schedule, Che describes performing "12 to 20 sets a week" and adapting to the challenges posed by the COVID-19 pandemic. With live shows largely halted, he pivoted to creating content on platforms like TikTok, which eventually garnered significant attention and led to managerial support.
“It is very much a grind... it's a long road of that.”
— Che Durena (21:27)
Che discusses his strategic shift to social media during lockdowns, which played a pivotal role in expanding his audience and career opportunities.
Social Media Strategy (26:21 - 30:25):
Che credits his manager, Rachel Helix, for facilitating his move to the United States. By consistently producing content—particularly "mirror rants, stitches, and duets"—he amassed a following that exceeded 900k followers, leading to representation and tour opportunities in New York.
“If it wasn't for her, I wouldn't be able to do what I'm doing now.”
— Che Durena (24:34)
Che reflects on the importance of staying positive and grateful amidst the highs and lows of his career trajectory.
Philosophy on Positivity (27:13 - 28:21):
He shares insights on balancing ambition with gratitude, noting how setbacks are tempered by the perspective of past struggles.
“I'm very much a grinding comic... I have to jump into it.”
— Che Durena (10:28)
As his career evolved, Che adapted his content to favor podcasts over traditional stand-up performances, recognizing the shifting landscape of comedy.
Shift to Podcasting (29:22 - 30:25):
Che introduces his podcast, "Dark Holes with Cheaterina," emphasizing its authenticity and his commitment to quality content. He discusses the high conversion rate from podcast listeners to ticket buyers, positioning the podcast as a central pillar of his career.
“It is some of the best... it is a really good product.”
— Che Durena (29:22)
Che provides an insider's perspective on various comedy platforms, including "Kill Tony," and the nuances of performing in different venues.
Comedy Platforms and Performances (37:16 - 44:09):
Che recounts his experiences with high-pressure formats like "Kill Tony," where comedians perform under significant time constraints. He highlights the importance of adaptability and the unique challenges posed by such shows.
“Kill Tony is like late night right now... the biggest thing you can do for your career.”
— Che Durena (38:50)
The discussion takes a brief detour into social issues, where Che shares his thoughts on recent events and societal behaviors.
Views on Social Issues (44:02 - 48:09):
Che expresses concern over rising hate symbols and the impact of influential figures' statements on public behavior. He maintains a belief in the inherent goodness of most people, despite observing negative actions in society.
“...most people are good. Most people care about each other.”
— Che Durena (48:09)
Che opens up about his passion for video games, revealing a different side of his personality and interests outside of comedy.
Favorite Video Games (50:00 - 53:32):
Che lists his top games, including "Elden Ring," "Bloodborne," and his nostalgic favorite, "Def Jam Fight for New York." He describes the latter as a hidden gem with a unique blend of wrestling and rap, appreciating its creativity and fun gameplay mechanics.
“Def Jam Fight for New York is... It is so outlandish, and it's just, at its core, so fun.”
— Che Durena (51:43)
As the episode concludes, Che shares information about his upcoming performances and ways for fans to stay updated.
Upcoming Shows and Contact Information (53:32 - End):
Che announces his tour dates in California and Salt Lake City, directing listeners to his website for more information. He also promotes his podcast, encouraging fans to tune in across all platforms.
“Find my podcast at Dark Holes with Cheaterina on all platforms. And, yeah, for tour dates, go to either chaterina.com or punchup.live/cheaterina.”
— Che Durena (53:27)
Notable Quotes:
“Security guard sees me and he calls the police. But he's like, this guy's like, scaling the walls.”
— Che Durena (06:26)
“I've been rocking this for a long time.”
— Che Durena (01:13)
“If it wasn't for her, I wouldn't be able to do what I'm doing now.”
— Che Durena (24:34)
“Kill Tony is like late night right now... the biggest thing you can do for your career.”
— Che Durena (38:50)
Conclusion:
In this episode of Digital Social Hour, Che Durena offers an unfiltered glimpse into his tumultuous journey from a wild arrest in Mexico to building a successful comedy career in the United States. Through resilience, strategic adaptation to social media, and unwavering positivity, Che illustrates the grind and passion required to thrive in the competitive world of comedy. His candid stories, insightful reflections, and diverse interests make for a compelling and inspiring conversation.
For more insights and upcoming shows, listeners can visit chaterina.com or follow his podcast, "Dark Holes with Cheaterina," on all major platforms.