From Open Mics to Headliner: The Grind That Paid Off

On this episode of Fit For Radio, Drew sits down with Brent Lowrey, a comedian whose path to the stage started with being the funny kid growing up in San Diego and turned into a relentless pursuit of something bigger.

Brent shares what it was like grinding through open mics and small gigs, learning the craft the hard way before making the move to Portland, Oregon. It was there, through the uncertainty of the COVID era and a competitive comedy scene, that he began to find his voice and build real momentum in the Pacific Northwest.

That momentum led to a breakthrough moment in 2023 when Brent won the Seattle International Comedy Competition, launching him into his first opportunities as a headliner and validating years of work behind the scenes.

But Brent didn’t stop there.

In one of the most unique twists you’ll hear, he took part in a comic swap—trading lives with a comedian in Philadelphia. They exchanged homes, cars, cities, and even comedy gigs, stepping fully into each other’s worlds. The experience changed everything.

Brent talks about why that leap pushed him to go all in, pack up his life, and drive across the country to Philadelphia to chase his dream at the next level.

This is a conversation about betting on yourself, embracing uncertainty, and doing whatever it takes to turn a passion into a career.

Transcript

Introduction

SPEAKER_03 0:00

Oh, do I start it? Uh no, but it's all right. I'll cut that part off.

SPEAKER_00 0:04

Welcome to the podcast.

SPEAKER_03 0:21

It is the Fit for Radio podcast, and who knows? Uh, it can go either way today. I'm excited to have today's guest in here, but first, let me tell you where we're at. We are at the Stafford Hills Club, right here in the suites where the studio is. You can work out here, and you can work here where work meets play, is what they say. And uh together, um, well, better together is the other motto around here, and you'll find that when you get here. Uh, it is a family. It's not like other gyms where they want to sign you up and then have you never come here. Uh, so check out the saltwater pool, all the new amenities. Uh, you can hit up the workout classes and even a kids' club with a highly trusted group of people that you can leave your little one with and have peace of mind. But right now, back to business. I've got a guest in here who I actually met. I was looking through my phone, and it's either 2021 or 2022. If I failed to get uh his number the first time around, it was 2021. Um, comedian and uh all-around good guy in here right now. Brent Lowry is in this in the studio.

SPEAKER_01 1:26

Thanks for being here. And I know that was an ad read, but this place is very charming. Yeah, it is. The Stafford Hills.

SPEAKER_03 1:33

Stafford Hills Club. And it means it's clean, it's nice. Um, and actually, I'm glad that we started the conversation right now because uh there was a Pilates reformer class going on next door to us right here. And these ladies were having, and so it's like Pilates, where you know you're working all the little muscles in your body, but it's on these pads and like sliding units. I'll tell you, Brent, I've been asked, and I did agree that in a week I'm gonna take one of those classes. Yes, and there's like this video that's gonna come out. And she just warned me straight up. She's like, usually it's people who think that they are like in good shape and they go to the gym all the time and they want to push and pull and do all these things. They're the ones who get humbled.

SPEAKER_01 2:17

So yeah, I mean, that's your whole brand, right? You did the whole push-up challenge. It was a similar story.

The Challenge of Pilates and Fitness

SPEAKER_03 2:22

But that's a lot different than working little muscles in the sides of your abs or like the inner part of my thigh. I think that I'm going to every time I do a quote unquote ladies workout, you get thrashed. They are they're much tougher in so many ways. I would much for me, I would much rather do push-ups or just like bench press or be a big meathead. Shout out to your wife. Yeah, exactly. I think you're trying to score points with the ladies, and I support it. Yeah, well, she's um I think the thing's gonna humble her too, because she's been talked into taking the class with me.

SPEAKER_01 2:54

So I mean, I think everything from a woman's perspective is a little bit more challenging. I think it's like yeah.

SPEAKER_03 3:02

Yeah, I I would definitely and being in the room for three births, I have nothing to I have nothing to share there other than like I was trying to clear out my phone rent in order because it was so loaded with videos um that I was just erasing and erasing. So I was deep in the well of of of my phone trying to like get rid of videos to free up space because it just randomly was freezing.

SPEAKER_01 3:25

Yeah, because you're a dad, you have videos of all of the Yeah.

SPEAKER_03 3:27

So I was like, here are your biggest files, and I clicked on it, and it was a video of like the moment my child like exits the womb and gets slapped onto the belly, which in the moment is very it's an amazing moment, but when it pops up on your phone, you're like, Good God! Oh yeah. I mean, it it's a it's a lot, right? I didn't know if I was looking at Italian food or that's my child. No, I don't show my actual children that, but I I would say that as you know, when they're in your phone, you have to be careful because they're like scrolling and scrolling and then waah! Yeah, a lot of action. Oh, so much. Oh, that's too much. It's actually too much, it is too much action.

Unexpected Family Revelations

SPEAKER_01 4:12

My girlfriend has this crazy story uh where she her parents were polyamorous. Oh, but they uh became polyamorous like her junior senior year of uh high school. They were like religious religious up until then. Then this woman just moved in and started living with them in Beaverton. Oh my god. She this is a story she should. I mean, she's told it a couple times, but whatever. It's a good podcast. You're here now, yeah. She senior project, she uh was gonna shoot a music video and so she went to borrow her uh parents' camera. No. And she like opened it up and she went to delete stuff, or she went to like, I don't know, she just pulled up what was on the camera and it was a sex tape. It was all the actors. Like the uh she's like sees two people and she goes, Who's holding the camera? Like, so she did the math slowly registering. Three people holding a camera and having a sex tape. It was oh, and that's how she found out. Yeah, and she was like, She chose a different senior project, she gave the camera back, she didn't talk about it. It was like that's like one of the crazier stories.

SPEAKER_03 5:18

So, does she confront them eventually on that? Just go into the dark. I hope they're not listening to this. Not well, I mean, now they can talk about it.

SPEAKER_01 5:26

They've never discussed that together. That moment. She's discussed it publicly, like on stage.

SPEAKER_03 5:33

Are they still because you're both stand-up comedians? Yes. And I've seen you actually both perform on the same show. She's highly talented. Oh, she's great. Um, so did did are they still doing that stuff, or are they did because a lot of times you try that out and then you move on.

SPEAKER_01 5:48

For sure. They it didn't work, I think. They it it they tried it.

SPEAKER_03 5:53

Uh it's hard enough to pick dinner with two people. You get the third person in there, really shakes things up.

SPEAKER_01 6:00

Yes, and then there was kids in the mix, and so it was the brady bunch.

SPEAKER_03 6:05

Shady bunch.

SPEAKER_01 6:06

Yeah, yeah.

Growing Up In San Diego

SPEAKER_03 6:08

All right, well, let's get back to you for a second. You grew up I'm all I'm already like, uh I should only tell my stories, but whatever. That one's too good. It was good. Um, now you grew up in San Diego, and I always wanted to live in San Diego post-college. You know, a bunch of my friends moved down there. It's just like it's so beautiful, the weather's perfect all the time. Right. It's like for people who want to be in the idea of LA, but really San Diego is better. It's a a little bit slower pace, but still enough action not to bet. Come on. And it's just it's it's my little piece of perfection.

SPEAKER_01 6:46

Yes. I mean, you're describing it 100% accurately. It's still Southern California, so there's still traffic and there's still people driving fast everywhere you go, but the pace is slower, just in terms of like LA is a bunch of people who haven't made it trying to. San Diego is a bunch of people who already made their money. You have to like, for the most part, you have to do pretty well to just even be in the game there. 100%. And so um the idea of going there and wanting to live there after college is definitely an aspiration uh most people would understand. What's weird is if you grow up there, you feel like you first of all you take it all for granted. Because of course, because it's all you know. Right. You don't even have seasons. There's no unbearable months, or there's no months where you would have to like switch out your wardrobe. Like shorts are always gonna be if they're not an option today, they were an option last week, or there'll be one next week. Like there's never a three-week stretch where you just couldn't wear shorts.

SPEAKER_03 7:57

It's like pants are for work and that's it. Yeah. Like, and that's you know, when we get into a summer month here, you almost don't think about it when you open up that drawer and you're like, oh, pants, and then you return to pants.

SPEAKER_01 8:10

Right. Or there's that exciting time around like May where you can even go grab your shorts or your like summer weather clothes, and that's exciting. And you can put your like big jackets away in like April or May, and that's you don't do anything like that in San Diego. It's so beautiful, but at the same time, because it's beautiful every day, you don't if you grow up there, you don't wake up and go, oh, today's a beautiful day. It's like, no, some beautiful days you're playing video games and you're like Yeah, you don't go outside and soak it in every day. You don't. And if you get to 18 and you become an adult and you didn't do anything to achieve this excellent life, it's such a weird feeling of being like, well, if the part of you wants to stay, right? Because it's the most beautiful weather, and you know, obviously you gotta have my my parents have money to be there. Uh but then you're like, I didn't earn any of this, you know, so I have to leave it's a weird feeling. You know, like mooch off the success of my parents and then get to live this lifestyle. But at the same time, for 18 years, that's what the that's the lifetime style I was accustomed to. Yeah, so going anywhere else is shell shock. Dude, when I told people I was moving to Portland in San Diego, like, are you okay? It must be the exact opposite reaction of when you tell somebody in Portland that you're moving to San Diego because they're oh wow, that's lucky.

SPEAKER_03 9:49

Yeah. Yeah. Instead, they think that you've you're ill. Why would you do that?

The Move To Portland

SPEAKER_01 9:54

And uh my reason was like, I'm already really depressed. I was in my like late 20s, and Portland is a place that I always had this kind of like appeal because of its kind of like dark charm. I went and went visited it in February, and it was just like very it was a beautiful experience. I didn't need it to be good weather. I kind of expected rain, but it wasn't like downpour. It was just sort of like navigable with wetness, and you know, um I was charmed by all the people. And so when things got like harder in the beginning of the first four or five years of my comedy career in San Diego, I had this kind of like escape plan of oh, Portland is where I could make it all work. And uh so 2018, I was I I was just kind of I quit my job, my job sucked. I was like merchandising gourmet popcorn. Awful. And uh so yeah, I was depressed, and that's what I told people when they asked why I was leaving. I was like, well, you know, I'm already sad, so if they're everybody there, uh, you know, maybe I'll I'll find joy. And what I think is true about Portland is it is a great place for people who kind of have been rejected or failed in other places to come find solidarity with uh low confidence people to kind of rebuild that. And yeah, it's a great place to recharge and regroup and refocus. And so for the last seven or eight years, that's what I've been doing, and it's been way more enjoyable than any stretch I had in San Diego, not because San Diego is not beautiful, but because I didn't really feel like I earned San Diego. And maybe one day if I could afford to live there on my own terms, like on my own success, I could live there and feel good about it. But I always felt bad and weird being like just a spoiled kid from San Diego. You know?

SPEAKER_03 12:03

Yeah, and I I see that as well. You know, I grew up um, well, I grew up in northeast Portland, but then the back end of my being brought up, I lived in Lake Oswego, which is a basically the place that you're describing without all the palm trees and the sunshine. But for me, the reason why, and we were all running for the hills at 18 to leave, but it was, I think it was we had a false sense of what we had there too, and took it way for granted. You know, it was like you're partying in mansions every week, whoever's parents were gone, you were partying in that, you know, four or five thousand square foot home, and then the next one and the next one. And it wasn't until I ran away to college that I was like, oh, that's a different world.

SPEAKER_01 12:48

Isn't that crazy that the people who have parties in mansions, wild parties in mansions, are rappers and teenagers.

SPEAKER_03 12:57

Yeah, nobody else actually uses their mansion for parties post-high school.

Teenage Parties and Social Dynamics

SPEAKER_01 13:03

Right. Or like the types of parties that we're describing, like ragers. Those aren't had in mansions unless you're like a rock star, a rapper, or the teenager of a rich parent who's on vacation. Yeah. And that's so crazy to be the third one. Because, like, I mean, it's crazy to be all of them, but you you gotta hate the third one the most out of the three.

SPEAKER_03 13:25

Oh, yeah, because they've gotten, I mean, at least the rapper or the rock star, they have some talent behind it that got them to that spot. They might be an idiot and they're wasting their money, but some group of people likes what they do. And they're likely the person who's rented or owns that home. Whereas in we were just decimating perfect strangers' home.

SPEAKER_01 13:43

Nobody, no group of people likes what teenagers of rich parents are doing, but at least, you know, some people like rappers or rock stars. Everybody hates teenagers of rich kids. 100%. And so when they're having parties, uh, gosh. It's like you they, yeah, of course they have no perspective on it. And of course they're like the worst. Ugh, yeah.

SPEAKER_03 14:06

Yeah, but at the time, you're like you're living for Friday night, and that was that that was the jam. But I I will say that um in this day and age, the land of the ring cam and uh the cell phone, it just wouldn't go down the way it went down.

SPEAKER_01 14:20

And yet I think that uh teenagers and parents are like cat and mouse or hackers and technology. It's like no matter how technology evolves, parents will use it to monitor kids, and kids will find ways to bypass what's going on. Whether, like, I remember I went out just like last year with my cousin, and he's been in some trouble. So his parents have his location shared. Oh, he's getting pinned. And he knows how like we were out and we went to go to get Dave's hot chicken, but I was supposed to take him home. So he was out a little later, and he said something like, Oh, my parents think I'm somewhere right now. Like my location is pinned somewhere that I'm not. So he's manipulated it. Of course, because every kid has nothing else to do but figure out ways to create trouble. So they'll find the app that does the thing that VPN or whatever that can like disguise their location. That's exactly the game. Like, so some ring cam. There is an app where some kid can hack into his parents' ring cam and just leave a still video that is calm or he can play the video from last week. Uh, I'm sure of it.

SPEAKER_03 15:42

Well, there is a way because when I had, you know, I have three kids. I got a 10-year-old, an eight-year-old, and then two years ago I had a sneak attack, my little two-year-old now, Millie. But while we were in the hospital, uh, when I came home, I had a 12-foot skeleton built in my front yard. You know, the ones you see at like Home Depot, they're massive. And I'm like, what is going on? My ring didn't even go off. And I go and I review all the footage. It's not that there's nothing there. And what I realized later is there is a, there is a like a couple seconds or like a second, that if you can get to the ring cam and you can cover the camera, it'll never turn on. So what my dad and brother did was they hit around the corner at my house and then they came with a piece of dark tape and turned and slapped it on that camera before it could flip on and catch them. And so I had no footage of them building a 12-foot skeleton in my front yard. And then they, you know, put up a whole like note about who was it. I'm like, nobody cares about me more than my family to go do 12-foot of skeleton. It's the small list of suspects.

SPEAKER_01 16:48

Uh I would imagine you could even do like there's probably kids who take a picture of the porch, like they were, and then they just tape it in front. And so, yeah. I mean where there's a will, there's a way. Yeah, they'll find a way. They're kids that all they want is to get together and do trouble.

Theater and Comedy Background

SPEAKER_03 17:08

That's true. And when you were a kid, um, you you wrote here, and you and I have some things in common. Grew up the class clown. You had you did some theater, and you know, now you're you're in comedy, so it's like you were being trained appropriately for this type of a life. I was also uh a class clown. I was voted funniest in my class, uh, which I don't know if they were still doing that.

SPEAKER_01 17:34

Mine was unofficial. They I did not win. There was a class clown. I that was not.

SPEAKER_03 17:38

Um, but I also think there were plenty of funny people there. It's just luck on that front. But I was I was in the theater. I was one of the few people. Um theater's a funny thing in high school, right? It's I loved the theater. Right. I did not love the atmosphere of high school theater. You know, it's like I would be like, okay, I want to act, but I also played soccer and I wanted to like I wanted to be cool and I wanted to be in theater straight up. And so I'd come in after class and be like, okay, I we're all friendly, and then there would always be the one girl in the toad rainbow socks who'd blow the door open and start singing rent songs. And you know, it just that wasn't my favorite part of it, you know. Right, but you know, every class had that girl.

SPEAKER_01 18:25

But theater allows for personalities that are bigger than most classrooms or sports teams to exist. So, like yours could exist, and so could this person, and so could like someone who wears, you know, cat ears every day. Yes. And the the the person who thinks they're like a TMZ Kardashian type. Yeah. They're all together in a class and they all want different versions of what theater could offer, which is like some people who actually want to be in the theater and they want to act and they like Shakespeare. And then there's people who want to be on TV and they want to be a movie star. Yeah. And then there's people who like uh just found a class that seemed pretty easy. And it's a way to slip through. And it they're right. They're all the theater exists. It doesn't require you to be one type of thing.

SPEAKER_03 19:23

And I couldn't agree more. And that's why I always allowed those people their space to exist in their I never told that lady to stop singing rent songs.

SPEAKER_01 19:31

Well, yeah, and she was probably like, who's this fucking jock?

SPEAKER_03 19:34

They did not she, I'm sure she did not like me or anyone in that realm just because they're sure some people did, but I'm sure even But they're coming in with the same preconceived notion that I am, you know. Correct. That Doey's this way or oh, she's that way. And you know, and you're also in high school, you know, like because I end up going from high school theater to college theater, and that's how I start college as a theater arts major. Oh, wow. And so I I went and hung with those people for another decade.

SPEAKER_01 20:04

Yeah, and you were obviously taking it seriously enough in high school that you decided to go majoring. So it wasn't just a class you took when you were 17, 18.

SPEAKER_03 20:14

Brent, I was living such a double life that listen to this. At one point in college, I was in a fraternity. Yes. And uh, well, I was, you know, all the way through college. Or it doesn't shock me. Well, yeah, and I'm sure it doesn't, but it's also another stereotype. Sure. Um, because guess what? I would be in charge of the like master of ceremonies, is what it's considered. So you're in charge of like all the ceremonies for the house. Yes. But it also was acting downtown in like legitimate pay-to-play acting gigs. So I cut I would come home in stage makeup and scream at frat dicks to follow the rules at two in the morning, you know, like still have all the like everything other than the costume itself on, right? Like, you know, hardly being able to be taken seriously.

SPEAKER_01 20:59

But I can imagine what they called you.

SPEAKER_03 21:01

But I also uh could hold my own there too, you know. So it was like I was going to do the theater and then roll in and be like, what? You know, and yeah, they could give me the churing it, but at the same time, I was both guys.

SPEAKER_01 21:14

That's great. And the confidence to be in both spaces without having to like conform to one or the other is great.

SPEAKER_03 21:22

Because the other space, while that seems awkward, the other space is also awkward when you show up and you have to prove to these people that you're not a frat dick or whatever they consider to be that, you know. And so by two, three weeks into practice, they realize oh no, no, no, he's not that. He's everything's fine, you know, and so you have to earn it.

SPEAKER_01 21:43

Yeah, and it is uh it's fun to exist in multiple spaces and not necessarily be all one thing or the other, you know?

Frat and Theater Life

SPEAKER_03 21:55

Uh and and to more and to be able to kind of morph from one thing to another. And be confident in it. It's not for everyone because I remember even trying to get people to come to my shows. Like, dude, I don't want to go sit. How long am I going to sit in there, dude?

SPEAKER_01 22:11

Probably an hour and a half. There's a classic story. I told it on one of the most recent podcast I was on. But we all played a lot of online poker, and we were poker players back in high school because this was like 2004 to 2008. It's the height of the moneymaker time. All of it's on ESPN. They got us by the balls. And uh We were doing it too. I was in a play junior year, and my buddies said that they would come. It ran every like Saturday, Sunday for four weeks. And then the last Sunday, it was their last chance to come. And I told my buddy, and and he called me right before the play. I was I was backstage and he was like, dude, I'm sorry. Our buddy Kevin kidnapped me. We're going to Verona. That's the casino. And I was so mad. Oh, yeah. I hung up. I called the casino. I called the poker room.

SPEAKER_00 23:01

And I go, my son Patrick is stuck off in 16. He's not old enough to be there. He he I think he just left. Bye. And then they boot him out.

SPEAKER_01 23:13

He shows up. He tells him the story the next day. He shows up and he goes, uh, Patrick for one, too. And then the woman goes, I know a secret about you. And then they tell him. And he was so mad. But at the same time, he was like, I should have gone to the play. You know?

Theater Memories and Friendships

SPEAKER_03 23:31

Yeah. You're listening to the Fit for Radio podcast brought to you by the Stafford Hills Club. It's a place, let's be honest. You gotta check it out. Of course, it's the premier indoor outdoor tennis facility where you can take lessons, you can play with your friends, tournaments, all kinds of stuff. Also, Saltwater Pool, an amazing kids' club with a group of people who take care of my wild kids. And that's saying a lot all by itself. So check it out, staffordhills.com, all the amenities, you're not going to be disappointed. Voted the best health and wellness facility in the Portland area. And of course, tell them Drew sent you for half off your initiation at the Stafford Hills Club. And I think that's part of it is having these buddies who they don't understand the amount of work that goes into a theater production or whatever. And you know, like I got buddies who you, because they were all playing football and baseball and basketball, and you go into their games and you understand that, you know, like this is important to them. And so I'm going to these games and I'll never forget we were doing these one act plays, and and your story just reminded me of it. And I told all my friends, I'm like, you guys got to come to these plays. Like they're all student directed. I'm starring in the thing. And like the the premise of the play was there's a hostage situation. So you're it's a peer into like this bus depot or something, and and so everyone's on stage the whole time. And my friends are there, and um, I can hear them giggling and talking and like you know, not paying complete attention. And I'll never forget I'm sitting there and out of the crowd flies a freaking gummy bear, dude, and it just drills me right in the chest and hits the ground. And I look down at it and I look up and I can see out into the into the abyss, this face. And he's my best friend. And I'm just in my head, I'm like, you die today. That's the and it's the you've broken the fourth wall, and anybody in theater do. So what I did, so my character was like this hippie stoner-ish type dude who's like sitting there spraying glade around sitting on a blanket. And so I just went, oh, gummy bear. And I reached down and tossed it in my mouth and just went right back into my line because I was already sitting right there, and it was like everyone saw like what had happened here. So I just hit the gummy bear and went back at it, and everything was fine. Wow, true professional, yeah, improving at its greatest. But then afterwards, dude, I was coming unglued. And he's like, I don't see why it's such a big deal. Calm down, dude. And I'm just like, I'm going to rip your ears off your head.

SPEAKER_01 26:19

That's how egregious it is. It is. But he was like, oh no, it's just a bunch of sussies. Exactly. I was just trying to be well, they're all froud dudes. And so this guy's.

SPEAKER_03 26:30

Well, this is in high school still, so and he uh he doesn't end up joining a frat, but he could have fit the bill all the way across. This was in high school? Yeah. So that's in high school, and but I'm also taking it seriously. Like I'm gonna go to college and and be in the theater.

The Journey To Stand-Up Comedy

SPEAKER_01 26:44

Right. We had a moment, student written play, senior year. It might have been the first moment that was like might have been the first like big, I guess it was junior year. I'm bringing flowers to the character, and I set the flowers down, and they knock over, and I go, I knew I should have bought a bigger vase. And and everybody in the That's great, everybody in the audience knows for sure he just made that up. It was very like out of the character. But I say it and then I go back into my line. Like, it got a big laugh. I'm sure I was like, but that's back into the line. But yeah, that was that one was the first laugh, maybe on stage. I mean, we were I was always chasing the laughs in the classroom. That was it. And so the next big one I remember was when we did a school. Every senior class would put on for the big rivalry game, uh, our version of like Saturday Night Live. So we would take the senior class every year, we would take like whatever popular commercials were going on, and they would satire them. They would do like their own version. Back then it was like the OC, Laguna Beach, those shows were big. So we were doing like our mock version of that. And so we would have like the hot girl be whoever the popular girl was, and the jocks would play these characters, and we wrote the whole thing, like it would fit a dynamic that tied into why we had to beat Mount Carmel for the game to be. And so I remember we had a a joke written in, and I someone else delivered it. I was backstage, but it's our school is 3,000 kids, so the auditorium, it's like a thousand kids in the gym. And I wrote a joke. We had written this for months, and so it finally get it finally happens, and um someone delivers the line, and I remember being backstage and hearing the whole audience laugh. And I remember just doing like a almost like a touchdown celebration. I just remember like, yes, and the adrenaline of being like, Oh, yeah, oh, that line. I wrote that, and now that's a thousand of my peers just popped at that. It's like, sure, I've gotten a big laugh like that in a classroom before, but that's 30 kids. The feeling of a thousand. It's can yeah, it's addictive. Oh, yeah. I mean, you don't forget stuff like that, and then of course, the fact that it all leads to where it is now. Stand-up wasn't the dream then. It was like Saturday Night Live, but the it was whoever the funny people were, I want to be the funny people.

SPEAKER_03 29:29

I always and it's it's wild how much our early years kind of go along the same path because before we started, I was telling you that Saturday Night Live was my jam too. I that first 25-year almanac, I used to sit and study it. And like they all had their headshots in there, and like they would little blurbs about skits and ones that worked and ones that got scrapped. And I just I wanted it so bad that I wrote that, I wrote a Saturday Night Live assembly with all parts in with mine being weekend update at the end. And when I I wrote it, and I was I was a clown, so the administration was on to some of my antics, you know. So I had to bring the whole thing down. And the I'll never forget the assistant principal went through with a red pen and just started axing scenes and changing scenes. And, you know, I I did have to work with her a bunch, but the amount of stuff that was allowed to stay, I mean, it was a very 20 years ago type of situation because I was still allowed to go on a smash sesh. And, you know, I'm I even had like the Matt Foley character come out of the the band pit, you know, with the the down by the river thing, the whole deal. So for me at the time, I was like, oh, this is what's happening. I'm gonna do this and then I'm gonna go to college, and then I'm gonna go to Hollywood, or I'm gonna go to New York, and then I'm just gonna work on SNL, and that's gonna be that, which is quite the dream, right? So I I went and started in college, and then um while I was there and I was still doing theater, I got my first radio job, and it was like, oh, well, this is kind of like theater because I can make people laugh and I can perform, but I can also prediction and projection. And they were gonna pay me to do it, you know. And whereas in downtown you're getting paid, but you're getting paid a very small amount. It's not paying the bills like it sh needs to. Right. And so when that opportunity came, I was like, okay, well, I'll just take a little break from the theater. And that's 23 years ago. And so I haven't done a production like that in forever. I've done many videos and where I've acted, but not like back to three months of stage production and choreography and the whole deal. But that was my jam. I used to just eat, sleep, and breathe that those hot lights on your face and just going.

SPEAKER_01 31:57

Do you see? Do you ever see like community theater around here and think like I could probably get back in the game?

SPEAKER_03 32:04

I it's gonna sound a little conceited. I know I could get back in the game, but do I, you know, like now married with three kids and like trying to.

SPEAKER_01 32:13

I think that was my next thought is how fun it would be for your kids to watch you do something like that.

SPEAKER_03 32:19

And it would be. Um, like, for example, so like I'm living vicariously through my 10-year-old right now because the first time I ever got a starring role in a play, there were 400 people in the cast of a play at Grant High School in Northeast Portland. And I landed one of the 12 leads uh in sixth grade. And so my daughter's in fifth grade right now, and she just tried out for this play, and there's a singing solo and a starring role, and she's practicing, practicing. And, you know, she's always had stage presence, but I'm like, we lack tone a little bit. You know, like she can project, she's so exciting. But we were lacking, we were lacking tone. And then she started to practice for this, and she's in the other room, and I walk in, I'm like, are you singing that? And she's like, Yeah. I'm like, that was perfect. And so I'm like, okay, well, let's work. So we start working on lines and we're working on the singing and the dancing and everything. And she tries out, she comes home and she's got giant bruises on her arms. And I'm like, what is going on? And she's like, I got nervous. So I was squeezing my arms and I bruised my arms. I'm like, you bruised your own arms? Calm down.

SPEAKER_01 33:30

Damn, that's how nervous.

Parenting and The Arts

SPEAKER_03 33:31

You're having like an anxiety attack. You need to chill. I'm like, hopefully that didn't like affect your ability to perform. She's like, hopefully. And so fast forward another week. We get the printout, and we're looking down the list, and I'm looking down. And it's just like when I landed the big one myself. I'm looking at what chorus I'm in, and I can't find myself. And everyone's like, oh, I'm in the She Poopy chorus. I'm in the Wells Fargo chorus, I'm in this and that. And then you're just panicking, right? And then I did the same thing I did when I was a kid, and I look back to the top of the sheet. Boom. There she was. She got the lead. And she just, I mean, she just into another room, like, singing like the the rent girl uh in my old acting class. But I I was so excited. It was better than any role I ever got.

SPEAKER_01 34:18

Oh. For me. Wait a second. So you were checking it with her?

SPEAKER_03 34:22

Yeah.

SPEAKER_01 34:23

That's I love it.

SPEAKER_03 34:24

Well, so she's she because it came out at five o'clock. And so you're just as excited as she was. Oh, yeah, right over her shoulder. I could see it before she found it, too. I was just like, yeah. And then Amy, my wife, looks over and mouths, she got it. Yeah. And they had a matinee and a nighttime, and she landed the nighttime. So that means I get to be there for it. Whoa. And this is her first time doing something like this? It's her first. I mean, she's done community theater where you know you're everyone's like acting around a yoga ball. Yeah. Like as a and I don't know if you're this way too, like because you've been in it and you've seen it on a higher level or like full productions. Sometimes when it goes back down to its infancy, and improv's important. I've taken every improv class at college will offer. But it's like, I just want more. Like I want, I want like the full production. I know that she could do all this, and then they're just like sitting there pretending that a yoga ball is the sun. And I get it, and you're gonna tell me it's part of the process, but I just like the full-blown production.

SPEAKER_01 35:23

Right. So you would the next step is if she likes this, then you take her to like a more serious program or school or we're in a slippery slope, though, because I I always wanted to be a kid actor first.

SPEAKER_03 35:36

Before Saturday Night Live, like I wanted to be Kevin McAllister. I wanted to be Macaulay Culkin, but you look at that now and you don't want to be them.

SPEAKER_01 35:46

No, even no, they all have really like they've been through some stuff. I mean, because the common denominator with a lot of them is a parent striving to recapture something they missed, and it doesn't play out very well. And that's why I refuse to do that. Have you seen that movie Honey Boy? I don't think so. It's so, I mean, it helps to have been like somebody who watched Shia LaBeouf when he was in his earliest stages of his career.

SPEAKER_03 36:16

Okay, I've heard of this one.

The Dark Side of Child Stardom

SPEAKER_01 36:17

So it's the movie he made, right? Right, where he plays his dad and someone else plays Shia LaBeouf being like on even Stevens and being this guy actor. So you're watching it, but the whole time you're like, oh damn. I didn't realize when you were a goofy kid on Disney Channel, yeah, that you were also like being verbally abused and maybe physically abused in this motel room and like none of this is fun for you. But he's also like he's playing the dad, so you're it's just it's epie, but you know, you the Nickelodeon stuff, and yeah, every the kids aren't if a kid decides that they want to do that on their own, and a parent and a family supports that, right. Yeah, if a parent is steering somebody into something that's so Hollywood is so cutthroat, and they're just using people, and you want to put your kid into that and have that be part of their formative years, that's dark.

SPEAKER_03 37:23

Yeah, and it's scary, and you know, the predators and everything that's out there now. I mean, you back in the day, it's like, oh yeah, you hear about these things, and then it was like 80% of the kids that you looked up to as a kid are either like massive drug addicts or completely broken or trying to pick up the pieces, or maybe they're still famous, but they've got a weird look in their eye. Like stuff happened.

Relatability In Comedy

SPEAKER_01 37:47

Yeah, these guys, I mean, my favorite show in the 90s or growing up was Boy Meets World. Yeah. And those guys all have a podcast now where they're more talking about what it was like to act on the each episode and things they remember from the shooting of it. And a lot of it, I I don't listen to it regularly, but when I see clips or stories, a lot of it is uh them realizing that what they were going through was not normal or really even that cool. Like, you know, Danielle Fischell, the girl who played Tapenga. Yeah, she was being heavily objectified and like sexualized and probably was not yet 18, and they got a whole cast, like writer's room, writing writing sexual innuendo about a 14-year-old girl. But it's delivered from the line, it's delivered from another 14-year-old or 15 year old. So this is just them joking about puberty, and and their jokes were so funny. Uh, they had really good jokes, and these kids, these teenagers were had a very like uh adult, their sense of humor was great, but it was because it was being written by adults.

SPEAKER_03 39:03

And it was it's gonna be weird for the adult writer to be in that perspective where it's like, okay, I'm 40 and I'm writing this stuff about this child, you know, but it's not from me, but it has to come from you in order to make it authentic.

SPEAKER_01 39:18

And it's still mostly wholesome, but the innuendo here and the innuendo there shows, you know, like, oh yeah, there was older guys doing all the like dialogue on this. And so some of that is odd, and you don't even think about it because when you're watching it, you're like, no, that's just six two 16-year-olds having a conversation. No, it's not. That was 30-year-olds and 40-year-olds, some guy named Dave. Yeah. And uh the things that they, you know, the workplace environments and things like intimacy coordinators, they didn't exist back then. So uh no one was helping these kids who don't have the faculty to process this. No one was helping them process it. And they were just kind of like, cut, all right, let's move them to the next scene. Um, and if they got too emotional or weird, they'd replace them with someone else. Yeah. They write them off and replace them. It's just like that's the business. And so it would be a weird thing to steer your child into if they didn't really want to on their own.

SPEAKER_03 40:17

Because there's a big gap between being excited about a stage performance and being at auditions and grinding it out. And you know, like even when I was started to find some success in it as a kid, you know, like my mom would have to take me around to local auditions. And it's not easy for a kid on repeat to hear no or hear it's not the lead or it's this or it's that. And it really is. It's like a peaks and valleys thing. And like when you land it, it's like a drug, but when you don't, you feel like a failure. And and part of it is, you know, even in theater on the local level, there's such it's so clicky, you know. Like you could walk into an audition and know you've lost because the the person who's looking for the talent knows the name of that other kid. And oh, little Randy, he's always here and he's always so great, and like you're fighting uphill. And, you know, I I want my kid to be used theater and things like that and choir as a vehicle to find confidence and to find her voice and to be, you know, because she's already super articulate. She was always the one, you know, even at like seven, she's standing there making the cheers at the table of 30 people in a restaurant. Like Pam Sando doesn't fall far from the tree. But I I don't want, I'm not gonna go to LA and grind it out with her, only to probably have her get her heart broken and then maybe worse. Um, so I think that for now, I'd just be happy that she landed this role and uh she can she can sing and dance with a bunch of other pirates on stage.

Success In Entertainment

SPEAKER_01 41:51

Yeah, the interesting thing you said about, you know, like clicks and stuff and uh politics playing roles and in how you know and all that stuff that maybe is too much for a kid to have to like see and be exposed to. They should at least have a period of time where they're incubating just their confidence in a place that's a little more insulated for them to succeed in it. But at the same time, you need some of it. You have to lose some of the clicks and the politics. You that's just a preview of every industry that exists, and so you want to say, hey, this isn't fair, what's happening in our community, but then if you really took it for what it is, it's a microcosm of what all communities are, which is like your talent alone, at least in America, is not going to necessarily dictate your level of success. 100%. In fact, if you are continuously frustrated by your talent not being rewarded, you're gonna just you better get used to that because you gotta look at all these other variables. What are the people who are succeeding doing? Maybe they're staying after, maybe they're going to grab a drink with all the other people and doing some form of networking or adding some sort of value. Maybe they I don't know what it would how it would apply to theater exactly, but I know in stand-up, starting in Portland and uh it was the pandemic, so their timing-wise things got I got lucky. But we started an open mic in a parking lot when there was no comedy, and then I started the website that housed all of the open mics and shows.

SPEAKER_03 43:46

So Which is lapspdx.com.

The Role of Kindness In Comedy

SPEAKER_01 43:48

Right. And so that's now uh it's been sold and resold, so it's on its like third owner, but it's it's sort of the hub of um comedy. Live comedy in Portland for people, at least comedians, to get information about where to perform. Yeah, I thought it was a pretty cool resource. And I think thank you. I mean, it's something like that can help differentiate you from somebody else who's also funny. And, you know, as much as having the perfect tone and the perfect voice will help you stand out, if there's somebody who's a little less talented, but can check a few more of those boxes, they're fun to be around. They contribute something that other people can't. It's like they're gonna get that, they're gonna get that role over the person who's more talented. And that's the business. And it's hard to to make an eight-year-old or a 10-year-old understand that. You want to do it with like more gradual lessons while you're also instilling this idea that hard work and talent will get them what they want because you want to believe in that, but you kind of know as an adult that that's it's more nuanced than that, you know?

SPEAKER_03 45:11

Like plus, with what you do and with what I'm doing here, it's that's the perfect example is you know, you can be a great stand-up comedian and never get your your your shot, your true shot, you know, and you can have a great podcast. And if people don't find it or it doesn't, you know, it doesn't get legs, you can fall flat on your face. And it's not, it's not just see, it's like sports are a little bit different than entertainment, you know, because if you're a great basketball player, it's gonna be hard to keep you out of the league. You know, if you can dunk and hit threes on repeat, well, you can hit you can dunk and hit threes. Like if you can tell great jokes, you might be lost in a in a mid-sized town in Tennessee somewhere, and you don't ever get your chance, you know, and it's I think that anybody, any, I mean, you need a little luck along the way. I truly believe that. Um, but I mean, obviously, what you say though does give you an advantage. It's like Conan O'Brien. I don't know if you've ever heard what he said about when he was hired by Lauren Michaels to write on Saturday Night Live. He was like, Oh, you've hired me because I'm super talented. And he's like, No. He's like, why? He's like, I you hired me because I'm talented. He's like, No, I hired you because I like you, because you're a you're you're a fun guy to be around. And I'd rather hire you than someone slightly more talented than you who I don't want to be around.

SPEAKER_00 46:35

Yeah.

SPEAKER_03 46:36

And he's like, that like hurt my ego, you know, because he was like, oh man, but then he was then when he had time to think about it, he would actually rather be somebody that someone likes and have them maybe think you're slightly less talented. Because in the end, you get to prove that if you're here. Exactly. You know, because if I'm not here, I can't keep I can't tell you you're wrong because you just picked the other guy, the nicer guy.

SPEAKER_01 46:57

Right. I uh you made a good distinction that I kind of like drifted off on. Like nobody needed Kobe to be a nice guy. They were still gonna come.

SPEAKER_03 47:06

Yeah, black mamba was black mamba. You're not gonna stop him from being a star.

SPEAKER_01 47:11

In sports, it's almost the less human you've seen, the more you appeal to the masses because it's like people are trying to aspire to be that hero larger than life. In entertainment generally, especially in comedy, people want to feel like you're there someone they would like to be around, hang out with. They're not just there to watch you like land punch lines like dunks, you know. They want to think that if they came up to you after the show, you would be someone that was at least like cool to them. Likeable.

SPEAKER_03 47:51

Yeah, I mean, at least relatable to them and their world, you know. And you can be totally different and still be something that they can they can latch on to. You know, like I love all kinds of comedians who aren't like me, but I have to have like this little part of me that likes them. Right. You know, there's it's like an underlying thing.

SPEAKER_01 48:11

Yeah, even if their character is dark or like I'm thinking of Jesselnik. I think most of his fans are still of the belief that he's not like that on stage. He's just on the inside, he's giving this like wink to them because they all kind of share this dark sense of like gallows humor. You know?

SPEAKER_03 48:30

My heart is not completely dead, is what he he that's the undertone, but he gives you the lines like, oh, well, this guy does not care.

SPEAKER_01 48:37

Right. But he does enough to where you can feel I think that's what his fans want. I don't know who he actually is. He could be awful. I was just I was just out with Mark Normand. Yeah. And the thing I learned, I was with him for the full weekend. The thing I learned the most from him was not on stage, even though he's a great writer and he works hard. It was how giving he was with his time off stage to anybody who came up and wanted to talk to him about this, that, or take a picture. He never made anybody feel like they were bothering him or wasting his time. Uh and I think that's the big that sells tickets at the end of the day. Oh, yeah, that makes people feel like you're their guy. And the minute you brush them off, even if you were somebody that they loved, the minute you make them feel small or like annoying, they're they're gonna go find a new person. Yeah, nobody wants to feel like that. And if you can make them feel like your friend, you can sell a ticket to them once a year for the next however long you do it. And it's like, oh, this light bulb went off. That is what a true headliner like is. Somebody who is on, and if if there's times where Mark doesn't want to deal with the public, he has to go in private. And that's like he I don't know that he's somebody who was he probably does have that, like we all do, but I didn't see it. And uh, you know.

SPEAKER_03 50:05

I'm glad you brought him up uh because I I did want to mention something about Mark Norman. The Fit for Radio podcast is brought to you by the Stafford Hills Club. And if you've never come here and taken one of their classes, you really should do so. Their instructors are really good. I took the Pilates Reformer class here, and she made me feel like I could be comfortable in the room. Let's get it right, though. I've got a lot to learn when it comes to Pilates, but that's how you do it. You just got to show up and give it your best, right here at Stafford Hills. They make you feel comfortable, and it's a family environment, not just being able to bring your family here, but also the people together feel like a family. Check out everything to offer at staffordhills.com. Tell them Drew sent you for half off your initiation. Do you remember years ago he came and did a TP Forever event? And for people who don't know what that is, that's a charity that uh Brent has has been at multiple times doing stand-up comedy for uh it's my buddy's charity for people who've lost a loved one, TP Forever.org. But we were at uh we were at one of the events. I can't remember exactly where it was. Part of me wants to say it was at like Spirit of 77, but Mark Norman did one of the events. Okay. And maybe it was the year before you came, but I thought you were there.

SPEAKER_01 51:28

No, I only did three. Okay, so the sportsman, Caitlin Palufo, and then Andy Haynes.

SPEAKER_03 51:36

Okay, and so the year before that, we had booked a comedian, and this is how cool Mark is. We had booked a comedian, and it was a friend of Mark's, and he was more of a mid-level guy, but still super funny, and we were really excited to have him. And at the last second, he got sick and he was he had to cancel. And so we've got this charity event, which is super important. They only do two events a year, so we need it to happen. And so he calls in a favor to his buddy Mark Norman, who says yes and comes out here. And at the time, I, you know, I knew of him, but I didn't like realize how much of a favor that was at the time. And dude, he was so chill. Like, he's over in the corner and he's like, when he's not on stage, just like just kind of like soft spoken, just kind of like, you know, chatting, doing that thing he does under his breath a little bit. And he made everybody feel cool. He made everyone feel like it was even keel, all the openers and everything. He's like chatting them up, making them feel good. And, you know, as a host of these events throughout the years, I've always tried to make it easy on the comedian, like, hey, you know, no pomp and circumstance for me. I'm just gonna tee it up for you. And he was, I think once he heard that I was gonna not try and like go over the top, he's like, okay, this is this is relaxing. Um, but I that was the takeaway I had with him, because I've worked with guys where it's not so smooth, or they're like, make sure when you get up on stage that you bring me my microphone and all of a sudden, I'm like, okay, all right, dude. Let's take it easy.

SPEAKER_01 53:11

But he's the guy. People can be all kinds of there's a whole range of what a headliner can be. And the helium green room. So last night there was a British guy who sold out his name's Ed Gamble. He's a uh a UK star. And so he sold out helium on a Monday, which is impressive. For he's never been there before. We had I got there like 45 minutes early. We had a great conversation, but that green room is so tiny. At the end of it, I was like, dude, thanks for being cool. Because sometimes the headliner can be like standoffish.

SPEAKER_00 53:47

Oh, yeah.

SPEAKER_01 53:47

But I still have to be in here. So, like that you're in a closet of a room with somebody who you don't, who you like look up to, but you don't know how to talk to. It's some of the most uncomfortable sitting on your phone.

SPEAKER_03 54:01

I've sat in those rooms with you a couple of times and I feel uncomfortable because I don't know how to interact with somebody that I don't know how they talk.

SPEAKER_01 54:08

But that mission theater green room is three times the size, maybe four times the size of the you guys were all. So if you don't like, or if you're not vibing with the guy, you're still like as close as you and I are right now. And the needs are close. So I literally thanked him for being like a cool hang because uh it can be bad. There's a whole range, and every time you come in, you have no idea. You can't tell from their picture.

SPEAKER_03 54:33

And I think that's something that's cool about you, though, is because you've put in the work and the time and the grind, and not to say a lot of these big comics have haven't, because they have too, but when you've been on the other side of the green room where you've seen cool comedian and icy comedian, I just I never want a people to leave my presence and be like, that guy was icy. What was that about? You know, I I really and now granted, some people do things that deserve ice, but I don't like to open my my interactions with anybody in that way.

SPEAKER_01 55:08

Yeah, I hate to leave a situation like that too, but I know that I have left situations, and certain situations can bring kind of a a coldness out of me where you're like, all right, I'm kind of just here to get done with this to do work, and then when this is over, I do just want to leave. But I mean again, shout out to to Mark. It's like if you really want to do this on a level that sells tickets and like works throughout the country, you gotta make the decision to be to to like if that's how you feel, it can't be how you act. Like you have to act as if you're just grateful for every opportunity because there's a reality where these opportunities aren't given to you. So you can be a little bit jaded about oh, this is kind of this in a great room or these people are half empty here. Yeah, but you could be at home not making any money.

SPEAKER_03 56:14

Yeah.

SPEAKER_01 56:15

And it's like it's so important to how you internally frame things to to kind of remain grateful. Sure, somebody could be bothering you while you're uh at the grocery store, but you're like, that's a sign that you're what you're doing is having an impact on just a stranger, and that's that could be framed as, oh, I'm grateful to be in demand, or you know, there's people who I know who are funny that are not being recognized. And so uh how you frame it is super important. Um because yeah, you could brush off some of the like awkward gigs and and be like a a little bit of a diva in, you know, Ashland or Hood River because you you know uh I think you deserve to be somewhere bigger. Right. But those people all have friends, and if they tell the story of how you weren't that cool, it's like, well, there's a whole community of people that are talking about how you're not that you're not actually that cool. And if the flip if it was the opposite, where you had a whole community or a bunch of communities around the country talking about how cool you were, those feel like the difference between success and failure, what as much as or more so than what you do, like the talent. And that comes back to our conversation with um clicks and politics and the things that you want to shield your kids from that like kind of learning too early. But they still need to learn it. And yet, if they don't, they're gonna be in for like a you know, a hard, frustrating reality, no matter what industry they pursue.

SPEAKER_03 57:56

And I'm always trying to teach my kids that whole the power of kindness. And it's not just on like the cupcakes and butterflies level, like take it back to the mark thing for a second. And even, and I I would even be willing to tell my girls this that you know, like I want you to be kind just to be kind. But even as a self-serving situation, let's go back to the Mark situation with me, right? He interacted in a way to where when I hear his name after how kind he was when he did a show with us, that I am a walking billboard for him, right? So when he, when his name comes up, I'm like, oh, he was so cool. It was like this, and then he was like that, and it was like that. If it's the opposite, you you become a poisonous billboard for him. And while it really is no skin off of his back, because if you were to ask him, he has no idea who I am. I mean, it's been that was 2021 or 2022, and you know, he's done a thousands of shows since then. And it doesn't matter if he remembers me because he's already planted the seed of who he is to me, and he doesn't realize in that moment that I've got this platform with a big microphone and a big voice and and all that. But to eat to your point, to each person who's sitting in a little nightclub somewhere and is like, oh yeah, we were thinking about going to that Mark Norman show. Oh man, when he actually he came down to Ashland and he played the place like he cared enough, it felt like he was in this massive venue and made us all feel great.

SPEAKER_01 59:24

They're gonna go.

SPEAKER_03 59:25

That's it. Yeah, it's done. But if you're like, well, it was a little cold and you seem like he was trying to get out of there, then they might not go. They might not go.

SPEAKER_01 59:32

Yeah, I mean, it's uh it's wild, but it's uh it's awesome and it's it's good. It's like, yes, you should be kind just for kindness' sake.

Darkness In Comedy

SPEAKER_03 59:43

But uh but it's tough though, because comedy is dark, you know. And one thing I've taken away from being around comedians for the last 20 years, and back when I still lived in Eugene, I used to host gong comedy. Yeah, with a gong on the stage. Let's just say after about a year, we ran out of comedians because everyone's getting gonged. But I was also putting on these shows with bringing Portland comedians down and bringing people in from out of town. And I did this thing called fat camp for years, uh, where Ph A T, it was no fat shaming in it, but I would bring these guys in. And one thing I've learned from having all these interviews with comedians over the years, and I wanted to be a comedian for so long, is there is like an aspect of darkness behind the eyes of comedy. Like, do you notice that? That a lot of good comedians have a darker side to them. It's not all, you know, sunshine and yuck-yuck jokes.

SPEAKER_01 1:00:45

For sure. I think well, comedians are sensitive. That's like at their core, they're all they seem like they're the most confident, the happiest, like, you know, they could talk shit to anybody and you could dish it, but they're the ones who can but at their core, if you think about it, anybody who has decided to get into this is somebody who really s values the val the validation of strangers. So at it's gonna bring out people who are a bit insecure, sensitive, emotionally, highly focused on how they're being perceived. Um that's just what they almost across the board everybody has in common, whether they're good or not. They're ready to uh be defensive at any moment. And that's why they, you know, um not I can't say that across the board, but Kyle Canaan, he he's great, and he lives in Portland, he's lived here for six years now. He said one night, he was like, everybody has a friend who's funnier than the funniest comedian, but a lot of people who are funny don't need to go out on stage and like present that in a way that they define as their career and their identity. Some people are okay just being hilarious to their 10 friends and their family, and that's all they need. Right. We like to assume that, like, oh, but you're not funny if you're not doing it at like we are at a at a nightclub selling tickets. And it's like, I don't know. That's not necessarily true. I think we are a group of people who decided that this was important enough to pursue with all of our energy and you know, that sacrifice other forms of income or stability to go do this. But I I don't think from I think a lot of people are lying if they're like, I just need to spread the message of laughter. It's like, no, you're doing this because it makes you feel good. Stop lying. Yeah. Yes, that can be true. It is great to spread laughter, and a lot of people come into this with something that they want to say. I'm not saying that nobody has a message, but I'm I would think that there are probably more a bunch of different ways you could get your message out. You're doing stand-up comedy because you feel great when you are holding a microphone and a whole room of people laughs. And it feels good. It's a great feeling. Yeah, of course. I mean, let's yeah, don't even play games about that being the reason, though, that you're doing it. Or at least maybe I'm projector. That's the reason I do it.

SPEAKER_03 1:03:45

I I feel the same way just with what I've seen and and the, you know, I haven't done nearly as much stand-up stand-up as you have, but definitely uh seen it on both sides. And I just didn't realize that there was so much of the darkness in it because, like, especially when you're doing morning radio and these people are forced to come in in their off hours, you know, and they walk in and you can some of them, some of them are true pros who can just the door comes open and it's like bang, bad-da-dang-dang. But some of them you walk in and you can just feel this Charlie Brown cloud come with them, and you're like, I used to pride myself on, all right, I'm gonna pull them out of that. Like we're gonna, I'm gonna, I'm gonna make them laugh and we're gonna try and pull out of that a little bit without being a cornball.

SPEAKER_01 1:04:30

I mean, you think about the road, it's so lonely. And then your days are like mostly in a hotel room. You could go out and interact, but a lot of people like their interactions are all at night. They're saving their social like gas tank for the evening because they're about to perform, and then if they're a headliner, they're gonna do the meet and greet, and then they're gonna do the whole game of going out with the openers and they're gonna be out till 2, 3 a.m. So uh yeah, I could see why it's 7 a.m. Yeah, they're they're not all bells on. Yeah, when they're about to face another lonely day, yeah, and uh they don't even remember which town they're necessarily in. Like that would it's not the healthiest lifestyle. So that would create a dark thing.

SPEAKER_03 1:05:20

And I I think that part of it is probably appears darker too because of time of day and being alone a lot. They probably during the day half the time only mumble uh like their bagel order, and then that's the conversation for the day.

SPEAKER_01 1:05:32

There's sometimes where the first people that you talk to are the people at night on stage, and that's that was just weird. Absolutely. But yeah, it is dark. It can be dark for sure.

SPEAKER_03 1:05:43

But harnessing it is the key, and you've you've managed to do that pretty well. You won the Seattle International Comedy Competition in 2023. That's pretty aggressive, right? Like that's a good title to hold. Sure.

SPEAKER_01 1:05:57

And we talk about like getting things getting dark. That is a three-week competition of it's just a grind. You're driving all around, it's not just Seattle. You're going Bellingham, you're going to Port Angeles. You go all the way down the Lawnview. Like you're and every night you're being judged by sometimes people who don't even watch comedy very often. And so it's competitive.

SPEAKER_03 1:06:23

It's like it's gotta be a lot of anxiety not knowing how it's gonna hit with these different judges.

SPEAKER_01 1:06:29

Right, or why they didn't score you well last night, but they did score you when you didn't think you did that great. It's a trip of a contest, and uh but it's been going for 50 years, and so it's had like a a long history, and a lot of great comedians have gone through either Seattle or the other one in San Francisco. Um I did not expect to win it. I didn't go into it thinking that I it was really even an option. I had a goal of making the semifinals, and then things just kind of it's a game at the end of the day. It's like it's got a point system, and there's ways you can use certain things that work better on the road to score better. And so uh I wouldn't have I wouldn't say I was the best comedian of the people that were in it, but during that three-week stretch, I was able to play the game. Found a way to win. I found a way to win. And uh from that 20 that was 2023, 2024 was where I got to start headlining around just kind of like the places we named, Bellingham, small places.

SPEAKER_03 1:07:36

Um and did that competition victory, did that help you secure some of those?

SPEAKER_01 1:07:40

A lot. Yeah, I think that gave me the credit to go to most of most of the small town comedy gigs and have enough. Oh, he won the Seattle International Comedy Confederation. We could go watch, you know. They're not necessarily people who follow me on Instagram most nights. Yeah. But they're people who want a good time. And I know the type uh I know the Pacific Northwest crowds pretty well at this point because of how many road opportunities that led to. And a lot of them went, especially in 2024, a lot of them were rough. Like going from somebody who's just featuring and getting to do 20 minutes, uh, and if it goes good, great. If it goes bad, the headliner comes up and sends them home happy. Yeah. Went from that role to the one who has to send them home happy, and some nights failing. That's a lot. Watching like a hundred plus people go out, like, you won the Seattle on the Aspen. But you're like, man, I won it with 15 and now I'm doing 45. Yeah. So it's tough. There's growing pains at all that. And I'm glad that a lot of those things happen in towns nobody's ever heard of. Those first moments where you're asked to stretch, they suck, but they're really where you find it's where you learn. Yeah. You hone the crap. You learn way more from those rough sets than you do from the good ones.

The Flop Swap Concept

SPEAKER_03 1:09:06

And so well, you um I've always one thing I've liked about your comedy here is you've done a good job of tapping into the Portland factor. You know, like um, I love your jokes about roommates, uh, woke roommates, um, and you know how they still go watch Blazer games and things like that. Like you have some really good Portland comedy. Um, and that's what I wanted to talk to you about before we get going too, because you did a comic swap, which I was following along with, where you and a comedian from Philadelphia switched places for a month, which is frightening in itself. Um, but I want to talk about that and how that has led to a decision for you to upend everything and leave Portland and head to Philadelphia. The Fit for Radio podcast is brought to you by the Stafford Hills Club. And when you come here, you will notice the difference. The sense of community is amazing, people smiling, happy. They hold the door for you around here. And of course, it's one of those clubs that when you sign up, they want you to come back. They want you to be happy and healthy, because then we can all be together for a long time. Check out all the amenities and everything they have to offer at Staffordhills.com. Tell them Drew sent you and get half off your initiation. How did that come about and what made you decide to make the big jump?

SPEAKER_01 1:10:30

Right after I won the Seattle thing, I was catching a lot of like weird energy in the Portland comedy scene, and it felt like maybe I was starting to develop my first wave of haters. And I was like, I don't want to leave Portland because all the work is up here now. But I gotta get out of here for a little bit. So I pitched this thing called flop swap, where I wanted to trade rooms, uh like a flop house. I wanted to trade rooms with somebody in a different comedy scene. I didn't care where, as long as there was comedy happening every night, you can come live in my place for a month. I'll live in your place. And people really liked the idea. And I caught like a couple leads, but uh one girl was allergic to cats, so she couldn't come. And I was gonna go to Brooklyn. Uh, somebody else was in Austin, but it like the timing, I didn't want to go to Austin, like it's gotta be just right.

SPEAKER_03 1:11:25

Like both of you have to be able to do it and have kind of like situations.

SPEAKER_01 1:11:28

Sure, and like a little bit of you gotta trust the person, right? They're gonna be living in your place, and it it went cold after the first couple leads, but I would share it every once in a while, or I would visit people in other cities and they would go, Hey, did you ever do that flop swap? So it stuck out as something that like people thought was a good idea.

SPEAKER_03 1:11:52

Yeah, I I loved your idea initially because I remember you bringing it up on social media and I was like, huh.

SPEAKER_01 1:11:58

Yeah, that was January 2024. And so I would share it every once in a while. I met a guy, when I went to New York City for a month. I got an Airbnb in Manhattan, and just it was like a closet of a room, but for a month I was just seeing every club and going everywhere. It was awesome.

SPEAKER_03 1:12:15

That is awesome.

Moving to Philly: A New Adventure

SPEAKER_01 1:12:16

Um, but New York is like at this moment prohibitively expensive and competitive for me and my girlfriend to move to. So I took another trip. Oh, and on this trip, I did go took a take a train to Philadelphia, and I met a guy named Adam Flick. Um in August, I shared the flop swap again because I just shared it every few months. And he saw that and was like, hey dude, do you want to come to my room in Philly? And I had already been there, I'd already met him, so I know the place is cool. I was pretty charmed by Philadelphia. And it had been a long year of traveling and taking these trips, but it was the first time that the flop swap kind of lined up, and so we set it for November 10th to December 10th, something like that. And uh right before it got super cold, that felt like the last time I would really want to go that, you know, um, experience the East Coast. So we did it. He he lived in my room, he drove my car, I lived in his room, I drove his car. Was this weird? Uh there's a lot. The car thing is the one thing that made me like, oh, please don't crash my car. Yeah, because then my insurance goes up and that and you know. But I host, you know, I got to take his car to my sister's in upstate New York for Thanksgiving. Um that's the other thing, is like, yes, he could do something to my car, but why would he? I have his car. And yeah, his car's a Lexus. Mine's a, you know, whatever.

SPEAKER_03 1:13:58

You you guys had a kind of a mutual situation that I won't mess up your stuff, you don't mess up my stuff.

SPEAKER_01 1:14:03

Right. Uh yeah, we both had guns through each other's heads, you know? And we were hosting each other's comedy shows. So like he ran a show for me out here. I uh hosted one of his shows and did his open mics, and it was an awesome, affordable way to experience a different scene. And yeah, at the end of it, everything kind of clicked. The Philadelphia is actually an affordable central hub to the northeast. We could move there and not necessarily have to go to the back of the line like we would in New York, maybe. And we can still get to New York whenever we want. It's a$20 bus for two hours to get there. So New York's the target, I think, still. But Philly is a great launch pad, I think. Yeah. And I really enjoyed the people, the comics, the city. You know, I have to be a little more aware and, you know, different demeanor a little bit, but I feel a little more grown up out there. I love Portland and I feel like I could stay like a grown-up kid in Portland my whole life, but I'm a little too young to feel as comfortable as I do in Portland, um, since there's still a lot more I want to accomplish comedically. Yeah. So Philly is the move. Two weeks away. Uh, we got an apartment. We're gonna be living on South Street, which is like one of the big busy bar streets, and we're not drinkers, but it uh yeah, we're gonna have nine months of chaos in downtown Philadelphia, and it'll be an adventure. I'm glad I'm going with uh my girlfriend because Yeah, that helps. Yeah, and she's a comedian too, so we'll both hopefully get to find our own lane. But there's a lot more questions than answers at this moment for the Philadelphia chapter. In terms of what you're asking about Portland, I'll definitely miss being able to do all those Portland jokes and like uh some of those don't even translate as hard on the East Coast because they don't they don't know West Coast.

Cultural Adjustments and Comedy Challenges

SPEAKER_03 1:16:21

Uh well I mean I think you can push into the stereotypes of us a little bit, and I'm sure there's a you'll just have to morph those jokes a little bit to be on their side of the comedy. Right, or frame them as more like liberals versus Yeah, exactly. Then they can they can understand that word. Yeah. Even though they're not they don't have an accent like that, but sometimes the thinking begs it.

SPEAKER_01 1:16:45

For sure. And it's Philadelphia, Pennsylvania's a swing state. We're gonna be in a place where there's a lot more range of opinions, so there's a dominating viewpoint.

SPEAKER_03 1:16:56

And with comedy, you want a little bit of an open perspective on some level, you know. So I mean, you go into the dirty south, you better change your whole set.

SPEAKER_01 1:17:05

I don't actually know that's the one region I don't know much about is the south. So I'll explore that. I'll explore that eventually. But the East Coast has its own. I mean, we got 10 times as many people in, you know, 100-mile radius, 200 mile radius.

SPEAKER_03 1:17:22

And that's what makes me uh nervous just a little bit about like I've always been the guy who makes people laugh in my job or my life, and you know, yeah, but it's a West Coast humor and I have a West Coast voice. And, you know, I always say it's the California accent because it's what people see in the movies, is how people sound here too. And so would it translate, you know, if I had a radio sh job on the East Coast, would it translate if I was in Florida or Texas or whatever? Or how quickly would I start putting some twang on it? You know, and because my wife laughs at me. If we go to like a Mexico, like all-inclusive, if there are people from Texas there and I befriend them, like I accidentally start speaking like them.

SPEAKER_01 1:18:05

Oh, I thought you were gonna go a different way. I thought you were speaking like the Mexicans.

SPEAKER_03 1:18:09

No, no, well, I mean, you leave me anywhere long enough, yeah, and I I will adapt.

SPEAKER_01 1:18:13

Right.

SPEAKER_03 1:18:14

Um survival. Exactly.

SPEAKER_01 1:18:17

But I think also going to the East Coast with your very defined West Coast perspective almost helps you be different. Who you are, because it's hard to distinguish yourself in a culture that's filled with people very similar to you. Because you're like, I I don't know, I'm this, but I'm like a lot of the people around me. But if you go somewhere where you're and you're unique, then you're like, well, yeah, I am all these things, and these things stand out because everyone else is a little different. And so Portland and the Pacific Northwest has been a really great fertile training ground, and the stakes are kind of low and the eyes are off. So it's like it's a great place to get good or get funny. But I really hope that the East Coast is a place where I can get like be myself.

SPEAKER_03 1:19:05

Yeah. And there's gonna be a bit of a trial by fire for you, too, because it's not just a getting used to the groups and the people. It's a lot like what's going on with me right now. When you reinvent yourself and moving across the country is a reinvention, yeah, is it's gotta be scary because you've got to find rooms to do do your shows and to earn money because like it's the same thing with this. It's a passion project until it pays the bills, you know. And so, like, when you guys get there, are you gonna have to find other jobs as well? Are you gonna be able to just do comedy? I mean, that's a tough thing in a new city.

SPEAKER_01 1:19:42

Right. I've for the last six years I haven't had to have an actual job in Portland, partly because of pandemic timing and some of the unemployment benefits, but partly because just that led to being a breakeven comedian and then being able to pay the bills.

SPEAKER_03 1:19:57

But you know Can we call the popcorn people back?

SPEAKER_01 1:19:59

You you go is not to call the popcorn people back. I already did that. I hear you were great times. I was excellent.

SPEAKER_03 1:20:07

Oh, I I can see it. I can see it.

SPEAKER_01 1:20:09

And what's funny is that where I'm moving is like the snack belt of America. Like there's a lot of it's a pretzel town. It's like there are a lot of chip makers out there. So there's part of me that's like I could probably make uh a snack company. I could be an asset to like a company. And is there a part of me that like could get back in the the game, like whether it's popcorn or chips or pretzels or whatever? If I have to, I will. Yeah, anything to keep the lights on. For sure. But I don't know, there's this part of me, and um we're fortunate enough to have some savings going into it, but like there's a part of me that thinks I just need to go all in on comedy and have a little faith. And yes, there's gonna be an adjustment period. There will be many different moments, I'm sure, where I go, why would I have left everything I had in Portland? Friends, work, uh a reputation that was, you know, like kept me working, you know. But I talked to a a manager recently who said, how you respond to that moment that will definitely happen, where you're why did I do that? How you respond to that will define how this chapter goes. So all of those are gut checks, and I kind of know that. I can't anticipate that, and maybe I can't anticipate how heavy it'll feel to be rejected on the East Coast, and sure that'll happen.

SPEAKER_03 1:21:45

But you're doing the right thing.

SPEAKER_01 1:21:47

And I took, I spent two months there last year. My stuff translates enough that I'm not like that you can't make people laugh. Yeah.

Upcoming Projects and Future Aspirations

SPEAKER_03 1:21:57

Yeah. And that's good to know ahead of time, right? That you've already tested it out a little bit. And I I really do think you're doing the right thing. And, you know, with my life right now, everyone who matters to me is coming back kind of like in turns as I'm going, am I making a mistake? Am I doing what I'm supposed to be doing? Should I be chasing other jobs? Should I, or should I be on this journey? And just seems like every time that doubt leaks in that somebody or something is there to say, yes, keep going, keep pushing, keep going. And so we're in a similar but different, but similar situation. We're gonna figure it out. Yes. I got faith. And we're gonna, I would like to have you on more often as well. The nice thing about technology is you don't have to sit here with your knees nearly touching mine in my little studio over here. It's a beautiful spot, but it's cozy. Um, but I'd love to have you back on. Uh, real quick, a couple of things about um what you've got coming up. You're about to you're about to film a feature in a special.

SPEAKER_01 1:23:00

No, well, maybe. Jackson is revising, reviving Deaf Comedy Jam. Oh, awesome. So like the 90s on BET. He's gonna do he he he doesn't believe there's enough people doing stuff like that where you're kind of putting on new comics. And so he's doing from his YouTube channel, um, is Nate Jackson, he's doing super funny comedy jam. So it's like at his club up in Tacoma, he's flying a bunch of people there, and he's doing, he's recording on Tuesday, Wednesday, and Thursday, 11 episodes of like, and then we're gonna be probably 30-minute episodes, but he's filming 11 of these. Each episode has three like featured comics and then a headliner. So I'm gonna do a five-minute set on Thursday, the 26th, and that's oh man, it's so cool to get to do uh like an official taping on my last night in the Pacific Northwest. That feels like, oh, it feels like the the region's sending me like uh sending me off in style. So I just gotta pick a good outfit. Because I was watching Def Comedy Jam. Like they all have these like iconic 90s crazy outfits. You're like, I gotta dress bold.

SPEAKER_03 1:24:17

Yeah, I think you gotta, yeah, you gotta step it up and bring it. Um well, it's so great to have you on. Thanks for having me. And yeah, I I good luck to you as well. Thank you. And it's a bummer that we'll be uh not seeing you here anymore, but you can keep up with him on social media. Uh, where where can people find you online? At ha ha. At ha ha ha brent. Three haws. Three haws. Yeah. And I follow him. You should do the same. And um, like I said, super funny guy. If you ever catch him on the list of comics here in Portland or anywhere else, make sure you go check out Brent Lowry. Thanks a lot, buddy, for coming on the show.

SPEAKER_01 1:24:55

Thank you. Cheers. Cheers.