Club Shay Shay

Club Shay Shay - Matt Rife Part 1

61 min
Mar 5, 20263 months ago
Listen to Episode
Summary

Matt Rife discusses his rapid rise from a 15-year-old comedian in Ohio to one of the highest-earning stand-up comedians, breaking Ticketmaster records and selling out arenas. He shares his journey through comedy clubs, Wilding Out, and the mental and physical toll of touring, while reflecting on his family's influence and the importance of mentorship in his career.

Insights
  • Early specialization and mentorship from established comedians (DL Hughley, Ralphie Mae, Dane Cook) accelerated Rife's career trajectory more than traditional education paths
  • The transition from comedy clubs to theaters to arenas requires distinct skill sets and audience management strategies; skipping steps leads to unpreparedness
  • Black audiences provide more authentic comedy feedback through cultural context and willingness to engage in competitive banter, making them invaluable for developing comedic chops
  • Television work (Wilding Out) serves primarily as exposure/marketing rather than revenue, with limited pay ($1,000/episode) but significant touring benefits post-appearance
  • Physical and mental health management is critical for touring comedians; extreme schedules (40-50 shows/month) can cause severe sleep deprivation and circadian rhythm disruption
Trends
Young comedians leveraging social media (Twitter, TikTok) for direct access to established performers and booking opportunitiesArena-scale comedy shows becoming mainstream with ticket demand breaking Ticketmaster infrastructure (comparable to Taylor Swift)Comedians diversifying into acting, producing, and content creation to balance touring exhaustion and maintain creative freshnessIncreased transparency around mental health struggles in entertainment, particularly regarding inherited depression and suicide preventionComedy tour economics shifting toward meet-and-greets and merchandise as revenue streams beyond ticket salesRegional comedy scenes (Atlanta's Uptown Comedy Club) serving as talent incubators with higher performance standards than mainstream venuesGenerational shift in comedy audience expectations: less tolerance for phone use, higher demand for presence and authenticityMentorship-driven career development in comedy replacing formal education and traditional industry gatekeeping
Topics
Stand-up comedy career development and progressionMental health and suicide prevention in entertainmentTelevision production and network approval processesComedy tour scheduling and physical health managementAudience engagement and crowd work techniquesSocial media's role in comedy discovery and bookingRegional comedy scenes and venue dynamicsRacial dynamics in comedy audiences and materialStreaming and special recording strategiesActing vs. stand-up comedy career pathsMentorship and early career guidanceTicketmaster and live event infrastructureComedy writing and joke development processWilding Out format and competitive comedyDental work and personal branding in entertainment
Companies
Ticketmaster
Rife's shows broke Ticketmaster's website due to high ticket demand, comparable to Taylor Swift's impact
Netflix
Rife has a limited edition series with Julia Garner coming out in 2025
MTV
Rife was the youngest cast member in the history of MTV's Wilding Out series
Disney
Rife appeared in guest episodes on Disney shows early in his television career
Live Nation
Live Nation inquired about Rife's pre-show routine and set preparation process
People
DL Hughley
Rife's first guest spot at age 15 came through a Twitter outreach to DL Hughley at Columbus Funny Bone
Dane Cook
Major comedic influence on Rife; later opened for Rife at Nationwide Arena, creating full-circle moment
Dave Chappelle
Primary comedic influence alongside Dane Cook; Rife studied Chappelle Show and early stand-up religiously
Ralphie Mae
First real mentor who took Rife on theater tour at age 19 and provided financial and career guidance
Eric Griffin
Rife lived on his couch for six months when first moving to LA; advised Rife to bet on himself creatively
Nick Cannon
Wilding Out creator and host; Rife discussed challenges transitioning from young to adult comedy material
Carlos Miller
Wilding Out cast member and talented comedian Rife considers among the funniest on the show
Chico Bean
Wilding Out cast member Rife cites as an absolute beast in competitive comedy
DC Young Fly
Wilding Out cast member; producer Niall Evans used him to build Rife's confidence during workshops
Cat Williams
Rife considers Cat Williams the funniest Wilding Out cast member of all time
Kevin Hart
Rife cites Kevin Hart as finding a balanced workload between movies and touring
Gary Owen
Rife studied Gary Owen's career but avoided being pigeonholed as 'urban comedian' for broader appeal
Julia Garner
Co-star in Rife's limited edition Netflix series coming out in 2025
Owen Wilson
Co-star in Rife's film 'Rolling Loud' releasing September 2025
Pete Davidson
Replaced on Wilding Out by Rife when Davidson left the show
Mikey Day
Wilding Out cast member replaced by Pete Davidson, who was later replaced by Rife
DC Curry
Comedian who taught Rife about the power of silence and patience in storytelling
LeBron James
Referenced as notable person from Ohio alongside other successful athletes and entertainers
Quotes
"Silence is one of the most powerful things you can have in stand up comedy. If they're quiet, they're listening."
DC Curry (relayed by Matt Rife)Mid-episode
"Stop trying to convince me. Just do it. Go on stage or go film the thing that you have an idea for. Nobody else is beside your brain."
Eric GriffinMid-episode
"By 30 years old, I've achieved 99% of my dreams. And you're not even half your life is not even gone."
Matt RifeLate episode
"Keeping it is harder than getting it. Anybody can get a flash in the pan. But once you get a taste of selling out arenas... that's a lifestyle you don't want to give up."
Matt RifeLate episode
"The more I drones on you, the more I fuck with you, the more I try to hurt your feelings, the more I actually fuck with you. Like, I genuinely love you as a person."
Shannon Sharp (on Black comedy culture)Late episode
Full Transcript
This is the biggest night in podcasting. The countdown is on to our 2026 iHeart Podcast Awards. Live from South by Southwest, March 16th, we'll honor the very best in podcasting from the past year and celebrate the most innovative, talented creators in the industry. It's truly a who's who of the podcasting world. Creativity, knowledge, and passion will all be on full display. And the winner of the iHeart Podcast Award is... See all the nominees now at iHeart.com slash podcast awards. Audible is a proud sponsor of the Audible Audio Pioneer Award. Explore the best selection of audiobooks, podcasts, and originals all in one easy app, Audible. There's more to imagine when you listen. Sign up for a free trial at audible.com. White people laugh. Yes. Black people laugh. No! No! No! No! Ow, ow, ow! Ow! All my life, been grinding all my life. sacrifice hustle pay the price wanna slice got the roll of dice that's why all my life I've been grinding all my life all my life been grinding all my life sacrifice hustle pay the price wanna slice got the roll of dice that's why all my life I've been grinding all my life hello welcome to another episode of Club Shay Shay I am your host Shannon Sharp I'm also the We're proud of Club Shay Shay. Today's episode is at the beautiful Lanx Bar in Washington, D.C. Stopping by for conversation on the drink today from club comedian to arena headliner. He's comedy's biggest lightning rod. He's one of the highest earning stand up comedians currently working. He joined Taylor Swift as the only other live act to break Ticketmaster's website due to high ticket demand. He's the youngest comedian to sell out two shows at the legendary Madison Square Garden in New York City. He's the youngest stand up comedian to sell out the Hollywood Bowl. He's the youngest cast member in the history of MTV's popular series Wilding Out, New York Times bestselling author, viral sensation, top creator, social media savvy influencer, prominent actor, popular producer, fame writer, superstar. Here he is, ladies and gentlemen, Matt Wright. Bro, that was credits I didn't even know that I did. Yeah, you did all that. You did all that. That's crazy, man. Okay, you were asking. What is this? This is a sidecar made with my cognac, shaved by Laporte. We normally do this, but now we're actually in a place that could actually do a drink. I want to know. Look at this. Look at this, y'all. Got a big old cube. That's cognac? Yeah. I don't think I've ever had it. I know you have it. This is the best on the market. Let me know what you think. That's not bad. That's not bad. Yeah. Why do you have it in a bottle that turned a donkey into a horse? That's terrifying. That's powerful stuff right there. Yeah, man. What's this in here? Is that straight? This is straight. This is straight. I'm going to try that. Hold on. I think there's a bug in mine. Yeah. You just said, yeah? What kind of production is this, man? Yeah, there'd be bugs in cups sometimes, man. That ain't bad. That's kind of smooth. Yeah, yeah, yeah. So we're going to be right. We're going to be right in this thing here. It's only 2 p.m., man. Let's go. I'm with it. So you have so much going on. Thank you. You had the show last night, and unfortunately, we weren't able to get in because it was a quick turnaround from us because we're coming from the west coast to get in and then we have had my show uh uh nightcap me and uncle no show and then to get in so next time i'm close by i'm gonna come see you man yeah because you were telling you went like three hours like hold on wait a minute yeah last night was a wild show i think we did like two hours 40 minutes something like that yeah i did like my show which is a little little over an hour like hour 10 hour 15 something like that and then it was just one thing after another things kept flowing into other things I kept meeting people, some fun people kept bringing gifts. It got out of control, but it was so much fun, man. That's awesome. It was one of those shows that you so locked in and focused on what's happening in front of you right now. At the very end when we took the picture together and all the lights came up and everything, I was like, y'all are still here? That's crazy. It was a little bit like 16,000 people, man. It was awesome. You got a film coming out later this year with Owen Wilson called Rolling Loud, drops in September. Your limited edition Netflix series with Julia Gardner. I love Julia Gardner. She's a beast. Ozark. She's amazing. Ruth Langmore, Al Truist, coming out this year. Any upcoming U.S.-Europe tour dates? Anything you got going on lately? Oh, man, a ton. I'm not sure exactly when this episode will drop, but I think our next U.S. dates are Jacksonville, Tampa, Savannah, and Raleigh. We got like a four-day weekend of that. And then we got Cincinnati and Louisville. Then we go to Europe for like a month, which I'm so excited for. We got like Romania, London, Sweden, Switzerland, Oslo. England, Ireland, Scotland, which is technically England, but I don't like hearing that. And a couple of other ones. Now, we're all over the place. Yeah, man, Savannah. You know, I went to school in Savannah, grew up near Savannah. I love it, man. It's haunted. It's haunted. You ever see any creepy shit? Nah, nah, I didn't see no creepy stuff. Really? No, no, no. You and I were talking early off camera, and then you're like, man, I'm from Ohio, a little small town, about 1,100 people. But when you go back and look at it, Bow Wow's from Columbus, Jack Nichols, Jack Nichols, the Kelsey brothers, Ben Roethlisberger, Pete Rose, Nate Thurman, LeBron, Steph Curry, Buster Douglas, Simone Biles, Luke Keekly. What is it in the damn water in Ohio to get all these great... I didn't even know half those people were from Ohio. That's crazy. We can't wait to get out. That's amazing. Shout out to everyone he just listed for getting out of Ohio. It's an amazing place to grow up, man. When you're growing up, you're so bored there and you can't wait to see what else is out there. But in hindsight, it was so wholesome, man. It was just so quiet. I'm so I'm so happy I got to be like the last generation of kids to like play outside yeah not have a phone have to bike across town see if somebody's even home like I'm happy I got that experience um no social media to get you no man distract you no I didn't really have social media till I was like probably 16 something like that when it started to come around but it wasn't anything like big like this was the time this is really how I like got a lot of my start in comedy that was the time where you kind of reach anybody on social media like everyone was just kind of getting on I got my my first ever guest spot was for DL Hughley. And that happened just on Twitter. I literally tweeted him. I was like, hey, I'm 15. I just started doing comedy. I see you're coming to the Columbus Funny Bone where I do my open mics. Like, would you want to, is there any chance I could do a guest spot? And he said, yeah, I showed up. And he was like, oh, you're actually a child. Right. I thought you were like a 35-year-old man trying to just get some stage stuff. Right. When you grew up in Ohio, your mom and your grandfather raised you. So that's your mom's dad, correct? Yeah, yeah, yeah. I had a stepdad, but we weren't that close. You weren't that close? Nah. It later found out that your father, unfortunately, took his own life. Yeah. Did we start the interview with this? We're going to start with it. Un omos. Dig in. How did you find out? Did your mom or grandfather break the news for you? How did that happen? It'd be pretty funny if I was just asking around. Has anybody seen my dad? And people are like, oh, he doesn't know. Right. I think my mom told me when I was probably, I had to have been an early teenager or something. I don't remember an exact moment when I found out. But I feel relatively lucky that it happened so early because everybody loses their parents eventually, right? And it's so hard. Like when I lost my grandpa like that, it still hurts. And that was a few years ago. So there's a part of me that's a little happy I don't have the memories because at one year old, I have no memory of this person. I barely know that I even met him. So I almost think I'm a little lucky to have gotten to skip that pain a little bit. So when your mom told you and it's like, damn, something. But and you see now everybody is seemingly more open with mental illness, with mental health. It seems like guys are not because for so long that he is in the shadows. You don't talk about what you're going through. You're a man. You overcome it. You deal with it. You make sure the family is OK. And whatever pain you might be harboring, you deal with it. But now it seems to be coming to the forefront. And so when you found out, you're like, well, damn. Did you feel any type of way? Like you said, you didn't have no memory of him. It's not something I really thought about when I was young. It was just like, oh, you know, he's dead. I don't have a dad. I didn't really understand the severity of suicide and what that means and what he could have possibly been going through. He was also young. I think he was 21 when it happened. Yeah, which is funny. A couple years ago, I was talking to my mom about how I still don't have a mustache. And she was like, well, you know, your dad never had one. I was like, he was 21. He didn't even get to grow into his face. Who knows what he was capable of? At the time, it didn't really affect me. But now as I get older and I'll go through little spats of depression or whatever. And I mean, I don't really, I've never really contemplated taking my own life right there. But you'll hit some low moments. Of course. And in that low moment, you're like, there's a bit of recognition of like, oh man, I wonder if this is what he felt as well. because they say a lot of mental illness stuff is passed down. So I'm like, I wonder if any of that depression is genetic or anything like that. But, you know, I try to think about it too much, not to let me bring it down anymore, just have an understanding of what he was probably going through. You know, he and my mom weren't really together. He didn't really have a good job. I think he was like a part-time job as a security guard or something. Wasn't that close with his family. His family was into drugs and stuff. So I just try to have a bit of an understanding of it as I get older. I think the thing is, is that for me is that I really did my dad and I only saw my dad once to know who I was looking at. I think I was about 13 years of age and it really never dawned on me until I got the things like football. And I see everybody else has their dad in the locker room. Yeah. Or I see their dad standing on the sideline or I see their dad in the locker room. And then it's like, man, I wish my dad could see this. I wish my dad could be there to see my brother. And that was the thing that that ever in a situation like where you're in school and you go to sporting events and you see dads at the game and they're cheering on their son to be. like now like you see so many comedians have their father yeah and you're like damn i wish my dad could see what his son became you know as a as a kid it didn't occur to me as much because i had a stepdad and even though we kind of hated each other to death i still like i knew him since i was five so like i i still said the word dad you know what i mean it's not like i never got a chance to say that yeah even though we weren't close it wasn't until the last like four years because my grandpa was like my father figure really like that was my best friend my favorite person in the world and he passed away like the exact moment within the same six months like everything started to happen for me i think he got to see me sell out a comedy club like the columbus funny bone where he actually started taking me when i was 15 to the open mics so he got to see me sell that out but like now getting to do these arenas and everything like that like i when i did the Hollywood Bowl, I had this giant backdrop that was probably 30 by 20 feet behind me that was like me and him when I was like a baby. Okay. Just because I was like, this is this was the first iconic moment in my life that I was like, I really wish he could. This is the biggest night in podcasting. The countdown is on to our 2026 iHeart Podcast Awards live from South by Southwest. March 16th, we'll honor the very best in podcasting from the past year and celebrate the most innovative talented creators in the industry. It's truly a who's who of the podcasting world. Creativity, knowledge, and passion will all be on full display. And the winner of the iHeart Podcast Award is... See all the nominees now at iHeart.com slash podcast awards. Audible is a proud sponsor of the Audible Audio Pioneer Award. Explore the best selection of audiobooks, podcasts, and originals all in one easy app, Audible. There's more to imagine when you listen. Sign up for a free trial at audible.com. I'm Daniel Jeremiah. And I'm Greg Rosenthal. And this is 40s and free agents. The games may be over, but the NFL never stops. 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You mentioned that he used to give you money. is that all you ever wanted to do did you play sports or you always like you know what this is my calling I want to be a comedian no I wanted to play sports for sure I played sports in high school football was my favorite for sure of course I had dreams of like let's go D1 play for Ohio State and then we'll see if we can go and then bro I went to the Ohio State Michigan game this year in Michigan and I'm on the sidelines with the players and I'm like I was never going to go D1 bro I'm 12 years older than these people And I'm still like, I can't wait to be like you when I grow up. They're gigantic. The kicker's like 6'4". I was like, this was never a possibility, man. I wanted to so bad. I have such a passion for sports. And since getting older, I've adapted new physical hobbies and sports. I love boxing now and everything. I try to keep myself as physically fit as possible. Because I miss, that's the only thing I miss about school is sports, man. Even when I moved out to LA, I was doing their communal flag football league. and shit like that, racking up MVP and everything. Just showing out on a Tuesday night. So who are you? Tom Brady, you B. John Robinson, Christian McCaffrey. Oh, I'm going deep, man. I was receiver. Oh, yeah. I loved it, man. You JSN and Chase. Yeah, bro. I'm multifaceted, baby. I miss it so much. I definitely have that Uncle Rico syndrome now. I forget that I'm 30, and I'm like, no, I can still put up a 4-7. Let's find some turf. Did you think your grandfather father you think you he knew that that was your calling that being a comedian because you said you started taking to the funny bone in columbus at a very you're 15 that's that's a prodigy thank you for saying that um there is a part of me that thinks that's possible uh in a really weird way i mean he definitely believed in me yeah i i found out what comedy was because i would go stay with my grandpa every single weekend from the time that i can remember okay so we would watch like Adam Sandler movies, David Spade, Rob Schneider, Jim Carrey, Robin Williams, like all these great comedians who turned actors as well. And it's like that's kind of what instilled like a sense of humor in me. My grandpa was also very funny. So he thought I was hilarious. That's definitely what gave me the confidence to try to make other people laugh. Yes. And I actually I have a tattoo of his handwriting that I found on a photo after he passed away. He had nicknames for all his grandkids like as soon as they were born. Right. As soon as they're born within the first couple of months, he has a nickname for all of my sisters, like Chip or something like that. My cousins got one. My other cousins got one. My nieces, my great grandkids have one. And for some reason, he chose Hollywood. Really? No idea why. This is before all the nicknames I could have given you. It could have been anything. You're in Midwest, Ohio. And he said, nobody's never even been to California. Nobody in my family ever has And for some reason to pick that name So that an odd manifestation I suppose But he was always very supportive Like I you know I still have some of his voicemails in my phone And every now and then I would go back and listen to one And I'd say most of them are checking in, like, how was the show last night? Did that new joke work? How'd your audition go? I hope you get this part. Like, he was so supportive. You know, I think there was a part of me that really hoped that I did a lot more than he did. Right. Yeah, I made the most out of this. I think the thing is that when you look at and you mentioned Chappelle, Eddie Murphy, Jim Carrey, Pete Davidson, Seth Rogen, all these guys started as teenagers. Most of the time, comedians get started in their 20s. Sometimes they don't get started until their 30s. And here you are, you know, reaching out to DL. Hey, bro, I hear you coming to Columbus Funny Bone. I'm a comedian. I'm 15 years of age. Let your boy get up there and open for you. Of course. Do something. Did you like you like at that? At what point in time did you realize that? You know what? My way out of Ohio is comedy. I'm not going to Ohio State. As a matter of fact, I'm not going to. Did not have the grades. I was going to go to Ohio Dominion, maybe. Ohio Dominican, maybe. I was probably, I had just went to L.A. for the first time, but I had a manager out of a comedy club in Atlanta where I lived in Atlanta. You lived in A? Yeah, my junior year. The summer between my junior year and senior year. Okay. I had a manager down there who owned the Uptown Comedy Club. Uptown Comedy Club, right? Yeah, you know Uptown? Shut up. Yes. Oh, man, so you know what I went through. it's like you you gotta earn your props at uptallet they don't give you no hell nah they'll boo the hell out they'll boo you take the car keys out jingle the car keys yes i won't say a word they don't this is all you got bro they don't care that you're 15 and white they're like we paid for the ticket or we got them for free at lennox mall because i passed them out um that was where i really got my chops and he he obviously wanted the best for me and wanted me to grow as a client of his so he had taken me out to la for the first time to like see the comedy store see the laugh actor do chocolate sundaes uh do mundy rays with d ray okay that's how he and i became really good friends um and then after that trip there i went back to ohio after and i was like that's what i want to do like i want to move to la and i took another flight out there and i took the it's like the california proficiency exam which in ohio you have to have like amount of credits to graduate high school right and in cali i guess you can just take a test that says like you learned everything you need to learn went out there took the test passed it and then i went back to Ohio, showed my principal, and he was like, I mean, I guess you don't have to go to school anymore. And then I moved out to LA like two weeks later. So I mean, I graduated early, I suppose. I don't have a diploma or anything, but... You don't get a diploma? No, no, no. It's like an equivalency to a GED, I suppose. Yeah. But I mean, didn't need it, thank God. The best decision I ever made was not go to college. When I mentioned these young comedians, Chappelle, Murphy, Rogan, Davis, and carry did you study any of those guys coming up or you charted kind of charted your own no no Chappelle was my guy like that what him and Dane Cook were like the epitome of what I wanted to be as a comedian growing up this was a little this was when like Dane was taking over the world yes Chappelle was in like the the heat of Chappelle show I was I was addicted to those guys that's it's all I would watch okay with the Chappelle show and his early stand-up or even even block party I was obsessed with and I didn't and like Dane Cook's like comedy central specials and everything. I watched that stuff like religiously. And then that's when my mom won tickets on the radio to see Dane at Nationwide Arena. She took me to see that and that like changed everything. That's when I was like, okay, now I kind of get what standup is and I want to do this. And then last year I got a chance to go play Nationwide Arena and actually broke the record for like most tickets ever sold there. And I had Dane come back and open for me. It was like such a cool full circle moment, man. It was unbelievable. He brought this email printed out that I didn't even remember writing until I reread it. It was this whole email printed out being like, hey, my name's Matt. It was like his fan mail email address. Hey, my name's Matt. I'm like a 15-year-old comedian. Same thing as I do with DL. And I was like, I'm a big fan of yours. I just didn't know if maybe you could take me under your wing and mentor me. I really want to be just like you when I grow up. It was the most like charmingly naive email you could have sent to somebody. He held on to it after all these years. It was unbelievable, man. I couldn't believe that. It was the coolest full circle moment do you remember the first joke that you told and became hooked oh first joke and got hooked or were you like a class clown in school did you make jokes in school so that's why you didn't do well in school because you was bulljot well what pissed them off is i did do well in school but i was still around that was what pissed them off the most i spent a lot of time being sent out to the hallway a lot of time in detention uh we used to have up to like six hour detentions so you would like you'd be that's the whole while you're in school yeah you get up so you had iss then in school suspension no that's happening during the day after school i what was that what do they used to call it it was like a like an all-nighter or something like that where you everybody gets out of school at 2 30 high school you'd be there till 8 30 at night and they had to go home and just go right to bed man it was awful i had so many of those i was so sick of school but i i couldn't help but make it fun man i was so bored you you get on stage you go to the comedy so so where did you perform were you at like a a talent show where you did your comedy stuff i did do a talent show you did in seventh grade this was another weird uh i guess coincidence in seventh grade i remember i had like i just started watching these comedy specials and falling over chapelle and everything and i sit down in homeroom in seventh grade next to my friend amanda and for some reason she asks me you know what do you want to be when you grow up and I was like, I think I want to be a comedian, and I'm telling you on cue, my teacher comes in and says, hey, everybody, I'm putting a sheet on the wall. We're doing a school talent show, and Amanda was like, you got to do comedy, and I signed up. I ate the biggest dick possible. It was terrible. It was terrible, terrible, terrible. I did a bunch of impressions of teachers and a bunch of terrible jokes of what I thought was material. It was awful, but that was my first actual performance. And I started real standup like a year later after that. At the start of every new year, I set my goals. I tell myself this year I'm eating right. I'm working out. I'm working hard, staying on track. Then reality hits work, travel, cravings, distractions. Life just loves to test your focus. I've been there. I've fallen off, but I don't stay down because Amazon helps bring me back up every time. Amazon is here to make sticking to your goals easier from healthy snacks I need to work out gear I like to have on hand. All of my everyday essentials are available to purchase in one place. Not to mention, I can get it delivered fast so I don't have to worry about making a trip to the store and adding to my already busy schedule. Great prices, no running around, no extra hassle. Now that's convenient. So when life tries to steer you off track, Amazon can help get you back to the plan, focus on your goals, and stay on your grind. Save every day with essentials from Amazon. So when you started, was your grandfather your audience? Was your mom your audience? Was your friend your audience? So who were the first people to ever hear Matt Reif tell a joke? Probably my grandpa. I spent so much time with him, and I was so free and confident. And like I said, he thought I was the funniest person in the world. So I used to love to try to make him laugh. And then that kind of moved back to like, okay, now I'm going back home with my parents. I'll try some of that on them. It'll work on my mom, not on my stepdad at all. My sisters weren't trying to hear it. And then it moved into school. But once I started doing like comedy clubs, I never really performed for like people my own age. Like my material ever since I was 15, 16 was always I was never like, you know, homework is crazy. I was always like, man, teachers are great. It was always a little bit more adult skewing, which I think helped the transition a little bit. I remember Nick Cannon was telling me he had a hard time switching from like being a kid. Yeah. Now being an adult. And that happens around age 21. You can get away with being 19, 20, and people are like, okay, this is kind of like a... Kind of cute. This is kind of cute. But at 21, people are like, no, I paid for the ticket. You be wrong. You curse. You got to be funny now. Yeah. So I think that helped with that transition a little bit is that I never really catered my set young or anything. Right. So with writing kind of a teen, obviously, you can't do a whole lot of cursing. You got to do... I did. Damn! I cursed a lot, man. At 15, 16, 17, you cursed? My parents didn't care at all, man. Not at all. It was a lot of freedom in it, which I curse all the time. It's such a problem. I cuss all the time. It doesn't even occur to me that I'm swearing. Is this an on-stage problem, or this is a real-life, like, actually I'm having a conversation? It's all the time. I've been trying so hard not to curse as much as this. And I know I can, but I'll say it's the word like. It's all the time, man. I've been trying to work on it. I know it's improper. So who wrote your first set? So did you have an idea of what comedy was or did you go out like, you know what, I'm just going to wing it. I'm going to tell this joke, I'm going to tell that joke. Or are you writing? I was writing, but I didn't know what a set was. So these open mics I was going to was usually five minutes. Yes. So I had no idea about what writing a set was. So the first probably three months I was going, so you've got to imagine it's the first probably 12 times once a week. I was doing a new five minutes every single show. And, I mean, most of it wasn't good, but every now and then I would get some big laughs, and that's what kind of kept it addicting. but it wasn't until a comic pulled me aside and was like are you working on any of these jokes and i was like what do you what do you mean work on like don't you just go up there and say them and then the next time try something else he was like no you're supposed to like formulate a set and then you can build on top of that craft it like going home and working on the jokes is the job yes not just the performance the performance is the reward right and so that that today is still my favorite part about there's nothing there's nothing more exciting than getting that spark of a new piece of material, a new idea, a new premise, and then going home and being like, I know how to make this better. It's so rewarding, man. It's the most addicting part to it. It's like, it's like bakers say, the first time you bake something is not the best time you bake it over and over and over. So you tell a joke and the first time you tell it, it's not going to be the best time you refine that joke. And over time it gets better and better. And you say, what this definitive product that I'm going to present. Exactly. The only problem with that is eventually it feels repetitive eventually you end up performing the joke depending on how many shows you do right chris roxie you're supposed to run a set like i hope i'm not misquoting this is what i heard from somebody else quoting him it's like you want to run the set like 300 times before recording it for a special really that's a lot man i mean and we do do that many shows but there's times that i'm like i don't feel like telling this joke at all but it crushes the audience loves this bit so now you're not really it's not as exciting to tell it the same but part of the job is you got to perform it you got to tell it like it's the first time every time but you know matt the thing is that when old comedians you could tell a joke over and over i could tell a joke and say i tell a joke in tampa i could tell that joke in jacksonville i can tell that joke in miami i can tell that joke in atlanta and nobody would have heard it but now i don't know if you have that like chappelle chappelle have that zip bag he gonna put your phone in there and you're not gonna hear this joke we we only do it for some i try not to do it because people hate it people complain they can't be without their phone they can't yeah what if there's an emergency they'll be fine crack the window in the car we'll be all right it's so annoying because it does make for the best show it makes people be so attentive there's no they can't even think about checking my phone to check the time or check the notifications or whatever it is 100 percent of the time the better show but i try not to have to do it unless it's a recording of some time but we do have a no phone policy at the show yeah we announce it a hundred times. It's all over the Jumbotrons. Do not have your phones out. And you look at the audience and somebody else. Happens all the time. Happens all the time. And I have little cues on stage that I'll do and my security knows that I can see somebody with their phone out right now. You gotta go, man. Just follow the rules. Just be present. So you kick them out? Yeah. I can't trust you, man. People record the show. They bootleg it. They try to post something out of context. And also, without the get you aspect, like, I'm working on a show. I'm building it every show. I'm trying to change it. I don't want you posting the the B minus version of the joke before I get to film it for Netflix. And it's the A plus version of it. Now you're not as excited. Right. So it's, it's just about privacy and respect and respecting yourself as well. You saved up money for a babysitter. You paid for parking. You, you came in here and bought drinks, bought the tickets, like just be here at the thing. Be with me, be in this environment. It's much more exciting. Did you ever forget a line? Do you ever forget a line? Um, when you first started, obviously now you're, you're a full-time pro. Did you ever forget a line? Like, damn my first time, the first time I was probably two and a half minutes in. and I literally, I gotta find the footage because I know it's out there somewhere. I remember saying like, oh shit, I'm like, I'm kind of freezing up right now. And the audience, this was the perk of being 15. It's like, they weren't really gonna boo you with the Columbus Funny Bone. I remember just, I remember it was just some old black lady just goes, you got it, baby. You got it. And I was like, that got a big laugh from everybody. And then that kind of helped me get back into it. But yeah, I froze up. I didn't really know what like memorizing a set was like. I was just kind of going up there and winging it. so when you started that so you're like okay i got five minutes i got 10 minutes i got 15 minutes and so you're like okay i swallowed that bug by the way i forgot it was in there so you're like okay i got five minutes i got 10 minutes i got 15 minutes and you're like okay i'm gonna go here's step here's one beat here's two beats here's three beats is that how you did it or you like or you just wink because some people marlon wayne says i don't write down nothing i'm just going up on stage and I'm winging the whole thing. I, I'll make a set list. I'll be like, I can bullet point a joke one through let's call it 12 or something like that. But I definitely don't go up there and I'm not as meticulous with like word for word. I end up memorizing it that way. Once I'm up there, just via repetition, but like, no, I want to be loose. I want to be, I want to be free when I get up there. I don't have, I had to do this video the other day, Live Nation wanted to know like my routine beforehand. Like, where do you write down your set? What's your motivation when you get up there? And I'm like, I, I'm not like sitting in a Float tank, 30 minutes before my show, playing tranquil music and everything, lighting candles. I'm back there. I just play some music. I'm hanging out with my boys that open for me. Like, I just want to be loose. Like, so much of my set is they're like, hey, you're on in five minutes. And I'm like, oh, okay, all right, I guess we'll just go do the thing. I don't want to be stiff. I want it to feel like we're all just kind of hanging out together. You also say that I'm not Justin Bieber in all your sense. This is the biggest night in podcasting. The countdown is on to our 2026 iHeart Podcast Awards. Live from South by Southwest, March 16th, we'll honor the very best in podcasting from the past year and celebrate the most innovative, talented creators in the industry. It's truly a who's who of the podcasting world. Creativity, knowledge, and passion will all be on full display. And the winner of the iHeart Podcast Award is... See all the nominees now at iHeart.com slash podcast awards. Audible is a proud sponsor of the Audible Audio Pioneer Award. Explore the best selection of audiobooks, podcasts, and originals all in one easy app, Audible. There's more to imagine when you listen. Sign up for a free trial at audible.com. I'm Daniel Jeremiah. And I'm Greg Rosenthal. And this is 40s and Free Agents. The games may be over, but the NFL never stops. This is my favorite part of the calendar. Yeah, mine too, Greg. Free agency, the combine, the NFL draft, pro days, trades. this is where teams reshape their future. This is where Daniel Jeremiah makes his money. On 40s and free agents, we break down every move that actually matters. From my draft evaluations, mock drafts, and team fits. To my top 101 free agents and how real rosters are built, cap space, contracts, and all the tough decisions included. You got quarterbacks on the move. We got teams rebuilding. It's hope season. Yeah, absolutely. It's hope season. We'll tell you what's real, what's noise, and what it means for your favorite team. Smart analysis, real conversations every week. I don't know about the smart, but definitely analysis. Listen to 40s and Free Agents on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Do people think that's who you are? In all my sets. No, no, no, no, no. No, that was like, that was one thing I used to compare in the very beginning. Because he was like, he was it at that time. He was. He was taking over the world when I was starting out. Not a bad guy to get compared to. Not a bad guy to be compared to. Wish I had that kind of success. Right. But bro, watching what he went through in like past documentaries and everything now versus kind of, it's not comparative, but I can only understand the stress I've gone through over the last couple years. To then times it by a thousand for what he went through, I have even more of a respect. Like I love his music already, but to see what he went through and how he's persevered. I know he's had his struggles and everything in the public eye, but like so much props to him. I can imagine what it like to be that global of a superstar Did you ever think that being a comedian would cause this level of stress have this level of anxiety No man I thought it was going to be so much fun I thought I was just going to get to be silly on stage at a comedy club every weekend for the rest of my life. I didn't know, man. I used to be so stressed. And as an artist starting out, as an aspiring comedian, actor, whether you're a singer, whatever it may be, you're so anxious and you're so stressed about like, oh man, am I, am I ever going to make it? If I could just make it, I'll be so happy and satisfied. But that's not true. You get, you develop new goals, new aspirations. And then you start to wonder like, can I keep it? Keeping it is harder than getting it. Anybody can get a flash in the pan. It can happen. One viral video can send you into, you know, a moderate level of fame. But like, once you get a taste of selling out arenas and hanging out with your idols and you got enough money to buy your mom a house, your sister's houses, your grandma's houses. Like that's a lifestyle you don't want to give up. Right. It's so addicting. I never thought it would be like this. I've, by 30 years old, I've achieved 99% of my dreams. Damn. Yeah. And you're not even half, half your life is not even gone. I know. And it's such a blessing. Like everything I get to do from this point forward is just amazing extra credit, man. Like I feel so blessed. But it also makes me think about like how much time I have left. Like what am I going to do with the next 50 years? Like the possibilities are endless. Is there a situation where you see yourself retiring or you just like, you know what, as long as I can tell a joke, as long as I can entertain an audience, I don't see myself slowing down. I don't see myself stopping. I can't see myself stopping for the pure fact that I love it so much and I don't know anything else. Right. Like this April will be exactly half my life that I've been doing comedy. It'll be the 15 year mark. Wow. So I haven't really known anything. Like I tell myself I want time off and how exhausted I am. I'm like two hours of sleep right now. Right. I can be like, oh, I'm exhausted. I take three days off. I feel like I fell off. I'm like, well, I got to get back to work. I have this thing I got to do. I got to do this thing over here. So I can tell myself that maybe someday I'd want to settle down, but maybe it's just a different pacing or maybe it's transitioning over to acting more. Maybe I just do stand up kind of when I feel like it. Like Kevin Hart's found a wonderful balance, right? He'll go knock out a couple of movies a year. And in the midst of that, he'll go tour, pop in and do spots, work on his set. Like that seems, I mean, it's a, it's a harder workload like i know he's like one of the hardest working people on earth but it feels like it's a more exciting balance he's not in he's not totally consumed in touring which is what i've been for the last right because that's a lot of travel at least that well like you do on your own location you're in one spot yes when you tour you're in jacksonville you're in miami you're in orlando you're in atlanta yeah yeah yeah i'm so sick of planes man if i can drive six hours i'll avoid flying really i would rather i would rather drive six or seven hours than i would fly for two hours I really would. So, I mean, you got a tour bus. Do you and the boys, the homies hop on the bus so y'all chill? We did the tour bus in 2024, and it was so much fun, but it almost killed me, bro. Because we were doing two shows a night, six nights a week with meet and greets after each show. Wow. So we were doing like 40 to 50 shows a month for like nine months straight. And it got to the point where like you get done with the last show at midnight, 1230. Then you got a meet and greet till 1, 115. Are you cutting off the meet and greet? So you got 100 in the meet and greet? You got 250 in the meet and greet? I think we did 50 per show. I think it was. Okay, that's what I had to do. But as amazing it is to get to meet your fans and everything and hear their stories and all that, it's like doing another show because you've got to be on. You want to be present. How are you doing? Where are you from? Yeah, you can't be the guy who's being like, all right, get in here for the picture. You might feel that way, but they pay for the experience. These are people that love you the most. But then you get done with that at 1.30, and now you get to go back to the bus. Now you get to light one up with your boys. Now you want to just enjoy yourself and decompress. fall asleep. So in other words, you're not going to bed until what, 4 o'clock now? 4, 5, 6 o'clock, get up at 2, walk to whatever the local gym is there, and then now you got to go back inside for a show. I was seeing daylight for like 30 minutes a day for 9 months in a row. It fucked my sleep up so much, man. Wow. Yeah. I had to cancel some shows in Indiana one time because I literally couldn't walk. I went 5 days in a row without a single minute of sleep. Couldn't do it. I couldn't perform. Had to go to the hospital and everything. Had to cancel. they were so mad they were so because it was like night of the show like people were getting sat i'm heading to the venue almost fell over in the bushes because like i couldn't see couldn't walk straight and everything and i got there they're like yeah you're you're exhausted yes i saw some sleep doctors they ran some tests and everything and they're like yeah you know how like your circadian rhythm is kind of what helps you find your sleep patterns and they're like you don't have a bad circadian rhythm you don't even have one like your sleep schedule is so your body has no idea when it's supposed to fall asleep. And I'm still struggling. I'm still struggling with that. I've had it my whole life, but that definitely like sent me over the edge. Definitely doesn't help. But I also don't know how to not be that busy. Like I would rather be exhausted from work than sitting around being bored. You mentioned DL, like your first start, you got DL was coming to the Columbus Funny Bone and you reached out to him and he put you on. I think you have a story with Mike Yelp. What's some of the best advice? Because DL has been at this thing 30, 40 years. Mike Yelp's been at this thing 25, 30 years what's some of the best advice these guys giving you some of the best advice i've ever been given is not to quote nike but like just do it yeah like you sometimes you'll have an idea of a piece of content you want to film maybe it's a script idea or just a joke idea run it by a friend they'll be like i don't i don't get it and you're like now you find yourself arguing yeah why you don't get it like no i'm trying to convince you it's it's and they're like just stop my friend Eric Griffin told me, he was like, stop trying to convince me. Just do it. Go on stage or go film the thing that you have an idea for. Nobody else is beside your brain. Nobody can picture and visualize exactly what you're trying to create, which is exactly why they're not in your shoes. You have to go show them and go do it. You got to gamble on yourself. If you're not committed to your own decisions, why would anybody trust them in the first place? I believe in just betting on yourself and what's another it's not like a piece of advice somebody's given um ralphie may used to tell me not to wear cool shoes on he used to tell me he was like yeah it's distracting from what people are trying to say i'm like you're 400 pounds you don't think people are distracted by what you're saying right now he was a little wrong on that one but he was he was a cool dude you ever get a chance to meet him i have not met ralphie but i hear great stories the body the best guy he was he was like my first real mentor like he took me on my first theater tour when i was 19 i used every bit of that check to pay for my teeth to get done immediately he was the best even when i was still living in ohio he would let me drive down from ohio to nashville where he lived and do his christmas shows with him at zany's so that he could pay me some money so i could go back to ohio and buy my family christmas presents with him he was the nicest guy when i I moved to LA he'd take me out to lunch and he'd make me order like five meals and I'm like is this this for me or for you and he was like no this is yours if you order five meals now you get to take the leftovers home with you right and now you don't gotta buy groceries this week wow he was the nicest guy man that is yeah man it's obviously the middle bunk on the bus and he will walk by open the curtain fart in the bunk and then go back to his room diabolical man but the greatest guy Yeah. You mentioned that the Uptown Comedy Store in Atlanta, Uptown Comedy Club in Atlanta. How did the Atlanta scene? Because, man, you know, as a comedian, you have to be able to branch off. You have to be able to get black people to laugh, white people to laugh, young people to laugh, men to laugh, women to laugh. It doesn't matter because funny is funny. And you have to. And so you coming up and they look at this young white kid. They tried to make me laugh because we laugh differently. Of course. It's more fulfilling to get black people to laugh. I got to say. Because white people laugh. Yes. Black people. No. No. No. No. Ow. Ow. Ow. Ow. God damn it, Shannon. That's how we laugh. We all. Man, we stand on top. It's the best. But when y'all don't with us, you don't with us. There's no pity laughter. Boo. from the back they don't care man it's so we don't feel we don't so to get in that to get to like grow up in in comedy in that kind of do or die environment it definitely helped me like carve my chops like had i not done that i never could have done wild now like atlanta's full of beasts man like i saw ryan davis come on here talk about ronnie jordan and everything i mean even special k back in the day like anybody who went through def jam at all i opened for them in Atlanta. So I'm getting to open for like Def Jam crowds in the middle of Atlanta when I'm 15, 16 years old. It was the best possible place to cut my chops, man. Had I gotten wild now like two years before when I originally auditioned for it, there's no way I could have survived, man. I couldn't have hung with like Carlos Miller, Chico Bean, DC on fly. There's no way. Those guys are absolute beasts, man. Atlanta's an amazing comedy scene. They really don't get the credit they deserve. Because you have to be out the car. But the comedy scene's amazing. Drive into Atlanta. Yeah, because when you think about it you got quake you got bruce bruce you got uh rns jay you got uh what's the guy from st louis uh no the guy that came on here oh said said the entertainer was the big guy i love said yeah dc curry i mean you got the heavyweights dc curry as a matter of fact going back to uh to great advice i was open for him at the cleveland improv and i was watching his show And, you know, he's a really great storyteller. Yes. He can sit in five minutes of silence building up to this one big punchline. I remember going back in the green room afterwards, just so naive. And I asked him, I was like, you know, there's like there's so much silence in the storytelling that you're doing up there. Does it ever feel weird that like, does it ever feel like you're like bombing up there? And he just started laughing to himself. And he was like, no, I'm not bombing. He was like, I've got their attention. He's like, silence is one of the most powerful things you can have in stand up comedy. Yeah, absolutely. If they're quiet, they're listening. It's when they start talking amongst themselves. It's when they start heckling. That's when you have a problem. It was like patience and timing is what I'm building up for that one big punchline. That never really occurred to me. I thought comedy was supposed to be like boom, boom, boom. It doesn't have to be like that. If your style is storytelling, grasp them. You know what I mean? Grab their attention. Hold them for that one big moment. That's so powerful. Because some people are storytellers. Some people, you know, 30 seconds, boom, it's gone. Some people, it takes a couple of minutes in order to build up to that crescendo. And then boom. Yeah, yeah. My set now is a perfect mix of that. I love stories. I'd say 45 minutes of my set right now is just stories. Like, I need you to follow me on that route. I got to practice that patience and timing. But you like that rapid fire sometimes, too. And that's just for me. You know what I mean? That's where, like, the crowd work is kind of fun. You know what I mean? Like, that's something new and refreshing I get to do every show that's just kind of spontaneous for me, you know? It mixes up the set a little bit. Because, like I said, you can get tired of your own set. So at 17, I think, if I'm not mistaken, you decided to go to L.A. And you're famous. So how was that received? You're like, Mom, Grandpa, I'm about to be like Jed Clampett. I'm about to move to Beverly Hills. Jed Clampett. Wow. What a reference. I'm about to move up out of here. I'm going to Cali. I'm going to maybe not Beverly Hills, but I'm getting up out of Ohio. They were so ready, man. My mom was like, one less mouth to feed. Perfect. They were so supportive. Because nobody in my hometown leaves that hometown. And nobody in my family has also ever been to college. So there was no expectation. It was like, okay, here's this thing that you're already kind of traveling to do. You're already making a little bit of money doing it. You're really passionate about it. We think you're good at it. So by all means, you've got some good mentors out there. I went out there. I lived on Eric Griffin's couch for the first six months I was out there. Then I moved to another friend's couch. Then I moved to a, what's that website called? So you can go on and just find anything up for listing. Craigslist? Yeah, Craigslist. couch. I did the whole crouch for like two and a half, three years, taking the bus. Like I had to grow up so fast. I didn't know about, I didn't know about paying bills. I didn't know about grocery shopping. You didn't know anybody in LA? I knew a couple of people, just comedians though. Just comedians I have met online or during that first trip to LA that were like, when you get out here, let me know. And I was lucky enough that they, uh, they fulfilled those promises. Wow. Yeah. I used to just walk to either the improv, the comedy store, the laugh factory every single night and just hang out, like just wait and see if maybe somebody didn't show up for their spot and somebody there would vouch for me and be like, you know, let this kid fill the five minutes until so-and-so gets here. And that's really how I, like, built up to being, like, I think I'm the youngest regular performer at the Laugh Factory besides Tiffany Haddish. Wow. Yeah, just from hanging out and people vouching, man. It was an amazing opportunity. And just getting to hang out with everybody who I had seen on TV and that, like, made me want to do this was just, it was amazing, man. You got some opportunities to be on Disney, but you hear these stories. A lot of these kids that own Disney, you hear them struggle, not only later in life. And so why haven't you, why haven't that befallen you? What was made you so mature that you were able to be in that environment and move forward and succeed? Well, I think it's because I didn't have my own show. I was a character on somebody else's show and they were struggling. But I'm checking in for a day. I'm like, what the fuck is their problem? Breakfast was great this morning, man. This set has everything. You're being pretty ungrateful right now. I mean, there was just less pressure on me. I got to show up on a couple of guest episodes on some really fun shows there. But again, that was my first experience with television. So getting to see what it's like to have a green room, getting to rehearse on set, learning what table reads are and everything, learning that you can get replaced at a table read. Damn! Yeah, I got invited back reoccurring on this show. And after the first episode went so great, second episode, I felt so comfortable. This is like the next season. So I went back in there, didn't know my lines. And the first rehearsal of it, the director comes over and goes, hey, man, if you don't memorize these lines for this network meeting we have coming up, they're like, they're going to recast you. I went back to my green room and just studied the out of every beat, every syllable. Because when the network comes in to watch it, you got to perform it. They want to see how it's going to be on camera. That's when I realized how serious all of this was and also how many pieces there are. That's why it's so hard to get work as an actor, I think, because as a comedian, you're in control of your own destiny to a certain extent. You write your own jokes. You book yourself for gigs. You are in total control of what you can and can't do for the most part, aside from getting on television. Whereas acting, it's like there's 30 people you've got to get approval of to get a spot. You've got the casting associate, casting director, the director, then the producers, then the network. It's such a complicated game. which is why I think stand-up has allowed me to get in the position I am now because I love to work hard. I woke up every day in L.A. for 12 years trying to create new opportunities for myself. So when it finally did break, I'm like, I want all the work now. Like, exhaust me, man. I wanted to be this busy. Is it a situation where, like, when you're a comedian, you write a set, you're writing that set. Compared to television, somebody else is writing a joke for you. And not necessarily, you wouldn't write that joke like that. So it's like, it comes off as strange or odd because that's not the way I would have wrote that joke. And so me, it's kind of. No, it happens, especially for network stuff. It's like, you know, PG, maybe PG-13 at most. It's some of the worst writing ever. I can't tell you how many auditions I've gone on for like a network sitcom that I'm like, I'm a professional comedian. I have no idea how to make this funny. This is this is such a terrible, terrible joke. And this person got paid six figures to write this joke right now. It's unbelievable. That's why, again, this job is so freeing. I get to just be myself. I get to just float out my sense of humor, project it out there, and God willing, people like it, man. Did you get an opportunity to get on Comic View before it got canceled? Yes, dude. That was my first TV credit ever, actually. Samore was hosting this season. Yeah, okay. I got found at the Comedy Union off of Pico. Okay. You know that one? Another Street from Roscoe's? Oh, no, I don't know that. Oh, it's an older joint. It's closed down now. it was one of the black clubs around LA which was one of the very few places I could really get stage time and I went in there and Amber Bickham is a great casting director she cast a lot of great shit and she saw me in there and said I want you to audition for Comic View this is when it was just coming back I went in we taped in Atlanta actually I got a standing ovation as the closer for my episode they filmed three comics per episode got a standing ovation I think I was I think I just turned 18 and And they canceled the season before my episode, so I never even got to see it. Damn. I know. I know. I think Carlos Miller might be the only person who got their episode actually aired. And they saw it and they were like, nah. Wow. That's unbelievable. I know. So in that situation, now you parlayed that, you get Wilding Out. You the youngest cast member so far of Wilding Out Did you like How did Because Wilding Out is kind of different because you like going back and forth Somebody bagging on you you bagging on me It a different so it like Yeah, the pacing's up, the intensity is there. Because like I said, everybody's a beast, man. Yes. And you're fighting for episodes too. It's like, it's literally like a team. You got a roster, right? But there's only so many starters. Yes. And you don't get paid unless you play either. Yeah. So we have these, we have these workshops for like a month before we start filming everything. And And that's maybe like two weeks before. We're going through all the new games and everything, teaching everybody how to play the games, how to write for each game or whatever. And I went in there as somebody who had never really been on a TV show outside of a couple of Disney episodes. I'd never done anything competitive in the comedy space either. And I was so nervous. I would go in there with my hands in my pockets and super slouched over. And the producer of Niall Evans was not having that shit. He was like, no, you got to come in here confidence like that show the workshops for that show like kind of taught me how to like be a man like he used to make dc young fly like get in my face like like about to like hit me like we he was really about establishing confidence in me because he was like if you can't be confident back here how you gonna be confident in front of a live packed out crowd for all these cameras where you get one shot and it was nerve-wracking but it definitely pulled the best out i mean it's one of those instances where like pressure makes diamonds right like the pressure was such an institution for how I developed as a comedian. Did you get turned down the first time you auditioned for the show? Yeah, yeah, I did. It was when they first rebooted the season. It was when Carlos and Chico first got on and everything. I drove down from Ohio because they had auditions at the Uptown Comedy Club. And my manager that was able to get me an audition, I drove down, which was like nine hours, and it was an okay audition, but didn't get it. I think Pete Davidson actually got on for that one, and then I got cast when he left as kind of his replacement. they just replaced white guy after white guy. So they replaced a white guy with a white guy. Because he replaced Mikey Day when he left. It was just one after another. So there was an opening, thank God. And I didn't get the first one. And once I got it when I was just turned 19, I think, bro, I was so barely ready at that time. You can go back and watch. I was terrified. So much of my stuff from episodes got cut because I didn't deliver it confidently. But I needed that. I hadn't been ready. And that's a reoccurring theme in my life where everything happens so young for me. Even the arenas and everything. When our theater tour for the Problematic World Tour sold out in the first 48 hours of pre-sale, we sold 600,000 tickets in 48 hours. My agents were like, oh, we could just transfer these to arenas. I was like, yo, I just started selling out comedy clubs. I'm not ready for that. You've got to take the necessary steps. I also want to experience theaters. A comedy club show is different from a theater show, is different from an arena show, is different from a stadium show. And I wanted those life experiences, you know. If I would have jumped right into arenas, there's no way I would have been ready. I was barely ready for the theaters. But the comedy club was where I was like just starting to like. This is the biggest night in podcasting. The countdown is on to our 2026 iHeart Podcast Awards. Live from South by Southwest, March 16th, we'll honor the very best in podcasting from the past year and celebrate the most innovative, talented creators in the industry. It's truly a who's who of the podcasting world. Creativity, knowledge, and passion will all be on full display. And the winner of the iHeart Podcast Award is... See all the nominees now at iHeart.com slash podcast awards. Audible is a proud sponsor of the Audible Audio Pioneer Award. Explore the best selection of audiobooks, podcasts, and originals all in one easy app. Audible. There's more to imagine when you listen. Sign up for a free trial at audible.com. I'm Daniel Jeremiah. And I'm Greg Rosenthal. And this is 40s and Free Agents. The games may be over, but the NFL never stops. This is my favorite part of the calendar. Yeah, mine too, Greg. Free agency, the combine, the NFL draft, pro days, trades. This is where teams reshape their future. This is where Daniel Jeremiah makes his money. On 40s and Free Agents, we break down every move that actually matters. From my draft evaluations, mock drafts, and team fits. To my top 101 free agents and how real rosters are built, cap space, contracts, and all the tough decisions included. You got quarterbacks on the move. We got teams rebuilding. It's hope season. Absolutely, it's hope season. We'll tell you what's real, what's noise, and what it means for your favorite team. Smart analysis, real conversations every week. I don't know about the smart, but definitely analysis. Listen to 40s and Free Agents on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I'm mad. Yeah, I'm a different person. And that's no shade. Gary Owen is a f***ing legend. Like, that dude murders. There's very few comedians that I would not want to follow. Gary's one of them, man. But he always has, like, the cachet of, like, he's a white comic for black audiences only, right? He's just an urban comic or whatever that means. And I just didn't want to pigeonhole an audience. You know what I mean? Like, I want to be for as many people as possible. now whoever finds me finds me if it's all black people amazing if it's all white people amazing it doesn't matter to me funny funny is just funny but i didn't want to be pigeonholed into like oh he only does urban stuff because it's it's so unfortunate that that limits opportunities in hollywood as well like gary was great and was a think like a man yes he was so good yes but because a lot of hollywood and the entertainment industry just thinks oh he only has a black audience i don't know why people will go see him i feel like that hinders a lot of his opportunities And I could be wrong, Gary, if I'm wrong, I apologize. But it's really what it feels like. I feel like he deserves a lot more. I agree. And from a young age, I just saw that. And I was like, I just want to make sure I leave all the doors open that I can. But he's, oh, he's a beast, man. Were you surprised by how Nick, the jokes that he would allow you to say on Wildin' Out? Yeah, that was my biggest problem with the show, actually. That show, everyone has their role, right? And my role was the white guy. and if you made any jokes outside of being the white guy, that shit was like not okay. It would either fall super flat that nobody wanted it or just kind of frowned upon. At a certain point, as a comedian, I want to say other shit. I want to say something kind of clever. Something that I actually put some thought into. Something that's not racially based. And that's all they really wanted after it. All they ever wanted out of it. So after it, after like three seasons of it, I was like, I just want to do other things. It takes up so much of my time. I'm not on every episode. It doesn't pay well. I need to go tour. I need to go be me on stage. So it was a little limiting. Yeah. But I mean, the exposure from it was amazing. You know, my first season on there, I mean, I bumped up thousands and thousands of followers that allowed me to tour for the very first time. So I'm so thankful for it. It was an amazing institution. It was a great opportunity to open so many doors for me. So I'm very thankful for it. Well, you got an opportunity to go against the 85 side crew. You got DC, you got Chico. I want to go do that show with them so bad. Those are some of the most talented people I've ever met in my entire life. When you look at the success of 85 South, and we mentioned those guys, so it strikes me as that you're not surprised at the level of success that they're enjoying. Not at all, man. It's so well-deserved. They're so talented, man. Sometimes I'll watch them just riff a freestyle song, and not only is it a good song, but it's hilarious. They're doing the instrumentals. They're doing the lyrics. They're doing the jokes all on the spot. They're so talented, man. I really do love those guys. I'm so happy for them. Who do you think is the all-time, who's the funniest member of Wilding Out cast? Of all time? Fuck, man. Oh, that's tough. Oh, I mean, Prime Cat was something else, man. Some people forget he was on that show. In the original seasons, Cat, Kevin Hart. But then, I mean, Carlos is up there, man. Carlos is a brilliant comedian, man. It's got to be one of those three, I think. Do you have a favorite? Probably Cat. Probably Cat. Probably Cat Alos. Because the thing is, is that. Did you see his new special? Cat Williams? Yeah, I did. I did. I watched it. Okay, good. And you know what the thing is, is that for those guys, I mean, it's just like this. It's just because you're on cue. And like for a comedian, like if I'm telling a set, it's one thing. But to just Joan, to just go back and forth. You got to grow up with it. You really do. If you don't got black friends, you're not going to laugh about it. There ain't no way, man. Because white people don't do it. They call it bullying. Yeah. It's so frustrating, man. We call it Jody. We go back and forth. I went to an HBCU. And so we go into the student center. If you if if you didn't have thick skin and you went to an HBCU, you're going to end up leaving. You're going to end up going to a PWI. Yeah, yeah, yeah, yeah. Because that's a for you. Because, you know, we you know, you've been around black people. We talk different to one another than where you guys communicate with one another. Oh, of course. And so we bring that right to you. Oh, well, you're right. So you will get this, too. Which is why black people are always the more fun comedy audience, man. Y'all know what jokes are. Yes. Context is everything, man. You realize it's not a personal attack. No, it's absolutely not. I'm just saying the funniest possible. The more I drones on you, the more I fuck with you, the more I try to hurt your feelings, the more I actually fuck with you. Like, I genuinely love you as a person. You know what I mean? Yes. It's so frustrating that white people don't get that. It's so annoying. They take a person like you're bullying him. Yeah, it's so frustrating. We're so f***ing sensitive. It drives me insane. If I ever get a complaint for any of my material, it's a white person. 100% of the time. 100% of the time. The pay. You mentioned that they didn't pay a whole lot of while they got. So what do you get? 250, 300 an episode? It's 1,000 an episode. But if you want three episodes a season. What can I do? And by the way, you can't go do other shit. You taping for a couple of weeks. So you're making. It's all perspective, right? So I'm making $3,000 over the course of a month. Which don't get me wrong. That's not bad. People pay their bills on that all the time. I imagine that's more the minimum wage, but you can't go do anything else. I could be going touring. I could be auditioning for other things that are going to pay more. So it's an investment. It's a gamble. You've got to hope you're on these episodes. So it's not $9 an hour or anything, but in comparison to what touring pays or what other TV shows pay, it is very little. And then you've got taxes on top of that. So it ends up being $300 an episode. Yeah. So in other words, you're going wilding out. It's really about the exposure. You're giving people an opportunity to see Matt, to see like, you know what? This dude is really funny. If he ever toured, I got to see him because I want to see what he really like. Because I see him go back and forth and he can join. He got the gift of gab and he's quick witted. So if he got a set, he can do something 30 minutes, 45 minutes. I want to see him. Yeah, it's more of a launching pad than anything else. The exposure for there is unmatched, man. What are they on, season 26 or something like that? That's not off luck. They have an audience. People love the show. People love the people from the show. We all tour together. As soon as you leave the show, it's like we'll go do shows on the road, five, six cast members at a time, sell off these big theaters, sometimes an arena. People love the show, dude. It's awesome. You mentioned that when you started Wild and Out, you ended up the first thing you did is about bought some new teeth. Yeah, man. After my first season, oh, bro, it was right after, it was in between seasons and Ralphie Mae took me on tour. I couldn't wait to get my teeth fixed, man. It was, I had Ohio teeth, bro. It was bad. I had them straight hands, man. Really? Come on, man. Bro, it was bad, bro. It changed everything for me, man. Because I had a beautiful 30-year-old girlfriend at this time. I'm 19 years old. I got these terrible teeth. I was like, I got to give her a reason to stay. Because it's not the money, for sure. It ain't the dick. There ain't no way. There ain't no way. She's 30. Yeah. There's no way. You said you would rather have died than smile. Yeah, man. So I'm still really bad at smiling in photos. I just didn't. But you got the grill now. You good. I know, but I don't know how to smile. I feel like I look weird in photos when I smile with my teeth. because I didn't grow up doing it. I didn't have, like, the practice of doing it. So how long you had the teeth? I got them when I was 19, so 11 years now. Well, you're good now. I try. Because, you know, you normally talk, you know, you got something, you got a missing tooth on the side, you got a cavity or gap. You got the Jack Hughes? Yeah, you're talking like, man, go head on with that, man. Because the thing is, as a comedian, the one thing, and you bag on people, the one thing, you cannot have any imperfection. Oh, bro, are you kidding me? God damn, they're going to get you. Oh, if you got something? Man, go ahead on. They call you jack-o-lantern. All of it. All right, relax. Relax. Okay. All right. All right, no more cognate. No more cognate for Shannon. That's enough. So why did you say, you know what, if I ever, because I said the same thing. If I ever get me some money, oh, I'm going to get my mouth fixed. Y'all ain't going to be ragged because I'm all of them people face-joining, talking about people, and they say call you snag-o-puss or jack-o-lantern, and you feel it some type of way. so I'm like I'm gonna get me some teeth is that how you thought about it was more just a confidence thing man like I knew they were f***ed up and I know how important teeth are when you meet somebody you look at eyes and teeth yes the two most important things and I was just so insecure about it I know there was nothing wrong like you people you don't gotta have a perfect smile you can be a wonderful person people still gonna like you but I knew the career that I wanted to have and by the way I checked in to get embraces first because I just couldn't afford braces growing up so I looked into that so you want straight gap teeth yes that would have been great That would have saved me tens of thousands of dollars. But they told me, they were like, you're going to have braces for like six years. I was like, I am not about to be in my early 20s with braces on. I wouldn't get laid ever. Are you crazy? My teeth were like, I think they were like $24,000. So I paid half up front and then I had payments for the next like three years, which was terrifying to miss a payment. The dentist is going to show up with some f***ing. Well, you can't take them out. They're like, oh, y'all stuck. Y'all teeth. So I missed them. I could have bought two pairs of fake titties with these tees. It's unbelievable. I got a Honda Accord in my mouth, man. It's unbelievable. But how do you feel about people saying that, man, you've had other work done? They ain't just fake teeth. You done have some jawline. You done have some Botox. It's the funniest thing in the entire world, man. Ugly people love to say that. It's the funniest. Oh, so you just get better looking as you get older? Okay. Yeah, not everybody peaked in high school, man. I don't know what to tell you. It's so funny. And it happened the weirdest way because when I first started to get famous, everybody's first thing was like, oh, he's not funny. People just like him because of how he looks or whatever. And then that caught on to being like, okay, I guess he's a good looking comedian. And people were like, nah, I don't like that. So now we have to find some way to make him not good looking. Right. So now I've had plastic surgery. I look the same. Right. I look exactly the same. You know, people do age. People do age. And I feel like I'm aging well. I like to think so. But just work out, man. Take care of yourself. We see what's going on now. Now Jim Carrey's gotten cloned. I don't know, man. That shit looks weird. Come on, man. No, listen to me. Come on, man. Listen to me, man. That shit, it looks weird. It don't look weird to you? The man got cloned? I don't know about that. His eye color's different. His nose is different. Face is wider. The one I would believe more than him, you see Britney Spears? Yeah. You see in her videos? How'd she get a gap in her teeth? She never had that before. yeah I don't know why they gave her my teeth that's just so weird to me man I listen I don't know I've never been invited to any any ditty parties I've never been invited to any Illuminati parties I don't I don't know how it goes I don't know what the weird conspiracies are in Hollywood I'm so far out of the loop I'm kind of mad right I thought I was doing well I haven't been invited to anything this concludes the first half of my conversation part two is also posted and you can access it to whichever podcast platform you just listened to part one on just simply go back to club Shay Shay profile, and I'll see you there. This is the biggest night in podcasting. The countdown is on to our 2026 I heart podcast awards live from South by Southwest. March 16th, we'll honor the very best in podcasting from the past year and celebrate the most innovative, talented creators in the industry. It's truly a who's who of the podcasting world. Creativity, knowledge, and passion will all be on full display. And the winner of the I heart podcast award is. See all the nominees now at iHeart.com slash podcast awards. Audible is a proud sponsor of the Audible Audio Pioneer Award. Explore the best selection of audiobooks, podcasts, and originals all in one easy app. Audible. There's more to imagine when you listen. Sign up for a free trial at audible.com.