The Three Questions with Andy Richter - Chris Fleming

Episode Date: November 3, 2020

Comedian Chris Fleming talks with Andy Richter playing off his androgyny, being featured in his high school’s film festival, putting in the work for his web series Gayle, and more.

All right, here we go. Let's start podcasting. 3, 2, 1, podcast. Hey, everybody. It's Andy Richter. You're listening to The Three Questions. And I have a a very very funny fella here today uh whose videos you may be familiar with whose comedy you may be familiar with whose joie de vivre you may be familiar with it's chris fleming hi andy it's uh it's uh massachusetts own chris fleming thank you so much for having me andy i'm happy to be here uh i i love your stuff you're very very funny and very unique too like i just um what i love best you know to call it absurdist like what you do it's like it just seems like you know it's like calling michelangelo's david a sculpture wow you know it's just because what you do is so fucking silly and so like uh just like goes deeply into nothing and it's just

my favorite kind of stuff deeply into nothing yeah but you know what i mean like you just join me as we explore nothing yes but i mean you mean, you know what I mean. It's like, I mean it as a compliment, and I hope you take it as one, but it's just like... Oh, no, no, I'm fine that very much under a compliment. It's very poetic how you said that. Oh, thank you. Because you just, you do follow, you follow like, you know, in all this sort of possible comic trails that one can take in one's work. You follow ones that not many others would follow. And it's fantastic. It's really great. I think it's the nature of working so

very alone for so long. I think that everyone's on my same page. And then I release these things, and it turns out I'm kind of, that's not the case. So I think it's this kind of like the ramblings of a hermit in some ways. Well, why so alone? Oh, I guess when I say alone, why so alone? I mean, wasn't there other people to be funny with? You have friends. I do have friends. I guess I just uh i don't know

i just started doing it alone because i started doing stand-up and then i then i then that turned to video production and or video making and i i was i guess when i say alone i mean like no um i did it so out of the uh any kind of industry or whatever you know it was it was very oh yeah yeah yeah that's kind of what i know exactly what you mean yeah i think it's i think i just didn't get notes for a while and i think that's why it's kind of unhinged well now let's oh andy let me also you complimented me earlier let me just say i love i i've been such a fan for so long and also i i you were on my favorite show of all time, Strangers with Candy. Oh, thank you very much. Yeah, that's a good one.

I'm a huge fan. Oh, my God. Yeah, yeah. Oh, my God. It's such a good one. Yeah, you want to, I mean, talk about absurd. That was like, that's the kind of show that when you look back on that, and if any of you out there don't know Strangers with Candy, it was a show starring Amy Sedaris and Stephen

Colbert and Paul Dinello kind of helped write it. know strangers with candy it was a a show starring amy sedaris and stephen colbert uh and paul danello kind of uh helped write it um but you could check it out it would the idea of the show was that there was a woman who had and amy based it off there's a film of this woman like it's like an after-school special yeah it was she but there's this woman who who actually says i was a boozer a user and a loser oh really it's like a it's like a scare film that they used to show kids and it's on it's on the internet if i find it i'll send it to you after this but she based the character on that on this woman that like would give sort of a scared straight talk to kids right and so it was this woman who had been give sort of a scared straight talk to kids.

Right. And so it was this woman who had been a boozer, a user and a loser, who at like age, I don't know, she's in her 50s or something, goes back to high school. And the whole thing is sort of like an afterschool special based on that. It's just so beautiful. I can't even believe it was on TV. The fact that it exists, it gives me vertigo that it was. You were in the episode, I think, where her dad gets eaten by wild dogs.

Yes. Yeah. I actually was in it like three times. Yeah. My ex-wife was. She was also in it. She was the gym coach. The gym teacher, yeah.

My ex-wife was – She was also in it. She was the gym coach. The gym teacher, yeah. She played Coach Cherry Wolf, who was like – who was very – well, I mean, she basically was playing like your classic sort of masculine female gym coach. Yes, quite butch. Yeah. Quite butch. Yes, a butch gym coach. And the best part of her history in it was that when she was pregnant with our son, our first child, she's like, guys, I'm pregnant.

I'm visibly pregnant. And they're like, meh. And they didn't do anything to change it. They didn't do anything to hide it. They're just like, all of a sudden, Coach Wolf wolf who has been very butch up to this point is suddenly pregnant yeah which i was in vitro maybe it was so great and i was so i it was funny because i was so much of a bigger fan of that show than she was which in many ways i understand because it's hard when you're a part of something to be a real fan of it and i think also too

stressed about making it right yeah and i also think too like for her that show represented like being picked up on a manhattan street corner at 5 30 a.m right in a in a in a in a like a 16 passenger van that had 17 passengers in it like just they because they didn't have a lot of money but the budget the budget was probably about three thousand dollars absolutely absolutely and they'd go out to new jersey to some like defunct church school or something and there's no trailers there's no nothing so yeah sarah it was like okay get up at 5 30 and then go sit on a folding chair in the corner of you know saint ignatius and paramus or something like that right

right um now tell me about your schooling you're from you're from stowe massachusetts that's right yeah yeah yeah yeah very people people often confuse it with stowe vermont but stowe massachusetts is which is stowe vermont is a ski place right that's right my family my family's very into skiing uh and i was always too cold I would get frostbite very easily. Well, you're a skinny thing. You're a skinny little thing. I am a skinny little thing. A skinny little thing. And my cheeks would be exposed, and they would put a cream on me to try and fight the frostbite. But I think in the 90s, they hadn not really, they hadn't specialized the cream enough. And what it would do would just give me frostbite quicker.

It was kind of just like putting petroleum jelly or something on my little cheeks. Like putting butter on when you're tanning. Yeah, yeah. Right, right. It exacerbated it. But I didn't have the power of language to explain. Like, you're just, you are just attractive. You're making it worse.

Yeah, yeah, yeah. You just put me in the lake, you know? Yeah. Classic parenting, you're making you are just attracting making it worse yeah yeah yeah you just put me in the lake you know yeah classic parenting you're making it worse yeah yeah um but in a situation but yeah so my yeah but so yeah and that's another thing i also like i was never like a skier but um i mean i did i taught skiing for a little while but it was so important to my family and it's still like something that i'm kind of you know i I kind of want to be more alt than that. You know, I kind of been running from that and I'm not very good at it. But I know I've been over served when I ask someone, do you ski?

That's when that's when auntie needs to go home. That's when I know. That's when I know it's showing, you know. Do you ski? Yeah. Yeah. And if I invite you to go skiing, that's when you need to take me to urgent care. Yeah.

That's like many people's southern accents. That's when their southern accents return. That's when it's time to go home. That's right. That's right. But yeah, no, Stowe, you know, it's a very Irish Catholic community. My schooling was a public school. It's a place called Neshoba Regional High School.

And then I went to a place called Skidmore College in upstate New York for theater and dance after that. And yeah, yeah. That whole East Coast sort of, especially like the East Coast, you know, like the references are lost on me as a Midwesterner. Like when somebody go, you know, like there are things that I know, like I know Worcester is a terrible place. Oh, yeah. Besides Providence, it's the worst city, I think. Yeah, I've been privy to, yeah. I think I've,

um, yeah, I've been privy to, yeah. But the whole, the whole, like saying that, you know, that you went to Skidmore cause you,

like I, um, there was, I just, I was rewatching some of the Gale videos last night. And there was one where you're like, where you're like, uh,

what do you refer to as some as like little Ivy leagues? And you say, yeah, yeah. The little Ivy is near like our boat. Like having to have a, put on a bumper sticker like bowden and all that stuff is absolutely i mean i get kind of what they're talking i get the point of like a overreaching parent but i don't like you know but like the actual sort of like you know how like when you make a reference like the point of

the references is like where there's some truth to it and i don't get any of those and the whole east coast college thing was always so weird to me when i moved to new york and i had friends that would and when i was you know i just had gotten to new york and i had a friend there um and he and he had gone to amherst and he would say like we're going to a party tonight but these people are all brown people oh wow you know and i and i i knew it i obviously i knew they he didn't mean their color he meant the school or it would be like we're going to this party and they're all you know oh oh i see what you're saying okay you're talking about brown university yeah yeah brown university yeah yeah i'm sorry i should have made that i should have picked another school okay or he'd be like oh these people are all princeton people and i would just be like what does that even mean i don't know what you're talking about and they're

kind of um yeah it's kind of they're really put up on a pedestal and it's like there's a crazy hierarchy um on the east i mean the east coast isal. And it's like there's a crazy hierarchy on the East Coast. I mean, the East Coast is so fucked up. It's so, especially where I'm from. It's like it's so, everyone's so tightly wound. And I'm trying to undo a lot of that. Why do you think that is? Why do you think it is?

Is it just because they've been there so long and there is like a sort of a strata that you have to kind of be respectful of or live either in reaction to or within it. I think it's a leftover from their Puritans at heart. And they think they're liberal, but they're not. Have you seen The Witch, the A24 horror movie? Which one is that? It's not the one with the woman sitting in the A24 horror movie? Which one is that? It's not the one with the woman sitting in the attic, is it? No, it's where she breastfeeds a crow.

Oh, no, I haven't seen that. Okay. I'd remember that. It's the best representation of what it was like to grow up in Massachusetts to me. I don't know. I think it's a lot of undiagnosed anxiety. Like in my family, we scream at night. And no one, I'm like the first to actually kind of,

or my generation is kind of the first to be like, oh, wait, I think we might, there might be some issue with us that we need to maybe get sorted out. In your sleep? Yeah, yeah. Or just like before you go to bed, the way you brush your teeth, you know?

You have a good bellow, yeah, out the window. No, no, no. Like we have violent night terrors. My dad and me specifically. Oh, yeah, yeah. I'm a real sleepwalker, yeah. And it's because we just bury it all and then let it out at night. Yeah.

I mean, I don't know. I think I was thinking about like um uh and talk about this in therapy a little bit about like uh i i have some ocd tendencies and that like i need to say the same thing over and over in my head to make to feel like everything's gonna be all right you know with my loved ones and stuff and um i i kind of traced it back to going to church a lot and just like you we just have to like repeat like the our father prayer or like the hail mary's like like 10 times in a row when you don't even know what you're saying you're right you need to say it to make things okay so it's like that's just gonna breed like such insane yeah yeah um feelings of of patterns and and habits that you feel like if you break

the entire fabric of your universe will unravel so and and also there's a lot of fear a lot of um imagined competition and stuff uh it's just i mean i'm really grateful for it because it's made me um you know a freak in a positive way but um i think if it hadn't been for the west coast i think i would probably be bedridden you know know, had I not moved on. Yeah, really? Yeah. I often, yeah, I think like if, you know, if I had, if I hadn't gotten into, like if I stayed in Chicago and, I mean, probably the most likely thing that would have happened was I would have ended up in advertising. Yeah, yeah. Yeah, because it was there and I worked in film production and it was, you know, that's what the Genesis of most film production in Chicago still is, is, is advertising. Yeah. And I just, there's so many times, I mean, I got, you know, I need to lose weight now. And I think if I lived there,

I would just be like the fattest alcoholic on earth. Just, you know, just because I wouldn't be, there would just be so much kind of existential dissatisfaction, you know, and just, and I also too, I got to a certain point, I realized I need to leave here. Like, just like kind of simple, you know, like. Also the winters. I think winters are just not good for the soul. Yeah, yeah. I do sort of miss them now now especially now that we're sitting in

la when it's a hundred and fuck you degrees um yeah but uh but yeah no but i definitely yeah i it was a stockholm syndrome because when i first came out here i was like this place the weather never changes i'm this winner and i went back to chicago for like a March blizzard. And I was like, oh, this is ridiculous. What the fuck was I thinking? The wind in Chicago. I mean, everyone talks about that, obviously. But there's a unique terror to feeling that. You walk in your downtown in a major metropolitan city in the wintertime and you can't walk.

Yeah, yeah. It changes your bone marrow. No. you can't walk yeah yeah it changes your bone marrow no i have to like if you have and you're completely concerned about windward and leeward and you're just like like okay i gotta walk six blocks this way and then just like really dash in quickly on this block you know walking almost you know the opposite like that michael jackson you know lean kind of thing but the opposite way you know can you do that in Chicago? You've done that in Chicago?

You've done the lean? No, but yeah, but forward. You have to lean like you're, you have to put your center, your body's, the center of weight of your body, like three feet ahead of you in order to just kind of keep your legs working. I've seen my friend Buck,

when I go to Chicago to do shows, he comes with me. And the way he moves around, he kind of uses his paws, like kind of burrowing through the air as he as he walks and he that seems to be how he's kind of managed it it's wild to see people existing in those extreme in those extreme climates yeah yeah it's like montreal is the same way montreal you know half of downtown is underground right which when you go there in the summertime you're like well this is weird and then you realize oh yeah but that's because

of the bad time you know like you know the seven months capital b capital t yeah the seven months where your face freezes i love how montreal always feels like it's role playing is Europe to me whenever I go there. Yes, which is what's fun, which I love. I love it. To me, it's like a more authentic Epcot. Absolutely. And I'm completely on board with all of that. I love Epcot. Oh, certainly.

I don't even know how much it still even exists. I have no issue with artifice. Oh, certainly. How much it still even exists, but like, oh, just. I have no issue with artifice. I have no issue with artifice and even materialism, I think, is the negative impacts of materialism, I think, are a myth. Because, like, I have a pair of boots that I got. Actually, these shoes right now. Here we go. When I think about these, these pink slide-ons.

They are pink slides with three embroidered stars on them. That's right. And they're a women's size 11, and I'm a women's size 13. So my ankle is constantly just in the mud when I walk around. But when I think of these, it brings me – these have sustained a fully – and unless I'm really out of touch with my soul, I've been – I wake up smiling thinking about these shoes for like at least a year now.

Now, you talk openly about kind of your androgynous sort of aspects of your life and your personality and your style. I mean, look at me, Andy. I look like a sorceress. You do. You look like a lion tamer from the Sonny and Cher show. No, I don't know. I don't know what that is.

Kind of like a Doug Henning, but more dangerous. Oh, you think I have an L in a danger tune? I do think you do. Yeah. Is that, that's the barracudas on the bike talking? It might be the barracuda. No, but was that something that like, was that something that's always been with you? Like when you were a kid, were you sort of like, and, and, and what did that do for you

to you? Was it difficult? Was it just kind of okay? Yeah. you was it difficult was it just kind of okay yeah i mean i i think i should have been a i should have had a lot more strife than i did socially um with it because based on what i've heard from other people's experience growing up in in massachusetts in that time or in the northeast in that time i grew up with um a sister and two female cousins very closely and there was one on one occasion i did weep because

i was not a woman uh when i was when i was like maybe five or six and i think it was i think it was probably because i just felt like um i was kind of raised as a woman in a lot of ways um really but still had the expectations of being chivalrous which which was kind of confusing expectations of being chivalrous which which was kind of confusing um and it felt like a weird power thing that i didn't like like being like i'm one of the girls but i gotta open the door for them it seems like i'm posturing above it felt very uncomfortable and almost like sexual in a weird way it just it felt very strange um because it was just me my aunt my mom and in these and my sister and kaitlyn and molly and so it was like wherever we my aunt, my mom, and my sister, and Caitlin and Molly. And so it was like, wherever we go, people would be like, hey, ladies.

Because I just looked like Pollyanna of some kind. And so, yeah, I think it was always in me. I always loved cross-dressing. I always loved dressing as a woman. And it didn't really take full effect until college, when I started. At the end of college, I started wearing, I just wanted to wear clothes that fit. And I have such a freaking like a small frame that I would just wear women's clothes. And I think I also got into British comedy at that point.

And I was seeing that there was a lot of androgyny happening. Like Noel Fielding. Yeah, Noel Fielding. Yeah. Love Noel Fielding. Yeah, yeah. And so I was just like oh wow yeah i don't have to wear like a hoodie and stuff and it felt um yeah it just felt kind of felt good

yeah yeah and nobody gave you and because you know oh yeah i got a lot of shit i used to do have to i was hosting a show at like a a sports bar in clinton Massachusetts. Oh, that sounds like a perfect place for it. I had a tally up in my room that was nights left that I had to host at the whatever. What was it called? God, I forget what it was called, but it ultimately got shut down because the owner put a fire extinguisher in the microwave to collect insurance money and blew it up

and like had to dive out of a window. That was after I left after oh man but one time i had to get escorted out by a local my my friend's dad who's a local policeman because there were men in the bathroom that were um after my performance uh they weren't talking about beating me up they were talking about just simply murdering me so yeah so that was that was a little tricky but um it is amazing like how like just that there is that i mean you know the phrase toxic masculinity gets tossed around to the point of where it almost becomes like i've heard that i mean yeah meaningless or something but it's like but no i mean right there it's like how can you sit there and think you know i gotta murder that

guy that willowy nafe i have to murder him and think that you're the one who doesn't have a problem you know what i mean it's just so bizarre i think that they've i think that's maybe changed slightly i feel like so too yeah i i felt i feel like watching queer eye it hit me like it seems like homophobia is way less of an issue as sex and sexism now it seems to me because it seems like even the deep south these guys are like well i'll take advice from this guy, even though it's a little light in the loafers. But I'm not going to. What if a lady tells me what to do? So I don't know.

So I do feel like it almost seems like more of a superficial hatred that I got and didn't seem deep or profound. And there was one guy in high school who was older than me who definitely did not like that I dressed the way that I did. And there was a couple harrowing incidences where I did think I was going to die at that point. He would learn my schedule and like, oh, God, it was spooky. He would follow me around and they cornered me in the locker room once and he picked me up. That just sounds like a crush. It sounds so much like a crush you know yeah i i that's kind of i think what was happening and so you can't really take

it personally yeah but yeah my only because i i mean i've always i was always a large person and a fairly amiable person and and i mean and all of my weirdness and brokenness is on the inside. Like I don't exhibit a lot of outward sort of misfit, malcontent kind of tendencies. I look like just your- What do you mean? I mean, I just look like, even in those days, like I didn't, I never dressed, you know, I listened to weird music

and I had weird ideas and I didn't, you know, like. You were a lady in the streets of Freak in the Sheets. No, I was, I was, I was just an average, you know, white guy. And I, and, and I, but I always have felt like, like when you say, you know, like the notion of like being a jock, like I played sports, but the, but the jock mentality always, I always, I never was at real risk of being bullied, but I always felt like,

Oh fuck, those guys are so manly. And so like, uh, just, I don't like being around them. Can I just go to the kitchen and talk to the women? Oh,

Oh my God. That's, that's, it's absolutely, but it just doesn't manifest itself in a an external way with me and the only guy in high school that that might be harder too in a way no i don't think so because i i know one like i say i had one bully and it was this one guy and he's about the same size as me he's a football player and for some reason he just had it out for me and and and like always was mean to me

and challenging me and and shitty to me and i was you know nobody there was no one else that really did that right and i remember there was like one time where i went to a party and i walked in and it was one of his friends and he had very they were very sort of like more of the pickup truck and and own multiple firearms kind of variety of fellow sure and I walked through the door and this guy was there and he and he goes Andy and he grabbed my breasts like grabbed my tits and just squeeze them as hard as he possibly could. And I was just like, ow! Right, right, right.

And it was just the most bizarre thing. And I was like- He opened a door and promptly did that? Yeah. And I literally was on the threshold and he just happened to be by the door and saw me and did that. And that was kind of the end of it and then like an eel popping out of a hole in the yes you know yes a halibut

eating a crab yeah yeah wow that's are you afraid of walking through doors now no no uh but i i that was i think when it hit me like i think there's a sexual component you know like you know i just it was like such a strange gesture that i has never been duplicated that i just was like okay i think like i think there might be some just like might be some weird crush stuff happening in some of these what's intersex uh bullyings the it's so easy like i i had that's kind of what i wrote it all off as stuff like that like just kind of very repressed um you know whatever sexuality things but then like i i've explored a little bit about how easy it is to repress any like sexual stuff yeah it's it's like i think we all have some some shit

that um that can be clear to other people you know um outwardly that like or especially are were you raised catholic no okay no very very just sort of generally protestant and a very kind of so you know what you're feeling and why you're feeling it a lot of the time right yeah most of the time and i and i also like that'd be nice a good a a real uh real serious kudos to my mother for always being open to therapy and counseling and and talk therapy oh you had that ass starting at a young age? And so I, from a very early age, just learned the value of that. And that's why, to me, it's always the fact that there are people that are against it or people that I just, and I just feel like there's, I can't even imagine not getting some benefit from some bit of the talking cure.

Like as happy as you could possibly be, there's got to be something that going to talking to somebody and and you know and you got to do it right there are certain rules you have to you know you have to be open you have to be ready to be self-critical and to do a real serious cold-eyed self-inventory if you want to make it better you got you can't it can't be like well those fuckers they're the ones that are misbehaving i'm the one i mean that's i constantly within conflicts of my children between you know in mediating which my son just the other day is like i don't want you to have to be a mediator between me and and his sister i was like honey i'm gonna be a mediator between the rest of you

for the rest of my fucking life. That's just how it goes. And so, you know, let me do it. But I will say to both of them frequently, like, well, then I guess you don't have anything to change. Everything you're doing sounds perfect. This fucked up situation can't be your fault. It must all be the other person's fault. That's crazy to think that you were so encouraged to do it because for me i just started therapy recently and because really and i feel like i'm betraying my ancestors

by even really i can hear them screaming i i truly it's the my methodology the way that our my family's methodology is to just act like everything. Like I once was very anxious when I was visiting my parents and I told my mom, like, you know, I'm going through some kind of wild anxiety and I'm having like a really hard time. And I went upstairs and five minutes later, she called up, she was like, Chris, are you feeling better? And it's like, it's that kind of like thought process

about, you know, yeah. Just everything off. Yeah, thanks mom mom i just need it yeah i was just constipated it's um yeah no it's it's uh i don't know what it is but i think it's just like the fear of looking under the hood and i and because because i was okay and i think like my a lot of i would get a lot of stuff out creatively too when I wasn't. And that's why I felt okay about not doing therapy because it would squeak out through my work and I liked that

and I felt like I had everything kind of lined up. But since I've started looking under the hood, it's really kind of changed things. Did you have the fear that, that going to therapy would, would break the spell of creativity and that you wouldn't be funny and all of that? Yeah. Yeah.

Yeah. I felt like I would never, it would never be the same. I was, I was really worried about just kind of fucking up the mechanism. Yeah. And I really like, and do you still,

do you still have that with you or do you think it's, you know? Oh yeah. I'm a real um i mean are you still afraid that that's going to happen like you know like you're going to get happy and your career is going to go down the shitter because you can't think of anything well no it's not even about happiness for me uh because i've i i have been i do believe that i've been happy even though there's been so much repression or whatever but i do think that um for me i never realized that anxiety could be getting in the way like without without you know with with kind of calling attention to the anxiety and pushing it aside it actually could open up um freer avenues

of thought yeah yeah in some way so i that's something that's the way i'm looking at it now and also just like not realize like i thought it was would be like some kind of psychedelic or something that would completely rewire my nervous system or something because of the way my family talks about it. Yeah. I think a lot of – I mean, it's just a hunch, but I think a lot of that fear, especially that generational fear about like, you know, some doors are meant to be kept shut. fear about like, you know, some doors are meant to be kept shut. You know, it's just like, it's a, it's like a fear of telling secrets, which, you know, which then telling secrets, I, you know, and I think that the telling secrets is like linked to like a complicity in

like, Oh, there was a crime committed generations ago and we have been perpetuating it and you know and now there there was like you know i think that they think like therapy is like the rico statutes you know like that it's gonna it's gonna unravel the whole organization and everyone's gonna have to deal with how they fucking did this thing that they know in their heart is fucked up yeah yeah it's like how our in third grade we were taught the entire year all we learned about was native americans but i mean it was about like wigwams and longhouses yes yes yes and not a fire water yeah and they ate maize yeah yeah yeah yeah they uh in california you know um i think it was fourth grade. Every kid had a, there was a whole section for the whole year on

the missions of California, you know, the glorious, however many there are missions of California. And part of that, and both my kids went, well, actually, I don't know if my daughter did. I think maybe she'd missed it. I don't think she did. But my son definitely had to build a model of the missions. You had to build. And then there was the day at school where everybody came in and looked at the mission models. And then somebody, I think, along the way was like, we're forgetting about the genocide part of this. And now kids don't make those models anymore at least not not in public school but it was probably like 2015 that stopped yeah it was it was just like that was part of california curriculum and you know i just what i like i like to listen to the there on sirius xm there's an old

radio show channel and i watched one that was like you you know, it was something like the, you know, the history of the ranchos, of the California ranchos. And that was, and there was so much about it. It was like, and, you know, all of the labor was done by the Indians who wanted to be paid in brandy, you know. And it's just like, you know, and then there's like cuts to characters like going i'd like to kill the fellow that first introduced these people to fire water like oh fire like you know what about the smallpox like how about that part of it or just like they wanted to be flu yeah yeah yeah yeah oh my god yeah no i mean and that was that's just for californians like yes oh there were people here for sure and they helped us work they wanted to work for us like right i

don't know about that right it's really hard to to face face some stuff yeah yeah were you were you funny in school like did kid uh oh yeah yeah i i was um i was kind of a fuck up in a way like i not a i mean i was very good in the in the place that's kind of where i um on stage is kind of where i found my little your thing My little thing, yeah. Yeah, yeah. And no, I had a really good adolescence and everything. I did try to be friends with the jocks in middle school for too long. And that was just, it's kind of like when you see someone trying to sustain a celebrity friendship on Twitter. It's kind of like, it's just too much work. Yeah, yeah. But then high school things really kind of, I went to kind of like it's just too much work. Yeah, yeah. But then like, yeah, high school things really kind of –

I went to kind of like an artsy school, so I had a lovely, lovely time. It was – but I didn't do very well. I was in like the higher classes, but I didn't do very well. And so that's when my mom was like – because she knew I wanted to be an actor. And she was like, how do you think you're going to be an actor? You need to start – you're funny. You need to start doing stand-up comedy.

Oh, your mom said that? Yeah, she made me do like 16 wow yeah so she took me to like an open mic for like high schoolers and and i remember the audience they sat in like um car seats that had been taken out of a van that was like that was like kind of the shtick you know and uh yeah yeah like that's yeah like that you know hobos do around the campfire like yes yes the most the least comfortable seating there is everyone had a single bean on a stick you know and a little fire very big bean yes yes yes pinto pinto and uh yeah so i started doing that and that um i didn't take that very seriously i didn't take anything very seriously i was kind of just like um like my friends always wanted to make funny videos and so i would be in them and like that would be like how i like i got kind of uh

known around town which was always important to me but i i wasn't that that was always to be known in whatever community i was i feel okay i needed that um were those youtube videos like that youtube wasn't around yet um so where were these videos being seen like were they just being passed around or we would have a like a like a independent film festival uh at our high school yeah wow in the spring, it was great. It was really great. Yeah, there was a lot of opportunity for like performance in my little town. Yeah, see, that's the weird dichotomy I think of New England too, is that there is kind of this artistic, creative, liberalism, you know, sort of a Unitarian history of, you of you know well no one's right about everything and and then there's also like you know a friend of mine that worked for well at the time it was the wwf he worked for vince mcmahon writing yeah and and he wrote for vince mcmahon yeah

although they call it booking you're a book booker. Booking in wrestling just means writing the story. He was a writer on the Conan show and then he did that for about a year. He said the worst place in all of America was for wrestling. Just the fans,

he said, was Worcester. They would do shows in Worcester and he said just like people apoplectic with rage at everything they would see. Yeah. Like, you know, you know, like every,

every female wrestler, you know, just, you fucking whore. You know, yeah. It's just anger, anger,

anger. And it's so crazy that those two things basically live next to each other in a relatively small space, you know? Yeah. Oh, yeah. Big time. It's crazy. And I think. Does that go town to town?

Like, is it like one town's kind of, you know, I mean, one town has independent film festivals and another town has, you know, chain snatching festivals? Yeah. Yeah. It does. It does. and other towns has you know chain snatching festivals um yeah yeah it it does it does um but but that kind of what you were describing like the i'm calling the lady wrestlers horse like that that that kind of stays constant like the the belief that the belief in horse uh that is is kind of uh ubiquitous around there's there's a lot of stuff around sex um but no uh i the way that that i i think would be i think it was also by terrain like lake people were always really scary um people that live by live by the lake right there was one one kid i went to some lake parties and my mom dropped me off and there was a kid on a bike that I think was on fire and he was waving a snake kind of in the air.

Just, ha! Ha! This is like maybe seventh grade. Welcome to the lake. Yeah. Yeah. So that was a very different world. Yeah.

Well, you could ride bikes on fire by the lake because you always had the lake to ride into in case it got too hot exactly exactly you have that cushion yeah yeah i mean you didn't enjoy that in the mountains you know no set yourself on fire what are you gonna do well you roll down the hill yeah yeah just feed it more oxygen yeah yeah but yeah no wister is what's it we i'm like 20 minutes from wister so uh yeah so that's that energy pervades um yeah but um right so then i started doing stand-up didn't really care too much then i had a friend who was this why do you think if i may just stop you there of course it kind of like not caring too much why was it fear of commitment to yourself kind of like why were you sort of like you know not really into any of it my sister was um very she was like uh salutatorian like she was she was just like cherished and like so good and brilliant brilliant and and was kind

of loved all over town and then so that i was it was great because i could kind of skate by on that when teachers would be like oh katie fleming's brother and then like it would like within a month they would start figuring out like okay yeah no this is a different situation but um i so i think i kind of gave up because i was like i cannot live in that uh footstep maybe and i think it was also ah I don't know what it was. I did care. I did get nervous for, for performing.

I think that I was always very invested in making people laugh, but I never really worked at it until my senior year. When I had a friend who was a faint, he was not famous, sorry, but he was like this, um, re like very good trumpet player.

And it's all he did. And he died. And so, and he was like always just doing this stuff. Like, like he was so devoted's all he did and he died and so and he was like always just doing this stuff like like he was so devoted to his craft and then he died and i my part of my at a young age i guess yeah 17 and i was like oh shit i gotta like i've been just fucking around and i felt really guilty and i oh wow and so i was like i need to like so i called like all the comedy clubs um the next week and started just like weekly doing the like sets and just started really kind of committing myself.

Are these Boston clubs? How far are you from Boston? Like 40 minutes. So, yeah. I mean, because, you know, when people like when I've talked to people and they say they're young and like when I was 16, I was doing stand up. Like to me, I don't know where that would have been in Yorkvilleville illinois so yeah you must it must have been in boston yeah yeah or cambridge was the big one this place called cambridge right sure yeah it's like this really funky place college town yeah yeah oh yeah best audiences and and that really kind of um the owner

of the club was all about idiosyncrasies and like kind of like having an interesting point of view and so it was less like um you know comedy like touristy and the giggle hut or whatever yeah the chuckle house yeah and so so that kind of helped me um find a voice and then uh i just got really really hardcore into it yeah obsessed with it and that became your thing yeah yeah yeah it just was like i need to just succeed in this. And so did you go to college as a fallback kind of thing? Or was it sort of just you had to and it was expected? I probably shouldn't have, but I'm very grateful that I did because I think for the community aspect of it.

But it was just kind of like an unheard ofheard of thing uh in my family to not do that yeah yeah and i think i think i would have been stressed had i not yeah i can't i mean i asked that question but i don't think i could have said to my family i'm not going to college i'm going to pursue something creative i think they would have been like yeah yeah, right. It just puts a lot of pressure on like every show. Yeah. Yeah, yeah, yeah. Yes, it does. You better do well.

It does. I mean, I think I was doing the Conan show and my mom was still worrying if I had a fallback. Like, you know, I'm on television. Doesn't that like. Really? Yeah, yeah. Seriously. Wow. And my dad even, you know, like my dad, when I, after being at Conan for seven years and I decided I was going to branch out and do something else.

I just was, I was, you know, I just kind of felt like I was doing the same thing over and over. I was young enough. I didn't have kids yet. I felt, you know, I had this ambition to go do something else. Yeah. had this ambition to go do something else. It felt frisky. Yeah. And I wanted to sort of, it was entrepreneurial sort of like, look, I know I have this kind of uncashed in capital of, because I just knew the way things work. If you're on a show for a long time and then you say,

all right, hello market, come and get me. Everybody's got to have a piece of you. Because I'd seen it happen with friends of mine that had been on the daily show like they they'd been you know like rob cordry's on the daily show and then he decides i'm going to leave the daily show and all of a sudden everybody's got to have rob cordry you know and and that's not when you have to worry about the work it's like a year and a half two years down the road when you the act when the dust settles and you what year was this i didn't know that you left. I left in 2000. I left in 2000. I was there 93 to 2000. Y2K.

Yeah, yeah. And then I came out here, and I was in three different sitcoms, and then he came out to do The Tonight Show, and I went back to work with him. And by that time, I was very happy to go back to making daily television. Who did he use besides you? He didn't use anybody.

I'm irreplaceable. So moments would just kind of sometimes just kind of fade into the abyss? I mean, I think he talked to Max more. You know, he kind of would talk to Max more. But it also became, you know, everyone. He didn't make an ai andy no no and when i start when he when i started working with him that was a throwback people were used to letterman and leno not really like having sort of like a band guy but they didn't have like a proper sidekick you know they right that letterman would have um paul kind of wandering the property yes yes or he'd have like a larry bud melman he'd have like you know like oddball sort of punching bags yeah but he didn't have like a you know like

a joke killer yeah yeah yeah a henchman yeah yeah or you always had your ankle piece ready yeah or i mean or a lieutenant you know basically like you know like kind of just like not quite the same status like a little bit less status but still sort of like an officer in the in the operation um so yeah but uh what was the my point started this, um, a fallback plan. Oh, oh, when I, when I told my dad, cause I, and I had wanted to, like, I had, I had been, I had been ready to leave. I had been feeling like, uh, like unsatisfied on, you know, unanswered ambitions. Um, and it had been bothering me. And I said to my dad,

when I told my dad, well, I finally did. I told Conan that I want to move on to something else. Did he put his fist through the drywall when you told him that? No, no. He said, oh, he said, and to me, this is a huge deal. This is a huge, scary, scary thing to do. And my dad said, Oh, well that's, well, that's great. I mean,

I know it's really been weighing on you and I know this is something. It was probably hard, really hard to tell him, but now you can go back to him. Right. If things don't work out. Right. Like maybe,

maybe a few months for that one, dad. You need to tell me that right off the bat. The fear of a dad. Yeah, yeah. Oh, that's brutal. I know. If things don't work out.

You can go crawling back. Yeah, go crawling back and shrimp his toes, right? Yeah. I guess I could, Dad. Thanks. Oh, well. Anyway, bon voyage, son. Dad's not really wild about a risk, you know?

You know, I, yeah. I mean, I can kind of understand it, but I also. Oh, you're a dad. I'm a dad. I'm talking shit about dads. I forgot you were a dad. No, no. That's, but I mean, I'm.

We got one in the room. I'm sorry. No, but I do like to think that I'm one of those dads that learned from previous, like, rather than like, well, I got hazed, so I'm going to haze these motherfuckers. You know, like, get in here, you fucking pledges. Now, you know, pick up that olive off that ice block with your ass cheeks. I always felt like I was hazed. I didn't like it. I'm not going to do that.

You stopped the cycle. I'm going to break the cycle of abuse. You break the cycle of abuse. And with my kids, I've always been like. I think I read that about Andy Richter online. He's breaking the cycle of abuse. Yeah, yeah, yeah. He's sniffing.

He's like Zorro cutting the string that's on fire before it hits the coal. It was a lifetime movie, Breaking the Cycle of Abuse. People said just the main beef was too many dick jokes. A lot of dick jokes. Oh, wow. Wow. Yeah, not the time. I still want it. I mean, I wanted to make it funny. Right, right. Still, I'm a

comedian. Yeah, yeah, yeah. But yeah, I think. Too much nudity from far away. That was the note that I read. If you're going to have it baby, why are you nude 100 yards away from the camera? Too tantalizing. That's haunting. I didn't know what you were trying to make me feel. Yeah, no.

I mean, with my kids, I kind of always been like, you know, do what you want. I don't care. You know? And my ex-wife used to be mad at me sometimes because i she'd say i feel like you don't even really care that much about their scholastic stuff and i'm like i kind of don't i don't you know i mean like she would whip out the word scholastic in casual conversation yeah yeah but i mean yeah but i mean i feel like you don't even care about their school things. I don't really that much.

I mean, I'd like them to get good grades. That's nice. And I want them to sort of work towards their full potential, but I don't care. If they decide they don't want to go to college, I don't care. Just follow what you want to follow. That's your business. decide they don't want to go to college i don't care just follow what you want to follow that's that's so you just have business you have faith that that that you've given them the tools and yes they can yeah i mean there are moments of abject you're a clockmaker god type thing yeah well there's moments of abject terror that like oh my god what if what if what if you know right

you see them like yeah what if they're yeah yeah like what if they're what if, what if, what if, you know. Right, you see them like staring at the screen. Yeah, what if things go terribly wrong? Or what if, you know, he ends up, you know, living in the garage? You know, it's just like all that. You do have those fears, but, and I think, and it's, my kids are pretty together. So it's like, I don't have a lot of reason to be fearful. And other people have kids that aren't so together. And I can see why they would be sort of more fearful.

So it's, I'm speaking from a place of privilege. But I don't know. I just, to me, parenting just seems to be like, it's one of those things where you're working towards your own obsolescence at all times. Like you're trying to, you know, you're working towards your own obsolescence at all times. Like you're trying to make it where they don't need you anymore. Trying to make a good system. You want a self-checkout. Yeah, yeah.

I mean, you've got to stick to that. My mom sort of, she changed her mind when the last kids were getting near to being out of the house. It's like, whoa, whoa, whoa, whoa, whoa. Hold on a minute. yeah i changed my mind i actually would like you to be attached to me at all here's how you fold a napkin yeah yeah yeah at 41 can't you tell my loves are growing so after college you just i mean did you did you have any other jobs or were you always making enough money as a stand-up oh certainly not andy no no no certainly not no no i know i don't know your life i was i was making um not not nearly enough money to survive until 2015 i had oh wow yeah when i first moved out to LA, I was an SAT tutor for some time. And then I was a caretaker for a man with Down syndrome for four years or so in tandem

with SAT tutoring. And while doing college gigs, that would, you know, make you like not like round, you would fly to Missouri to basically break even um yeah yeah and then um yeah i didn't really start making enough to like uh youtube really took off for me and then that was when i was able to to quit those jobs um when you came to la what was i mean what what was like the the main like what did what would have been your kind of the utmost fulfillment of your expectations and ambitions? Oh, wow. Okay.

Like when you came out here. Yeah. And by the way, is it true that you had a manager who became a chef? Yeah. She signed me in Boston. And then she kind of got me to move out to L.A. And then as soon as I got there, she became a chef in Times Square. Not only a chef, she left town.

Yeah. So that's like. That's probably not entirely your fault. No. No, it is. It is. She Facebook messaged me recently. Oh, really? Yeah. she facebook messaged me recently oh really yeah i got like like my deactivated facebook

was like you have you have a message from anna i was like oh my god how dare you um were you upset by that no i was like oh okay oh yeah see that's got to be scary though because i mean that's your lifeline to the industry you know for me it was about so that happened and then i uh i also found a dog uh and in in the street um who i still have um and so i had to take care of a dog and i was like i need to get my shit together i have like no prospects um i need to that allowed me to get outside of myself as having a dog and so i started so i turned it's amazing i have a dog too it's amazing like oh just especially for a male it's i can be very very self-absorbed and um and and not not very so um i don't i'm never inclined to take care of myself, you know? Yeah.

But that really was like, oh shit, okay, I need to do something. So I turned this, I was doing this character Gale in standup. That was part of my, what I would do in the clubs. And so I just like put, it was like putting forks in a cannon and stuff and just like desperately trying to make something that hopefully the industry would notice. And they did. And then, but I did get some fans from it or some following from it. But that's, yeah,

that's how that started. When you, when you started putting, was Gail, the Gail videos, was that the first thing you kind of put on, on YouTube? Pretty much.

Yeah. There were a couple of like one-off sketches that got nothing, but that was the first, pretty much the first big thing. like one-off sketches that got um nothing but that was the first uh pretty much the first big thing yeah and when you shoot that do you is that that's all out of your own pocket and you just kind of i mean you obviously is that in stow all those oh yeah and you just enlisted everyone in your neighborhood to yeah you know yeah and isn't your mom is bonnie right yeah yeah she Yeah. She, she's the, the second lead. Yeah.

Yeah. These people are good actors. She's incredible. I mean, they're all incredible. Yeah. I mean, it's really, it's really something like to just kind of know how DIY it was. And also, but you know, nobody really overplaying it. Everybody like real subtle, good work, you know, nobody really overplaying it. Everybody, like, real subtle good work, you know?

Yeah, because Gail, to make it work, like, I never wanted it to be about, like, oh, I'm in, you know, I'm playing an older woman. Like, I wanted it to really be a believable world to make the joke. Yes. And I think that's why, I mean, thank God for my mom being that good, because that balanced it in a way that it did not deserve to be balanced, you know? Like, to not even, we weren't working with any actors it was just people yeah my my friend's parents and stuff and yeah yeah like people in my town and yeah who was shooting it did you just melissa melissa stripe no um okay yeah she she directed everything and she's in it she she plays my daughter oh okay yeah so she would the shots that she's not in, we had to put the camera on a tripod because we had no...

It's awesome. Yeah, it was so exhausting. Yeah. Yeah, and it was a lot of fun in hindsight. It was something that I could not do post-30 in terms of endurance. I understand that yeah yeah no i think to just do it all ourselves was like yeah almost like it made me afraid to like when people talk about like making a tv show or something like my idea of like what that is like with having like no help it's like oh i can't do that again. Yeah, yeah, yeah. But you're, I mean, also, too, when you're shooting that thing,

your plan is to just spray it out into the ether, you know? Yeah, there was no plan, yeah. There's no, it's like you're doing all this, like, and to me, like, in looking at it, like, you know, especially, like, in the, what serves as the voiceover, the sort of race walking. The power walking narrative. Yeah. Yeah.

And the way that you cut on different sides so that you can cut the different lines. I look at that and I think, oh, that's work. Oh, that's multiple, multiple takes. And like, okay, now let's do the other side of it. And I'd be sucking down car exhaust because I'd be power walking in winter behind the car and the tank top and falling in snow and yeah i was yeah i had to be in really good physical shape um at that time yeah and i lost that after doing it i i yeah no it was it was so much work and um yeah yeah i mean worth it it's it's really maybe maybe no i think so i think so it's really funny stuff thank you it's really really funny stuff i'm proud

of it yeah yeah yeah i look back and i and it just it brings me a lot of joy and i'm always you know when you look back on things and you're like i don't remember writing that doing that oh boy do i you must i can see myself in video in elaborate costume and be like no recollection oh it must be like ubiquitous with you because you've done so many things yeah the most recent one was because now you know conan got possession of our old archives which for the longest time he did not have because of an acrimonious relationship with nbc right so there will be on this day in conan history you know the team coco the digital people put something out and there was one where uh apparently there was a bus that would take you out to the hamptons on the hampton jitney or whatever yeah but but this one was a spa so you

could while you're you know you'd kill two birds like you'd get your nails and your hair done while you're on the road out to the hampton and a eunuch would sing to you it's you know no i'm like a man with an accent that would cut your hair and uh but there's a whole segment and i did a whole remote of the thing no recollection at all like you did in a fugue state you think i i don't i know just there was so much that you just kind of and and the same thing with bits you'd be in the middle of a day and you're writing stuff you're you know or and then you have your life going on and and then it's kind of like we need you down to two for pre-tape or 130 or whatever so like okay fine oh shit it's 125 you get down there okay put this on and it's like emelda marcos

costume you know like okay and then what is it show me the cards okay and you just have like a horrible fight with your family right before and you're wearing like a powdered wig yeah you do it and it's like it takes 15 minutes to do it and then you you take all the shit off and then you're like okay now back to what i said to mom you know right right right right and then and then you know 12 years later you see it on video and you're like what what when did i do that and it is i guess it is kind of a fugue state you're just it's just kind of and because it's not so much of that stuff it's not like it's a kind of performing that takes a lot of preparation you know like

i don't need to really search for anything with most sketch you know what i mean i'm so precious about what i put out though that i've always been blown away um by the fact that you just show up at like a certain time every day yeah and you you just you do it you sit down you you like you can't like i'm just it's terrifying to me you don't have any choice right no right right i've said it's a it's laying tracks for a train that's coming you can see it here comes the train you got to put these tracks down quick quick quick quick uh and then you ever look at yourself and like like do you ever like see your face and quick quick quick uh and then you ever look at yourself and like like do you ever like see your face and like a clip back and you're like you remember

like something in your life that was going on that was in your head at that time yes yes or things about the shoot like that had nothing to do with like you know like you know like a remote and then you remember like that cameraman that got drunk and yelled at a waitress, you know, that night and just, just stuff like that. Yeah, definitely. Because the actual, and there's times, you know, and then there's times of it. And I just think this is the human condition where I look back and I think like, I wish I'd been more present in the actual doing of this thing, the thing that I'm actually living on, which is the sketch or the bit or the piece. And I wish I'd been more present in that rather than whatever.

But I just think like... But maybe you couldn't have been if that's the way it was. I just think it's the human condition. And what amazes me too is like, here I am in my early 50s and I just kind of feel like i'm getting the hang of it you know like wow well that's inspiring yeah and i and i and you know

and maybe 10 years from now i'll be like oh boy that back then i really didn't know what i was doing but it just i think that just you know the life she is so long there's like there's a there's a uh uh there's uh the the um in disneyland there's a uh the hotel that we would go to disneyland all the time with the kids yeah and there's a hotel called the grand californian which is like a big again like completely fake looking craftsman you know like you like how all those craftsman buildings that were eight stories tall with an eight-story atrium frank lloyd wright was really into that uh and like and it's it all supposed to look like oak beams but of course you know it's girders like fiberglass oak beam around

it but there's a restaurant there and and it is a quote it's like a quote from you know uh you know the guy that came up with i can't remember his name but the the guy that uh designed all the mission furniture i can't think of his name but um but it's it's like uh it's a it's like the life it is so short and the craft so hard to master. Like that's in the breakfast restaurant. That quote. But it really, I am like, I always, and I just, but it kind of sticks with me. It's like.

You have to face that over a Belgian waffle. I know. With Minnie Mouse coming up to shake your kid's hand at the same time. Yeah. I ran away from one of those character breakfasts i ran away from the villain from robin hood into the kitchen as a three-year-old that was a um that was a traumatizing thing for me into the kitchen yeah because he represented just evil to me i that was a big thing i was always running away this is what's terrifying about my nature

is that one time during a storm outside the optometrist my mom was like a crazy tropical storm in like new england and my mom was like okay at the count of three we're gonna run to the car together and then when she made it down to two i just took off in the other direction just running into the into the deluge and whenever i'm acting erratically my friend jair is like oh chris no you're running into the storm man you're running into the storm wow yeah yeah that's um do you do that still do you think do you do that on a real yeah oh yeah i'm a i'm a real i'm a real flight risk is therapy helping like to keep you from running why why do you think you run into the storm are you going to fix the storm

are you succumbing to it you know um uh no i i think it's just um you like scaring your mother is that what it is i think i like to frighten my family. I just think my panic, I just panic irrationally. I think that's all it is. And I think that I don't trust any, I think that I trust my anxiety more than I trust anybody else. Really? Yeah, yeah. Have you ever thought of medication for anxiety?

Or if I may ask, I mean, you can certainly. My medication right now is boba tea every day around 1 p.m and i just hit that stuff and it's yeah yeah that's you need to turn that into cash buddy you need to become mr boba tea boba spoke for all for all the yeah when you were describing um the the cameraman and all that stuff an image came into my head a memory we used to tour gail uh live we would do live shows and melissa and i um it was we had to strip it down to just the two of us and we were um on stage uh and a crowd was waiting in the lobby and we um i was dressed as gail and she was dressed as you know as her character and we were in a blowout fight and i'm just i'm just

like it's we're just absolutely going at it. And, um, about like the show. Cause I think she was, she's very practical and she'd be like right before we were about to do like an hour and a half show, she'd be like, is this funny? And I would just, I would just lose my mind. Not now. Yeah. And so I'm just like, and I didn't realize that, uh, the stage was being broadcast.

There was a video screen in the lobby. And everyone could just see this fight that we were having before the show that we had to do. But luckily, there was no audio. And so, I think they just thought that we were rehearsing because that kind of was the nature of the character. Yeah, yeah. Yeah, there was a lot of just like absolute, like, I don't know how you were able to, like the emotions that run high right before. Like I have to do the smallest thing. I'm like so vulnerable and so fragile.

And then you can just do it daily and just like, yep. And then just head home and hop on the 134 and just, yeah. You got it. Yeah, you got it. just head home and hop on the 134 and just yeah you gotta yeah you gotta i mean well and now time time has gone on that everybody's much more settled just everybody's older nothing is as important anymore which is a lovely lovely thing you know low stakes that sounds yeah just it's like i mean it's not that it's not that quality control isn't the same. You just know that like you get to a point,

and I should just speak for myself. I just get to a point where I always, like when my ex-wife, she would have flight anxiety. And I would say, and I understand why this would make her nuts, but I'd say like your anxiety isn't keeping the plane in the sky. Right. Which is like so easy for me to say, because I just happen to be lucky enough to be able to work through that kind of rationale.

I would argue. In that particular thing. I would argue that my anxiety is keeping the plane in the sky. Well, but that's, you know, you're you, you're magical. You're magical. You're the magical, you know, barracuda wearer. I'm the Sherbert King. I just think that it's like, I don't know.

I just, in that, you know, there's other areas in my life where I'm not so good at just putting the anxiety aside. But there are lots of places and work is one of them and doing shows is one of them and i don't know i think i honestly do think that improv doing years of improv where you're going to go on stage and you don't know what you're going to say yeah makes you pretty i wouldn't say fearless but certainly makes you comfortable less less apt yeah exactly or i was going to say less apt to be rattled because you're like look i've done i do i've done a million hour hour and a half shows where i didn't know what i was going to say before i got on stage i can handle this you know i can handle right television or whatever all right and it is weird it's like my my comfort levels now are more

uh situational in that like uh like it's way more nerve-wracking for me to do an improv show at ucb than it is to do to you know to go be on a talk show. I mean, a talk show that's not me. Why is that? Or guest on it. Because I'm comfortable. And I know what's there. And also, too, I have the structure of it's an interview.

I know how that works. I know I'm going to say something decent, you know, I know. And I've, and I've also bombed before. And I know that like, you know, nobody took away my show business card. I can still get to work. Yeah. I like that feeling of saying one or two good things. You're like, I can go to bed now.

I can go to bed now. It's like, okay. Well, and I used to, I used to do that. I used to do that math on the, on the Conan show when I'd feel guilty about it because in the beginning I was expected to write as many bits as the writers. And after a little while I was like, wait a minute, I'm also on the show. How come I have to do as much as these guys? But there were plenty of times where I would go in my head still with the midwestern guilty like I really didn't keep up my end of the bargain and I would think okay let's look back okay you said

that one thing you said that other thing and you you know at the after that other bit you said that other thing those are three big laughs yeah that's in terms of like just like filling the vessel yeah that's like and filling the vessel like like any of the other writers would be thrilled with Three Big Laughs. Absolutely. Yeah. So like, yeah, I did my part, you know, I had to kind of work through it. And now it's just, it's easy.

It's, you know, it's, you know, you're not all, you're not swooning in love. You're not working over the rough patches where you're just in a long-term functional marriage you know and you're just yeah you're just getting up and you're doing the work and then you know and you're going home so yeah um well let's go on to the um the the uh the the uh where are you going like what what what do you want to, what do you want to be doing with it? You know? And that doesn't, I love it when these aren't, cause I mean, I'd, most of these conversations end up being kind of show business oriented. Cause I'm talking usually to show business people, but I mean,

I'd love it if it was, you know, the answer went beyond that. Like what, you know, where you want to, you know, start a, you know, a turtle sanctuary or something like that, you know where you want to you know start a you know a turtle sanctuary or something like that you know right right right like a like a pig racing type thing yes exactly um exactly as a metaphor yeah i think um well when you said that what what flashed into my mind was i taught at a camp once and the guy who was in charge of the camp, I think I was just talking to somebody about this. Maybe that's why I took my head. I didn't really know him very well.

He looked just like Teddy Roosevelt. And he said, when things go bad for you, go here. And he whipped out a map and he pointed to Missoula, Montana. And did he have a reason or did he just like cryptically walk away he said he was he was seated and he was like giving me my last check um and i was like wow oh okay and he just said like i think best place on earth yeah and so i've always uh i've always dreamt about that i've always i'm a i'm a big fan of this film called crazy Heart, and things do not go well for Jeff Bridges in that film. And so I don't know why, but I really, really saw myself in that in 2009 when I saw it. And I've seen it maybe hundreds of times since.

And I have this premonition that things will go awry for me in whatever, in my personal life or something. I don't know. Maybe it's just as weird. I don't know what it is it's it's this weird premonition i have and so i do find solace in the idea of starting starting over in missoula montana even if it's just an absolute kind of impish fantasy but yeah in terms of like where where i'm going i mean i never have an idea for my career about, I never really have like a dream. I think I kind of gave up on that because it's so unpredictable. I just kind of like making things

that I'm proud of. And I think, I think feeling stronger in my voice, I think is something that I'm, I revel in and, and, and, you know, mastering the craft or whatever craft that is and making things that people aren't making um i like uh i spending time with freaking loved ones has been like a real like just even friends like i unfortunately because of the times it's harder now and zoom hangouts are like really blue balling in a horrible way. Yeah. In a unique way. But yeah, trying to expose more of, I've been really guarded for like the first third of my life. And I think I'm trying to, even with really like loved ones. And I think I'm hoping to kind of put an end to,

to that. Well, that's good. I mean, well, and obviously, I mean, I think,

I think that most people would be surprised to hear you say that you're guarded because you do not seem, you are like, you are very unique. You're very much yourself. And you seem to be very sort of like sure footed in, in your self ness. Oh, sure. yourself. And you seem to be very sort of like sure-footed in your self-ness. Oh, sure.

Yeah. So, you know, I mean, it's kind of – but I can completely understand how – With matters of the heart, I think I'm more – Yeah, yeah. Yeah. I think I'm a little more protective of that. Yeah. If I was courting you, I'd be a lot more.

I'd be a lot coyer. You've been pretty coy. I'd be winking behind a fan like that whole thing where you said you had to go get your plug because your computer was dying just just to show me the shorts i know what that was about you just wanted to show me the shorts and they were not in their beautiful shorts really nice yeah i wanted to see these things and now and you turn a computer so i can see your washer dryer so i know like i can do my laundry over there yeah yeah yeah yeah yeah and i have a mat there set for you and you see the little you see the stepping stool up to the in case you want to peek into the dryer really get in there yeah yeah you want to really get involved yeah yeah um well i guess i don't you know i i you know therapy kudos to you for doing that because i mean that's gonna don't you think that

that's kind of going to be the thing that that sort of gets you there oh big time it's already changing everything for me in terms of interpersonal stuff i feel a lot um i'm starting to be able to recognize what I'm feeling and why I'm feeling it, which is a gift that I've never had. Wow. Wow. So that's nice. How long ago did you start? I think it was March or April.

Oh, really? Wow. Oh, yeah, I'm a spring chicken. Wow, wow. I'm nubile. And so it's all been kind of COVID times, too. Yeah, yeah, exactly. Yeah. Wow. I don nubile. And so it's like all been kind of COVID times too. Yeah. Yeah, exactly.

Yeah. Wow. I don't even really know what my therapist looks like. Wow. Did you, and was it because of the pandemic? Is that, I think, was there, I mean, if I may ask and you can, was there a trigger or something that like. An inciting incident?

Yeah. Yeah. I think it was, it did happen because of uh quarantine i think um and uh trying to kind of like being forced to sit with things and i was you know i was touring so much before yeah yeah and um i was feeling things uh that I felt like, yeah, I think I was being kind of dishonest with myself in unique ways and like just repressing feelings. And I was kind of tired of it. And so I think I just had to sit with it. Like, I don't really like being still at all.

I didn't stop moving until I was like 30. I was always kind of pogo sticking around. And so, yeah, I think it was COVID related. What's the point of it all? I mean, what do you think like, what does someone come away, like they look at a Chris Fleming and and they come away with blank what would that be oh i'm so bad at knowing what like the way i'm supposed to be perceived or or well which yeah i mean what what you would well what you what you would want people

like what you would want you want people to get to know you and then think this is what i've learned from from chris wow okay um uh i think that it's um okay the way that i work is i don't like i've kind of aligned my um a lot of things with alongside prince the way prince lived his life um i try um i try to ask you're a jehovah's witness i'm gonna go door to door wear pajamas all day yeah yeah um but like in terms of uh always uh evolving and not um or trying to throw out, you know, the formula and whatnot and, um,

trying to have a sense of integrity about what you do, how you do it, uh, or, or, um, not being afraid of, uh,

you know, losing what you've like a fan base or whatever, just because like thinking a little bit ahead i don't know um trying to be uh i like i like ambiguity a lot um i kind of like the idea of not being understood i don't really want uh people to know too much about me i think that's part of the guarded thing um i uh i want people to think i'm quite funny and innovative, I guess. Yeah. And stylish.

You got all those things going. I mean, those are all done deals. Okay. Yeah. Then I'm happy. I'm happy. Yeah. And I want to be a good time at parties, honestly.

I like doing that. I like... Remember parties good time at parties, honestly. I like doing that. I like. Remember parties? Yeah. Oh, parties. Yeah. This whole thing is just, it is the strangest thing. There's nothing to really compare this pandemic times to.

Not even like 1917 or whatever you know it was like that didn't have this i mean there's really been nothing like this and there's no i just find myself uh giving up on thinking about what life will be like after it that's that's kind of um for me it was a while i was like, oh, I'm so sick of this. I'm tired of this waiting around. But now I'm with you. Making plans almost seems ridiculous. Or doing anything the way that I once did.

Or even loving anything the way that I once did seems ridiculous. Yeah. I don't know. So I hear you. I think, oh, yeah, it's scary. I mean, I look forward to it being over. And for me, too, because probably a bad emotional habit that I have is isolating, is isolating myself. Oh, same, yeah.

bad emotional habit that I have is isolating, is isolating myself. Oh, same, yeah. And whether I think I, you know, like I will maintain, I have contacts with people and stuff, but I mean, but truly isolating myself and not even kind of, I mean, when you talk about parties and stuff, like, yeah, enjoying them, but usually like feeling more comfortable going home, you know? Oh, sure, sure. And.

That's good that you like home. Huh? that's good that you like home huh that's good i know home yeah no i mean and i but it is it's like well it in the short term seems more comforting and more easy in the long term it's not doing me any favors right um do you feel like you have a controlled way of relating to people? Like you've learned the way that you want people to see you, and so you put that forward? I think so. I don't know. I think it's just kind of like it's just easier.

It's just easier. And especially in the last couple of years, I've got divorced. So I'm at a huge crossroads in my life. And the isolating, I think, was just out of just general sort of – I mean, I've suffered from depression my whole life. And the isolating kind of – that makes it easier. If you're a bruise not being touched, it seems like healing, you know. But this period has really made me feel like, okay, when this thing is over, I got to get out there.

And I mean, I don't mean like I got to get out there and, you know, and start to party and meet some chicks. And I mean, like I need to, you know, this blossom needs to open, quite frankly. Yeah. And I and I and I want to make sure that I don't forget that. And because this does feel like such a weird. Locked in a chrysalis kind of way, because all the notion of like and i and i see other people talking about this um and i hear other people talking about this this should be the time when like well i'm i'm there's so little distraction so let's let's be creative let's make a big burst of production you know like let's just be productive and write all kinds of shit and and

i just feel like no let's see what else is on tv. No, exactly. I just don't, it's not in there. There's just like, I think like I should. But that's smart. You're in a time of input because you're, to think that. That's a good way to look at it, yeah. To think that now is the time. I mean, a lot of normies are doing that. I'm getting a lot of like manuscripts from my normie friends who have now been creative

the last, you know, 30 odd years who are now like hey i'm writing a jukebox musical about kesha you know and it's like okay now that's not a good a good example because i'm there a jukebox musical about kesha but that's okay that's kesha's job you know i think i feel like i should be up to kesha it's just like a it's just like a lot of empty lines that say insert kesha hit, you know, where it's like Is that really a thing that somebody came up with? Yeah, and he hasn't even named the characters. It says like male lead one,

male supporting lead. I'm like, just, if you're going to send it to me, name the character. It looks great. I'll take it down to the Pentagis right now. Yeah. That's now. Yeah. That's great.

Yeah. But no, I feel the same way. I feel like I've only been working on things that I conceived of pre-corona. I feel like I don't want to have an original idea yet. And during this time, I'm worried about what that's going to be. Yeah. I'm not. I can't wait.

Well, Chris, thank you so much much I've kept you long enough here and this was really delightful and thank you for putting out into the world what you put out into the world you do such funny great stuff thank you I've had a lovely time with you

thank you so much for chatting with me yes and let's you know when the world writes itself. Let's go to a water park. Yeah. Let's get some boba and go to a water park. Although I think I'll just, I'll watch. You'll watch me get boba?

Yeah. No, the boba I'll have, but you can go down the slides and all that. Oh, okay. And go down the giant toilet bowl and all that other stuff. I do it face first backwards though, Lady of Shalott style. Arms crossed, pennies over eyes. Yeah. We're going to have a good time.

All right. Yeah. All right. Look out, water world or whatever the hell. Raging waters. All right. Well, thanks everyone for listening. That's been Chris Fleming and I'm Andy Richter.

And this is The Three Questions. And next week, you'll hear more. Bye. I've got a week, you'll hear more. Bye. I've got a big, big love for you. The Three Questions with Andy Richter is a Team Coco and Earwolf production. It's produced by me, Kevin Bartelt, executive produced by Adam Sachs and Jeff Ross at Team Coco, and Chris Bannon and Colin Anderson at Earwolf.

Our supervising producer is Aaron Blair, associate produced by Jen Samples and Galit Sahayek, and engineered by Will Becton. And if you haven't already, make sure to rate and review The Three Questions with Andy Richter on Apple Podcasts. This has been a Team Coco production

in association with Earwolf.