Starting Standup in Maine with David Walton

#24 Caleb Sherman Interview - An Open Mic Master Class

• David Walton • Season 1 • Episode 24

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Caleb Sherman is a comedian and has worked for almost a decade at the Empire Comedy Club in Portland, Maine, where he's become something of an accidental anthropologist of the open mic scene. 

In this conversation, we explore the strange and beautiful world of amateur comedy, what it actually means to "find your voice," and why the grind of showing up night after night might not be such a grind after all. 

From philosophy degrees to ass play, Caleb shares his journey and what he's learned from watching thousands of comedians try to make strangers laugh.

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David:

Hello, welcome back to another very special episode of Starting Stand Up at Maine with David Walton. Today I, david Walton, am sitting down with Caleb Theodore Sherman Very powerful name for a powerful man, a fascinating figure in Portland Maine's comedy scene. Okay, caleb works and performs at the Empire Comedy Club. It's a 140, 30-seat theater that gets huge names. Caleb has been there since 2016. He was born in 1992. He was born to mental health professionals in upstate New York.

David:

Caleb grew up in the Poconos with an almost clinically perfect upbringing His words, not mine. He's been nurtured by very conscientious parents who have obviously screwed him up because he's in stand-up. He studied philosophy in college, which is a worthless degree, as we all know, but he discovered through a poetry reading, his love for performance. These poetry open mics, but he found himself more interested in getting laughs than finger snaps. Since 2016, caleb has seen it all, and when I say that I, I mean it quite literally.

David:

I won't give away the number yet, but I believe Caleb has seen more open mics than any other human being on earth, and we had a fascinating conversation. I loved it. One of the coolest things about doing this is that I get to meet people like Caleb, not know him, invite him to my home, trust this man with long hair down to his nipples who looks a little bit dangerous in a good way, but then turns out to be a extremely soulful, kind, intelligent human being. So what you're about to listen to is two men getting to know each other for the first time. So, without further ado, please enjoy this conversation that dives deep into the craft of comedy, specifically open mics and their value. Here is my chat with Caleb Theodore Sherman oh man, that's rubbish.

Caleb:

That's rubbish. Was born. I was born in a bathtub at home on purpose mama hippie uh, they were my parents. By the way, caleb has long hair.

David:

I would say nipple length, and he's got a good, some good facial hair, but nicely manicured. He's not, doesn't look homeless. Really. You do have something going on with your eyes which is interesting.

Caleb:

Oh, vitiligo I have vitiligo facts that is that when I was 14. It's a harmless autoimmune disorder where your body, your immune system, destroys your melanocytes so you have patches of your skin with no pigment.

Caleb:

Oh uh, michael jackson claimed to have had this disease but was probably just like early on the korean skincare trend of skin lightening, sure, uh. So we don't vitiligo people. I I speak for us all when I say I'm not sure that that was who we would have picked for our spokesperson, but that's who we have as a point of recognition.

David:

Yeah, yeah, I've a bit on the hands and then on the eye everywhere, oh everywhere.

Caleb:

That's exciting, ladies.

David:

No, no, but it looks just as a a first impression, it looks like you have six sunglasses that you're just like rocking that's.

Caleb:

That's my favorite uh interpretation of what it might be on on site, because I I do fear I get insecure, that people will think that I'm tanning like I'm just laying in a.

David:

Well, you just had a disastrous tanning bed session where, like this is a spray tan catastrophe.

Caleb:

That happens I don't want people to think I'm no vain enough to go, not not to all right, I derail, but that's cool.

David:

no, it looks cool. I think it's a good look, so anyway, it's in fashion for sure. You have witnessed how many open mic performances estimate Back of the napkin. Holy crap. Years and numbers.

Caleb:

We got to do some maths. Yeah, because let's see I'll speed this part up, bro, take your time. Four or five open mics a week? For how many weeks? Let's say an average of four mics a week. For how many weeks?

David:

let's say an average of four mics.

Caleb:

Okay, a week with an average of, let's say, 12 people on them.

David:

Okay, 12 that's 48, jesus christ. That's a lot of hours. That's 48 a week. Sounds like you've been going to six years of open mics. It's a lot. At 50 weeks a year, obviously you're not going to every week. So I would say you're somewhere between 200 and 250 times 42 weeks. Wow, wow, wow. So let's just call it low parameter.

Caleb:

We'll go 200 times 42 which is 8,000, that's a lot never thought about it that way.

David:

Yeah, wow, wow, wow 200 times 4 is 800, so 200 times 40 is 8,000. Ok, I just wanted to you're in the top .001% of the global population in open mic witnessing and I would say maybe top 100 on earth.

Caleb:

There's thousands of us.

David:

Dude, I think you're number one in the world Number one. No, but so. So this is an incredible insight. And I think when you mentioned when we, when we had this idea to come on, I had just done an open mic I think it was my 18th or 19th ever and then we just started chatting and I was like I fucking hate open mics and you were like I love open mics. And I was like yeah, and so I was like, oh, this is going to be great. So it's like Crossfire on CNN right now.

Caleb:

Okay, no, no, we don't have to argue about it, but I would love to know why?

David:

what did it? What is it about open mics that you love? Yeah, what have you learned watching open mics? You know, I'm just gonna, I'm just, I just want to extract your experience and especially for listeners, because there's it's a ton of value for versioning stand-ups and just people who are who are now interested in the whole world of stand-up comedy yeah, what do I love about open mics?

Caleb:

oh, the humanity of it all. Yeah, um, if you're a hardcore comedy fan, you like I think even through, uh, someone's like nervous jitters because it's their first couple of mics can see a good premise and a good joke. I love that. I love to see people facing their fears right. People who, um, do it one time, like these, these people that come in with all sorts of bravado, who you don't expect to just crumble as soon as they get up there. That's great too. That's a part of it. Yeah, uh, this shot in freud a little bit of it but also just the the vulnerability of it

David:

be like yeah, big tough guy like this is hard and that's okay and we support you anyway, man sweet, you're much more of a sweetheart than I thought. Now I feel like a real asshole. No, not at all.

Caleb:

No, go, keep going uh and I love uh. Also like people getting their first laughs, like seeing people light up. They're getting their first laughs. Um, I love uh watching the downfall of uh, the itinerant alcoholic piece of shit that you wish wasn't as funny as he is and over time gets less funny and less coherent. That's a, that's a perfect open mic experience over the course of years.

David:

You mean so he comes his first guy up. There's all this like promise.

Caleb:

Right, and then his alcoholism. The potential there's so much potential and he goes the other way and then you realize that two years in he hasn't written 10 minutes. And uh is doing and doing crowd work at an open mic. That is increased. It's just devolving, yeah, week over week. Yeah, there's all that. Um, that's a valuable lesson too um it's all, it's all learning.

Caleb:

Right, I love that? Um, I definitely. I think earlier we we asserted that maybe I had some sort of natural inclination to be funny, but I didn't recognize it and I think that I would say, to whatever degree I've improved in my stand-up, writing, delivery, performance, doing stand-up, especially at open mics, I had to learn it. I'm a student of it.

Caleb:

None of it came naturally to me yeah, and I was as insufferable as a lot of other open micers are when they start doing, you know, hack shit, doing dirty, gross stuff for the sake of being perverse and shocking. And I still revel in that to some degree. I mean, like I've featured now for like national headliners at Empire Comedy Club. I've had the blessing to be able to do that and like my A material I always pull out is about putting an ice cream scoop in my ass. You know like I think that's fine.

David:

It's true, it's the true story.

Caleb:

So, but that all came out of open mics and that culture of the open mic.

David:

So where are you at in your career? I'm gonna just, I just want to sort of oh, let's start there. Where am I? I mean, how many? So? So you started when? What year? 2016? Okay, and then you took a couple years off during covid yeah, uh, I.

Caleb:

So I was, like in 2018, a semi-finalist at the Empire Comedy Competition and like, did a half hour because that was the prize for the semi-finalist.

David:

You had a half hour materials two years in.

Caleb:

I didn't, but I certainly performed for 30 minutes. I did my time.

David:

That's amazing, that's terrifying.

Caleb:

It wasn't great. Looking back on it it could have been a lot worse like, but I was dedicated to going to the mics and I would write a new five minutes every week for my first couple of years whoa yeah and no matter if it and a lot of it. You know ate shit, of course, but you never retested material, never until I started getting on shows in 2018, I would do a new thing every week. Okay, but hold on a second.

David:

How do you know that it's funny or not? Because this is my big problem with open mics Like, for example, the one we just were at together. Those were all ostensibly other stand-ups. I was looking at the audience as people were being you know it wasn't bad some of the stuff looking at the audience as people were being. You know they were it wasn't bad. Some of the stuff, yeah, and no one's paying attention dude everyone's like looking at their own notes, so how on? Earth? Do you know that a joke is good or not?

David:

you don't not based on one's uh open mic performance for sure so do you wish you tried more of those out, or were you like the pipe metaphor where you're just, I need two years of unclogging my shit pipe I did need that I think, I did.

Caleb:

I think it was an outlet for me. I think I also had no ambition um, beyond getting better at public speaking, right like being a little less nervous every week, and, uh, the only agenda I had was to like say my ideas out loud to a room yeah uh, for those for that time. So it was a lot.

Caleb:

It was like an outlet thing and yeah, I was just writing uh and like, uh, getting it out, but, amazing dude, once I started to get shows, uh, then it's like well, I would like them to laugh. Yeah, the open micers, I didn't really. I did care a little bit. I wanted to like get into those circles and I wanted that. I did want them to laugh, but I was more preoccupied with like writing little rants.

David:

Yeah, I'm very ranty. I was rant, ranty too and I thought that was enough.

Caleb:

Yeah and no, we can't all be bill burr, but, um, you don't. And comics are not an audience that paid to come to a comedy show either, so it's not doing you any service. Uh, you can glean plenty of useful information right from just the performance, the, the I would say 80 of the utility of going to an open mic for the first lot of time that you're going to open mics is just comfort, getting comfortable on stage. Yes, speaking, hitting the points you wanted to hit in a bit. That's like a huge chunk of the usefulness.

Caleb:

It's not about identifying what's funny, and I would also say uh, my, my point of view on it is I do, I do know that something is funny when I write it and it it's more dependent on me successfully saying it, delivering it, than it is the, the word. Like I know, like you know, you can identify a joke, you know what the laugh line is right and and it might be not as funny as you thought or it might be funnier than you thought, but it's funny. You know that when you write it.

David:

Well, it's like, you know it's a joke, you know that there's a rhythm, that you have released the tension, and either there's a laugh or not, but you have stated a joke and if you've done it with courage, you have stuck it yeah and then you're there to see, yeah, what the reaction is we.

Caleb:

I don't know if we were recording, but I was talking about how I used to canvas and ask people for money at the door and when I was training college kids to ask for money door to door in our practice I would be like, how did you feel about that ask when they would?

David:

get to the ask right.

Caleb:

Did you feel like it was a good ask? Very similar, I feel like yes, you just know, I fucked that joke up the joke is funny, but I fucked it up or I nailed it. Didn't get the laugh that I thought it would. Now we have to think what other factors went into why this room of people in this context today looking at me, laughed only this much at this thing. That I think should be like the finale to this big five minute set or whatever you know, um, but you can't judge.

David:

Again, back to those open mics. You can't judge the lack of laughter on anything, that's true, because no one's paying attention unless some people are. And like I've noticed as I've gotten, I've progressed and gotten objectively more, you know, uh, playing by the rules of stand-up and like saying actual jokes, right, I? I now see that some people are like, you know, you hear a couple and that's why the recording I you know gary goldman's 366 tips, yeah, that we talked about. Yeah, the number one is record your things and listen back. And my friend al madrigo's done hbo specials. He's like, he's like record and listen where the laughs are and where you're not getting a laugh. That isn't important information. It's just gone. Cut it, cut it.

David:

I have the book Stephen King's On Writing, book that we were both praising Same thing. It's just like get rid of all extraneous everything, and that seems to be a lot of the game. It's more almost science, it's more like tinkering in an automobile shop.

Caleb:

Something that I recall from stephen king's own writing is he describes it as like archaeology like just brushing with a toothbrush, uh-huh off the stuff, right, revealing exactly the structure of the thing that's already there. It's like a subtractive sculpture art, right. Like you, it deforms. In there, you got to chisel it, right yeah uh, and if you chisel too much, you have a deformed thing. If you if you don't chisel enough, you don't have a formed thing at all.

David:

Yes, yeah, totally okay, so, so all right, I'm buying the open mic. The value of it, yeah, uh, and, and you're and totally about getting comfortable. I think, um, at my stage I don't have the confidence you have that the the joke is funny, meaning I can think it's funny you know, but if it's, if it bombs, it bombs. I know in talking ad nauseum with so many people in the last year, like sam morrell, who's so good and so funny you talked to sam morrell no, oh, he's so good he's so good yeah whoever's listening, go watch sam morrell.

Caleb:

But he was just in portland.

David:

Yeah, he was but I know that uh val over at the comedy cellar sam his comedy seller shows is he's a writing machine and he's, he's got, he's got five alts and he's like which one val? Which one should I go? Which one did I?

Caleb:

go with, like what set, he should do.

David:

No, no, which joke he should do what's like, what's funny like he's constantly and gary goldman's other tips is just like the minute you have a laugh, like there's more laughs in there. We were talking about that. There's more ways to you can probably get three laughs where you didn't think there was any. You know and you can change a word whatever, but Val's statement was Sam doesn't know what's funny until he does it.

Caleb:

And he.

David:

I think let me preface it by saying I've witnessed people testing jokes.

Caleb:

They're all funny.

David:

Yeah, I think what he's saying in his brain is what's the funniest?

Caleb:

What's the one?

David:

Yeah, yeah, yes, and they don't know what the funniest is. They can think it is, but they all know that they're jokes that will get chuckles totally, yeah.

Caleb:

Yeah, that's the level, that's the only level of confidence I have. It's like this is not. Nobody is going to throw something at me and tell me to leave after I say this, you know what I mean.

David:

Yeah, bare minimum. They will see, they will appreciate the effort that went into crafting a joke.

Caleb:

Quote unquote yeah, yeah yeah, I'm, and I'm by no means like I would say samorelle, really brilliant joke writer I don't know where this distinction lies in my brain exactly, but like I don't think of myself as like a a great joke writer, I'm, I, I am, I can write, I can articulate things yeah, obviously to some degree. Yeah like, but like it's not gonna be like 1970s joke book, right formulaic that's done.

David:

That world is over.

Caleb:

But so I think like joke jokes a pretty nebulous, but I don't think that I'm the strongest joke writer. I am a fucking weirdo. And that goes a long way if you're able to bring people into your point of view. I'm much more interested in that than I have endeavored to nail the structural parts of it. Not that I don't want that challenge too, um, and I do trim some fat and think about where to change words here and there, but never been a great wordsmith me neither and I and I constantly, when I wake up in the morning I'm like what?

Caleb:

am I doing like I don't?

David:

because I have a friend who's a comedy writer professional. He's written scripts, he's written movies with ro De Niro, like big comedy films, and I will reach out to him and I'll usually record something in my car or something. And I'll be like what do you think of this? Does this feel hack? And within like a nanosecond he's got like three like it's like blank. That are just tight ass fucking jokes. Yeah, and I'm like is this your? I'm gonna have him on the podcast.

David:

So I'm like is is your brain just auto training joke. It's like all day and he's like kind of yeah, I was like oh yeah, because he's been in room.

David:

He's been in sitcom rooms, you know for that's his 8 000 you know, thing of just like pitching jokes to 10 other good comedy writers, yep, and so that that brain and I know that that's not how my brain works I'm more like with you, philosophizing, thinking deeply about things. My brain naturally goes to either like fedex middle management logistics, like how do I get to my kid's school 20 seconds faster, or I'm just off in the clouds thinking of just not jokes things I will say if I'm writing every day I start to get more of the downloads.

Caleb:

The accidental?

David:

oh that would be funny. It's sort of like.

Caleb:

I have to keep my brain in that context do you feel, when you're in that context, that sometimes they just appear fully formed to you and there's, there's. There's no wordsmithing, because you're just like well, there it is. I don't know where that came from rarely, but yes, it has happened.

David:

And just like, yeah, that's what I want that yeah because I'm I'm a lazy mother like I want just to be downloading constantly. I know people.

Caleb:

Uh, I say this sometimes and I think that there's kind of a worthy stigma surrounding it, like but? But I think of comedy as like a low effort, high reward thing really I do, yeah, which people hate? I mean, I don't. I haven't felt like going to all these open mics has been a great effort, because I'm enjoying it I genuinely enjoy it, I love that's beautiful comedy, so it's not felt like but so I have to pretend that that's the grind.

David:

But I put in my reps uh-huh uh, but really like, I just like writing, so I'll write some crazy down, if I can get laughs, that's how my friend, another comic, kevin christie, who's been uh known forever and he's a staple at the uh comedy store in la and I'm like how do you? He goes up three times a week. He has a, he has a neil brennan uh kind of mic, that that's all for big stand-ups to test new material. And I was like how do you just keep going? He's like I don't know, I write it and I'm like I need to see if it's funny.

Caleb:

I just need to. I relate to that Like yeah, are other people thinking this? Or do they not realize they're thinking this? Or when I say this, are they going to think it's really funny that I thought that. Yeah, all that.

David:

I think I'm in the stage and I've said this on the podcast but I think I'm in the stage where I'm trying to figure out my life and story, almost like in a memoir-esque way. I'm like, how have I gotten here? Because I've kind of been a a I don't know. I just try to live in the moment, try to have fun, try to do what's enjoyable, and then I kind of wake up and I'm like I'm 46, I have a wife and kids, I live in maine. Like how the fuck did this happen? Right and um, and so a lot of the writing that appeals to me is kind of mining my personal experience, which I know from stand-up point of view. Is there a? I sense this, I don't know why. Is there like a looking down on people who kind of like bring their own personal life? Is there like a snobbiness about that that you are aware?

Caleb:

of. Maybe what I think you might be sensing is that low level open micers are often really have a hard time being vulnerable, and that they have always had humor as a deflective self-defense mechanism. And so what they? When you talk about your life, they see it either as self-absorption or vulnerability which terrifies them. And they will then go to the mechanism they've relied on their whole lives, which is to humiliate, not humiliate it. What's the word? What's the word? They need to put it down yeah right, they need.

Caleb:

They need to be like oh this, you're talking about your kids. Yeah, gay yeah, I mean yeah like um, I don't know if it's snobbery, I think it's actually just a kind of neuroses that they they can't take anything seriously. How unfunny would it be to like think you know? This, I also think, is why, like the people, the, the rare comedians who like able to do deep social commentary and like have a point, are people that are really really friggin funny but are not debilitated by their funniness you know what I?

Caleb:

mean like uh, you'll meet people you probably know, comedians who can't turn it off never turn it off it's annoying and it's annoying, it's like a it's it's kind of tragic yeah, it's like you'll, you'll, they're just bidding all the time all bits all the time and you can't even have a conversation with them or like shit will be going on in their life and you are trying for just a moment to check in with them as a friend and they're like mom died, whatever, dude, it's not no, big deal like and you're, that's actually tragic.

Caleb:

So yeah, I don't, I don't know, I can't speak to like broader comedy community outside of the one that I've experienced, but I have noticed that that happens in the main comedy scene. There are a lot of comics who are just not able to get vulnerable with you yeah, so maybe that's what you're sensing yeah I've done a lot of like mining of my personal experience too.

Caleb:

You don't see it as much. I mean, we're all coming from our own point of view. It's all autobiography, yeah. So if you're doing it intentionally, I think you probably have a.

David:

You're a little head up on the folks that are doing it unintentionally well, it's a good segue because I want to talk about this idea of in our cars we're like amazing and we rip and like I've had rehearsals like a half hour before an open mic where I'm like ooh, fuck, yeah, it's going to crush, let's go, baby, of course. And then you get in this room and the energy of the room and you're like nothing I did in my car will work, because the energy is totally unmatched to this. Somehow I have to take the energy, transmute it, transform it into something where now my set works. Can you speak to this idea of taking control of a room or being having to match your set to something in ineffable, almost in a room? Yeah, what, what do you know about that and what, how do you see it and how do you deal with?

Caleb:

it. Wow, yeah, no, that's a big. I mean in the vacuum of your car you were all crushing. If we could, if, if we could all be who we are alone in our car, we would all be stand-up comics professional. Yeah, if we could do that in front of people, that would be pretty wild, I don't.

Caleb:

It's an interesting way to frame it that you that you framed it like is it that you need to take command of the room and then transmute the energy, or do you need to meet the energy where it's at? And I think that's like a great, that's a great frame. It's probably something like both at once. Like I think maybe taking taking command of a room involves just instantly demonstrating in your body language, your countenance, your cadence, immediately your cadence, that you are like you're a part of the room. You recognize the energy that's in the room and you're consciously bringing it to where you want it to go.

Caleb:

For a moment you have the mic right, like what that it is. That feels ineffable to me to to really describe how people can do it. You witness it, you recognize it when you see it, but you're but it's. You know it would take, I think, a bunch of analysts could talk about. Oh, the body language and their tone, or like, I have a deep voice, or like, like, what is it that is commanding the the attention of the room? I would stop just short of saying it's magic, right.

Caleb:

Cause there's definitely thing quantifiable things that we could like appreciate about how it transpires that someone just can go up there and in a room that was could appreciate. About how it transpires that someone just can go up there and in a room that was giggling about stupid puns a moment ago, talk about some serious topic, and get huge, crushing waves of laughter from a room, just to really quickly take control of the room. In that way, we are trying to make people laugh, make them, make them, making them do it. Uh, it is an involuntary response laughter right, so like um I don't know.

David:

Yeah, that's such a cool answer. I think it made me think of the advice or that I've read, or whatever, that you know there's certain techniques, right, like the person before, if you've been listening, usually there's a way to tie your first joke to what they've done. Yeah, uh, gary goldman's advice was usually, I find it very effective to get up there and make an observation about the either the room or the the stage or something that no one stated. That is honest and funny. Yeah, and and I will say that the blink moment it's blink moments when you see a professional get up there because they are exuding like you're in safe hands and it usually is immediately they find a way to make everyone laugh and they're just like oh okay, this guy is funny and he's comfortable and he's poised and this is a professional.

David:

Now I can relax and I think if I had to state what is the value of open mic land? It's getting good at that. It's just going into hostile environments and being like I'm gonna learn how to in 10 to 15 seconds, 20, 30 max. Yeah, just have everyone on my side yeah, well said.

Caleb:

That is a great insight on the value of open mic, I think. That is one of the definite takeaways over time that you get is that it's interesting because I see a lot of the national headliners that come through Empire Comedy Club.

David:

Yeah, just for people listening, Caleb works at the Empire Comedy Club, which is the one real comedy club in. Just for people listening. Uh, caleb is works at the empire comedy club, which is the one real comedy club in portland, maine. Yeah, and you guys get big people yeah, huge names huge names come through punching way above our weight class.

Caleb:

I would say for a 130 seat little club to have like joe List annually come through. I have had Big Jay Ogerson do like four sold out shows Incredible.

David:

Who is the guy that you took me?

Caleb:

Kyle Canaan yeah, awesome, we're going to have Doug Stanhope in October, I think. Just yeah, awesome. Legends Ari Shafir we had Really cool, really cool club. Wow, I got derailed. What was I going to say? Oh, just that, those folks, those heavy hitters, there's a certain degree to which they still do that because it's like a reflex to them. I think at that point, when you're a pro to riff on the room in in some way, to do like you're saying, uh, in the first 10 or 15 seconds, just make sure everyone's like, yep, we're in good hands, this is a pro there's a degree to which they have less of an impetus to do it at all because they're them just being the ticket that you bought yeah it already kind of did that for him yeah I see this especially with, like lucas zelnick, rachel uh, I almost said rachel rachel scanlon, uh, people who have big online followings, who are there for them.

Caleb:

That are their fans, who watch their content, their podcast, their clips, their crowd work. They are so excited to be in the room with them. That it's immediate, it's just immediate. Whatever the first thing out of their mouth is, it's gonna get applause.

David:

You know that's sort of the world of the netflix special, it's like yeah, you know what I mean. Like all those high ticket, those people love this comic.

Caleb:

Yeah, they're like bitter open micers who have no right speculating. We'll often be like at that level. How do you even know if it's funny? They're just laughing because you're Tom Segura. It's like okay, dude.

David:

Sure yeah, keep telling yourself that.

Caleb:

Yeah, no, it's fun, it's a wow. Yeah, that's a really great one. I'm gonna tell noobs that about open mics. It's like getting comfortable on stage is the value of it and learning how to uh bring the energy of the room where you wanted to go and like little things like that. You also pick up from hosting shows yeah, there's a lot of value to hosting, isn't there?

Caleb:

I've hosted a ton of shows and that was something I had to. To learn was like what? I have to change my opening bit. I have to do the kind of call and response like, oh, come on, guys, we can do better than that, or something to that degree. I have to ask them aren't you guys excited? You know I have to uh, freaking, project my voice a little more and like yell yeah um, that all is valuable.

Caleb:

Or just like the economy of words, like to to get through house rules, even like if you fucking fumbled the house rules and then five minutes later you get on stage to host. They're already like who's this fucking guy?

David:

yes, I have. I'm trying to figure out a way, because when I speak there's certain moods and you know when your brain's cooking that you're you know more, more articulate, and then there are times where you're, you know, tired or whatever, and like I am now, like it's like halting and you don't really know what you're saying. There are certain comics like woody allen comes to mind other where, like almost the whole the, the, that thing becomes the part of the act yeah and there's a part of me that's like I think I'm gonna have to do that because totally I can't be crispy cream.

David:

You know what I mean? I I could just yeah I don't have that and I, when I listen back to my sets, like I'm the filler words, I'm like dude, what are you doing? Like the amount of filler words, and sometimes not yeah and I'm just like shit.

Caleb:

Like because the filler words deflate and I think they show amateurism and you're losing trust if you're going uh uh, At the very least you're thinking about the next word you're going to say that goes away just from repetitions to a certain degree.

David:

Yeah, and there's stories I've told maybe 10 times where I know the story and I can change a little bit. And that's a lot of what it is right that fluidity is good.

Caleb:

there's also the other side of that coin where, uh, you've told that you're telling the joke for the 50th time and it comes off too polished, right? So, um, like, really, really strong joke writers I think have to will intentionally include a filler word. Yes, I have a bunch of bits where part of it is that it's like oh, I'm, what was I going to say? Oh right, the punchline.

David:

Like I knew exactly what I was going to say.

Caleb:

Knew it right yeah, so it is. I've noticed. So when I was I don't know why I keep coming back to this it was valuable for my stand-up when I was canvassing, knocking door to door. I was training people to do this political, political donations.

David:

Right, talking about my version of stuff yeah, it's not.

Caleb:

You know, nobody wants you interrupting their dinner time and and it's hell. But one of the things that I saw was completely unhelpful in training people how to canvas was pointing out filler words. It would just completely destroy the confidence.

David:

Yeah, because they would say one and then they'd panic.

Caleb:

Yes, so it was like not the feedback that a lot of people needed to hear, that, um, I wouldn't, I wouldn't worry too much it's so funny.

David:

You say that because I remember my third open mic or something, and you may have been there. It was at empire and I it was my first time, maybe, at empire and I was like, oh, my first two, there were so many uhs, it was so messy, I gotta be chris, like the pros, and I went and it was like this robotic, perfectly stated thing that was just not. Not a single laugh, you know, like just like just crickets for five minutes, dude, yeah, and I remember being like, okay, I guess crispy isn't the whole Right, you know, so, so, and now, yeah, the, the, the whole thing. One of the guys that I really like, uh, his name's Fox Uh, I'm spacing his first name, but he's, he's an LA really good writer. And Kirk Fox, uh, if you've never heard of him, you should check it out. Go to his Instagram.

Caleb:

Yeah, and Kirk Fox. If you've never heard of him, you should check it out. Go to his.

David:

Instagram. Yeah, really funny and he's got a really good reputation. He started late, like he started he was a tennis pro and then he started in his mid 40s and now like is big with all the big hitters. He had DM'd me because we have mutual friends and he was like I'll help you write some jokes. And I was like I got to learn how to write a joke for us before I started pulling like super pros, you know.

Caleb:

Sure.

David:

But he said um, he said just talk it's, it's like it's just talking with people as opposed to at them, and that was like the only thing he said and and that you know, it's like this simple thing that you're like, that's like a nothing statement, right, right, talk at them. Well, of course I'm talking with them, but there's something there that's very deep and I've noticed in all my open mics. If I go up and I have some set in my head and I just like to get through it properly, it it's not nearly as good or as satisfying as being messy, but I feel like I'm like dude, we're talking and we're having a we're having a little chat ski right, you want to guys have a little chat ski with me up here you know, like that kind of thing, and you can say it, you know.

David:

And then then you feel like after our interview to like I'm gonna have being a great move because I've connected with you in a very real way yeah and then the point is like you can do that on stage, yeah, and anytime I I just go up with the intention to connect. There's just more goodwill coming my way, you know totally.

Caleb:

Um and that'll also change what you want to write about, because, uh, if you're writing autobiographically, it's like well, we got to talk about how this is like the human experience, not just my autobiography, right, but like what's funny about this that everyone can talk about, or, or if you're doing, or you're at least more self-aware to be like that was just just this is a just me experience, right, y'all like in the room. And then there's also a thing there, uh, which I've heard like comedy teacher types talk about, where you're like training them that their input is a part of it. Uh will encourage the laughter and reactions. Who's Oz? If you're having a dialogue with uh, you're asking them, you hear it Standups do this all the time, even if it's completely rhetorical, is like, right, like yeah, what.

Caleb:

Nodding with folks just to connect that connection as opposed to just reciting at them.

David:

Yeah.

Caleb:

Uh, reading lines to them.

David:

Yeah, I would say, the premise setting up is always in the sort of you language, like you know, when you blank.

Caleb:

Now I just I want to write a five minute set where I only say when one goes to the post office, when one, when one, no, you, yeah, so I'm going to, because we're I'm going to be nearing my children's school pickup, so I do have to.

David:

Kind of I could talk for another couple hours. Hell, yeah, if I may, I think people would be interested. You've witnessed. Did you watch my set on Thursday? Yeah, it was about meditation. Yeah, like just you know the premise is, I've done so much meditation to try to become a better person. All I'm doing is becoming more mindful of what a degenerate I am. And then you know various things. I would be very grateful if you just either, maybe in the context of, like, what are you noticing that I'm doing? Well, what do you? What are you noticing that I should work on? And what are you noticing Like, is there any raw? Is there anything that you know hit you as like a I don't know, kind of a, an area that is worth mining, if you will.

David:

And I don't want to put you on the spot because you may not even remember what I said or anything I did.

Caleb:

But any kind of impression. I've always had positive impressions of your sets. I feel like I'm not usually digesting people's sets in a in a way of like oh how can I give them tips, right? Yeah um, nor am I super, super critical if you, if you're doing so, what maybe? Maybe the feedback then is I think you're doing a lot of the fundamental stuff right, which is just that you're, and maybe this is learned. I remember your Millennials Need to Fuck More. First, open mic, hot take as being really funny and it going well.

David:

Oh, interesting.

Caleb:

I don't remember any crickets sets from you, but I haven't been at every single one.

David:

You haven't been at every one.

Caleb:

No, the first yeah, I would say you're doing a lot of the fundamental things right, and maybe just from this conversation too, I would say, if you've got a premise that's that loose, it feels like you're opening yourself up to the possibility that when you get up there, what you wrote down isn't what you're going to say and that that kind of playfulness can go a long way and create more connections and have a more conversational uh feeling, which can be really, really fun for people with, where you still have a few punch lines in your back pocket to deploy, if the right energy and moment appears in, in just bringing the topic up with people, like if the premise is.

Caleb:

I've done all this meditating and now I'm just more aware of what a degenerate I am. I've done a lot of open mic sets with nothing more than a premise. People sometimes would call that like writing on stage. I don't know to what degree I do that, but sometimes my only goal for an open mic set is to say it out loud in front of people in a room, see what reactions just the premise starts to bring and go from there.

David:

Do you start doing crowd work a little bit?

Caleb:

after I will occasionally. I don't know how useful that always is for writing, but I guess what I'm saying is like occasionally, I don't know how useful that always is for writing, but I guess what I'm saying is like how comfortable are you with, like the extemporaneous? Writing yeah based on a premise, because I think that you would really thrive in that, and then you come away with something that you could do less improvisationally later oh, this is beautiful because I that's a really cool idea.

David:

It's ballsy and I I think I it's ballsy in the sense that you're kind of like I don't know what I'm gonna say yeah, but it's low stakes it's super low, you know I think my challenge is because I'm recording them all and I think it the the premise of this podcast was that I share them all. It feels weirdly high stakes every single one but I don't have to share and I've stopped sharing every open mic.

Caleb:

I do, but you don't need to go like full.

David:

hey, let's workshop this premise together, guys, yeah, yeah, yeah.

Caleb:

But you don't always need to know the punchline. If you mull over the premise and what you think is funny about it, you can, I think.

David:

I don't know, that might be horrible advice, but no, no, I don't think it is, because ultimately I get my enjoyment and I try to north star, like what is exciting about this for me? Yeah, and I think one of my great challenges is is repeating jokes. I don't like doing it in life. I mean there's a couple that you do because it's almost like a parody of the joke. Yep, you know, like one of my friends has a line where where his pickup line, oh no, he'll be with a group of his buddies and and there'll be a table of girls like with an earshot and he'll be like guys, guys, enough with the fucking donkey dick jokes. It's old, you know, so they can hear and like that dumb shit. Like I could hear it 50 times and still find it you know, um.

David:

So there's certain jokes which I won't tire of saying, I would say on stage, but for the most part there's a sort of a almost like a shame that I'm doing the same thing. And that's a problem with standup, I think, because you are all constantly tinkering and doing the same thing.

Caleb:

One of the things.

David:

That's hard. While you think about a response, is that I that that gave me a bad feeling was watching Louis CK do this amazing set and his performances are so good because they're so coming out of his head like there's such a. I'm talking with you and this is just coming out of my mouth for the first time and then this damn instagram person put on another night the same exact thing and it was like exactly, yeah the same.

Caleb:

He's master of that.

David:

He's a master, it's every nano beat is mapped out oh yeah and I was like, oh shit, like I wonder if that's obviously he enjoys, that, he obviously has a profound love. I want to. I I worry that I won't have that love and I have another friend who started stand-up. He's like really famous dax shepherd and he he started uh doing he.

David:

When I said I was going to do this project, he was like I did stand-up actually right when my kids were born and he was like I challenged myself. I just do new stories every night and he got hooked in Vegas, but he never repeated it right and we sort of have a he's a master improviser, sure, uh. But anyway, my, my that's really my long-winded way of saying there's concern I have going to bed at night.

David:

That, like stand-up, is an amazing art form that I'm clearly intrigued by, but I'm just like, oh shit, like yeah, is it? Is it going to be enjoyable to to? Keep repeating to to have some tight 10. That I repeat 30 times yeah, I.

Caleb:

So I'm only recently beginning to struggle with this because it's been. I have like I've got this like 20 minutes. I have like that. I do the same way every time and I've started to get sick of some of them. I hate all of those jokes now to some degree, but I, I would, my, I don't know, I would see my suggestion would be like that.

Caleb:

This, uh, stand-up versus improv dichotomy is a false one, and both muscles are really important to to exercise and that you, like I said I did a new five minutes for like every week, multiple open mics sometimes for like two years. I was not interested in repeating stuff. That's wild, and I had the same sort of fear too. It was like, well, that's not gonna be fun, like I said the thing and I don't need to go back there. But there is a ton of value, of course. That is.

Caleb:

The stand-up game is in the tweaking and the wordsmithing and then performing it as though it's the first time you've ever said it every single time. There is a lot of value in that, but there's still, I think, because of that energy in rooms where we keep talking about, there's a ton of value in the improvisational stuff as well, and like you don't need to become a crowd work guy to mine the value from whatever you can get out of that, right, I would say. So I think, think you, and also I mean you've done how long have you been doing this now like, well, I did my first open mic about a year ago, but I'm still below.

David:

I'm nearing the first 20 open mics yeah, yeah, that you're.

Caleb:

You're your first 105 minutes that you write aren't going to be the ones that you want to like, immortalize, yeah, you know, don't be so sure, yeah I, I think I'm almost done.

David:

I think my life's work's almost complete so I start commissioning the equestrian statues well, I, exactly, I, uh, no, I. I was down at the bitterford open mic, uh, mulligans or whatever, and and it was the first time I had a real set, that was like I, I really focused on the writing and and then all those guys asked me to come do like the real you know set or whatever where there's paying customers yeah which was which was a really cool feeling of, uh, validation of the hard work that I felt like I had done.

David:

That being said, they're like so you got 10 minutes right and I was like what? So now it's sort of like okay, I had this thing that was probably took six minutes to perform, but if I do it right, it's probably four minutes or three and a half, yep, and now I need another seven to kind of be that minimum. Would you say. 10 minutes is kind of the minimum where you can start being asked to to join shows uh, no, we'll do guest spots that are five on some showcases yeah.

Caleb:

Yeah For, like much newer people, people who want to see how they handle it. Yeah, 10 feels really short to me now. Yeah, but it isn't. It's so much time you can do so much. Yeah, just watch the first five minutes of any of your favorite specials. There's so much.

David:

There's so much packed in. That's what my friend Kevin says.

Caleb:

He so much packed in and that's my friend kevin's day, he's just like, at the end of the day it's last minute. Yeah, you know, and you're like, oh, and those guys, that's what they're doing. This is another great thing I had early on was that at bull phoenix in portland when there used to be comedy upstairs run by this awesome guy, mike mike levinsky, I think his name a really cool guy he would do at the end of their showcases, anybody in the audience who wanted to could take the one minute challenge and he would give a dollar to whoever had the best one minute. That's fun, I think.

Caleb:

Starting to think about minutes of comedy, because one time I was like I'm going to win the one minute thing and I went there and this awesome comic in Portland, amelia, that I love, just showed up out of the blue and everyone was like, oh my god, amelia is making an appearance like we haven't seen her in months because she kind of comes in and out, she's got a busy life, uh, and she just crushed me oh based on like telling just a story from her day.

Caleb:

Like casually, I was like fuck, I wrote six ten second jokes for this and it was really really good lesson and I have a file on my phone to this day that is just one minute challenges where I'm thinking in terms of laughs per minute. I'm not a one-liner guy. I don't. I don't even think of myself as a great joke writer, but it's.

Caleb:

It is important to think about it minute by minute. And even if it's a, I'm notorious among the comics in Portland that I work with a lot for just making a thing way too fucking long and just having like a seven-minute rant about Amish people that I don't need to have. So I constantly need to be thinking more, yeah, like what's the tightest version of this that I don't need to have? So I constantly need to be thinking more, yeah, like what's the tightest version of this? Where's the setup, where's the punch in it? And that's a really fun exercise to do is just like give yourself a one minute challenge and then write 10 of them and then you'll be all set for your comedy mill gig.

David:

Nikki Glaser was on Howard Stern, yeah, and she just explained one regret she had, which is that she didn't ask friends to help her with her sets earlier, like she just did it all alone and she thinks it's like so much more fun. I would have gone so much better, so much faster. Yeah, and that was all I needed, because I've been trying to prove to myself that I could be good on my own and, like you know, I want this all to be me. It was like almost egoic and then I started just saying fuck it, reaching out, sending a rant to a friend what do you think is this hack? And just the joy and enjoyment and the just collaborating and not being so precious, totally.

David:

And the other thing my friend says like dude, if you're in two years and this is your, your walking testament if you're in two years still performing these jokes that you wrote in your first year of stand-up, like you are failing dude, right, like it, that is not the game. And so I think, like you, you just did it, naturally, without that advice. You just kind of had an intuitive sense like I just gotta fucking get unclog the pipe. Man, I, man, I did, yeah.

Caleb:

Yeah, and I've only recently become less precious about like accepting tags from people.

David:

Only recently.

Caleb:

Yeah, so I totally agree with that. It resonates that you're going to have awesome people around you who are very clever too, and you're going to hopefully you're like carpooling to some gig an hour and a half away. You got all that time. You're just riffing like stuff. That's the best thing ever, that's if you can share even a microsecond of that joy that happens in a car, just driving with another comic on stage like don't deprive audiences of that. It probably was really fucking funny.

David:

Yeah, I think it would supercharge development to just be around comics all the time, and I think those guys are you know I think the top guys are. That's their friends. They're just constantly hanging with them at the clubs.

Caleb:

Yeah, they talk about the good hang, the other part of this work, the social networking aspect of it, where it's like you can be really really funny and talented and, uh, absolute, uh, displeasure to be around and then you're not gonna get far yeah, uh, that is something I've had to reckon with too. Not that I'm like not fun to be around, but I'm just like not as motivated by companionship as I ought to be, and I've worked on that.

David:

Are you a lone wolf?

Caleb:

Definitely like a homebody and just very isolating, self-isolating. Yeah, I've working at the. Actually working at the club has helped with that a lot too. It's like now these people are like my coworkers. I'm not going out to the mic and sitting alone, I'm like behind the bar. There's like a customer facing aspect to it.

David:

That's four times a week, right? Yeah, four.

Caleb:

Monday, yesterday went pretty well. It might be five soon, but yeah, but it's been good for me. I completely agree. We all need to be better collaborators with one another and just share in that, in the joy of it. We all have this shared joy for humor and funny and the craft like 100. Yeah, nikki blazer said uh, she's.

David:

you don't blame an interior decorator for, like, borrowing the tapestry or the fabric, and so she sees it more as like you're a designer as opposed to like, and I thought that was cool For her to say that. You know it felt from someone in her position. It's probably more better for her career to be like. No, this is like me, like yeah, there were writers at the golden globes, but like that was my stuff, you know.

David:

And she was just like no, um, so anyway, well, caleb theodore sherman, thank you. Where can people find you? Your instagram is caleb the sherman at caleb the sherman yeah and do you have any of your sets on uh on the interweb?

Caleb:

I do have quite a few clips up on youtube.

David:

Uh yeah, on youtube as well, on instagram too oh, instagram is the place to see some of your stuff talk.

Caleb:

I went through phase I was throwing content up like three times a week and very quickly got discouraged by that. But oh, it's awful the grams there, and you can know I'm always at empire comedy club in portland, maine go say hi to caleb at the empire comedy club in portland.

David:

Yeah uh, he's tall, he's, he's handsome, he's fit, he's what? 220 6'3 did you?

Caleb:

did you know that because I say that in one of my jokes, or did you just? No, I'm a weirdo I I just 6'5 220 6'5, 220.

David:

Guess what big boy I am?

Caleb:

6'4 and a half, 230, dude taller than me I'm like a half inch taller maybe I don't know, maybe you're 6'5, I'm 6'5, yeah, you're tall, you're taller, I don't know, I don't five.

David:

Yeah, you're tall. You're taller. I don't know. I don't know it's all posture, but I, um I'm on an all sugar diet and I'm just gaining rapid weight, so it's great.

Caleb:

How many large Papa John's pizzas do you eat per week?

David:

Oh, no, no, pizza dude, I'm not allowed to eat that. No, no, I can't eat.

Caleb:

I'm like I can't eat grains Averaging more than one large pizza myself a week.

David:

Well, it's a nice price right, it's good value. Calories per penny.

Caleb:

Yeah, yeah, yeah, 2,500 calories 2,500 calories.

David:

What is it? You probably have a coupon. It's like eight bucks, right.

Caleb:

Nine ten. If you're loyal, you get a free medium pizza from Domino's every like 20 pies.

David:

Dude Dom loyal. You get a free medium pizza from domino's every like 20 pies do domino's I miss domino's.

Caleb:

What's your go-to pie? Uh, in portland. Well, papa john's, what's your go-to? Pop it, oh, and pop just garlic stuffed crust with uh so there's cheese in the crust?

David:

oh yeah, and it's garlic. Sure, I think they mean they claim to have garlic night terrors.

David:

But and um, you can't eat grains, your uh well, sugar, no, no, I, I yeah no, I, if people who know me well like I'm always doing, uh, some sort of weird thing to try to, you know, try to feel better. You know I can't do drugs anymore, so it's like you have to feel better for what you eat. Super fun, yeah, this was a lot of fun. Yeah, so I'll be seeing you. I'll see you at Empire man. Hell. Yeah, all right, brother, peace. Well, I hope you enjoyed that as much as I did.

David:

I'm leaving a little Easter egg for everybody, because I assume Caleb's parents would probably listen to most of this, but if they're anything like my parents, they would tune out eight to ten minutes in. So I've left an Easter egg which they will regret not hearing, because it's a secret that Caleb revealed probably about seven minutes into us getting to know each other, and I'm going to leave you with this wonderful little clip. One more thing I'll say about Caleb. In re-listening to this episode and getting it prepared for the World Wide Web, his words seep into my consciousness, and so I found myself today, wednesday, writing new stuff for an open mic, and because of the freedom with which he explained his own open mics, it inspired me.

David:

Caleb inspired me to take some more risks on stage and to not be so hung up on being perfect or looking professional. Open mics are low stakes and they are a place to push the envelope and to explore If you can be terrible for four minutes and 58 seconds, but if there's one nano moment where you realize something, you discover something, then that time is worth it. I think that's what I've learned on this from this interview. This isn't about becoming perfect. This is about doing it your way, and there is only one place left where you can truly experiment and do whatever the fuck you want, and that's open mics. So what am I saying? I've gone from an open mic hater to someone who mildly respects them. No, I see a lot more of the value and I thank Caleb for that.

David:

Is there anything you've hidden from your parents that you'd like to reveal right now.

Caleb:

I've reveled in revealing those things to them over time so much that there's almost nothing left there's one thing that I do, that I do bit about on stage all the time that still hasn't made its way back to them. That is the last. What is that bit the? Uh, it involves butt stuff yeah, anal.

Caleb:

Yeah, okay, yep, and um receiving or giving um, being a teenager that was shoving random common household objects in their butt, in your own butt, in my butt, at a boy, yeah, at a boy, as one just exploring the bit is about.

David:

It's like a psa to parents, so that In your own butt, in my butt, atta boy, yeah, atta boy, as one does, just exploring the wonderland, the bit is about.

Caleb:

It's like a PSA to parents, so that hopefully they go home from a comedy show and they see everything in their house in a new light Glistening, have some kind of a talk with their kids.

David:

Harm reduction, I'm just doing a service. Yeah, I was imagining your parents hearing the bit and then looking at all the household objects.

Caleb:

In particular, a specific ice cream scoop that I know is still in their silverware drawer.

David:

Good Lord.

Caleb:

Yep, it's out there now. That's fantastic.

David:

It is most certainly on the pod. Yeah, it just makes me want to wish everyone an incredible week full of anal venery.