WTF with Marc Maron Podcast - Episode 1110 - Ben Sinclair

Episode Date: March 30, 2020

Even with the popularity of his HBO series High Maintenance, Ben Sinclair is still not great at taking compliments. He gets a lot of them, considering the show is one of the early success stories from the world of DIY web series that crossed over to mainstream television. Ben tells Marc how he lived a classic struggling artist life in New York before making the show, complete with a failed audition for Blue Man Group, an apartment with bedbugs, and sleeping on a futon in a lobby. They also talk about how he fell in love, got married and got divorced, but still maintains a close working relationship with his ex, series co-creator Katja Blichfeld. This episode is sponsored by Scotts Turf Builder Triple Action. Sign up here for WTF+ to get the full show archives and weekly bonus material! https://plus.acast.com/s/wtf-with-marc-maron-podcast. Hosted on Acast. See acast.com/privacy for more information.

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It's hockey season, and you can get anything you need delivered with Uber Eats. Well, almost, almost anything. So, no, you can't get an ice rink on Uber Eats. But iced tea, ice cream, or just plain old ice? Yes, we deliver those. Goal tenders, no. But chicken tenders, yes. Because those are groceries, and we deliver those too. Lock the gates! all right let's do this how are you what the fuckers what the fuck buddies what the fucksters what's happening it's me mark maron this is my podcast wt WTF. Welcome to it. How's it going? What are you up to, huh? What's new?

What's new? That's not something you're hearing a lot of people ask. What's new? What adventures have you been on since I've last talked to you? Where have you gone lately? Do you have any stories of your travels nope no i've gone to all of the rooms in my home and out here to the garage at least once this week just to say that i did it what's new i guess people are really figuring out who they are I don't know

I've talked about this before and eventually shit is going to grind down you know people it's amazing it's only been two and a half weeks isn't it? but it really has I think it's only been about two and a half weeks

since the major lockdown at least out here and again my thoughts go out to everybody struggling with isolation a major lockdown, at least out here. And again, my thoughts go out to everybody struggling with isolation, with family, but most importantly, with sickness. Talk to my mother. Her best friend has the sickness and is dealing with it. She's an older woman and she's doing okay, I guess, but the fear becomes about not giving it to her husband. And it's a real thing.

And it's going to affect everybody eventually. By the way, Ben Sinclair is on the show today from the HBO show High Maintenance. We had him scheduled. I'm trying to think what day it was that he was scheduled to come on, but it was right at the beginning of like the distancing. And like, maybe we shouldn't be being around other people, but he, he, it was like a Sunday even, but we were already sort of like, I don't know, man, we should really be isolated. We should

really be shut in. And I gave him the option. I said, man, I'll do it. You know? And I don't know, man, we should really be isolated. We should really be shut in. And I gave him the option. I said, man, I'll do it. You know, and I don't know where I'm at. I feel fine, but I don't know if, you know, I'm, I got it and I'm going to give it to him or if he's going to give it to me, but I'm willing to do it. If we go about it carefully. And that day, day of he decided no, that he wasn't feeling well. And I had not been feeling well a little before that, but it was just one of those things where it's like, all right, okay, well, open door. You know, if you're going to be in town, because he's a New York guy. And a few days later, we did it. And this is the conversation that you're going to hear

a little later and then just a few days ago he actually texted me he said i just realized coming out to do our interview got me out of new york and may have saved my life he's still out here and he's seeing uh got a a woman he's seeing out here as well but i did tell him that i was happy to talk to him but i'm sorry we didn't talk about death more because death is sort of a big through line big theme in high maintenance and initially when this show started i didn't know what to make of him i didn't know what to make of the show but then i got into it and i really started to realize that, you know, I'm old and that it was a fairly accurate and interesting and intimate depiction of, of all the different types of lives

that inhabit New York city. And I think it's fairly honest to the subject matter. I, I, after watching many episodes in a few different seasons, I realized that this is, you know, in a broad sense, how some directors or people that shoot in specific places really go out of their way

to make the environment a character in the show. I think that high maintenance really shows New York in its current state and the people who inhabit it and their lives. I just think it's a very beautiful and poetic and honest, and dare I use the word authentic, characterization of that city at this point in time.

I think mostly Brooklyn. But look, you guys, I talked to my dad, checked in with my dad, checked in with my mom. She's in Florida. She's all of a sudden nervous and scared. She should be. There's a moron running that state, a few of them. And I'm really a little scared for Florida right now. But I guess it's going to pop up everywhere.

But what have I been doing? What have we been doing? Lynn and I are in this house together. We're in this isolation quarantine trip together. We made another pot of stock. And we've been watching stuff. I've got the Criterion channel, and I see a lot of high-minded people have the same. And people are kind of like, these are the movies I'm watching.

And I've been bouncing around with the things to watch. But the one I did watch last night was a Michelangelo Antonioni movie. And I'd only seen, I'd seen two of his films years ago. I'd seen a blow up. And when I was in college, we saw red desert. And I remember being sort of in awe of the way it looked. I remember very little of the movie. And I was sure, not unlike many movies I saw, studying film, that I was missing something. I did not get it. Why wasn't it more entertaining? Why did I not understand why this is good? Why? Why am I dumb? Why is this such a special movie to so many people? I don't even know what the fuck it's about.

But that kind of softened and evolved into, maybe that's just not for me. And then it evolved into like, maybe I'm not appreciating the context here. We gotta, there's a battle. We have to fight appreciating the context here we gotta there's a battle we have to we have we have to fight to maintain the context is it still important to assess a film on its own terms within the context of the history of the medium yes has to be at least for keep your brain active, right? I mean, can't all be Spencer Confidential, can it? Can't all be just, we're all doing TV now, man.

The best and the brightest of the visionaries, they're all doing TV. But what about the movies, man? What about those wide-angle lenses, man? What about that depth of field? Everything's in focus from this cup on this table to that fucking guy sitting outside 50 yards away through the fucking window. What's going on out there? I watched The Passenger, Antonioni's movie starring Jack Nicholson. And I just remembered the scope of Red Desert and I

remembered I think that blow-up really in and of itself is all about lenses but I think he uses a lot of these wide-angle lenses for these deep shots and they're just stunning but it's really the story of the movie is is poetic in what it leaves out everything is tight and over explained and you know kind of the disbelief you have to suspend in order to engage in something meant as entertainment fodder on a story level is profound and it's not for art reasons but this is a it's an odd story it's a about a reporter a wartime reporter on assignment i think in chad and you know he's covering a government there that's under attack by guerrillas leftist guerrillas perhaps or just uh opposition forces

and he's just staying at this hotel and he's friends with the guy you know i guess across the hall and uh he goes in to say hi to that guy that guy's dead and then you know nicholson his character or nicholson himself as well looks enough like this guy that he just assumes that guy's identity switches out the pictures in the passport without knowing anything about the guy just so he can get out he can escape his life back in the day where it was sort of possible you just switch the pic on the passport you have the locals bury the body you know they report you dead with your stuff there and you just kind of wander the world with this falsified passport and you know kind of

tricky for people to find you i guess but that really wasn't what it was about the backstory of it is he's got a wife that he is no longer really with. Who's fucking some other dude. Who looks just like an alpha dude. Monster dude. And I think there's some element. Of a study of masculinity there. And you kind of find out. That she didn't think that. Jack Nicholson the character.

He was playing the reporter. Really had much courage. Or balls. Or the ability to take a stand or pick a side. Then it turns out the character, the guy whose identity he took, is a gun dealer, a gun runner. And he's sort of mired in this arming the opposition of this kind of autocratic leader that Nicholson had interviewed. And you see pieces in the interview. It's sort of complicated, but it's really about who we are.

What do you stand for? You know, when it comes right down to it. But it's one of those 70s movies, man. One of those existential explorations where I can walk away from a movie like that and think like, you know, I don't know, man, it's kind of sparse or maybe I didn't get something or I can accept what's given to me by a master and artist and and think about it. that was popular at that period of time in film and really kind of being able to make it contemporary and make it relevant to me. What do we stand for? What is your identity?

What is that based on? Shoes? A name? A job? What are you made out of? And I think that in some ways, this time alone may give us, or at least isolated, or at least, you know, with out of the, I guess, out of the routine. I know not everyone has a time to meditate on, you know, what's important to them or their purpose in the world but but it is sort of a time to be out of the routine you know it's a beautiful thing in the

midst of all this horror that we're experiencing on a governmental level and now on a health level and on all the levels is that um everybody's kind of living the same shitty life right now in a way with the same real fears. Most people, most smart people, on some level, you're not missing anything. The competition is over. Everyone's fucking doing the same thing now. everyone's fucking doing the same thing now. Trying to transcend fear.

Stay cool. Stay safe. Hope for the best. Don't get too fat. So, Ben Sinclair, a nice guy, didn't know much about him. Turns out we got more than I thought in common.

I thought he was a little, you know, I thought he might be a little odd. Of course he's a little odd. But as I said, he canceled once because he didn't feel well. And then we eventually got it together. And I've been doing that. I mean, we're allowed to do these podcasts. We are an essential service under the media service in the media subcategory. And if people want to come over, I can provide them a clean, safe environment. I won't touch them.

This is a little before it got more crazy when Ben came over. But it was the beginning of it. And we had a nice talk. And this is me talking to Ben Sinclair. His show, High Maintenance, is in season four. It's the fourth season. It's on HBO. It's on now. The season finale is on this Friday, April 3rd. You can watch all the episodes of all four seasons on HBO Go and HBO Now, but now you can hear me talk to him. Ben Sinclair. But iced tea, ice cream, or just plain old ice? Yes, we deliver those. Gold tenders, no.

But chicken tenders, yes. Because those are groceries, and we deliver those too. Along with your favorite restaurant food, alcohol, and other everyday essentials. Order Uber Eats now. For alcohol, you must be legal drinking age. Please enjoy responsibly. Product availability varies by region. See app for details.

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I think you'll find the answers interesting and surprising. Hear it now on Under the Influence with Terry O'Reilly. This bonus episode is brought to you by the Ontario Cannabis Store and ACAS Creative. I even had, like, I had these really cute face masks. I was like, oh, maybe we'll wear face masks for this. I got them in Japan. Yeah. I actually have them with me.

You want to see them? They're cute face masks? You'll see. We can still wear them if you want. I would. Oh, that's nice. I would keep hold of them. They're kind of a tough item to find now.

Oh, yeah. People are stockpiling. Purell is gone. Exactly. So I was on my way to see you on Sunday, and I visited my friend at a gymnastics place where he brought his kids. You were coming over here, but you weren't coming over here. I was on my way. Listen, I was you were you were coming over here and you weren't coming over here i was on my way listen i was on my way to come over here but i woke up at 6 a.m because i flew in on saturday night okay so i woke up my friends like hey we're my kids are doing

gymnastics right down from the apartment i'm staying in so i went down there with these face masks right visited them i leave i'm like oh fuck where are the face masks i left the face masks with the germy kids in the gymnasium but they were in package they were in package but i but i even well it doesn't matter the face masks are good they're right they're an option for us well let's well good let's see how we feel going into it yeah i think already with this mic in my face whatever damage that was going to happen yeah it, would have happened. You know, oddly, for that morning, my producer, because I was sick. I mean, that was the issue. And I really was sick.

But I was willing. And, you know, you agreed. And my producer goes, well, maybe you should change out the windscreens. I'm like, I don't know if I have one. But that's actually a clean windscreen. There's no goop in there. Well, but we were joking that it was a breakthrough that I didn't come through here. Yeah, well, explain that because here's the message I got.

Let's just get to the truth of it. Let's get to the truth of it. If you want transparency, we can do that now. That's all I want. Okay. So I got set up. I was ready for you to come, and then I get a text or a call that you weren't feeling well. You had agreed to do it, even though I was sick, which I took a bet

with Lynn. I was like, do you think he'll do it or not? And I'm like, I think he'll do it. I was about to do it. I think he'll ride out the storm. I don't think he's afraid. I wasn't afraid of coronavirus,. I wasn't afraid of coronavirus. Yeah. But I wasn't feeling well either. But that's what I got. He doesn't feel well and the car didn't come. The car didn't come.

That wasn't my thing. The car was our thing. Whose fault was that? HBO? Let's blame HBO. Yeah, HBO's fault. HBO fucked up the car situation. You know, it was HBO Max, actually. They fucked it up.

No, the car didn't come. I couldn't find my face mask. I got a text earlier that morning from a jilted lover from the past. How far back? The last relationship before the relationship I'm in now. Okay, so not before the marriage. Not before the marriage. The marriage ended almost four years ago.

Marriage is a Trump era. We are a Trump era divorce. The day we decided to separate was election day, 2016. Did you have the discussion before the results were in or after? Before the results were in. We decided to separate and then we watched the news. We watched him take it. And then we watched Friends. We watched an episode of Friends afterwards. And then we slept in separate beds. It was actually a great way to consolidate all of my grief with the rest of the, like when something bad happens to you, you know, it's one thing to like go outside and everybody else is going on with life as usual. Nobody was. But nobody was. I left my apartment and everybody was upset.

And I was like, well, at least everyone's upset. Right. Not just me. Yeah, for different reasons. But yours was compounded. Consolidated. Oh, you consolidated it that day. Because I was going to be upset about both.

So why don't just, you know. Oh, so you just, well, yeah, right. But okay. It's like i had twins horrible horrible stressful sad twins yeah but so so the jilted lover the jilted lover texted me with uh whatever they they how long were you with that person about a year oh so a year and a half nothing it was not nothing yeah and uh and i was told by my PR people, like, get in. I'll just take an Uber, and I'll pay for it.

Right. And I thought, I lost the face masks. I'm all emotionally twisted up. Yeah. And Mark's sick. Yeah. I don't have to do this on Sunday morning at 11 AM. Wow.

You know what? Then old me would have just charged right through and be like, no, I made a promise. And they're going to think I'm like scared of coronavirus. Right. And I just put all that on hold and said, I don't really feel like doing this right now. It's so good, right?

Yeah. And I have only just started in my life acting in accordance with my own best intentions and the best way and also just saying no it's a it's a weird kind of i don't know what it is about certain types of people or maybe just people that are have fought it their way through uh and sort of landed in show business in a positive way but there's always this idea that you will be judged and punished if you if you say no and and that's also the truth is no one's really thinking that much about you except for yourself nobody yeah and it's like what so what you're gonna make a publicist upset it's like you and then if you really want to get into it judge yourself against all the

other fucking whack jobs and prima donnas that they have to deal with from that particular outlet. I mean, you know, no matter how crazy I am, I'm not as bad as some of the things they're dealing with. Yeah, I try to- On a talent level. I try to compare and not to project too much. But I think that being on this show and being in this room with you is a big deal to me I think I probably that morning even psyched myself out

Because you think that but you said they you did feel ill. I felt I didn't tell her to tell you that I felt ill, but I felt bad So I I was just not feeling on there's the transparency we needed. Yeah, she decided to lie I know and say that you felt no that's a publicist job she tried to make it the the responsibility of the germs and the biology we were both sick man yeah maybe it's just better for both of us yes exactly i also i also imagined like man this guy's sick is he gonna want to like already i'm like does mark marin really want to plunge into every

success narrative of the person in front of him that he's talking with or does some days he feel like i don't really feel like digging here or i don't feel like well for you though because like you know i gotta it's really you know i don't know what the narrative is really going to be you know i just have to figure out for myself what the through line of of a conversation could be right so you know for you i wasn't that concerned about you but also when i get sick i get i'm actually a little more relaxed oh yeah yeah and and like i do not do drugs anymore or drink but when i'm sick there is a a shift in perception that's sort of like hey i'm a little fucked up i do i do my best acting when i'm sick is that true oh definitely definitely

because there's a uh an unavoidable vulnerability and you're not trying you don't have the energy to try right yeah so do you get sick on purpose to act? Yeah, I just have unprotected sex with everybody I can. Oh, that guy that's sick is going to shift here. I just lick doorknobs. Oh, there you go. No, there was one for the season finale. There's one day on set where I- Hasn't happened yet.

Hasn't happened yet, but there's one day in a Chinese restaurant. I shoot this Hanukkah dinner or Christmas dinner in a Chinese restaurant I was so sick that day yeah and I looked at the footage and I was like oh okay here we go that's a leveling up here yeah so I do and I think Nicole Kidman even said something about that like she does her best work when she's sick as long as your voice doesn't sound weird and your eyes don't look all fucking sick did you know that who was singing in the rain gene kelly yeah oh yeah i heard that like you had the flu or something like 102 fever the day he shot the singing in the rain yeah i don't know if i could do that that seems a little more demanding than what you or i do really do you want to train for that scenario to swing around

swing around on lamp pubs yeah i'd like to be able to do that. Are you a song and dance dude? No, I wish I was. You could be. You know, we all could be. You know, once you have a certain amount of talent, it's really what you want to apply it to. I mean, I think that what stops me from being a song and dance man is what's stopped me from being huge my entire life. What is that?

Fear of looking stupid. Uh-huh. Yeah. Well, you don't have to worry about what you look like on a podcast. No, I know that. I'm doing a little on-camera work. Yeah. But there is that weird, that's a different type of vulnerability. It took me years to sing in front of people. Years. Yeah. And you do it now? Yeah, I can do it. Karaoke? I've done kind of karaoke, but I've actually played with a combo of sorts. And, you know, I've taken opportunities to, when people put together evenings of jamming in front of people and have people sing, I'll play and sing. I've done that.

Well, this is, you know, I've seen episodes of Marin and I've seen, and actually I am staying at my friend's house who I will not say who it is, but they work at Netflix. Oh yeah. And I got to see your special. Oh, you did? I got to see your special. The end of the world. And then I was walking by a cafe and I was thinking about this interview and then there was a neon sign in the business office that said, end of the world. And mine's end times fun.

End times fun. It felt like it's all about the end. Did you enjoy the special? I did, but that was the first time I really got to study your physicality. Oh, yeah. I was like, interesting. He chose the stool.

He chose to bring a stool on stage. I'm always in the stool. And you had the boots. You're tucking the heel of your boots up onto the highest bar yeah there was a perched yeah a perch for sure there's a little there's some arm crossing happening yep there's some like uh pulling in kind of sure yeah hunched over yeah but then when you got in a role like on like you step up from the stool and you move around and you take up more space it It was interesting to watch you.

That's evolved over many years. I've been stooling it for a while. That was a conscious decision based on the history of comedy. And what do you, tell me more. Well, there's this idea, you watch a lot of specials from the 80s and upwards. Not only will people, it's just, there's this idea that you gotta run around. You know, that you're in a big theater,

you guys move side to side. I did it. But if you really look at some of the great comics, they sat down. Like Shelly Berman in particular. That there was a time where that was part of the trip. That generation from the 50s and 60s, if they did stand up, they weren't moving around. And a lot of them would sit on the stool and just talk.

And I thought there was an intimacy to that. And if I could make that work in a room of 800 people, that would be something. Oh, yeah. So that was that. I mean, it was a very good special i think you should be very proud well thank you very much i'm enjoying your work as well thank you man yeah i've watched uh i've watched all of i'm up to speed on the new season i've watched most of the last season in and out of the first couple the first season is definitely our growing pains but i'm glad that happens right i was very happy to have it happen i was thinking recently

i'm like the the pilot episode of our hbo show was supposed to be the fourth episode of the show and maybe it was the weakest episode of the season i don't think the weakest but the second weakest of that season and i really i don't know what it is about this might be illuminating to you as a pointer of how i am as a human being but i try to start with my worst like i like to i don't know i don't know if it's testing people but i like to be like well here's the worst that i can do first on purpose or it just i think you you you you know it i don't know the the one of the best episodes of the season was supposed to be the pilot. It was called Tick. It's about two families.

And we moved. We switched places. I don't know why that is. I have the impression that I give not the greatest first impression. I would have thought that when I first met you, I was like, I feel like I made a bad impression on Mark. At the movie theater? Yeah. Yeah. I didn't feel like when I first met you, I was like, I feel like I made a bad impression on Mark. At the movie theater? Yeah. Yeah.

I didn't feel like, I don't know. I had that weird moment where I'm like, how do I, I know this guy. Yeah. And then I'm like, oh, you're on television. Oh, I had the moment. And actually in your special, you described the moment of when people meet you and then they're telling their friend about who you are. In front of you. Yeah.

And I have that all the time too. I was like, oh, we have the same perspective on this level of recognizability that we have in the public. Right. Where people are like, oh, hey, wait. You can actually have very dedicated and passionate fans who have friends that have no idea who you are. Exactly. That has a lot to do with the fragmented media landscape. Yeah.

You know, like if High Maintenance was a popular show on one of the three networks or even just on HBO when it was only HBO, there would not be that problem. There would not be that problem. But then you give people the gift of getting to explain your show in front of them, which people really like to feel like they're in the know. If anything, we've learned from this Twitter, Facebook, whatever generation. Oh, there's a lot of know-it-alls out there? People love to talk. Yeah.

They like to- Discover. Right. But they like a lot of last worders. Yeah. It's the last word. Nobody, never ends. Everyone's always going to. There's a lot of deep geeks and nerds for a lot of different things out there.

That's the weirdest thing. I've never been that guy. Me neither. I investigate and learn enough to be proficient and knowledgeable, but I'm not going to make a life out of it. Would you say you're a person who knows a little bit about a lot of things yeah i mean there's some things i don't know about but the things that interest me i it's actually been sort of an issue for me lately like why don't i know more like about certain things but that's just the struggle of life but my feeling about this meeting

was yeah i don't know where you come from, man. I have a similar background to you. I'm a middle class Jew from the desert. Come on. Yeah, dude. I grew up in Arizona. Which part? In Scottsdale is where-

Do we have this conversation? I don't know, man. You had a Diet Coke. That's what I remember the most. At the movie theater. Yeah. Right, the Diet Coke. But I have family connection in Scottsdale.

Go ahead. We didn't talk about that. You don't remember. So my mother spent the last 25 years of her career as a cantor in a reformed synagogue in Scottsdale. Oh, my God. Yeah. And then my dad was a public school teacher in Arizona. But before that, my mother taught music lessons out of our house. So we would

have piano, voice, and guitar students. She was the lady cantor at a reform synagogue. Yeah. So where were your parents from originally? They were army brats. They met on Andrew's Air Force Base in Washington, D.C., or outside of D.C. Both of them, parents were in the military? Air Force. Both of them Jewish? No, my dad did not grow up jewish he he you know knows all the prayers and stuff but he didn't convert until a couple years ago so but he did convert he did convert here in the last quarter yeah he thought why not and then uh she's she's dead now but his mother one time I joked about him converting around his mother and he was like, your dad was like that. Yeah. Yeah. Yeah. That's, and that gives you

another preview of how I was raised. We didn't, we weren't in the, in the spirit of transparency. My family, uh, wasn't, you know, they were repressed. i would say it came from and now i'm only now in my 30s understanding that the military upbringing had a lot to do with that keeping secrets acting you know acting strong right discipline acting strong and discipline yeah both of them yeah but your mom i would think being a cantor at a reform synagogue had at at least some sort of way of communicating. Sure, but also there's a lot of routine built into that schedule. There's a lot of, you know, she graduated from Juilliard. She wanted to be like a folk singer or a performer.

She went to college because she loved music and she loved the arts. Really? Went to Juilliard for all four years? Yeah, I think. She went to American University and then she transferred to Juilliard. D.C.? Yeah her really went to juilliard for all four years uh yeah i think actually went to american university and then she transferred to juilliard dc yeah and then to juilliard that's pretty highfalutin it was highfalutin after she got out of school she went on tour with andrew with leonard bernstein's uh show mass it was like uh it was like a choral thing and she went on tour with him with him and then they came out of that show experience and my dad was driving up from getting his education certificate to teach out of university of maryland so he'd drive up every other weekend to come see her in new york and

they were trying to decide should we start a family in family in Arizona or should we go for it in New York? And they chose Arizona. Wow. Gave up the fucking nightlife and the big dream. And they've been in Arizona ever since. They were in Scottsdale when Scottsdale Road had like four cars on it an hour. Right. You know, I witnessed sprawl growing up.

Oh, and it's like one of the great examples of sprawl. It's the, I would say, chef's kiss of sprawl. The only good thing about sprawl in Phoenix, in the Phoenix area, is that for some reason, either it's a law that they can't, they can only paint three colors of brown. Yeah. So, like, there's a never-ending strip mall, but a lot of times you don't even notice it somehow. It's an odd thing. I will say, you know, Frank Lloyd Wright was... Great.

He was banging around down there, and I think that culture of architecture is exciting if you're an architect. I mean, all that space. Isn't the Biltmore him, or a student, or partially him? Yes. And there's some... The houses out there, yeah.

I've always... I like Arizona. I like the heat for the same reasons that I like being sick. Because. Because it alters my perception because it's so daunting that to walk outside in 110 to 120 degree heat

for any amount of time, eventually you get delirious. Oh, yeah. And I kind of like it. I like it for the same reason. I think that I'm drawn to altered states as well. And the one thing that really chaps my ass in my childhood is that we didn't go camping at all because we had to be, you know, school Monday through Friday, Shabbat services Friday night that my mother had to go to. Oh, because we had to be you know school monday through friday shabbat services

friday night that my mother had to go because she had to sing and then on sunday was hebrew school yeah so there was never time to go out into like the arizona wilderness which is like yeah astounding i didn't go camping until i went with my friends when i was in high school and then i was like holy and then there were you guys go i i used to like t went with my friends when I was in high school. And then I was like, holy. And then there were. Where'd you guys go? I used to like Tucson. My brother went to school in Tucson. Tucson's sweet, man.

It is, man. Yeah, I like it. It's like real kind of. There's a lot of cowboy shit in Phoenix. You know, in Arizona, it's definitely not. It's not Jewish by nature. It's definitely some. By infiltration.

It's Jewish by infiltration. For sure. You know, wherever the old people who need doctors go. Yeah, or need to breathe easier. Yes, exactly. But did you ever get a sense that your mother was bitter about her choices? I wouldn't say bitter. In fact, I look to her as an example of somebody who has managed to marry their community, their spirituality, and their art into one job.

And I really admire that about her path. Does she see it that way? I think she sees it as... Because I think that's a beautiful thing you just said. And it's specifically non-selfish thinking if she is indeed thinking that. I think like I come from a family of overachievers and part of being an overachiever is speaking sometimes harshly to yourself and saying it's not good enough and having the spirit. Doing that now. Yeah.

You're so good at it. We're achieving, man. We're achieving. you're so we're we're achieving man we're achieving uh so i feel like uh when i speak with her and she's the one i go deep with fast like i'm like okay what do you think about dying or whatever yeah uh i her feeling is in our philosophical conversations is that she knows all that information but i don't know that her heart is open enough necessarily to feel it and to really feel a almost divine satisfaction with what her choice is. And you think that that's an issue of allowing yourself to experience it on an emotional level? Yes, I think it's a, it's a vulnerability. We don't do that in my family,

really. We don't, we're, we're not, we don't, like, I remember because we would tease each other a lot. Humor and being smart was very valued in our house. But you felt that a lot of that was masking an inability to emotionally communicate. Yes. Or to be vulnerable. Yeah, a lot of coping strategies. But did you feel cared for? Well, am I going to say it on this podcast? Maybe.

I don't know. I felt like the fourth child. I am the fourth child. My sister is nine years older than me. My next brother is seven years older. And then my closest brother is two years older. So my parents, who I think always battled financial struggles, I mean, I don't think. Four kids. It's a lot, man. They put a lot on their plate. And it was the same kind of thing that I told you about wanting to come here is like, oh, I got to do it because I said I would do it. And they didn't exercise no a lot in their lives lives they felt like they had to accept everything as like charity or as a gift or whatever and be thankful and and you know maybe it's not what you really wanted but just be happy or blah blah blah and see that's i mean that was the sense i got of you you know in

talking to you now but also just that you know you know, that the boundaries are porous. Yes. Very flexible boundary. Porous is a good, healthy word. Flexible is a good one. Faulty. Yeah. Faulty. Well, I mean, it's, I think, don't you kind of use a similar strategy with how you get people to open up to you is that you offer, you offer a sense of openness and vulnerability. Well, sure. I mean,

I think, I think, but that was learned in a way, but, but, but, but, but conversely,

I generally want to be them. So, right. So, so whether or not I was vulnerable for whatever years of my life that, that, you know, that I would adapt to who they were, become more like them, almost instantaneously.

It's a strategy. I don't know if it's a strategy, but it's a yearning for modeling or for parenting that I didn't have. Yeah. And I don't know, do you identify with that or are you just understanding me? The thing that I yearn for in terms of what I feel like I missed out on in my childhood is my parents modeling what it looks like to make yourself happy. Modeling what it looks like to go out on a hike and take care of your body. We had a lot of health issues on my dad's side of things. And I really wish that I witnessed my father take care of himself and do the things that made him happy and not always seem like he was acting out of sacrifice. And the same thing for my mother. But see, the thing is, sometimes happiness is not the priority.

I agree. Sometimes I'm not sure it should be. Sometimes it should be, though. Not all the time, but sometimes. No, I think that's true. And to characterize everything as a slog, to come home and be so tired and say yes to helping everybody.

Every grandparent that died would die in our house. You saw them die? I didn't see anyone die in our house. I witnessed my dad's brother die when I went to the hospital because this was in my adult life. But he, whatever, he flew over New York

and his aorta bisected and then he went to Jamaica and then he went to Cornell Y and I was the only one in New York and I went to his bedside and watched him die. But our grandparents, great-grandparents died in my house. Um, we were always caretaking. There was, um, I, this is a sensitive topic. So if anybody who's going to get triggered, they should turn off now, but like around, so we took, we took a child into my house that my, one of my mother's music students, uh, her husband was getting out of jail and she was worried about the welfare of her son. So my mother said,

your son can live with us until the smoke clears or whatever. So we had a child living with us for a while who was older than my sister. So at least 10 years older than me. Yeah. And when I was three or four, he used to abuse me like in a, in a sexual manner. And I grew up having this memory of this happening, but forgetting that that kid stayed there. Yeah. Uh, so I asked my brothers, I'm like, hey, I'm not mad about this or whatever,

but did something weird happen in the bathroom when we were younger? And then they were like, no, no. And then finally we made the connection that this kid was staying with us. And then I was like, oh yeah, that's who that was. Oh shit. That's who that was.

So if the answer is, did I feel safe? I think coming to the realization that well because the big thing is I didn't and I was I made a joke out of it after that I was like oh this just happens to people like you know that's true but it's not funny it's not funny but I was trying to be stronger than yet by making a joke yeah you got it I mean how you know how else do you deal with that PTSD? But I didn't want to tell my parents about that until in the recent years, because I didn't want them to have to feel bad about that happening unbeknownst to them. them. But what I have been turning over is that they, A, were doing the best they can, and B,

were trying to help somebody. They were trying to help my mother's music student avoid problems. They didn't understand that they were inheriting the problems of the person that they were trying to avoid through that that person's child and so the father was in prison for that who knows i think he was in right for assault or murder or something like that but but that being said it's con it's confusing on it on the level of trauma and responsibility in terms of the question of safety sort sort of navigating what you do with that trauma, because like you said, your parents took on more than they could handle, really. Yeah, it's true.

And that they sacrificed sort of the safety or at least the emotional attention that they should have been given to all of their children. Well, the question was, why are you trying to help this other kid when you have a kid of your own right here who has never been camping? And it kind of continued on.

My mother would do every kid's bar mitzvah in the community. We were attached to a community. And everyiday night and saturday morning there was an ushering of this kid into adulthood yeah and i got that one weekend right but uh also my mother taught voice piano and guitar and i think when i was younger she tried to teach me piano and i was you know a kid and not responsive to those lessons. And she tried to have me learn piano through another teacher. And I just wasn't, I, my finger hand-eye coordination is not my strongest suit. So there was no trying to teach me guitar. There was no more lessons for

me. I taught myself guitar. I, the music was a huge thing in our family and we all are so independent. All of the four of us are so wildly independent that we would teach ourselves things and educate ourselves. There wasn't so much support of one another, which is so, I think that my parents will probably be heartbroken to hear this, but it's just kind of how the chips fell. And I think they're really wonderful parents and I love them so much. But I don't think I felt safe. I think I felt like I was on my own, especially when the health problems came when I became 12 or 13. My father had a myriad of health problems that lasted through high school.

health problems that lasted through high school. So I felt like I was raising myself and developed a myriad coping mechanisms and defense mechanisms during that time, which I'm very lucky to have the wherewithal to look at them for what they really are. I experienced a similar thing in that, like, there's certain questions in my head about a period of time when my folks, when we lived in Alaska, my dad was in the service and there was some, you know, something happened with some babysitter. And I'm not clear what, you know, like, I know that something bad happened. I know. And we told on him, you know, and we were able to do that. But it's not completely clear. But I do know that they stepped up and, you know, what are you going to do?

It's just so fucked up about, you know, and then you realize why parents are so scared is that these impulses of these older kids, you know, who the fuck knows. fuck knows but but what but in terms of the self-parenting thing which i'm a little hung up on um for my own life that my parents were just kind of you know self-involved really uh and because of that i don't feel the appropriate closeness that one should have with a parental bond you know i it seems like you feel some of that oh definitely when you came out on your special and people are clapping for you and the first thing you said out there was like, I don't know how to take love in or I don't know how to accept love. I'll try to let you love me. Yeah, I felt I really felt for you in that moment. And I feel that often. I feel very much that the that it's hard for me to take compliments,

although privately I'm so hungry for them and so hungry for attention and validation. But when it's there in front of my face or when somebody like this person who texted me before I came to your show or like a lot of my relationship issues are just me like accepting that this person loves me and holding that and sitting with that

and not running away because it becomes too much or too overwhelming. So you have to practice that. It is a practice. But I've been able to track the fact that most of that is because of self-parenting that I don't know how to receive it because I was not trained in that way. Yeah.

And that my self-parenting coping mechanisms were actually necessary but bad parenting. That I was badly parenting myself because I assumed there must have been something wrong with me. And have you reparented yourself and you know that you're great and all that? Some days. Yeah? I think you're great. I appreciate that. I really love this thing that you've been doing for a while. Well, thank you. I appreciate that. And I think you're great as well. It took me, you know, there's something that you do that, you know, to make yourself available as a conduit for these stories and also to sort of wrangle what you wrangle creatively and also take care of you know the types of personalities that you explore on

your show over these seasons like i was talking to uh to frank in there that you know what you do is it's it's a very diverse all-embracing very forgiving and accepting space you create with the stories that you have on the show. I don't think there's any single show that captures what contemporary diversity really looks like on all levels than your show. Well, I won't accept that because I don't know how to accept that compliment, but I'll take it. Do you know what I'm saying? Listen, I think the best. I'm talking about gender. I'm talking about ethnicity.

I'm talking about age. I'm talking about emotional diversity. I think you are also complimenting my colleagues a lot in this statement. my ex and co-creator and present collaborator. I think that she is so sensitive to the ills of other populations. She is very awakened in her sensitivity to those people who are not being represented. She came from the casting world, So she is very aware of representation. And, uh, and a lot of the people I work with, we have an extremely queer set. Um, a lot of the people who work with us, the most department heads are women. We have like

pretty left, pretty left up in that place. and it was her guidance to make it not a show about a weed dealer but to make it a show about the people to whom he delivers do you like that grammar and uh it was nice to follow her lead on that and be like because I do want to express myself. I do want to be like, I am feeling, you know? Yeah. And- I think you do, though. We do, we do, but we, most of my personal emotions get lived out

under the skin of somebody else's situation or somebody else's identity. Essentially, you're, you know, porous boundaries, and you're almost, you know, that you have to almost, you know, fight your own empathy to maintain your sense of self. Yes, for sure. And I think, you know, I'm super into meditation right now. I listen to Sam Harris every day. I am trying to shrink my ego to the lowest possible need.

You know what I mean? I define ego as anything that separates us from the great totality. My ego is made up of my likes and my dislikes. It's made up of my identity. The great totality. The great totality any my ego is made up of my likes and my dislikes it's made up of my identity the great totality the great totality yeah so you separate your ego from the great totality well your ego separates it's anything i am i get it from the great totality so the last vestige of the ego is you know or or the the primary function of the ego is sort of like, if we're not careful, this great totality will crush us. So, but if you open up and accept the great totality as you being part of it,

and it's a beautiful, enlightening thing, then, you know, then that shield is gone. Yes, exactly. So let's go back to, because I don't know where you come from in show business and like how that all started. But before we go there, like in retrospect, in dealing again, trigger alert in dealing with with the sexual abuse and the trauma of that at that age. that age, what did you find once you mind that and understood it and contextualize it and felt, did you go through a period of grieving what you lost through that trauma? A little bit. I guess my question is, how did it affect your life in that chunk of time before you realized the impact of it? What part of your personality you're like that's that's a reaction i think a fear of being alone was a huge i think that had a lot to do with it i it's not a total fear but a a sense that if

when i was by myself that there was, it wasn't all right. There was a feeling that I needed to fill. Someone was going to come in and. Not even, maybe that. Oh, yeah. But. Just a general unsafe. A general unsafe feeling.

And, you know, I can push boundaries. I think that people have described hanging out with me as fun, but sometimes challenging. Yeah. And... I used to do a joke about the verbs for my comedy. Draining. I felt a little drained at the end.

End fun times. End times fun. Yeah. Uh, but, uh, yeah, I think my,

probably I coped with it by always trying to be funny by trying to be strong and by trying to be, uh, in control of, of, of situations. There was a threat both by, because of how you were brought up and because of that of, a sort of nebulous threat to vulnerability.

And I think one of the reasons that I like altered states and that I probably veer towards addictive tendencies is because in those moments, I don't feel the need to have that control. You know, I am off the hook for the time. So what was the journey to show business? Because, like, you know, I mean, your show's not a comedy per se, you know, really. And I can't sort of associate you with the creators I know, but you're not making a drama.

You're not making a procedural. You're doing something in the wheelhouse of many of the people I know, but you're not making a drama. You're not making a procedural. You're doing something in the wheelhouse of many of the people I've known, but I don't know where you come from creatively. What was the development there? Okay. I'll start probably at age 18. I went to Oberlin College. Now, my niece went there.

Is that a sort of a liberal arts, but it's got a pretty powerful hippie contingent. Capital L liberal. It was this beautiful bubble with which to explore the elasticity of your paradigm by really being able to go out far left. And my freshman year, I had a gender neutral bathroom. We were talking about everything we're talking about today. Everything was on my orientation week. A lot of that started... Consent, consent culture, everything. It all started, right.

That all started with, you know, lefty 18-year-olds. Yeah. You know, blogging about feminism. And this was during... I was shielded from Bush times because I was there at Oberlin. So it was like it was almost an experimental lifestyle? In a way, but it was a lifestyle that very much fit where I was already going. And I kind of was a contrarian. Before that, I went to a public high school in a red state and I was willing to wear

dresses, willing to go against the grain. Willing to or wanting to, did you? I mean, like what was your high school like? I wanted attention and I was getting attention by acting really progressive. So that was it. So fourth kid of emotionally distracted parents going to high school in a dress. Yeah.

Or I wore like, you know, I was very involved in the Jewish community, but I was also kind of like, you know, that was Jewish youth group culture is a lot about. B'nai B'rith or B'nai? Nifty. National Federation of Temple Youth. Oh, that's the reform version? Yeah. Like, you know, there was a high overachieving thing, but also all of my other brothers and sisters had claimed the safe ways of getting attention like getting good grades or being well

behaved and I sought my identity and the opposite of what they were doing what were you doing creatively other than these costs marching marching band show choir arching every play every musical team, social youth, NHS. Really? I did everything. I did everything I could. Everything that you could do to- Because I didn't want to be alone. That involved people looking at you or being around other people.

Exactly. Yeah. I mean, marching band, you really, and choir, you really go into it. But yes, I was developing a showmanship there. Yeah, but also you were developing uh you know like for me you know i i wanted to be around other people but eventually i would push them away like i you know i don't know if i was using them or you know trying to figure out who i was or whatever but i didn't stay long do you know what i mean i'm not i was not you know and as it leveled out i

was not an ensemble player i wasn't a team player you know i chose a solitary profession you're a poet also in that way yeah i think that's probably true yeah there's a distance of and commenting that is built in right that yeah but you like immersed yourself around other people and found yourself there. Yes. And there was a bit of, I think at that time of my life, I was aware of the social climbing and the ability to get the attention of a bunch of people and started even thinking about it quite scientifically. But it seems like the areas that you chose to express yourself in

were people who were marginalized by mainstream culture and jock culture. And so, you know, so you were already part of the other, you know, in that sense, not the other in sense of ethnicity, but the other in sense of the status quo. Of course. Right. Always looking to occupy that space. Yeah. So I came to Oberlin. always looking to occupy that space.

So I came to Oberlin. I was waitlisted everywhere else and in Oberlin because I made like a funny essay for college entrance that people, I guess, didn't think was funny. And I ended up going to Oberlin and I had never gone there. I knew nothing about it. And it turned out that it was exactly that space that I was occupying in high school. 2002 I went and then 2006 I was out.

So I did 9-11 in high school. I was like, oh my God, are we going to get drafted or whatever? And then I just moved to the, not far, politically I wasn't left. I mean, I was definitely, but I wasn't like radical about politics. I did feel strongly that. Right. You weren't, you weren't dug in. You were more about you, but you knew what you identified with and the, and the, the

tone of it, but you didn't know the, you weren't a wonk. No. Or somebody who was fighting for a particular cause. And when I went to oberlin i found myself being contrarian to the left being like you know that when everybody is i just i wanted to be different right than everybody else always i found myself balancing that out so i definitely have a fascination with the marginalized with the different with the, with the people who are not usually in the spotlight in that community or what have you.

Because you wanted to be one of them. Yes. And then, yes. And then I'm obsessed with community, I think. And then I became a theater and dance major there and I got really into Chekhov. I got so into Chekhov. A dance major? Theater and dance. That's just what they got so into checkoff dance major theater and dance

that's just what they group it together do you dance yeah i did a year of ballet i did some modern dance there i've been to contact improv things i love to dance in fact i was in show choir in high school and i really i think that was one of the most important creative uh what is show choir it's like jazz hands and glitter vests and cummerbunds and you know like medley my we did a miami sound machine medley and ever since then i've been i i really love to sing and dance um mark i think it would be actually pretty entertaining to see you join a show choir in la the east la yeah yeah i think you would really like, Ira Glass does it. He loves to dance, man. He joined a dance group

in New York, and I was like, really? And I'm like, oh yeah, makes sense. He seems to be having a fairly, a kind of a just post-middle age rebirth of sorts. Definitely.

His hair grew out. His hair grew out for sure. His hair grew out. He's got a new relationship. Yeah. He's doing, you know. I like them. He introduced me to my current girlfriend, which is, he has a special place in my heart. And you, well, you did a whole episode revolving around this American life crew.

It's true. I wanted, I thought it was a great, anyway, we're jumping around. I'll get back to Chekhov. So, show hands. So, you're at oberlin i'm at check i get into check off i go to russia to study check off because i love it so much i go to williamstown theater festival because they used to have great checkoff plays there with nico sakharov what was it about checkoff that so grabbed you i think uh he's all about life is meaningless and full of meaning at the same time. He's really paradoxical in his Quetodian fascination with the banal. I think when I read it, I remember thinking, oh, you mean a bunch of upper middle class people talking about how someone should fix all the problems and no one does anything the whole time and they're just bored. It just felt like- What does quotidian mean? Every day. Okay. Yeah. I like it. Yeah. La peine quotodienne. So I loved it. I went to Russia. I had a bad time in Russia. I think I got too drunk often because that's a real thing over there. I went to his

grave, Chekhov's grave. Drunk? I think I had something, but I wasn't drunk. And then I did a little rubbing with the crayon and I had a rough time in Moscow. We were there in the winter. And I- What, you were depressed? I was depressed. And then I went to Chekhov's grave. Do you come from Russian people? Odessa. Well, Ukrainian, to Chekhov's grave. Do you come from Russian people? Mm-hmm. Odessa. Well, Ukrainian, but the other- Me too.

My great-grandfather had nightmares after watching Fiddler on the Roof when that pogrom breaks up the wedding. Pale of Settlement. Yeah. Belarus. Oh, really? Yeah. Well, I mean, a lot of the Russian Jews come from the Pale of Settlement. Some of mine came from Galicia, which was Ukrainian.

Belarus is a wild place. I haven't been there, but I hear it's... Oh, yeah? I hear Minsk is... They love Russia. They're like, why can't we be Russian again? Oh, yeah? Yeah, yeah.

I think a lot of people crave that. Yeah. Daddy. Here, too. Yeah. That seems to be what's happening. I know. Okay, so you're at the grave.

I'm at the grave. I mean, the momentum has gone from this story, but I think I expected to feel something at Chekhov's grave, and I felt nothing. And I was like, this is the most Chekhovian moment of my life. This is exactly what he would have written. And I walked away from it. That was the end and I walked away from the end of that that was the end of that I walked out of that great that graveyard yeah and I kind of left theater I came out to have graduated school I can't

was the end of theater not the end but close to the end I went I went to I went to I got out of college I went to LA for like nine months. I had some friends who were doing okay here. And my brother was a writer's assistant here. Is he in show business too? I have two brothers in show business. One is a writer on Chicago Med, the Dick Wolf Project. And my other brother is general counsel at UTA.

He's like the lawyer at UTA that's a big deal they're all yeah what's your sister she is a nurse she was like went through nursing and became like a nursing essentially a public health professor at ASU so she's very involved and she ran for congress in Phoenix she had a congressional bid that she didn't eventually get. But, yeah, we all are overachievers. We all want it. We all want the prize. So that's good.

So you come out here for six months? Came out here. You know, probably wouldn't have a good time anywhere, but this place can be pretty lonely and you don't want to be lumped in with the masses. Not as bad as Moscow, though, huh? Nothing's really as bad as Moscow. Nothing really is, i can honestly say um and then uh i had a blue man group callback i auditioned for blue man group and they were like you're you can drum you're pretty interesting you got a good

shaped head yeah it seems like you were the actually that was if you were to really look at your training and interest blue man group probably would have nailed it yeah marching band meets show choir uh meets meets wanting attention yeah uh so i went out for a long callback for blue man group did they had to put the blue on you got blued up i and the three of us, there were two other guys I was with and we were auditioning for the guy who, one of the creators, who was trying to select the next blue man. I think I talked to a blue man.

Yeah? Someone who, like, it was surprising that he was a blue man, but he was a blue, I can't remember who, go ahead. It's a sweet job, but blue handcuffs, they pay a lot.

You get health coverage? Yeah, probably blue handcuffs, they pay a lot. You get health coverage? Yeah, probably blue cross, blue shield. Good one. That was quick. But I didn't make it. I apparently non-verbally yelled with two, what are they called? The flight flashlights that the air traffic dudes use. They have a whole thing with that and

i guess i banged them too hard together to get this guy to clap non-verbally yelled he goes stop yelling at me and i didn't yell i would just i banged these two things together was that a revelatory moment that you've been non-verbally yelling for how long how long then uh i don't think it was relevatory because i was like he caught me he caught he caught me doing that thing i do again and after that i knew i didn't get it and i went out and i got a knish from one place and then i went to another place and i got some combos from a duane reed and then i went to new york yeah and then i got a pizza yeah and then i overate which is what i do i call it bodega crawls where i get stressed and then i go from one bodega to another just getting a snack thank you bro thank you uh and then i stayed in new york

after that and then i went up to columbia i so the not the la thing was not eventful nine months worked at kendall's brasserie under the mark taperaper Forum and the Dorothy Chandler. I was a waiter for a while. One night I wasn't tipped well and I chased the people out. And I was like, come on, man. And then I got fired. And I was like, sounds right. Sounds like it's time to leave L.A. So it all coincided.

And then I've been in New York for about a dozen or more years. or more years so all right so in college the arc was you know uh education self-discovery creative education drugs drugs the whole time throughout the whole drugs through high school drugs from age 13 14 till now yeah what what do you land on with the drugs? Pot. Yeah, that's it. And I'll do psychedelics quarterly. So you're one of those tune-up guys. Tune-up. I like to tune up. Uh-huh. Yeah.

I think I had a rebirth. I didn't do psychedelics quarterly again until I was in my 30s. I took like a break in my, like a 10-year break. But you still, you believe that this is the way? No. I believe it's probably something I'll be fiddling around with my whole life of how, how much to embrace or deny myself. Drugs.

Drugs. Yeah. Altered states, really, I call them. Well, how does, so you're in New York. Are you, are you performing? Are you going out for auditions so i go i go to new york i start messing with the columbia directing mfa program they need actors with which to practice directing so i start building my creative community out of there

while this is happening as an actor as an actor i'm i couch surfed for about a year, got an apartment. Good friends. Well, I learned how to, what is it, companies like Phish, they stink after three days. Yeah. So I learned that fast. Yeah. And then I found an apartment that had bed bugs.

And then at the time I moved into that apartment, I was giving up acting to become a New York teaching fellow. And I did the training for teaching fellows. Does bedbugs make you a crazy person? Yeah. Yeah, it makes you crazy. New York bedbugs, Blue Man Group, all of that makes you a crazy person. But driven, not lost.

Very driven. Well, what happened is one day I was hanging out with my- Driven and lost. I've never even thought of that combination. Yeah. You can be all of those things yeah uh my i was sitting at my friend lou's house and lou and i had joke this was like the beginning of derrick comedy the beginning of youtube really youtube came out as i was coming out of college yeah and my this democratized filmmaking was just hitting the ground. And my friend's friend was running a Diet Mountain Dew spec commercial contest. And my friend Lou and I, Lou had just bought a camera. We were like, we can try it. We can make this happen. And I had learned how to edit a little bit from trying to get my acting reel together. So we made this commercial for Diet Mountain Dew and we got it.

We won. So I made the next two years of my life about making low budget commercials and then identifying commercial contests that had low entries and then flooding that commercial contest with my videos. So while this was happening,

I couldn't afford rent. So I agreed to live in a theater and take out the garbage and kill the mice for about a year. Which theater? It's this little black box in the bottom of Kipps Bay called the Richmond Shepherd Theater, 26th and 2nd, near Bellevue Hospital, slept on a futon in the lobby. It was a really weird time of life. I was working in a cheese shop to pay off a credit card bill. I quit the teaching program because I was like, wow, I'm really not well suited for this. Everybody's going to lose if I do this. So you're sweeping on the floor, eating cheese and bread that you've taken from the store?

Yeah, and trading that cheese for other goods with friends. Cheese and- Bartering cheese. Cheese and theaters in rehearsal space. I'd be like, okay, you can come here in 10 and we can do this, but you got to help me work on my commercial. So you had the run of the place during the day. Oh, so you had the run of the place. Yeah.

During the day. When the show was done, whatever they were doing, I would invite my friends over. We would put on all the costumes, play with the lights, do a Phil Collins dance party on stage. Two nights a week, the guy who owned the theater, who was a mime in his 80s, he was such an interesting guy um his ex-wife would sleep on the stage on a piece of foam two nights a week so we had to and you were in the lobby and i was in the lobby on a futon why was she there with two nights a week because she was a birthday performance a children's birthday performer and she had a dora the explorer costume and an elmo costume right and she kept those up

and we also dressed in those and danced in those as well. But still, why did she sleep there? Because she had a place in Bridgeport, Connecticut. Oh, so she had to put on the shows. Yeah, yeah. She had to go and put on the show and do it. Wow, that life in the theater, man.

Yeah. An 80-year-old mime that no one knows who owns a theater space. In the bottom of a, like a basically housing project. Yeah, it was just a really wild... Specifically New York, but see, sort of informs the possibilities of the show. Oh, yeah, dude.

That, I remember sleeping there, watching the shadows of the rats crawling up the grating that the streetlight was pushing through the window. And remember thinking, wow, this is, I'm going to look back on this and think this was the most romantic time of my life. The most, I knew going into it, I'm like, this is what this time is for. Ratatouille came out during that time or a little after. And I was like, yeah, that's what I'm doing. I'm doing the exact same thing. But just to meet those personalities as well.

Of course. Of course. You know, that there's something about, I think, the show and seemingly about your experience with New York that really kind of gets where New York's at now. And it's still this weird, thriving, almost unexplainable community of of incredibly diverse humanity and and i think that you know you see you used to see it more before people had to leave yeah yeah which is like you know why brooklyn is brooklyn but i mean but at the time you were there maybe it was already starting to happen but like when i was there in the 80s you know people could still afford to live there of all different kinds. So you had all of that weird ass theater stuff.

I also got to New York right as the recession hit, which was, again, not unlike when I separated on Trump's election day. I also got into like the least skilled portion of my life, my years after college in New York when everybody lost their jobs too, you know what I mean? So it did feel like there was this spirit of, I know I did everything right and it still didn't work out. So I'm just going to fuck it and do what I want now.

And that was the prevalent attitude when I was making those videos. I was like, oh oh this is democratized filmmaking i don't i can just make a thing and i don't have to ask permission i can say fuck and show a dick and an asshole on the internet and it doesn't matter louis ck had come out with louis not too long after which was this auteur comedy thing and it was that it really was the moment of a populist uprising in content creation. Yeah. And that's where it began.

For me, that's where it began. I learned how to make things fast and good. Sorry, cheap and good, not fast. Fast, cheap, and good. You pick two. Yeah. I picked cheap and good. And how did the early YouTube versions of iMaintenance evolve? Well, I met my ex-wife

Katya in LA. I had just won a contest out here. I was seeing family. I was feeling like hot. Commercial contest? How many of those did you win? That was my salary. I was really taxed very poorly. I shouldn't have done it, but it was my salary for two years. I was really tacked very poorly. I shouldn't have done it, but it was my salary for two years. Yeah. I made a couple of tens of thousands of dollars over two years off it.

Not enough to live on, but enough to feel- Just by winning commercial. Enough to feel good about inside. Commercials for what? Would people know them? Nissan Cube, Diet Mountain Dew is one,

Sun Chips, Compostable Bag. Yeah. yeah you really had figured out an angle huh oh yeah that was the angle it was my film school yeah i was just like all right what's the assignment okay they want this okay so if i can just ask this person to do this and maybe if you shoot it like this and then i'll edit it the editing was the most powerful tool that I gained to their editing is everything Wow for me so okay so you meet Katya what did I go in for a role Katya was she had worked on 30 rock as a casting assistant for a couple of years she was changing her life and moved from New York to LA

to kind of try something else. Not casting? Working in the NBC casting office, but not on 30 Rock. Okay. And I met her via my brother who lives out here, works in Chicago Med, and his wife. His wife is an actress. She was actually in the first ever High Maintenance. Her name is Bridget Maloney Sinclair.

I love her so much. And Katya was a fan of Bridget's as an actress. And then Katya moved out to LA and Bridget's like, let's be friends. And they started hanging out and Bridget and Dan, my brother, were trying to set Katya up with their friend, Alex from college, who I'm also friends with. I was in town. Alex was like, come over and hang out at this party. I'm dating this woman. And then I went to that party. i was sleeping on my friend mike's couch at the time here and but still feeling like hot shit because i won two thousand dollars yeah and then that was 50 taxed and then uh yeah and then i met katya and she was a functional stoner i was a functional stoner and then there was functional stoner. And then there was like a magnet.

I think looking back on it, we realized there was this creative spark in both of us that fell in love with each other at that moment. And I feel like there was sexual attraction there too. There was everything that goes into it. We were just, it was one of those moments. And this was around my almost 25th birthday. She's six years older than me. So I was like, wow, this cool woman kind of likes me what's going on this. And, uh, and this was, she is probably the first time in my life where I was feeling very unstable. I just moved out of the theater. This woman was into me. I was on my way to do the tempest at my alma mater oberlin for the

summer theater thing and i just back in the theater back in the theater that was the last play i ever did before this one i'm doing up in june which i'm excited about but uh i i was like all right i'm signing on to this person. This is the first person that I'm going to let take. Honestly, she took care of me in those times. I was sleeping on couches. I was living in a theater. I was like, from a non-romantic point of view, out of control.

You know what I mean? Or without a net, flying without a net. But you're not a boozy guy. Boozy? No, it wasn't about booze. You were just sort of like unformed. Yes. And high.

And she, her God-given talent is to identify potential. And she still does it. And I feel like she identified my potential at that time. And then she was willing, she was like, uh, maybe I was amused to her. Maybe I was, uh, I don't know what I was to her, but I do feel like I jumped into that in a, in a way that I haven't ever jumped into anything before, which was just let her catch me. So you let your guard down, you opened your heart for the first time. Probably the first time. It was my 25th birthday.

And then we were married like a year and a half after that. And when did the creative partnership begin? Well, when she came to visit me at oberlin that summer she was like maybe i should be your manager like what should i do she was trying to figure out like what we should do together and then business wise business wise and then after we moved in together we moved back to new york together we uh realized that we had, I had even said, fuck acting. I'm going to do Brooklyn. I said, fuck acting. I want to do something that matters. So I got into composting big time. I tried to start a compost pickup service in New York that would, with a bicycle powered delivery

mechanism and decentralized compost heaps all over this i really wanted to do something that wasn't acting but wait now let me ask you about that because acting does feel like sort of um uh there's something about acting that if you're a certain type of person that makes you feel like like i'm getting away with murder here and i'm not doing much to help anybody yeah also coming from being with a casting director, she went back to work on 30 Rock and I got to see from the other side of things how little agency an actor has,

especially in TV and film. It's the worst. I don't know how they do it, dude. I don't know either, man. How do they fucking do that day to day? I don't know. They must really want it. Or I guess,

or it's a certain type of delusional. I mean, but- I guess they really want it want it but i mean how much rejection can you take and at what point do you realize like i don't i don't even like talking like this but it's just like at what point do you realize like i can't it's not you know i got to do something else yeah i mean that's what i did at that time i was like i got to do something else like this can't be just yeah. Yeah, this can't be the life. So my compost company was going middling to okay, but I was still making videos. I was doing bar mitzvah videos. I was doing-

Really? Yeah. And she was okay with this? Yeah. She was like, all right, I'm going to go to my job and then you're finding it out. I was 25, 26, 27. You're composting, you're shooting videos at bar mitzvahs.

Exactly. And she identified a potential that was trying to figure itself out, I guess. And then when we got married, six months after, we started writing the first time maintenance. What was the sit down discussion though? Whose idea? Was it because a weed dealer came over well we would order weed a lot we were we were like true blue stoners yeah uh i was also working at a plant shop so i would deliver plants and and flowers to people's apartments in brooklyn and then i would

stay there to plant the thing in the pot in their apartment and I would talk with them and I kind of created the persona of the guy while doing that because I was very happy I was just married I didn't have this acting monkey on my back of feeling like shit I was like oh actually I don't need that I I'm I'm fine without that world and I was just feeling like I was doing something that was more important than just being in somebody's play or movie. So I felt really good and I had a very optimistic attitude. And this was 2000 and Obama times. We were in Obama now. So I felt very optimistic. And that summer we were also watching Six Feet Under and Party Down. And, uh, that summer we were also watching six feet under and party down. And,

you know, in the beginning of six feet under there's somebody dies. We were like, that's a show. Yeah. Like right there, just on the web, just like a little short story where,

you know, something's going to happen. You know, this person's going to die. And then they do. Uh, we thought about just isolating that moment and making a web series that was like, you know, a weed deal is going to happen, but we don't know how it's going to happen. And we don't know who it's going to be when we dropped into that world.

And then I think we were biking around Brooklyn. I remember the day we were biking around Brooklyn and we started talking about this weed delivery show. And then I remember we would have long silences in between talking to each other riding bikes next to each other and i think it formed on one of those bike rides huh and so you just started doing short episodics yeah we invited bridget my sister-in-law to come to new york and do this with us and i my friends were in mfa programs at nyu and we, hey, you want to help make this with us? Yeah. And then we released the first one

in November of 2012, coincidentally a week after weed was legalized in Colorado and Washington. So Kismet. A week after? Yeah. We didn't even know that was on the ballot. But didn't that reality become a threat after a certain point?

People keep asking us, what are we going to do when weed's legalized? I've been getting that question for five years. I figured. Yeah, but it's not legal in New York yet. No, that's what I mean. Yeah. So, yeah, when it's legal, we'll figure it out. But yeah, but it might have been the run of it anyway.

Yeah. Right? Who can say? I don't know. I mean, there's still people that prefer it to get by it illegally yeah well yeah well to buy it from somebody who's going to come over i definitely am very skeptical about big business coming into weed and ruining the whole well well not just big business but whether big business comes in or not, it's developing a new big business. And with a new big business comes big business thinking. So I don't know if it's a new paradigm. I don't know how much the old paradigm is getting involved in it.

But there are classicists who really want to keep that old paradigm going. Sure. And if you've been buying weed illegally for some time now, and now there's a legal way that only the people who haven't been arrested for weed dealing are like, why would you change over the legal way when you've been doing it illegally to success for years anyway? It's like, you're going to do illegal in the past. You're going to do it illegal now. It's, I would still, it's like the same risk. I guess so. I guess, yeah. But okay, so how many episodes did you do online? We did 19 total. Well, we did 13 online.

How long were they? Self-funded. Six minutes to 12 minutes. Those were. Yeah. We then, right before we made our 10th. They're still up there, right? They're on HBO now

everything's on HBO all the stuff you did on YouTube is now off? it's off Vimeo we did it with Vimeo oh okay so we had a deal with FX to make a TV show briefly

and it was clear that they didn't watch the show or weren't fans of the show but for some reason that's interesting so you did it with Vimeo so you were able to get it yes because I think it's kind of tricky to get your shit back oh we are please if anyone's

listening who is like oh that's how i'm gonna do it the way that we did it is an anomaly and it's and it we got very lucky we are very lucky to get your shit back because we were able to maintain the rights because we had made the thing already. The thing already existed as it was, the web series. So while we were stuck in development at FX, I was like, hey, can we still make web series shows? And they were like, oh yeah, we don't care, whatever. So I was like, all right, now we're going to make stuff that they'll never let us make when we go to FX,

if we ever go there. So we started making, we really started testing our own filmmaking ability and the limits and we made episodes called cassim matilda and rachel and i think those are to this day some of our best work because we had this thing of being like hey i'm going to show you we had the i'll show you mentality of like actually here's what you can do when you're not dealing with commercials well it seems like that the the sort of context you've created really enables you to do whatever you want the format is the best part of the show is in that like like i don't know if i mentioned this

earlier like it it's essentially an anthology show oh it's absolutely but it's not though you know because you know anthology shows by and large don't really work certainly not for four seasons you know but you are the thread and the city is a character and you made the country a character as well and we have we try to reflect life as it is we try to tease out my character and try to give you little bits and pieces uh because he's the only through line at it but we also recognize that the success of the show is the format which is to say there is a format but not much it's just this the weed deal right but also but but like it's not unlike you know directors have claimed that you know environments are characters. But that's true.

It is true. That the consistency, mostly Brooklyn, I guess, right? And just that you really feel that. That because of the nature of the way people live is that there is no place like New York. No. Well, I'm trying to get this format going in non-English speaking cities as well. I'm working on Mexico City right now. Oh, yeah.

That makes sense. And I want to see how that goes. But I would love to see. So you would sell the format. Mm-hmm. Yeah. Huh. I love to, traveling is, you know, who doesn't like to travel, I guess.

People don't like to travel. But every time I go to a city, I'm like, all right, what has high maintenance work here? Like, how does it? Yeah, I mean, you know, it's, yeah, who's, create the thread. Get the guy. Yeah, but it's very important because there's a lot of what we don't do is what defines the show.

We don't get too saccharine. It doesn't get too anything. We really try to pull back right when it gets to be. There's a cleverness and a sort of subtlety to the way it's written. Yeah. You know,

I think that's the real trick. Well, thank you. But, you know, and how you can recreate that, I don't know. I don't know either. What are people's instincts going to be

once you start entering environments with the new guy who doesn't, you know, who lives in a culture that isn't yours? Exactly. How do you let that go? I don't know, Mark. a culture that isn't yours exactly how do you let that go i don't know mark okay all right i don't know well now let's you guys were married how long

six years and you know a year into the hbo show was when it yeah it started crumbling it started becoming untenable during the post-production of the first season of High Maintenance. And I would even say the first HBO season. And I would even say during production. How did that manifest itself? Arguing. Oh. You know, the typical disillusion of a marriage.

You know, one thing that became a problem was as I became more recognizable in Brooklyn, people would stop us but wouldn't know about her involvement. You know, they would look through her, and that was very uncomfortable. Plus, you know, I won't speak for her side of the thing, but we were both having identity shifts, you know? And I was struggling with taking success on and, and leveling out during that. I feel like everybody has a period of time when they're adjusting to that. And I think

similar for her, but the truth is, I think we recognized in each other the creative thing. We were both a man and a woman who were used to putting sexuality on top of a relationship when we found an attraction to one another and weren't used to just being attracted to each other creatively and just letting that ride out. So that thing is very alive and well still, that creative attraction and that respect. very alive and well still, that creative attraction and that respect. But the sexuality was kind of something we did out of habit, I think, based on every other... Interesting. But that's something, looking back,

you've decided that. Looking back, I decided that. I think the first couple of years of our relationship, we were... And I really liked being a husband, man. I liked it so much. I thought it was great. I don't know that I'll ever be one again, but i really liked being a husband man i had i liked it so much i thought it was great i don't know that i'll ever be one again but i really liked it uh i think that there was like a conventional relationship in there for about a year and a half and then after that it was

something else yeah yeah what does that mean we were were creatively combined. The show took over. Oh, I get what you're saying. The show took over. And then, so, but where does heartbreak stand? I mean, was there heartbreak? Yes. Incredible. Incredible. I would say- And she came out, correct? to separate and while we were doing counseling that winter uh there was this her feeling this realization that maybe she uh was uh not a straight person and then once that came into the fold it was like a oh you know part of me felt relief about it not only just how i would seem

to the public and not feeling like there was nothing I could do, you know what I mean? Sure. But the truth is, I participated in negative back and forth that also led to the end of the marriage. I also, you know, became bitter and resentful and fought and like, I'm not off the hook. I, I didn't treat that person all the time. The way I treat would want to treat something or somebody that I loved. Yeah. And that's the heartbreak is, well, I'll say this, like we were texting this morning, like after, well, after we broke up, we were working together 60 hours a week, 70 hours a week. So immediately, while, after we broke up, we were working together 60 hours a

week, 70 hours a week still. Immediately. Immediately. There was no break. I think because, um, we just finished, finished the show this year, like last week, this might be the first time longer than a couple of weeks that I've spent away from her. You know, we never actually got to break up as people break up. We broke up and we were right in each other's face. I would even call it exposure therapy of just learning how to be around each other and not together immediately after.

It's rough, dude. It's rough. The truth is I think I'm a little traumatized in love from it, just a little bit. I would think so. Yeah, but I also wouldn't trade it. I wouldn't really do it differently because— No, I dig it. To kind of assess the trauma of just basic love dissolution. Oh, well, I would argue that I have been able to assess it,

but in the presence of her and a room full of writers. Okay. Maybe I'm saying you haven't been able to meditate on it with alone time. Yes. Alone time is, and there are a couple of episodes this season addressing directly alone time. I would subtitle this year, season four, joint custody, because there is this feeling where Katya and I agreed to direct every episode this year where in the past two or three seasons no two past two seasons we had other directors come in we agreed to direct every episode and as a

result of that choice we were one was offset while the other was on set you know there was more of a this is the ones that I'm working on and these are the ones that you're working on and I will you had to be in all of them yeah as well that well, that's tricky. Well, I'm used to that part of it. That's probably, the acting, I'm like. No, but I mean to go back and jump in and out. So, but largely like, whereas in the past, we would both always be on set directing every episode. Now we were directing separately

and not present for each other's episodes, except when I was in the thing or I would drop by. Right. And it's really cool. There's a Lennon and McCartney thing going on, but we also, going out on our own, want to make sure that all the things we learn from each other are present in the episodes that we directed solo as well. And that is, it's so cool to watch that part. that we directed solo as well. And that is, it's so cool to watch that part.

Like I really, I feel so much like, you know, a big thing for me was I never could trust my own taste because I was a younger brother. I would just like look at my older siblings taste and like copy it or whatever. And I was really worried going into the season. Like, what if I have terrible taste and I was just copying Katya this whole time?

Or what if I, what the fuck? what if I have no idea what I'm doing and I was just saying something and then looking at her face to see if she liked it or didn't like it? When there wasn't a face there, I had to trust my own gut. And I think in doing that, that is the kind of the meditation you're talking about, the solo journey. That is the kind of the meditation you're talking about, the solo journey. It's hard, man. I mean, I experience that in the sense of more of a, it's broader for me, like, you know, just my whole life. I'm like, you know, the who am I?

Why do I dress the way I do? Is this, you know, is this, do I like this stuff? What do I like? You're ignoring that totality. We both are, I guess. Yeah. But I guess that's what we're celebrating here. We're celebrating people's likes and dislikes and what they think works and what they don't work. Well, just also this, it falls in line with the sort of not being able to say no thing. There's a lot of things you think you should like. And there's a lot of things you've sort of, because of things you've identified with or people you have identified with, you like because of them. So to really, and I'm 56. And now I have the freedom to sort of do

things I have not been able to do. So the idea of what makes me happy and what do I like are questions that have been unanswered for my entire process. But I would even go further to say that taste is more about what you say no to than what you say yes to. No, for sure. Yeah. But that's also closed- know, closed mindedness. Yes, it can be. It can be until you go into that closed minded person's living room and then you're like, oh, you have really good taste. Good for you keeping that other shit out of here.

But somebody told me a while ago that at a certain point, the password to yes is saying no. And I really I held on to that for a long time and mostly when people were like oh we want to buy high maintenance so we want to put it on this and it was i'm sure you've had it with this thing you're like no no no no no until that thing comes along until for us that hb deal of hbo6 episode promise comes along and then we're like yes but you have to say no a million times yeah i say no a lot too but like it's not you know i don't there's not many things i've i've created that don't require my immediate engagement do you know it seems like you know because of your ability to

work with an ensemble and also your you know the collective of of you and your crew and you and your uh now ex-wife you're bringing a lot of different people in and in in in in a really great way i i still don't do that trust people enough no no it's just like it's not the world it's not the you know i'm not living in that world of creativity what about your show marin well yeah but that was that's done and i think that was kind of limited. I made some mistakes in that. It was still sort of like, how do I do this? I didn't know how to do any of that.

But I'm reckoning with the idea that I'm sort of an old man in certain ways, and I don't really know how I fit into the whole thing, and I don't live a regular life, and I've never been that sociable in the sense of like, you know, I'm like literally watching high maintenance. I'm sort of like, wow, there's a lot going on out there. And I'm not part of it. But that whole show is about being alone and that feeling of like loneliness is one of our most oft used themes. Yeah.

And I think that that alone together feeling is a lot of new york and it's just a count the the current condition will that i get yeah willie staley wrote a great article in the new york times magazine about how our show and master of none and russian doll fit into this fantasy of new york now and the thing that really that I was really heartened by what he wrote was that we are talking about the modern condition that we're all alone, you know, seamless, grub hub, everything. Amazon has driven us into our homes. Coronavirus. Just the internet. Period.

Just the internet. So that's just, that's just being alive now. And you have to actively fight to not be alone. I guess so. But the one benefit, and I think the organic nature of what still is the city of New York is that you got to be up against other people. Yeah. It's like alone is one thing, but you step out of your house or just to get somewhere. You're like, boom. But you also build a wall around you because you need of your house there just to get somewhere. You're like, but you also build a wall around you because you need to get from point A to point B. I guess so, but you still are got

you're still in it. It's true. It's true. And I'm also coming, you know, whenever I come to LA, I I go, I walk on the LA River walk. I love that. I like seeing people. The Uber drivers here are so talkative. Oh my God. They talk. They are the most talk seeing people the the uber drivers here are so talkative oh my god they talk they are the most talkative people in the world it's a different trip man you know out here you

can really you know you you don't have to see people man yeah do you i mean where do you find your community where do you get it uh well you know i got I got, I got friends, a few friends. I got my comedy store, which I go to. Uh, you know, I, I don't, my sense of community is not tremendous. I, you know, I do, uh, I do the AA trip and not as regularly as I used to, but, uh, it doesn't, it's not, I'd say when I need a clubhouse vibe or I need to get out into the world, I'll go to the comedy store and see my people. That's cool you have that. I wanted to be a stand-up comic when I came out here.

Did you try? I did. I went to the comedy store. I went into the, is it called the Belly Room? I did that night, and then I went into the Bringer Sunday night slot, and then I did a couple things there. And I was like, I don't like how I feel in this green room. I don't like the end. Like, did you do stand up in New York? No, I didn't. I think it's probably something that will happen to me again one day. I think I was watching you do stand up and I was thinking about the camaraderie there. And that's like

something that I remember watching the comedians of comedy when I was younger and watching that and being like, Ooh, I want that. So, you know, I kind of like, you know, I check in with them and we all understand each other to a certain degree. It's kind of a, a weird bunch. Uh, but, but I, I know that I can go there and feel this is my people in that place, which is cool. Yeah. Great talking to you, man. Nice talking to you too, man. Thank you for inviting me. And I'm glad we're both not sick. Oh, me too. Yeah. Smart guy.

Creative guy. Interesting guy. Glad he came by. Ben Sinclair. I hope you enjoyed that. You can watch all four seasons of High Maintenance on HBO Go and HBO Now. The fourth season is underway. The season finale is Friday, April 3rd.

And now I will play raw guitar for you. I think I'm really getting a handle on this new guitar. We'll be right back. Thank you. Boomer lives. It's winter, and you can get anything you need delivered with Uber Eats. Well, almost, almost anything. So, no, you can't get snowballs on Uber Eats. But meatballs, mozzarella balls, and arancini balls? Yes, we deliver those. Moose? No. But moose head? Yes. Because that's alcohol, and we deliver that too.

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