< Ben Sinclair: High Maintenance And The Battle Of The Podcast Stars

JONATHAN COULTON: This is ASK ME ANOTHER, NPR's hour of puzzles, word games and trivia. I'm Jonathan Coulton. Now here's your host, Ophira Eisenberg.

(APPLAUSE)

OPHIRA EISENBERG, HOST:

Thanks, Jonathan. It's time to welcome our special guest. He's the co-creator and star of HBO's "High Maintenance." You know him as The Guy. Please welcome Ben Sinclair.

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EISENBERG: Welcome.

BEN SINCLAIR: Thank you. Welcome.

EISENBERG: Welcome to the podcast festival. So I thought this was pretty interesting. I read that you're a great admirer of the film director Steven Spielberg.

SINCLAIR: Ah, yes. Yes. Yes.

EISENBERG: And as a kid, you would write him letters with pitches.

SINCLAIR: You know, I am from Scottsdale, Ariz., and he grew up very close to me in Arcadia. So when I would watch those movies, I was like, I know this feeling because it was just kind of based on the same place. And then I thought that was, like, we were soulmates. And then...

(LAUGHTER)

SINCLAIR: ...I got a book of, like, the addresses that you could write to people to get their autographs. I wrote to Steven Spielberg with this, like, scrawled note that was like, hey, I got this idea. If you want to know about it, I'll tell you.

(LAUGHTER)

SINCLAIR: But, like, I'll just give you a little taste. It's "Rookie Of The Year 2..."

(LAUGHTER)

SINCLAIR: ...Except he's a werewolf.

(LAUGHTER)

SINCLAIR: And his grandmother is Whoopi Goldberg. What do you think? Anyway - and then I got a letter back - was like, thank you for the pitch, young man. Unfortunately, we're not able to read this because of our lawyers or whatever. And I - but I appreciated being treated like a professional. That really...

EISENBERG: Yeah. That's for sure.

(LAUGHTER)

EISENBERG: So between high school and college, you spent some time in Mongolia.

SINCLAIR: True. God, what's going on?

(LAUGHTER)

SINCLAIR: You know, here's a - here's - I'm going to get this off my chest.

EISENBERG: Yeah.

SINCLAIR: I went to Mongolia for 45 days. I've been telling people it was three months my whole life. I don't know why I'm rounding up a month and a half.

(LAUGHTER)

EISENBERG: To a solid three.

SINCLAIR: But I've been lying to everybody that I was there for twice as long as I was there.

EISENBERG: OK. So then you go to Oberlin.

SINCLAIR: Yeah. I went to Oberlin.

EISENBERG: And then in your junior year, you...

SINCLAIR: Go on.

EISENBERG: ...Do an intensive theater program...

SINCLAIR: Oh, yeah.

EISENBERG: ...In Russia at the Moscow Arts Theatre, where you did a bunch of Chekhov plays.

SINCLAIR: Yeah. I'm cuckoo for Chekhov. I...

(LAUGHTER)

SINCLAIR: I thought it was so fun to be in a Chekhov play - maybe not to watch one, but, like...

(LAUGHTER)

SINCLAIR: So I went to Russia to study it, and then I don't know what happened. I was at Chekhov's grave, and I did a grave rubbing of his name with a crayon. And I was expecting to feel something, and I felt nothing.

(LAUGHTER)

SINCLAIR: And it was the most Chekhovian moment of my life, I think.

(LAUGHTER)

SINCLAIR: The exciting thing is I've been asked to be in a Chekhov play with the New York Theatre Workshop.

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SINCLAIR: Yeah. Yeah.

EISENBERG: Which one?

SINCLAIR: I've - in the "Three Sisters" that Sam Gold is directing. I was asked to be in it. I didn't even audition. I just was asked. And I know the "Three Sisters," like, backwards and forwards. This summer, I'll be doing that.

EISENBERG: That's amazing.

SINCLAIR: Yeah. Yeah.

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SINCLAIR: I'm so excited. Yeah.

EISENBERG: So "High Maintenance" is a series about the lives of New Yorkers which are all connected by a weed delivery guy played by you. So...

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SINCLAIR: Got a fan over here.

EISENBERG: I have to ask you just because of obviously the role you play on the show, when you show up just around as a regular person, yourself, do people sometimes think that you are selling pot?

SINCLAIR: I don't know what people think.

(LAUGHTER)

SINCLAIR: I'm not going to pretend like I can assume what anybody thinks. So there are some pot dealers who will come up and be, like, hey, I'm doing it.

(LAUGHTER)

EISENBERG: Now, I believe you spent a few years as a flower delivery guy...

SINCLAIR: That's true.

EISENBERG: ...In Brooklyn. I'm sure that influenced this character.

SINCLAIR: I worked at Sprout Home on Grand Street between Kent and White for three summers. I was...

EISENBERG: Did you hear the gasps?

SINCLAIR: ...Their summer meat man. I would come in, and they would be, like, move this. Take this over there. Be nice. And...

(LAUGHTER)

SINCLAIR: And I would go from apartment to apartment in Williamsburg just hanging out in people's places. And I was - I'd just gotten married, and I was in a really good mood, and I was wearing toeshoes. People would be like, you're the help. And I'd be like, no, I'm in your house. Let's talk. And...

(LAUGHTER)

SINCLAIR: And then I just - I kind of - I think The Guy came out of that time of life because I felt like, yeah. And I was like, I want to help. So I went to Annie Novak at Greenpoint Eagle Street Farms. It was a rooftop farm. I'm like, what do you need? She's like, I need compost. And I said, well, let's get some compost for you. So then I got together with a friend I went to college with, and we started a compost collection service that was on a bike. It was like a bicycle. We would pick up your - whatever. It was...

EISENBERG: Yeah.

SINCLAIR: ...Too hard.

EISENBERG: Yeah. That sounds...

(LAUGHTER)

EISENBERG: ...Super hard.

SINCLAIR: It was too difficult - too difficult. I was going over the Williamsburg Bridge with, like, almost a thousand pounds of trash.

(LAUGHTER)

SINCLAIR: And my - it was hot. And I was like, what have I done?

(LAUGHTER)

SINCLAIR: Anyway...

EISENBERG: So you dipped your...

(LAUGHTER)

SINCLAIR: Anyway, yeah. I like Chekhov or whatever the other question was.

EISENBERG: You dipped your toeshoe into the compost...

SINCLAIR: Yeah. I dipped my toeshoe into the compost business. And then this show happened, like, right after I dumped that crazy uphill battle for...

EISENBERG: (Laughter).

SINCLAIR: I did not die on that hill.

EISENBERG: Right.

SINCLAIR: And I'm not dead yet.

EISENBERG: Of compost, right.

SINCLAIR: Yeah. Yeah. But this season is about - anyway, I...

EISENBERG: Yeah.

SINCLAIR: I'm talking too much.

EISENBERG: Oh, yeah.

SINCLAIR: I'm sorry.

EISENBERG: So, well - so I - but I have a question. So weed is becoming decriminalized slowly more and more over the country. How are you going to address that in future episodes of the show?

SINCLAIR: You know, the thing with this show is it's so tempting to put it in that box because The Guy is a weed dealer. But it's just so not about that.

EISENBERG: True.

SINCLAIR: So, you know, it's just an excuse to tell any - it's a portal topic to talk about any other story. And really, at the end of the day, it's - oh, God, I can't believe I'm about to say this - it's about human suffering and people...

(LAUGHTER)

SINCLAIR: ...And people relieving - people looking for a way to put a pause on human suffering just so they can collect themselves a little bit.

EISENBERG: Yeah.

SINCLAIR: So at the end of the day, that's what it's about - or something.

EISENBERG: Yeah, that sounds good.

SINCLAIR: Yeah, yeah, yeah, yeah.

EISENBERG: I'm excited. I'm very excited.

SINCLAIR: Cool.

EISENBERG: OK. So we're at the Brooklyn Podcast Festival. You're a huge podcast fan. You listen to a lot of podcasts.

SINCLAIR: Podhead (ph).

EISENBERG: Do you - podhead.

(LAUGHTER)

EISENBERG: Do you - a lot of people I know - I don't do this, but a lot of people, although they listen to them on their commutes and while they're doing things, but they also listen to certain podcasts - like, actual people talking or what have you - to fall asleep. Do you do that?

SINCLAIR: Yeah.

EISENBERG: What podcast is your favorite to fall asleep to?

SINCLAIR: I listened to Tara Brach. She's a Jewish Buddhist psychologist who really just talks about presence and just trying to get out of the cycle of suffering.

EISENBERG: Sounds great. Sounds great.

(LAUGHTER)

SINCLAIR: Yeah.

EISENBERG: OK. So we have a game where we took the titles of popular podcasts and made up Bizarro World versions of them. And you just have to guess what the real podcast I'm hinting at is.

SINCLAIR: I know.

EISENBERG: OK. So, for example, if I said Exposed Heart, you'd answer Hidden Brain.

SINCLAIR: Oh. Yeah, yeah, yeah, yeah.

EISENBERG: Got it? Got it?

SINCLAIR: Oh, this is going to be much, much harder than I thought.

EISENBERG: Yeah.

(LAUGHTER)

SINCLAIR: Yeah. Oh, yeah.

EISENBERG: Well, I would say you're setting the stakes, aren't you?

SINCLAIR: Oh, yeah. OK.

EISENBERG: And I have plenty of hints just in case.

SINCLAIR: All right.

EISENBERG: All right. And if you do well enough, listener Ryan Goluch from Ames, Iowa, will win an ASK ME ANOTHER Rubik's Cube.

SINCLAIR: Wow.

EISENBERG: Yeah. Come on.

SINCLAIR: Talk about getting out of the cycle of suffering.

(LAUGHTER)

EISENBERG: All right. I'm going to start with a gimme - Visibilia (ph).

SINCLAIR: All right, Invisibilia.

EISENBERG: Yeah, exactly.

SINCLAIR: Yeah. All right. All right.

EISENBERG: How about this? Stale Vacuum.

SINCLAIR: Fresh Air.

EISENBERG: Yeah.

SINCLAIR: Fresh Air. Oh, yeah.

EISENBERG: Yeah. OK.

SINCLAIR: See, I keep looking at this handsome man in the front.

(LAUGHTER)

SINCLAIR: He doesn't crack that much, but every now and then when he cracks, it makes me really happy.

(LAUGHTER)

SINCLAIR: You know, he holds it together. I appreciate it.

EISENBERG: (Laughter) That's how you know if you it's really working, right?

SINCLAIR: Yes, yes, yes.

EISENBERG: How about "Gail's (ph) Bad Body Non-Communications?"

SINCLAIR: What's the opposite of Gail? Like a wind?

(LAUGHTER)

EISENBERG: Oh, like a person's name, Gail.

SINCLAIR: Oh, "Oprah's Adult SuperShow" or whatever it's called.

EISENBERG: Yes.

(LAUGHTER)

EISENBERG: I like it called Oprah's Adult SuperShow.

(LAUGHTER)

SINCLAIR: Yeah.

EISENBERG: That should be her festival.

SINCLAIR: Yeah. Cool, cool.

(LAUGHTER)

EISENBERG: It's close. Right - Oprah's SuperSoul...

SINCLAIR: SuperSour Power Hour.

(LAUGHTER)

EISENBERG: SuperSour Power Hour Of Conversations.

SINCLAIR: Yeah, yeah, yeah.

EISENBERG: Right. "Oprah's SuperSoul Conversations," yeah.

SINCLAIR: OK. Yeah.

EISENBERG: All right - Your Despised Resuscitation.

SINCLAIR: My Loving...

(LAUGHTER)

SINCLAIR: My Beloved Housemate. My Beloved Resuscitation - death?

EISENBERG: It's hosted by Karen Kilgariff.

SINCLAIR: Oh, "My Favorite Murder."

EISENBERG: Yeah, that's right.

SINCLAIR: "My Favorite Murder" - see, I've never listened to it. I just know about it.

EISENBERG: Yeah. Are you a true crime podcast person?

SINCLAIR: I don't know, man. Hearing about somebody getting killed doesn't, like - it's not better than "The Daily." "The Daily"...

(LAUGHTER)

SINCLAIR: That's what that's about. You know what I mean?

EISENBERG: (Laughter) All right. Your next clue is, The Sporadically.

(LAUGHTER)

SINCLAIR: Oh, yeah. The Constant. "The Daily."

EISENBERG: That's right. I had to. I know. You basically answered it before.

SINCLAIR: Yeah.

EISENBERG: All right. This is your last clue. This Russian Death.

SINCLAIR: La petite mort. This American Life, yeah.

EISENBERG: (Laughter) That's right. I know. Cold War's back to make that clue work.

SINCLAIR: Aha.

EISENBERG: Hey; you did amazing.

SINCLAIR: Russophobia is alive and well. Thank you so much.

EISENBERG: Yeah.

SINCLAIR: Thank you.

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EISENBERG: You and Ryan Golak (ph)...

SINCLAIR: Did they get the Rubik's Cube?

EISENBERG: Oh, yeah.

SINCLAIR: Good, good, good, good.

EISENBERG: Then you and listener Ryan Golak won ASK ME ANOTHER Rubik's Cubes. So Ben will be back to play another game later in the show, but for now, give it up for Ben Sinclair, everybody.

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