Since 2009, three longtime friends — rapper Alec “Despot” Reinstein, comedian Ashok “Dap” Kondabolu, and rapper Aleksey “Lakutis” Weintraub — have brought the sensibility of Howard Stern to covering emerging hip-hop. Like Stern’s iconic radio program, their long-running underground radio show Chillin Island is hard to describe if you aren’t already a listener. It’s chaotic, nonsensical, and sometimes a tad problematic. In a culture that feels overwhelmingly polished, it’s also one of the more essential cultural products of the past decade. Which probably explains why HBO is turning Chillin Island into a TV show, premiering this Friday.
Produced by Spotify and Elara Pictures, the production studio founded by the Safdie Brothers (among others), Chillin Island builds on the raw and unpredictable magic of the radio show. The series is intended to be a rap version of John Lurie’s cult series Fishing With John, with guests like Young Thug, Lil Yachty, and Gunna joining our hosts on adventures in the wild. In the series premiere, Young Thug joins the troupe on a camping trip where we learn, among other oddities, that Thug has an encyclopedic knowledge of animal facts.
“When Alec approached me and [Elara co-founder Sebastian Bear-McClard] and said he wanted to do a TV show of the radio show, it was a unique challenge,” said Josh Safdie, who worked as one of Chillin Island‘s executive producers. “How to synthesize the show while also becoming something else.” The task was a good fit for the Uncut Gems co-director, a devoted fan of the radio show. “I would often call in and bother Alec, Dap, and Lex to try to tap into that strange tropical vibe,” Safdie continues. “I heard the meandering yet deeply revealing conversations with people who would soon coup culture.”
Chillin Island was indeed an almost frighteningly accurate cultural barometer, serving as proof of human curation’s superiority to any algorithm. Who else could have guessed that, in the summer of 2014, iLoveMakonnen’s eccentric, stream-of-consciousness rap would dominate the charts and gain a Drake co-sign? Chillin Island.
Similarly, Safdie remembers going to see a then-unknown Lil Pump perform at the behest of Despot, who saw the rapper’s potential for success early — very early. “Alec knew there was something futuristic about Pump. Something strange,” he recalled. “Pump came on and performed 4 songs in the most deadpan nature I had ever seen. Repeating the same word over for a few minutes at a time. It was trippy.”
While this version of the show doesn’t include live performances or straight-ahead music, it does still feel musical. Evan Mast a.k.a “Evax” from Ratatat, scored the entire series. A welcomed treat if only for the comfort of knowing the guy who made the “Pursuit of Happiness” beat is still doing his thing. To top it off, the legendary narrator Steven Wright offers the kind of dulcet voice-over work that dreams are (literally) made of.
Chillin Island restores something unexpected and jagged that the prior generation used to go to networks like MTV for. Back when network television was still interested in surprising people. Ahead of their show’s premiere, the hosts spoke to Rolling Stone about a dizzying number of topics. They talked about their new TV show, too.
For the uninitiated, how did Chillin Island start?
Despot: Dap, you go.
Lakutis: Dap should go.
Dap: In 2009, we did a residency at East Village Radio through a guy named Peter Ferraro. They let us do a month. They were like, “All right. Well, what’s your show?” And we were like, “We want to do a show, like Stretch and Bobbito, but in 2009.” He was like, “Okay,” and that was the beginning of Chillin Island. Our four weeks went really well. We constantly had people calling in and it just became a thing, and then we did that until 2014. So between 2009 and 2014, we did the show on East Village Radio, and then I think they tried to do some sort of… What was it?
Despot: Well, they were losing the space, and then they were going to partner with a radio app or something like that. And then Aaron [Bondaroff] had the Know Wave idea and he needed help, and we did the show on Know Wave for a while.
Dap: Yeah. The way I think about it is it was like a torch-passing, basically. Because Alec has much better taste, and way more connections, and is cooler than me, and I was like, “Dude, why don’t you take over the show?” I never said that, but it was kind of understood. (In 2018, Bondaroff resigned from his L.A. art gallery amidst allegations of sexual misconduct.)
What was the biggest change between those eras of the show?
Despot: When it was Dap’s show, we would switch off playing music and booking guests. Then it gradually became me always playing the music and mostly booking all of the guests.
Dap: Yeah. Alec kind of made the show the A&R secret weapon to steal from. They basically stole all the playlists, and I guess went up to their superiors and were like, “You should check out X artists. You should check out Y artists.” It was like when people talk about how the Sex Pistols only had 30 people in the audience when they played the U.S. for the first time, but each of those 30 people started their own band. We were like that, but for rap.
Lakutis: That’s what I was thinking. Yeah.
So you guys have been friends and doing this show for a decade-plus?
Despot: Yeah, more than a decade, yeah.
How do you make it work for 10 years?
Despot: Like, relationship advice?
Dap: It’s a lot of acting exercises and a lot of like —
Lakutis: Team-building exercises, and we go to yoga together. We make sure to coordinate our meals.
Despot: We actually did do yoga together a few times, me and you in my house.
Lakutis: Yeah. That’s right. Yeah. We just do everything together, man. It’s really beautiful.
Dap: Indian people invented yoga. So I was like, “You guys, I’m good. You guys go ahead and have a blast.”
Despot: We see each other every day. We do a check-in in the morning. We call. We say, “How are you feeling?”
Lakutis: It’s like, you know the thing where you walk and then there’s only one footstep, and it’s because God was carrying you?
Dap: Yeah. G – O – D
Lakutis: It’s like that, but with two sets of footsteps and it’s the two other guys, but for each guy, it’s the other two guys.
Lakutis: You know what I mean, Jeff?
Dap: Alec and Lex take turns carrying me often because they’re strong men, beautiful men.
I feel like you guys had the radio format pretty dialed. There were people who would call in every week. I remember there was a guy who kept calling to talk about his cat’s asshole or something.
Dap: That guy, yeah. We had a lot of very derelict callers.
Despot: We had some regulars. Yeah, the cat’s asshole guy.
Dap: We had a fire firefighter.
Lakutis: Yeah, that guy.
Despot: He collected fireman gear, like vintage, antique. He worked in fireman gear or something like that.
Dap: Worked in fireman gear?
Dap: Because he was a firefighter.
So now, with the TV show, you guys are leaving the callers behind for something different. What was that like?
Lakutis: It wasn’t by choice, man. I tried to get them to let us have call-ins on the TV show.
Despot: Didn’t we talk about that originally? We were like, “we’ll start the TV show in like a tent doing the radio show remotely and people could still call.”
Dap: That was it. It was gonna be like a weird device where we wanted the radio show to be what sets up that episode’s adventure.
Despot: I think it would’ve been cool, but we didn’t do it. I think it was like a gradual change, though, because we talked about making a TV show for a while. We had all these ideas that were not the best ideas, and we tried them out, and we had the little YouTube thing that was pretty much made. That was us doing all sorts of sketches.
Dap: We had like three or four iterations of the show that were wildly different from each other before we kind of ended up with this. We had a sketch show. We had a —
Lakutis: Walking-around show.
Dap: Yeah. We had a walking-around show. We had a show that was basically like Howard Stern where we were filming us doing the radio show, and that would lead to little breaks where whatever we talked about on the radio show would lead to a little sketch-like thing. Each version was more sensuous than the last.
How did you guys land with the version that’s premiering on HBO?
Despot: I decided I wanted to make a fake version of Fishing With John, and I talked to two of my friends at Elara [Pictures] about it and I was like, “How could we make this TV show?” And they were like, “I don’t know, really.” And then we made a pilot.
What inspired you about Fishing With John?
Despot: My dad really liked that show, and he used to watch it when I was really young, and I thought it was weird and cool. I just thought the idea that a guy could just hang out with his friends on TV and be weird with them was cool.
Dap: Like fish out of water. When OD city people who have no business being out in nature come on the show.
In the Lil Tecca episode, he seemed pretty bummed about being in nature.
Dap: Yeah. He was not feeling it.
Despot: Oh, did you catch that?
Dap: Yeah. He wasn’t feeling it, and then he didn’t like being on the water.
Was he seasick? Did he throw up?
Lakutis: Nah, but he seemed close.
Despot: It’s hard to say. It’s possible he threw up because he left and, you know, we didn’t get to see that part. He probably did later.
Lakutis: He probably threw up in a paper bag or something.
Dap: He probably picked up a fish and threw up in the fish’s mouth, and then the fish threw up back in his mouth.
Lakutis: Yeah. I still have that fish’s body.
Despot: Like in Stand By Me at the pie-eating contest.
Lakutis: You think he did that?
Lakutis: I’m sure he did.
Dap: And then the fish threw up, and was like, “It’s a living.”
Was it hard to explain to the guests what you guys were trying to do?
Lakutis: I don’t think anyone really explained it to them.
Dap: We never explained shit.
Lakutis: That’s what it seemed like when they got there. Nobody told them, not even a couple of minutes before.
How do you guys deal with the awkwardness?
Despot: Just talk as much as we can; just don’t stop talking. Just keep going.
Lakutis: Yeah. Just drown them out, right?
Lakutis: Blast them.
Despot: Just don’t let them say anything-
Despot: … because then people who are watching the show can’t tell that they’re having a bad time because they’re just being quiet and looking around, so it must be fine.
Lakutis: And as long as you keep introducing new dangers, they have to deal with them before they can get too upset, you know?
Despot: They could be upset with the danger, but that’s not really our fault.
Dap: Right. If anything, they don’t have time to think, “oh, these guys are actually my problem.” Superficially, we’re the ones helping them.
Despot: We’re their only hope. That’s the idea.
Dap: It’s a big part of the show, hope.
So you trap them?
Lakutis: We like to trap and tantalize our guests.
Was there one episode in particular where you guys were surprised by how well it went?
Lakutis: Yeah. The Thug episode was sick.
Despot: Thug is just the man, and he was mad fun to hang out with, and he had a great time. He’s mad interested in nature, and animals, and stuff, so he was just very engaged.
Dap: He had a lot of facts up his sleeve. Left and right, he had facts up his sleeve.
Lakutis: He owes me $500.
Despot: He made Lex eat a bug and he told him he’d give him $500, but he never gave it to him.
Lakutis: That’s right. Just so you guys know, Young Thug owes me $500.
Despot: Yeah. Now you don’t have to write that whole book about it. You can just say it here.
Were you guys worried at all about bringing celebrities into a context where they might say something a little too loose?
Despot: Yes. I think that in the edit, we were pretty conscious of that, and tried to make sure nobody looks crazy because that’s not what we’re trying to do. I don’t want this to be a “gotcha” sort of thing.
Despot: So I wasn’t nervous about it because we have control over it in the end. I’m not trying to catch anybody saying anything crazy.
Musicians especially are often so sanitized in interviews. How do you get them out of their element and still avoid pushing them into saying something they might regret?
Lakutis: That’s our forté.
Dap: I mean, that part was kind of the biggest thing that was related to the radio show. Because we don’t do regular interviews or ask people what their influences are.
Lakutis: No. What producers are you dying to work with?
Dap: Right. Because I feel like when you do that, people just switch into their automatic press mode or whatever.
Lakutis: We don’t want them to get into their media training shit.
So what’s the secret to getting rappers out of their element?
Dap: Ignore them completely. The three of us will have a conversation, and it’s up to them whether they want to participate or not. They almost always do.
Lakutis: And then they decide they like us or they decide they hate us, and either way the pressure’s off.
Despot: Our interview style is to just yell at each other until the person we’re supposed to be talking to decides to interject.
Dap: Right, and in the last 10 years there have been mad times after the show or during a music break, where they’re like, “Yo, this is the best interview that I’ve done.”
Despot: Don’t gas yourself up, man.
Dap: No, I’m just saying. That’s how it often works out. At first, they’re like, “we don’t know what’s going on,” and then in the last 10 minutes of the show they’re like, “this is the best interview that I’ve done on this trip.”
What do you hope viewers take away from this television show?
Despot: I mean, I think the goal is for them to learn something about the guests that they’re not going to learn on No Jumper or in a DJ Vlad interview – not to shit on either of those outlets. It’s cool that you now know that Thug is really into cheetahs, and their small hearts, and you know what the first time Thug smoked a cigarette is like. I just think the idea with the radio show has always been to go beyond “when is your next album dropping?” “Who are you working with?” “How did you come up with your rap name?” I don’t care about any of that shit. Everyone’s heard those answers 6 million times. So it’s like, let’s hear something else.
Lakutis: Let’s hang out and fry a fish or throw an egg at a dog.
Despot: Yeah, I think the goal is to kind of humanize these people a little more, and you get to see them being people, instead of just talking about whatever.
Dap: Great answer.
Lakutis: Great answer; well phrased.
So, you guys are HBO stars now. Have you gotten to hang out with the Succession cast or anything like that?
Despot: I saw Kieran Culkin at Bowery Hotel. He was drinking with Michael Cera and I thought he was Macaulay Culkin. I was like, “What’s up, man? My friend was in Home Alone 2, and I hung out with you back then and shit,” and he was like, “Uhh.” I was mad drunk, and Michael Cera was looking at me like “damn, you got the wrong guy.” But he wasn’t saying anything, and I was just like, “alright, man, cool.” But that’s the only Succession cast member I’ve ever met.
Lakutis: I have the same answer, Jeff.
What’s a weird moment that happened during filming?
Lakutis: We got naked in a cave.
Dap: With each other.
Lakutis: Butt naked.
Despot: Yeah. I’ve never been with you guys fully naked before until we were naked in that cave, but now I have.
Lakutis: I’ve seen Dap’s dick a bunch of times.
Despot: Me too, but I’ve never seen his whole body naked.
Lakutis: Right, right. Me neither.
Has working on the show strengthened or hurt your friendship?
Despot: Hurt. Definitely hurt.
Despot: I don’t really like you guys anymore, and yeah, it is getting worse, steadily.
Lakutis: It can only get worse.
Thinking back to the Fishing With John comparison. That show famously gained a cult following after the fact. Is that how you see this going?
Despot: Yeah. That’s what we’re going for.
Dap: I want to make sure I die in poverty.
Despot: We want people to like this in 20 years.