‘Chillin Island’ Is A Vacation For Your Mind

No more than five minutes into a conversation with Alec Reinstein, Aleksey Weintraub, and Ashok “Dap” Kondabolu, they’re animatedly discussing the memory spans of different animals, recounting a news story about an elephant attack, and quoting lines from Mrs. Doubtfire in a goofy lilt (“It was a run-by fruiting!”) To talk with the three New York natives even briefly is to step into their freewheeling world: a place — or rather a state of mind — known as Chillin Island.

Such is the basis (and the name) of the group’s off-kilter docu-comedy series, which premiered on HBO earlier this month. Roughly a decade before its arrival at the network, Chillin Island originated as an independent radio program conceived by Kondabolu and his cohorts. The three hosts, all active members of New York’s indie rap scene, particularly at the height of the blog era — those who recognize Kondabolu from defunct alt-rap trio Das Racist also likely know Reinstein as Despot and Weintraub as Lakutis, both of whom are rappers in their own right — used the show as a platform to highlight other underground artists, curating music and conducting interviews with their now-signature non-sequiturial banter and affable languor. As the show evolved across stints at various New York radio networks over the years, and after a failed attempt at a pilot for VICE, Chillin Island was ultimately adopted by Elara, the production banner of the Safdie Brothers and Sebastian Bear-McClard, who helped successfully translate the show and its unique disposition to television.

The series retains the irreverence and loose structure of the radio show, but incorporates some enticing new elements afforded by a bigger budget and televisual format: snakes, swamps, all-terrain vehicles, and prominent rappers such as Young Thug, Gunna, and Lil Yachty, just to name a few. Each episode clocks in at under 30 minutes and follows Alec, Lex, Dap and their guest on a roving expedition into nature, where rather than discuss album cycles or industry gossip — which, against the backdrop of a sprawling desert at dusk, would feel not just contrived, but frankly absurd — the group indulges the casual and frequently existential conversations that emerge as they build a fire or handle exotic animals. Topics range from the zoological, as when Young Thug reveals his knowledge about cheetahs and horses in the inaugural episode, to the theological, as when teenage rapper Lil’ Tecca discusses his fear of God during a fishing trip.

Eccentric, awkward, surprisingly intimate, and sometimes surreal, Chillin Island is an inviting departure from the traditional media landscape for host, guest, and audience alike; a journey into the unexpected that, in its informality, feels thrillingly human. Fame is a mantle that innately shapes how entertainers interact with other people (and vice versa), especially in front of a camera, but Chillin Island seeks to relate through the nature within and around them.

Chillin Island is now streaming on HBO Max.

How did you guys all initially meet?

Dap: [Lex and I] met when we were 15, I think in 2001.

Lex: Then we met Alec later through rap music.

Alec: That's accurate.

Dap: The very first time I met Lex... I think it might have been the second time.

Lex: It was the second time.

Dap: We drank a bunch of cough syrup for the DXM. Then, outside of the Express that used to exist on 83rd and Broadway, we found a bunch of mannequins.

Lex: Banana Republic.

Dap: We dragged these mannequins to Riverside Park and we had an aluminum baseball bat or a pole or something. We would take turns beating the mannequins and then hanging out on a bench and talking to each other.

How did that lead to creating the radio show?

Lex: Same exact thing, pretty much.

Alec: Instead of mannequins, it was people. Then we were like, "You know what? We should just start a radio show."

Dap: "We should verbally beat rappers into submission."

Alec: Yeah, with using our tongues as the metal poles, as it were.

Dap: And our brains as cough syrup.

Lex: It's pretty much the same thing, but now there's people with cameras.

When did the idea emerge to take it from radio to TV? Take me through how that developed.

Alec: Dap started to slowly push it into a TV or visual thing by making these little video collage type things that were part of the Chillin Island world. Then he had this idea to do this sketch show that we would all do together that would be called Chillin Island. We started talking to VICE about doing this reality TV type show, and we shot a pilot, and it was bad. Then that led to me approaching Elara with this totally different idea.

Dap: I think the spiritual center of the radio and the TV parts of Chillin Island were passed from me to Alec as I continued to spearhead failed iterations of both of those things. Now we're on HBO.

Alec: I applied my entrepreneurship to it and then I gave it that final push.

As the show has evolved across time and mediums, what’s changed, and what has stayed the same?

Alec: I think we're slowly learning how to still do the freewheeling type of thing we've been doing, but under these [different] confines that are sort of necessary. There's cameras pointed at you, there's a whole crew of people working, there's multiple takes. It's not exactly what we're used to. I don't think we quite got it yet. What has stayed the same is we're definitely still just doing whatever.

Dap: I think we're getting used to it going from a sub-cult radio show to a multimillion dollar HBO production. I think people can fill in the blanks about what might be different between those two things.

What role have Sebastian Bear-McClard and Josh Safdie played in shaping the show?

Alec: Sebo has been instrumental in putting it in front of the right people. I can't really sell the show the way Sebo can. He has done a great job selling it up the ladder. Both of them have had extensive creative input, but I would say Josh is maybe solely on the creative side. He's been pretty involved in what edits come out like and post [production] stuff, shaping what it ends up being like. He's on all the emails every day, tailoring the trailers and the Coming Soon spots.

Dap: He's the trailer tailor, if you will. Josh is the archetype of the delicate genius who only deals with the content itself. And Sebo is involved in the nitty gritty production angles, as well as being a delicate genius.

Alec: Sebo is a wheeler and dealer, plus a delicate genius.

I’m curious about the production process. What kind of writing or preparation happens before shooting? It seems very informal, of course, but that can sometimes be the product of very thoughtful planning.

Lex: That would be crazy if it was.

Dap: [Sarcastically] Preparation and rehearsal are the absolute cornerstone of the show, whether it's radio or television.

How are you being directed while shooting?

Alec: There are directors, and we kind of take or leave what they tell us to do. But we do listen. And there's some very light writing, but the writing is basically like, “We want you to do these things, and in the process of doing these things, whatever happens is what's going to happen.” There's never like, “You should ask this question,” or “You should say this.” There's no script.

Is there any technical training you had to go through? Alec, you’re driving some crazy vehicles. Lex is handling exotic animals.

Lex: I mean I think we all decided we're going to die filming the show.

Alec: That's kind of the goal.

Dap: We got close a few times this season, but obviously it didn't work out the way we wanted it to.

What’s the closest you’ve come?

Alec: I mean the dune buggy crash [in Episode One]...

Dap: Very close.

Alec: Dap really almost died.

Lex: Did that look real?

It does look real.

Dap: It was.

Alec: To answer your question about whether or not there's any training, obviously, no. That's why I flipped the thing over. I had no idea how to drive that thing.

Lex: It's a good thing you didn't flip that [swamp buggy in Episode Two]. That would've...

Alec: That thing also was broken, remember? Every time I pushed the gas, it stuck, and I had to kick the gas pedal out. We could have easily died on that thing.

Dap: Or killed someone else.

Lex: You did a pretty good job considering you didn’t know how to drive the thing.

Alec: Thanks.

What are the conversations like in terms of coming up with locations and activities for each guest?

Alec: We didn't have that much money. This is our first season, so a lot of that was relying on who's closest to where; what's the easiest place for this particular guest to get to? I think we were a little more ambitious in the beginning, then as we ran out of money and got deeper into it, it was just like, "Let's shoot somewhere close to where the person lives." That's pretty much what we did, because we're not flying people around. Because we can't. [Laughs]

What attracts you to nature? What do you find rewarding or interesting about bringing rappers, including yourselves, into those environments?

Lex: I feel like a lot of stuff that [the media has] musicians and especially rappers do is usually pretty prescribed and pretty boring. No one's really taking them out of their comfort zone like that. We're all city kids, so nature is a fish out of water thing for us [too]. When Yachty came out, he was like, "I've done more here with you guys than I’ve done in my whole life." I don't know how hyperbolic he was. But we're having them do something that they wouldn't normally do, and we're doing a lot of stuff we wouldn't normally do, and you get a different perspective than, like, a million interviews in front of a mic in a radio… Radio room? What's that sh*t called? Recording studio.

Dap: Radio room!

Lex: Classic radio room sh*t.

Dap: I feel like it's an extension of the ethos of the show, which is like, we're going to continue having the conversation that we’d have even if you weren't in the room, and you can feel free to join in — it'd probably be best for you if you eventually did. Then we took it to an extreme where they have no alternative, because they can't go outside or leave or call an Uber or anything like that.

Lex: They can't call for help.

Dap: We kidnap guests and bring them into the middle of places with no cell phone service.

Alec: [With] the radio show, despite having the option to leave and it being in a radio room, I think that we still did a pretty good job of making these people feel obligated to participate in this thing we were doing, and [also] distinguishing ourselves from other radio shows in that we're not asking the typical questions. We're not even necessarily asking any questions. We're just talking. There's been a lot of instances when we did the radio show where a rapper who we didn't know beforehand is just sitting there looking at us, and we're talking, and they're just like, "Alright. I guess I'm just here." And eventually, they'll be like, "I like that cartoon too," or whatever. Then it's like, "Alright, well now you're here." They always respond well to that. Afterwards, they always end up saying, "That was very weird and different. That wasn't like a normal interview."

Dap: The classic first talk break of Chillin Island is a lot of staring and one word answers. By the end, it's just mad laughing and saying stupid sh*t.

Alec: I think we come off as these goofy whatever dudes, so it's not this stuffy, “Hey, I'm going to ask you some questions” thing. I think initially, that catches people off guard. But then it's like, “Oh, we're just a bunch of people in a room.”

Lex: Just a bunch of dudes hanging out.

Dap: Yeah. Inclusive men.

How do each of you view the mission of Chillin Island? Whether in terms of your own relationship to the show, for the guests, or for the audience — what do you aim to accomplish?

Alec: For me, the goal of the radio show has always been to have a stage for these new musical discoveries, because I like to discover new music. I think that part of it went really well. I think people started to notice that it was a go-to show to hear something new that you wouldn't have found on your own. I like that, and I want the TV show to eventually be that, too. But right now, that's not really what we're doing. For the TV show, [the goal is] just to humanize these larger-than-life personalities and be like, “Here's Young Thug sitting on a sand dune, talking about how he'd rather be a gorilla than a bird.” That's what I want to hear from these people. Not like, “Have you been to jail before?” or whatever. I don't care about that.

Dap: For me, it's a shared journey of improvised, idiotic, self-discovery, an excuse to hang out with my friends, and a way to avoid getting a real job. Those three things.

Lex: I get really frustrated with the way the media interacts with celebrities the same way all the time. It's just always very prescribed. It's so much more interesting when you're with people whose art you like or who makes sh*t you think is cool and just hang out with them.

Dap: It's a cure for loneliness.

Lex: Yeah. A lot of it is, whether consciously or not, born of a frustration with how boring those media interactions are and how much of it we are exposed to.

Alec: Maybe you do a lot of those boring interviews, and that's not what we're talking about.

This interview has been edited and condensed for clarity.