Chillin Island Is a State of Mind

I can’t remember when I met the guys from Chillin Island. If you spent enough time lurking at New York City underground-rap shows in the late aughts and early 2010s, you eventually encountered the rap whisperers Ashok “Dapwell� Kondabolu, Alec “Despot� Reinstein, and Aleksey “Lakutis� Weintraub. Their longtime internet interview show graduated to HBO last month, and the premise is simple: The trio meet hip-hop movers and shakers in exotic locales that carry interviewers and interviewees far beyond their comfort zones. Out in the wild, all sorts of absurdities and profundities bubble up; this iteration of Chillin Island, which airs its first-season finale tonight, is a drug journal, nature documentary, and hip-hop interview series all at once. The scenic locations and all-terrain vehicles never distract from the trio’s core values: friendship and a love of rap.

I got Dap, Despot, and Lakutis on a video call to trace the zany trajectory of their show, but you don’t interview the hosts of Chillin Island. You quickly get absorbed into their world of elaborate New York City lore, outerwear, and deadpanned absurdism. Your conversation becomes the show. Really, Chillin Island is a state of mind.

I remember seeing one of you post a photo with Young Thug in the desert and thought you were just up to your usual adventures. How’d you get a show? 

Alec “Despot� Reinstein: You have to have incredible adventures. Eventually someone shows up, and they’re like, “I gotta film this.�

Aleksey “Lakutis� Weintraub: An old witch gives you a secret key.

Despot: Between the three of us, we had a bunch of different ideas about an internet show, like a YouTube show. We did a comedy version of it. There was a reality-TV version. At some point, I stepped to Sebo Bear-McClard and Josh Safdie at Elara, like, I wanna make Fishing With John but not Fishing With John.

Ashok “Dapwell� Kondabolu: Fishing With Dons, if you will. Peace.

I want to ask how you met the Safdies, but I feel like the story is just that you know half the city. You’re key points in a game of six degrees of separation in New York culture. 

Despot: I met Josh through my very good friend Sebo. I couldn’t tell you exactly when I met Josh or why or how. Fun fact, though: The Safdie brothers are originally from Forest Hills, where I’m from. They moved to Manhattan when they were very young. Lex is also from my neighborhood but moved to Manhattan.

I would’ve guessed that you were born and raised on the Upper West Side.

Despot: Lex is, technically, absolutely from the Upper West Side.

Lakutis: I don’t count as Queens. I moved when I was, like, 5.

Despot: We don’t claim him. At all.

Lakutis: Zabar’s, baby.

As someone who was once a guest on the Chillin Island radio show, I like that the HBO show feels like the same property even though it has a different setting and players. Was it important to make it feel like a natural extension of the original series?

Lakutis: That was the most important thing because the magic of it is our rapport. We thought it would be cool to hang out somewhere beautiful but still act the same.

Despot: Our interview style is us yelling at each other and talking over each other. Then, if the guest feels brave, they can try to jump in.

Lakutis: If they happen to have a certain secret key.

I couldn’t always tell whether you’d met the guests prior to filming. They seemed unprepared for the wilderness experience — except for Young Thug, unflappable in the cowboy outfit. He completely committed. He seemed relaxed in the wilderness.

Despot: He was having a great time. Even with the people I did meet prior to filming, I don’t think anyone was really expecting what it ended up being. I don’t know if there is any prepping for being on this show. It’s different for us every time too. I don’t know what’s gonna happen.

Dap: The guests cling closely to the hosts when they have no idea what is about to happen and what the show is about: I might as well talk to these gentlemen here because I have no idea what I came for. There’s nowhere to go, like a hostage situation. Basically, we capture famous people and hold them hostage in weird locations around the world.

Lakutis: Nobody tells them what they’re about to do.

The wilderness is disarming. When you get outside, really outside, you have to mean business. I want to ask how scripted the weirder parts of the show are, but I also don’t know if I want to know.

Lakutis: Everything is 100 percent real, Craig. This ain’t CGI Island.

I want to know the truth about the Grape Ape — I mean the Skunk Ape from the Lil Yachty episode.

Despot: You’re high on weed, aren’t you?

Never heard of it.

Lakutis: It’s legal now, baby! You could say you smoke weed all the time.

You don’t really spell out what locations you visited.

Despot: We never want to say specifically where we are because the idea is that Chillin Island is a place that exists in the minds and hearts and souls of us and our viewers and our guests.

I’ve been watching nature docs in the pandemic where a narrator explains everything happening, where it’s happening, and who it’s happening to. When I watch your show I’m going, Where are we? What animal is that? What is that rock formation called? But that’s not the point at all.

Lakutis: We went out of our way not to do that. That’s already every show.

Despot: Yeah. I don’t like that [suspenseful voice] “Here we are in — whatever — the Amazon …� Fuck that.

Your show touches on this wild dichotomy where most rappers love animals but not necessarily nature.

Despot: I mean, I would argue that I don’t like it, either. There’s definitely a fish-outta-water element to the show, and I think the fish-outta-water element applies to all of us because we’re three guys who grew up in New York and don’t have that much experience being in the wilderness. The common understanding of most rappers is they don’t really want to be sleeping in the dirt in a tent, either. There is that dichotomy: Yes, I would love to have a pet cheetah, but I’m not trying to hang out in the desert around cheetahs. Why would you wanna do that?

Lakutis: Nobody’s really trying to make rappers do stuff like that. They’re trying to make ’em comfortable or whatever. We take ’em out of that. Also I really wanted camping gear, so that was a huge element of wanting to do a nature show.

Despot: To get free things.

You never looked totally out of sorts because you were dressed well on every occasion.

Despot: I wore a lot of clothes I’ve had since I was in seventh or eighth grade. That’s how I always dressed. I have clothes that are designed for wilderness adventures.

In New York City in the ’90s, you had to dress like you were going on an expedition.

Despot: It was a store downtown called Tents & Trails that was very easy to steal from. It recently closed. They managed to stay open for a really long time despite getting robbed constantly by people like me in junior high school. That’s where half the wardrobe for the show came from. Special thanks to Tents & Trails, who are now closed because I stole everything.

Lakutis: Yeah, I remember folding my spiral notebook into my North Face backpack. After a while, I stopped pretending I was taking notes in class and just didn’t wear a backpack to school.

I never had North Face growing up, so one time a few years back I got a big check and balled out in the exact 72nd Street location where I couldn’t afford anything back in the day.

Despot: My first North Face purchase was just a black bubble. I got it at Jimmy Jazz on Main. I remember thinking, I got it at Jimmy Jazz; it might be fake. As soon as we came outta Jimmy Jazz with the jacket, mad people were scheming on us. I had to call my dad and be like, “You gotta come get us.�

Dap: When that Jimmy Jazz on Main Street closed, I went there. It was my sophomore or junior year. Barely anything left on the shelves. I turned around and Noreaga walked in, looked around, made a piss-smell face, and walked out. I turned to my boy Mike and he was like, “Yo, that was Nore!�

Despot: I haven’t met Nore many times despite living a few blocks away from him. One time I was standing outside of the candy store everyone always stood outside on 108th and 63rd. He was already a famous rapper by then. He rolled up in, like, six Escalades. They went in Candyland, bought all the dutches they had in the entire store, said hi to everybody, and got back in his car. It was sick.

Pulled up in the presidential cavalcade.

Despot: To buy dutches!

Lakutis: They tried to rob me for my North Face backpack. What was the one everybody had? The Hot Shot. They tried to rob me for my Hot Shot! That was the most expensive North Face thing I had. I couldn’t afford the bubble. I got beat up, but I didn’t give them that Hot Shot. Outside Bronx Science.

Fights outside school were always events.

Despot: I used to fight outside my school a lot. I had a heartbreaking moment where some kid told me to beat up Scott ’cause Scott played strip poker with his girlfriend. It had nothing to do with me, but I was like, Whatever. He was on the ground, and I was jumping on his head. My brother came by to hang out and just happened to walk up when I was jumping on this kid’s head. My brother looked horrified. I felt really bad. That’s the story. Scott’s alive and well.

Lakutis: His gait is a little iffy.

Dap: But he a good dude.

Lakutis: Really good heart.

Despot: I didn’t jump on that.

So, the geoduck from Chillin Island — how did it taste?

Despot: Honestly tastes like a clam. You know, clams don’t have that much of a taste. They taste a little bit like bad breath maybe.

Lakutis: I was not with that. I thought you were gonna get sick or something.

I learned about those on Bizarre Foods With Andrew Zimmern.

Dap: Yo! He did an interview after the show came out, and they asked why he ate all that nasty shit. He was like, “I used to be the ill crackhead in New York. I would rob you in the street. I’d do anything for crack. For me to eat these weird foods is not a big deal compared to when I was a crackhead in New York.�

There’s cooking wild animals and there’s eating things you’ve just pulled out of the ground …

Despot: You gotta rip the Band-Aid off. You gotta just go for it. I’ll eat anything. I don’t care.

Lakutis: He’ll eat the Band-Aid.

Something lightweight terrifying happens in every episode. What was the scariest thing during filming?

Despot: We flipped over a fuckin’ vehicle and Dap almost died because he didn’t have his seatbelt on.

Dap: I was, like, two inches from having my head severed by a pole.

Despot: I wonder if we’re not supposed to talk about stuff like that …

Lakutis: My mom watched it and she was really mad at all the dangerous stuff. I had to be like, “Nah, it’s TV, man. It’s fake. Don’t worry about it.�

Alec: My mom asked when we flipped that thing if it was real, and I was like, “Of course not!�

I questioned whether certain stuff was staged, but I knew that happened. I felt that.

Despot: It was my fault.

Lakutis: I don’t think it was your fault. You took on a lot of guilt behind that.

Despot: A guy told me to flip the switch to four-wheel drive. And apparently that was the wrong thing to do.

Lakutis: I feel like that was a psyop. We were set up.

Dap: It was our last go-round. We’d been in that thing for, like, two hours, and they were like, “Go on one last crazy run and make it look insane.�

Despot: The guy was like, “Flip the switch. That’ll make it easier.� I was like, “Okay.� Flipped the switch and then we died.

What about the guy who fell off the boat during your fishing trip?

Despot: He was a safety guy, like a medic. And he fucked up and fell off the boat. I thought he was gonna get chopped up by the motor. He lost his phone. His phone is in the bottom of the ocean, poor guy.

Lakutis: Nore’s calling it right now.

Props to Nore for staying in the conversation.

Despot: Nore’s a famous podcaster. It’s sick!

I like his interviews. A lot of people come into interviews very guarded, and you have to have negotiations about what they’re willing to talk about. Nore gets people to say stuff they had not intended to say. 

Despot: As a concept for a rap podcast to just be like, I’m gonna get mad drunk and ask questions, that’s it, that’s great. I love that.

You’ve been doing Chillin Island in one form or another for over a decade. How do you keep that going and keep growing it every year?

Lakutis: We’re really good friends and we fucking hate each other and we all want to die. And that part stays consistent throughout.

Despot, where is the album?

Despot: The album is at the bottom of the ocean next to the medic’s cell phone.

Watch Chillin Island for clues.

Despot: Maybe this entire show is a long scavenger hunt that leads you to my album in the end. Maybe the show is the album. It’s scored by Evan Mast, who makes all my beats. And it’s a love letter to hip-hop.

The show has a great score.

Despot: Evan is a genius. He’s having a renaissance now and producing for everybody. He’s doing a lot of Kanye stuff now.

Lakutis: Great guy, great job.

Dap: He’s reborn, if you will.

Despot: He produced the Kids See Ghosts song “Reborn.� That was Dap’s joke.

Something I like about Chillin on HBO is that I can’t always pin down exactly what kind of show it is. Sometimes it’s an interview thing, and sometimes it’s a nature show. Sometimes it’s a drug show, but it can be this absurdist humor thing, too. It can be all of that at the same time.

Despot: That’s what hanging out is like. You don’t hang out with an agenda. I don’t meet up with my friends and be like, “Now that we’re hanging out, let’s talk about the first rap song you ever heard.�

What was Ski Mask the Slump God playing on Nintendo Switch during the peyote ritual?

Despot: It was some street-basketball game. I kept looking over.

Lakutis: They have Street Hoop on Switch, and it’s fire.

One of my favorite moments, aside from basically anything Young Thug said, was Ski Mask saying, “Acid is like an electric guitar.�

Despot: He said mushrooms are like the bass and acid is the electric guitar. That was really good.

He seemed very comfortable in a wilderness scenario, him and Thug.

Despot: It’s possible, but I don’t know. He was having trouble with that hill.

I was impressed when Young Thug didn’t so much as blink when the torch came out.

Despot: He’s a very calm person. I think he’s very well adjusted.

Lakutis: I was trying to make a fire on this island we were stuck on between boat things, and one of the guests’ friends ran up and poured gasoline on it. Almost burned my face off. Was it Lil Tecca’s people?

Despot: That was when we were with Yachty.

Lil Tecca has that New York thing. We like flat ground, respectfully. I would entertain the boat but I would be trying to get out of there, too. 

Despot: I didn’t want to be on that fuckin’ boat. It was hot.

Lakutis: We were on that boat, bro, for like two days. No food on the boat. Prop food we had to eat.

Despot: I was brushing my teeth in a hotel after the first day of shooting on the boat and the whole room was shaking. I never experienced that. I ran out in the hallway in my underwear like an asshole because I thought there was a giant earthquake happening.

Lakutis: Yeah, that’s why.

Dap: And it was Earthquake from “Smoking That Shit� by KMD.

Despot: And I let him in, and we hung out in my room for a while.

What new local rap are you playing?

Despot: RXK Nephew.

Lakutis: Lot of RXK Nephew and Rx Papi in the car.

Despot: He’s the best rapper, right? That Papi and Gud album is sick. Those guys are the best.

This interview has been edited and condensed for clarity.