Photo:Brandon Kline

Brandon Kline
Caleb Simpson asks strangers, “How much do you pay for rent?” and follows it up with, “Can I get a tour of your apartment?”
Simpson has more than seven millionTikTokfollowers, two millionYouTubesubscribers and nearly two millionInstagramfollowers and also hosts the “Free Rides” and “Pizza Reviews” series, but his home tours have struck a chord with viewers — and even caught the attention of A-list celebrities.
In addition to stopping strangers on the sidewalk, he’s collaborated with stars such asScarlett Johansson,Barbara Corcoran,Jared Leto,Deacon PhillippeandDwight Howard— and even cuddled withDrew Barrymoreon camera.
Simpson spoke with PEOPLE about his viral home tour series and his future plans — and addressed the one question he gets asked: Are his chance encounters real?
PEOPLE: Was the home tour series a slow burn in gaining a following, or did it blow up all at once?
Caleb Simpson: This specific series was not a slow burn at all. It was the second I posted the video, it blew up, and everybody in New York City saw it. And then within two months, Barbara Corcoran’s DMing me like, “Come tour my home!” and then all of a sudden I’m with Scarlett Johansson, and then I’m with Jared Leto. I’m like, “What’s happening? Is this reality? Is this what it feels like?” It was about eight years of trying different things online and working with different people before it popped off.
PEOPLE: When you’re filming, is it one continuous take, or are you redoing clips?
CS: I show up and just start filming, and what I get is what I get. I don’t really do any retakes too much. It’s kind of just the camera’s rolling for an hour, and then I cut it up into a minute and a half.
PEOPLE: Are you shooting the series on your iPhone?
CS: When I first started the series, I had no money, so I was like, I’m just going to shoot everything on my cell phone, and it’s kind of just stuck with that. But if I’m making a long-form YouTube video, I’ll have one camera guy typically, and we’ll be mic’d up. But for the most part, I just show up with my cell phone, and people are like, “That’s it?”

PEOPLE: Are your seemingly chance encounters real? Are you stopping people on the street, and they agree to show their home right away?
CS: Everybody always asks me this question. Like, “Caleb, is it for real? You’re stopping people on the street? There’s no way." And I think that’s the beautiful part about the series. I do and I have stopped people on the street, and I’ll just see if I can go into their home that day. So to answer your question, with celebrities and stuff, for the most part, it’ll be like, I might run into them and ask them, and then we’ll do it on a later date. But I do run around and just ask people on the street and see.
For example, tomorrow, I don’t have much to do, so I’m like, “I’m going to run around and ask people.” I think it keeps the ethos of this series and the [feeling of], wow, I can’t believe people are actually doing that. But then sometimes, yeah, I’ll have it pre-set up. Definitely not everybody has the time right then and there to drop their entire life to be like, “Yeah, let’s go film this thing.”
I feel like I gave you a roundabout answer, but the answer is yes, it’s real . . . and sometimes it’s not.
PEOPLE: Now that you have this platform, do you have people reaching out to get featured?
CS: All the time.
PEOPLE: Do you take those requests?
CS: Sure. I mean, if someone’s presented me with something that’s sick, and I’m just like, “Wow, that’s cool. I want to go experience that.” I’m kind of looking at it through the lens of, is that an experience I want to have? Is that something I would like to see? Is that something I’m interested in? I think I’ll just have more fun, and that will shine through in the video a lot more.
PEOPLE: Why do you think this series is resonating with people?
CS: I think there are a couple of reasons. One: the rental housing market has just been crazy, fluctuating, really expensive top-of-market prices, especially in New York, so it’s just top of mind. And two: I realized it’s the one thing everybody in the world can relate to. We all live inside a box, and we’re all curious about how much money gets us, how much space — and then how we design this space, and how do other people live. Typically I hit on those three questions.
And then I think [people] just have curiosity [about] moving to another city. One girl stopped me and said ot me, “Oh my God, I was thinking about moving to New York, so I was watching a bunch of your videos to see what price gets you this and that.” And I was like, “Wow, you’re using my videos as a research tool. That’s insane. I just think about it as entertainment.”
It’s also very localized, so when I go [to a different city], everybody in the region watches it, and they’re like, “Oh, I know that building.” It’s pretty funny.
PEOPLE: You shot an episode with Drew Barrymore, where she touredyourapartment and you ended up cuddling. How did that go down?
CS: Really, we were both a fan of each other’s work, and we wanted to collaborate on something. She didn’t want to show off her home for privacy concerns, which makes complete sense, she’s a big star. So I said, “Hey, how about you come over and tour my home? I think that’d be fun.” And she’s like, “Oh, that’s a great idea.” She showed up with a huge entourage. I was like, “What is happening outside my apartment right now?” And we just started filming right away, and within two minutes we’re just cuddling on my cuddle cushion.
PEOPLE: How did you get from meeting her to snuggling so quickly?
CS: I’m not really even sure how it happened. I’m like, “Oh, there’s the cuddle cushion.” And then she got on it, and I was just like, “You want to cuddle?” She’s like, “Yeah.” We hadn’t even talked beforehand. I just met her. She walked in my door, and now I’m cuddling with Drew Barrymore. And then we’re just having a full blown conversation. We probably had a 15-minute conversation in that position.
And then the tour, I have a pole dancing pole, and I shot a money gun at her. Then we did a cold plunge together, and I was just like, this is a ridiculous thing that’s happening right now.
PEOPLE: How did the Scarlett Johansson interview come about?
CS: I ran into her in a hallway while going to visit my friend who lives on the floor above where her office is, and I was just like, “No way.” She’s standing right here. I explained to her everything off camera, so she wasn’t like, “Who the hell is this guy?” But that one was real.
PEOPLE: What’s been one of your favorite places to travel for the series?
PEOPLE: What lessons has this series taught you?
CS: I’ve stepped into a stranger’s home almost every day for a year and a half, and that is just so many lessons learned on how to talk to somebody, how to be respectful in somebody’s space, how to navigate a conversation and really just how to listen to someone’s story. For the most part, I’m just listening to how somebody lives their life and asking questions. I’m so grateful for those conversations.
I do think there’s this stranger danger that has been, well, it was taught to me as a kid for sure, and it’s taught to most American kids, and I think people are just cooler and kinder than you would believe. And I feel like I’ve proven that point, time and time again.
I try to structure the videos in a very non-judgmental way. I never judge someone’s apartment or the way they’re living, unless it’s an obvious joke with a comedian or something, which I’ve done before.
PEOPLE: What has the success of the series been like for you?
CS: I am super grateful that I popped off online, but it took almost 10 years. I recognize how things ebb and flow now, and I don’t think I would be in it for the long haul if it happened in my first year of creating stuff online. Emotionally, it’s such a rollercoaster.
I know a lot of people think you pop off overnight, and for some people that does happen, but I’ve asked every person that I’ve connected with online how it popped off for them, and only one of them told me their first video popped, and they just became famous. So I think that’s just an important factor to figuring out who you are and the type of content you want to make.
PEOPLE: Where do you hope to be 10 years from now?
CS: In a perfect world, I just keep building out this idea of Caleb’s world, which is interviewing and hosting. I’m really basing a lot of what I’m doing off of James Cordon’s approach toThe Late Late Show, where he had variety shows and he came in and was like, I want to change up late night and come up with all these new ideas for late night. So in my head, that’s what I’m doing on social. I’m just creating different series ideas that different people can participate in, and then ideally those worlds can jump into other places.
So just continuing to interview people and come up with fun show ideas that we can all play in. Whoever I’m interviewing, I want them to come in and have fun and have a good time, and leave like, “Wow, that was a great time. I want to come back and tell my friends about it.”
This interview has been edited and condensed for clarity.
source: people.com