On a freezing November weekday, a few dozen teenagers are sitting cross-legged on the floor in New York City’s Webster Hall. Robin "Robbie" Skinner, aka Cavetown, walks in wearing jeans rolled up at the ankles with checkered Vans, and greets the room as if we’re all gathered at a club after school. (Actually, most of the attendees either came directly from class, or got to skip school entirely to make the late afternoon arrival time.)

We’re gathered here as newly-initiated members of the Cave Club, the name for what functions as Cavetown’s pre-concert VIP package -- a chance for some of the the English singer-songwriter’s more devoted fans to have one-on-one time. It’s a few hours before one of two sold-out shows at the venue, and Skinner is totally at ease.

The 21-year-old makes small talk with the group, recounting his own grade school days -- which weren’t really that long ago, either -- and admitting he hated Chemistry. A short while later, Skinner plays a few songs by fan request, and one asks for “Dear,” adding that it’s her favorite song. “Really? That’s so sweet,” he says, soft-spoken and sincere, before launching into the acoustic ballad. “I’ll try my best for you.”

Robin Skinner is about to blow up. He’s been spending the past year honing his skills as a touring act (selling out dates across multiple continents) and releasing singles ("Boys Will Be Bugs," which features some impressive kazoo-playing, has 39 million streams on Spotify), and he recently signed with a major label in order to launch his next round of ideas -- of which he has enough to power a small continent.

Skinner was born in Oxford and grew up in Cambridge, England (“I'm from two prestigious places -- I'm definitely a privileged white boy,” he acknowledges). Both of his parents are classical musicians and teachers, so there was always music playing. “There's videos of me dancing to Bach or whatever at the age of one, just bobbing my head out of time,” he says.

As a kid, his dad showed him how to play some basic guitar chords, which was way less boring than the formal lessons for piano, trumpet and violin he’d been subjected to. He eventually began teaching himself. “I liked the whole DIY feel of not following books, and figuring out things as I went along -- as I needed things, I would learn them myself,” he remembers. Soon, Twenty One Pilots' Tyler Joseph inspired him to pick up the ukulele, too.

Meanwhile, Skinner had a group of friends on Twitter in the music fandom scene (early favorites: Pierce the Veil, All Time Low, Sleeping With Sirens) that also followed YouTubers. Some of his pals had started channels and tried their hand at “quirky, vloggy videos,” a la Charlieissocoollike (Charlie McDonnell) and Vlogbrothers (John and Hank Green). “So I did a few of those,” he says, cheekily adding, “which are very much private now and not accessible to the public.”

He hit his stride, though, once he started posting covers of songs by Twenty One Pilots, Ed Sheeran and Justin Bieber. “My channel grew very slowly and gradually, which I think has translated through into my music,” he says. The result was that Skinner landed in a sweet spot where he wasn’t too famous as a video personality -- some YouTubers struggle not to be pigeonholed once they get serious about a music career -- and already had the sort of fierce following that every artist covets. “I never thought, ‘I want to be a YouTuber,’” he says. “I thought, ‘I want to be a musician, but I'll use YouTube as my way to get out there.’”

Skinner is a self-taught producer, learning out of necessity the same way he did guitar. He started on GarageBand as a tween, using preset sounds. He managed to upgrade when his dad gave him an important Christmas present (though not without a patented dad joke). “He did that classic thing where you put loads of boxes in each other to make it seem like a big present. And I kept opening it and eventually it was a brick and I was like, ‘Dad, why would you…’ And then taped to the brick was the receipt for [music production software] Logic.”

Today, Skinner is most self-critical about his producing, aware that if it sounds too professional or clean, he might lose some of the rawness he’s trying to convey. To that extent, he aims for more of a “homemade” vibe. “[That] adds something really unique and genuine to it,” he says. “It's endearing almost...it feels down-to-earth, [like,] ‘This is just a person who's just making this.’ It doesn't need to sound perfect to be a good song.”

No matter where Skinner is -- on stage, backstage, with the Cave Club, in an interview -- he makes whoever is in the room feel like his guest. He’s comfortable and practiced when performing or speaking about his music, and he never, ever shies away from feeling. After the last show of his fall North American tour, he says he “just kept hugging everyone [in the crew], going around in a circle and hugging again. Because I didn't want to say goodbye. I started crying in front of them, went upstairs, and just sobbed all over my boyfriend, and just snotted everywhere.”

He isn’t any different around his fans. Skinner has always talked to his audience on a deeply personal level, whether via vlog or at the meet and greet table. “It still feels pretty much the same. They're all so sweet and I've hardly got any hate, which is quite incredible and confusing to me,” he says. “You can't say anything mean to me. I'll cry.”

Skinner met his manager Zack Zarrillo in January 2018. Again, an emotional connection was vital. “He made me feel really protected and safe and he really cared about what I wanted to do,” Skinner says. “That’s when it truly felt like, ‘Oh, this is my job now.’” He played his first major concert in London in May 2018, and caught the ear of Sire Records president Rani Hancock. “I was talking to some of the parents [at the show], and they were telling stories about how they’d flown in from Stockholm and Prague and all these places -- because their children just would not leave them alone -- to see Robin live,” Hancock remembers. “It was just amazingly inspirational to see this beautiful community of kids coming together.” Instantly drawn to Skinner’s fantastical world, Hancock made landing Cavetown a priority.

In about a year, Skinner went from playing New York's 575-capacity Bowery Ballroom to selling out two nights at the 1,400-cap Webster Hall. With every show, he becomes more comfortable in his performing skin, with the help, as always, from his fans. Skinner gets very animated when this is mentioned about halfway through the interview. “The audience plays like 50% of the role in making it a fun time,” he says. “If there's people in the front just going crazy and screaming all the words, I'm like, ‘Hell yeah.’ And it feels like I'm a rock star and it just goes really well.” Whenever he can, Skinner tries to impart some advice, giving back to the audience who has taught him so much. “You are the most important person in your life,” he reminds the passionate Webster Hall crowd that first night, “So be kind to yourself.”

But his empathetic nature means that when something goes wrong in the crowd, he’s shaken up, too. At one show on the last tour, an audience member had a seizure -- something that hits close to home for Skinner, whose mother also suffers from the affliction. “I got a bit emotional, thinking about my mom and stuff after it happened,” he says. He watched as others helped the attendee exit safely, but felt uneasy having to continue the show. “People [yelled] out ‘you're doing great’ and ‘I'm so proud of you,’ just keeping me going.” In that way, his symbiotic relationship with his fans helped him get through the rest of the set.

At first, Skinner toured with his guitarist/keys player, using a loop pedal to create drum tracks, but he wanted more energy from his live show. The Ed Sheeran comparisons didn’t help: “I'm already ginger and have glasses and British,” he jokes.

More importantly, he’d been dreaming of having a full band since he began playing music. For the most recent tour, he brought a drummer on, and the whole mood changed. At Webster Hall, his boyfriend Avery moshed with fans in the pit (“he moderates and makes sure everyone's having a good time”), and the energy was palpable during hits like “Lemon Boy” -- which he says was inspired by the tomato breed of the same name -- and “Boys Will Be Bugs.” “Now when I watch videos from the crowd, it sounds like I want to sound, whereas before, I would watch videos and be like, ‘I'm bored.’”

As his live show has evolved, so too has Cave Club. Back when Skinner was playing smaller rooms, he’d wait afterward and talk to every individual. “It was really cool to have that human connection with these people that have made everything happen for me,” he says. He would meet hundreds of fans, hearing their stories, giving hugs and taking photos. But as the venues grew, it became harder for him and his crew to accommodate everyone who’d waited -- “I like to talk to people properly, rather than just take a photo and leave” -- and so the 30-odd-capacity Cave Club was born. “I want it to be very casual and feel very like we're just hanging out, really,” he explains.

At our session, Skinner chatted with the group as they sat cross-legged in the venue lobby, played a few songs acoustically by request, took Polaroid photos, and of course doled out plenty of hugs. By the end, the Cave Club fans had stars in their eyes; not because they’d met a celebrity they admire, but because they got to know Robbie, someone they might regard as a friend, a little better. “I still feel weird about having to charge more to meet me, because I still have that feeling in my head that I'm not a special person,” he admits, “but I guess to these people, I am special, which, like, thank you. That's cool.”

A few years back, Skinner was publicly reluctant to sign with a major label, afraid he’d have to sacrifice his creative freedom. But after a few years, he realized he’d reached the threshold of independent growth, and the conversations began. “I had built a really good ‘product’ to present to labels,” he says, tone devoid of arrogance. “I've built this audience by myself. I do everything by myself out of my room, still. We were in a very advantageous position where we had them in our hands, basically fighting for us. They really had to just convince us what they could do for us.”

Hancock concurs: “Our mission [is] to keep the roster small and boutique, and to allow every artist to get all of the attention that they deserve.” This was important to Skinner, who writes, produces, mixes, masters, and creates his own artwork, merch and video concepts. “Everything comes straight from him -- I assured him that he would maintain that level of creative control.”

In the end, it came down to the personal connection he felt with Hancock herself, a fellow vegtearian and cat lover, and Sire, a team of four. “It feels like a good mix between a major label and an independent label -- it was a good balance. We have the power of the major label if we want it, but also at the same time, it's like a small family,” Skinner says. They put pen to paper on his 20th birthday: Dec 15, 2018.

Skinner’s vision for Cavetown was formed long before the labels came knocking. In December 2017, Skinner released his signature hit "Lemon Boy," centered on a titular character who represents “the negative sides of myself,” he explains. “I'm a sad, anxious guy. And so it helps me to mentally be like, ‘These sad, anxious thoughts are just a friend who's coexisting with me, who I just have to comfort.’ Because I find it easier to comfort friends if they're feeling down rather than being self-critical.”

The soothing but nonetheless upbeat track, which also features an unexpected guitar solo, would have been right at home on the Juno soundtrack. “It’s actually pretty easy being nice to a bitter boy like him/ So, I got myself a citrus friend,” Skinner croons. Simply put, it’s a song about trying to get along with the sour parts of yourself, and the lemon character now appears in much of Cavetown’s merch and other imagery across the project.

A Cavetown song is deeply personal, and often written with an impressive perspective for someone so young. For Skinner, it was never a question of how to hide, but of how to share as much as possible. “I write songs about things that I find hard to talk about in person with people. It's my way of getting it out,” he says matter-of-factly. “It's not something to be ashamed of...everyone goes through it, and it's okay.” Depending on the song, “it” can be anything from anxiety to sadness or depression. "Sometimes I think I'm dead," he sings on "Home," "'Cause I can feel ghosts and ghouls wrapping my head."

Indeed, 2019 was a year of transitions for Skinner. He took Cavetown to new levels by signing with a label and strengthening his live band, but he grew beyond the music, too. He moved to London last spring to live with friends, and while he admits he misses the family’s cat Fig (“He's a bougie cat that my dad bought from Poland, so it doesn't leave the house”), he did recently adopt a kitty of his own named, incidentally, Juno. While on tour Stateside, he kept an eye out for where he might want to live next -- currently, he’s leaning towards the East coast, perhaps near his Philadelphia-based manager.

Where will Cavetown go in 2020? He'll tour Australia, New Zealand and the UK this winter, and come summer, he’ll play a few major festivals. His full-length debut album with Sire is due this spring, and it was written with his live show in mind. “I’m trying to do more songs where I’m not required to play an instrument,” he says, “because I really like being able to move around on stage -- that helps me increase energy in the crowd.”

Whatever he creates next will be for himself, but for everyone else -- his crew, friends, fans -- too. “I'm so lucky to have found such nice people who just care about me and care about my art,” he muses, “and just want to lift me up and show everyone what I can do.”