Billie Eilish has run from him. Doja Cat stopped her security detail to allow for a sidewalk serenade of Paint the Town Red. Charli XCX let him sing a few bars from I Got It before telling him “You need to work on it,” turning on her heel, and strutting back to her car.

Harry Daniels stakes out celebrities such as Dua Lipa, Katy Perry, Ellie Goulding – and, uh, Joe Biden – and serenades them while filming their responses for TikTok. Most of these interactions appear spontaneous, as if the celebrities are genuinely surprised to be accosted by a 20-year-old man singing at them, usually terribly and oftentimes with their own songs. When Daniels found Jacob Elordi at a restaurant, the Saltburn star stayed across the room next to a bodyguard-type, looking amused but slightly wary as Daniels crooned Murder on the Dancefloor his way.

Daniels’ videos alternate between old-fashioned trolling (Daniels once thanked Lea Michele for “all you do for the community of people who can’t read”) and displays of genuine love for an artist. In an era when celebrities maintain strict control over their images, his improv manages to reveal whether there is a sense of humor, a lick of personality, or anything at all going on beneath the surface. To quote a popular genre of comments Daniels receives on TikTok, “HOW DOES FIND THESE PEOPLE?!?!?”

Daniels has long cultivated an online obsession with pop princesses. “I think there’s a big element of escapism to stan culture,” he told me when I met him and his sister Madeline Daniels at a Lower East Side cafe in New York last week. “I found solace in other people’s careers and work, because oftentimes I felt like I was insecure in my own life.”

Daniels grew up in Long Island, the son of an accountant and stay-at-home mom. “Harry was around 11 when he first enrolled in stan university, where he has a PhD,” said Madeline, who acts as his sometimes camerawoman and manager. He loved Demi Lovato, Billie Eilish, Fifth Harmony and Haim, and engaging with their fandoms on social media taught him how to follow his faves in real life.

Two years ago, Daniels started using his stanning education to wrangle face time with superstars. “I was going to everyone’s shows and meet-and-greets and engaging with them to feel like I had a sense of connection with them,” he said. But he found the interactions too formulaic. “How many times am I going to tell someone, ‘I love you so much?’ I wanted to make a lasting impression so I thought, fuck it, I’ll be a troll and be entertaining.”

Daniels filmed his first TikTok serenade at a Sabrina Carpenter album signing in 2022. In the video, he sings the nascent pop star’s diss track Skin while she sits behind a table, clearly holding in nervous laughter. As soon as Daniels finishes, Carpenter lets out a very diplomatic “thank you”. At that moment, a shtick was born.

Daniels soon became “more clever” than meet-and-greets. He waited outside a Broadway stage door to land Sarah Paulson. Sometimes he got lucky: while eating at a diner one night, he ran into Ethan Cutkosky, who played Carl on the US version of Shameless.

“I think people think I’m like, hiding in bushes, but I really just show up places I know they’ll be,” he said. (It helps that he lives just outside New York City.)

Eventually, Daniels reached a level of virality such that some artists’ teams started reaching out: The music industry’s overreliance on TikTok as a promotional tool means labels are more likely to back an artist who can generate buzz on the app. A smartly planned “surprise” run-in with Daniels, who has over 1 million followers, is catnip for artists looking to go viral or curate relatable online personas.

Lipa’s team invited Daniels to surprise their star during press tours. Likewise, Daniels went to Coachella earlier this month with backstage access that allowed him to sing Taylor Swift’s Anti-Hero to Jack Antonoff, and Paris Hilton’s Stars Are Blind to the heiress herself. Daniels says that a lot of his videos “are just for fun”, meaning he doesn’t get paid. The money comes in when a sponsor pays him to film with artists at an event. (Daniels declined to reveal the most he’d been paid for an appearance.)

According to Daniels, an artists’ team might know what’s going on, but the artist “legit has no idea”, which he claims helps the manufactured situation retain its authenticity. “But lately, people have been trying to tell me how to do my own content.” He’s had artists ask him to promote their new song or name-drop a product. “I’ve had to put my foot down, because I want my videos to be more culturally relevant than commercially blah, blah, blah,” he said.

Daniels prefers to stick in the pop culture realm, though he recently filmed a video with Biden after receiving an invitation to his star-studded Radio City Music Hall fundraiser in March. Daniels was able to get close to the barricade where Biden walked around shaking attendees’ hands so he could sing Lana del Rey’s National Anthem to the 81-year-old politician. “He was very present, but I think he was just like, literally what the fuck?” Daniels said.

Daniels would sing to Kamala Harris too, given the chance. What song? The Wheels on the Bus, of course, alluding to the vice-president’s apparent love for buses, loudly laughing, and loudly laughing about buses. But we shouldn’t expect a Trump video. “I don’t think I’ll ever get that close to him,” Daniels said.

Not everyone appreciates the Harry Daniels treatment. At the Biden fundraiser after-party, Daniels tried and failed to sing to the inimitable Vogue editor-in-chief Anna Wintour: “I knew going into it that Anna doesn’t do that. I may be a troll, but I’m not stupid,” Daniels said. “So I introduced myself, said that I’m a fan, and she was like, ‘Thank you, you’re so kind.’ She just walked away.”

Daniels also got some flak after asking America Ferrera if she’d prefer having “a gay son or a thot daughter” at the People’s Choice awards; his critics accused him of being “not funny” and “not a real journalist”. He shrugged it off, telling Rolling Stone, “My job is to create content that will generate clicks and views.”

Daniels has an ulterior motive for his posts. As he first told Rolling Stone, he’s a singer himself, and not a bad one at that. The magazine described his vocals as possessing a “similar innate melancholy as Troye Sivan’s”.

“The only reason I really started all of this was because I wanted to pursue music, and basically everyone I’ve ever spoke to in the business consistently told me I needed to have a following on social media,” Daniels said. “So if people want a following, I’ll give them a following.”

Daniels doesn’t seem annoyed by this give and take; he respects the hustle. Still, there’s something bleak about his outsider-y bit inevitably becoming part of the star machine. The more celebs get tipped off about a potential Harry Daniels interaction, the more the videos feel like SNL shorts – less gonzo fun, more fuel for PR campaigns and album release calendars.

Regardless, Daniels says “the music comes first”. He describes his work as hyperpop, the bubblegum-meets-chaos genre typified by Charli XCX and Kim Petras. “It’s larger than life, and reminds me what music should be: it’s supposed to soundtrack something bigger than you, and make you feel things you can’t put into words,” he said.

He hasn’t released any tracks yet, but says 2024 will be the last year for his current shtick. It’s not that he’s over it; he knows he’ll have to create content forever if he wants to stay relevant, and that’s fine with him. He just sees an opportunity to “strike when the iron is hot”. He’s currently in talks to expand his homespun team to include professionals who aren’t just his sister.

As Daniels left the cafe, one young woman and apparent fan standing near the exit quietly said, “I love you.” Daniels cooed back a breathy, saccharine, “I love you, too” – the sort of delivery I bet he picked up from the celebs he’s sung to.