Billy Eilish is Running away from him. Doja Cat Stops her. Her security detail made the sidewalk serenade of “Paint the Town Red” possible. Charli XCX Let’s him sing a few bars of “I Got It,” then said, “I have to try,” and turned on her heel and strolled back to the car.

Harry Daniels stakes out celebrities like Dua Lipa, Katy Perry, Ellie Goulding, and Joe Biden and serenades them while filming their reactions on TikTok. Most of these exchanges are spontaneous, as if the celebrities are genuinely surprised to have a 20-year-old man sing a song to them (usually horrifyingly, often about themselves). When Daniels found Jacob Elordi, who was at the restaurant, said the Saltburn star stayed next to a bodyguard-like man across the room and watched, amused, as Daniels headed off to the dance floor singing “Murderer.” I was a little wary.

Daniels’ videos alternate between old-fashioned trolling (Daniels once gratefully sang to Lea Michele, “All I Can Do for the Illiterate Community”) and an expression of true love for the artist. In an age when celebrities tightly control their images, his improvisations manage to reveal whether there’s a sense of humor, a lick of personality, or something going on beneath the surface. To quote a popular genre of comments Daniels receives on TikTok: “How do I find these people?!?!?”

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

Daniels grew up on Long Island, the son of an accountant and a homemaker. “Harry first attended Stan University when he was about 11 years old, where he completed his PhD,” said Madeleine, who also serves as his cameraman and unofficial manager. He loves Demi Lovato, Billie Eilish, Fifth Harmony, and Haim, and learned how to follow his favorites in real life by interacting with their fans on social media.

Two years ago, Daniels used his superior education to compete for face time with superstars. “I went to everyone’s shows and meet-and-greets and engaged with them in a way that made me feel connected to them,” he said. However, he felt the interaction was too formulaic. “How many times do I say ‘I love you so much’ to someone?” Wanting to leave a lasting impression, he decided to entertain himself by being a damn, a troll.”

Daniels’ first recorded TikTok serenade was at Sabrina Carpenter’s album signing in 2022. In the video, Sabrina Carpenter sang her diss track “Skin” while sitting behind a table. He suppressed an obviously nervous laugh. As soon as Daniels finished speaking, Carpenter issued a very diplomatic “thank you.” At that moment, a fool was born.

Daniels quickly became “smarter” than he appeared in person. He was waiting outside the Broadway stage door. He serenaded Sarah Paulson. Sometimes he got lucky. One night while he was eating at a diner, he ran into Ethan Cutkosky, who played Carl in the American version of Shameless.

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

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

Ripa’s team invited Daniels to surprise their star during a press tour. Similarly, Daniels used backstage access to go to Coachella earlier this month and sing Taylor Swift’s “Antihero” to Jack Antonoff and Paris Hilton’s “Stars Are Blind” to the heiress herself. Daniels says many of his videos are “just for fun,” meaning he doesn’t get paid. Money comes in when sponsors pay him to take pictures with artists at events. (Daniels declined to reveal his maximum performance fee.)

Daniels said that while the artist’s team may know what’s going on, the artist “legitimately doesn’t know anything,” which makes it difficult for the created situation to remain authentic. He claims it’s helping. “But lately, people have started trying to teach me how to create their own content.” He says he’s been asked by artists to promote new music or promote the names of products. “I wanted my videos to be less commercial and more culturally relevant, so I had to put my foot down,” he said.

Although Daniels prefers to stay in the pop culture realm, he recently filmed a video with Biden after receiving an invitation to a star-studded Radio City Music Hall fundraiser in March. Daniels was able to get close to the barricade where Biden walked around shaking hands with attendees. So he learned to sing Lana Del Rey’s national anthem dedicated to the 81-year-old politician. “He was very present, but I think he was literally like, ‘What the heck?'” Daniels said.

Daniels also intended to sing for Kamala Harris if given the chance. What song? Of course, the wheels of the bus are “The Vice President’s Obvious Love” laugh out loud about buses, laugh out loud about buses. But don’t expect a Trump video. “I don’t think I’ll ever get this close to him,” Daniels said.

Not everyone appreciates Harry Daniels’ treatment. At a Biden fundraiser afterparty, Ms. Daniels unsuccessfully tried to sing to the incomparable Anna Wintour, the editor-in-chief of Vogue: I may be a troll, but I’m not stupid,” Daniels said. “So I introduced myself and said I was a fan of hers, and she was like, ‘Thank you, that’s so sweet.’ I started singing and she just walked away.”

Daniels also came under heavy attack after the match. Ask America Ferrera if she wanted a “gay son or creepy daughter” at the People’s Choice Awards. His critics accused him of being “uninteresting” and “not a real journalist.” He dismissed that, telling Rolling Stone, “My job is to create content that generates clicks and views.”

Daniels’ post has an ulterior motive. According to Rolling Stone, he’s also a singer himself, and he’s not bad at it. The magazine said his vocals had “an inherent melancholy similar to that of Troye Sivan.” “The only reason I really started doing all of this is because I wanted to pursue music. Basically, everyone I’ve ever talked to in this industry has told me that you need to get a following on social media. I said it consistently,” Daniels said. “So if people want a follow, I’ll give them a follow.”

Daniels doesn’t seem annoyed by the give-and-take. He respects the hustle and bustle. Still, there’s something dark about how his outsider side inevitably becomes part of the star machine. The more celebrities are tipped off about a potential interaction with Harry Daniels, the more the video feels like an SNL short, less gonzo fun and more fuel for PR campaigns and album release calendars.

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

Although he hasn’t released any tracks yet, he said 2024 will be the last year of his current idiocy. He’s not done yet. He knows that if he wants to stay relevant, he’ll have to create content forever, and that’s fine with him. He just sees it as an opportunity to “strike while the iron is hot.” He is currently in talks to expand the Homespun team to include not only his sister but also the pros.

As Daniels left the cafe, a young woman who appeared to be a fan standing near the exit quietly said, “I love you.” Daniels breathlessly responded with a sweet, “I love you too.” I’m sure it’s something he inherited from the celebrities he’s sung to.