The Terrence O’Connor Touch

Once upon a time, in a Williamsburg apartment with more roommates than square footage, Terrence O’Connor could feel his life starting to change. His boyfriend and closest collaborator, comedian Benito “Benny Drama” Skinner, had just uploaded an impression of Gossip Girl’s Serena van der Woodsen to Instagram. “Blake Lively liked the post and we were literally jumping up and down on our bed, almost crying, like, ‘We made it,’” he tells me over drinks at Nine Orchard. Now, almost a decade later, O’Connor’s work as a photographer, creative director, and digital strategist has led to fruitful collaborations with the likes of Charli XCX, Troye Sivan, Mark Ronson, and Omar Apollo. But Skinner will always be his favorite client. “We’ve worked together ever since then,” O’Connor, 31, says. “Our careers grew together.”

The couple first met at a party in 2016, when they were both new to the city and newly out of the closet. Their connection was instantaneous. “I really had a That’s So Raven moment where I was immediately like, ‘I’m going to marry him,’” says O’Connor, who had just taken a job in digital marketing amid the influencer gold rush. “He told me he wanted to be an actor. I was like, ‘I don’t know how I could help you become an actor, but maybe we could try to get you a following on Instagram?’”

Skinner had been posting Dubsmashes— a TikTok precursor — and other clips since college, but under O’Connor’s tutelage, his Instagram became a legitimate enterprise. “I’d race home from my job and help him film and edit. We’d run small paid campaigns on his videos or pay meme accounts to repost him,” says O’Connor, who also made the occasional cameo. “There was a tin can in our early apartment with all loose change in it. One day, I got back and there was a huge gash in the middle where Ben had stabbed it open — because he had zero dollars in his bank account — to buy Dunkin’ Donuts so that he could [stay up and] edit. I take it with me to every house we live in.”

“Creative director was one of those fake jobs that seemed so unattainable to me.”

Thinking back to those early days, O’Connor’s gap-toothed smile beams so beatifically it could serve as an anti-veneers campaign. But when I try to commend him for his Boyfriend of the Year-worthy acts of service, he swigs back a big, embarrassed gulp of chardonnay. This is just his thing.

“I have a strong sense for people’s potential. I’m able to see the best version of every person because I had to do that for myself when I came out of the closet,” he says. “I was extremely depressed, extremely suicidal, and I had to do a lot of therapy to get out of that and start to accept the things that I did like about myself.” He fiddles with the Ray-Bans nestled in his loose black curls. “So through that journey, what I have carried with me, from Ben to everyone I work with, is seeing what they could be.”

His belief in Skinner eventually led them to relocate to Los Angeles in 2020. O’Connor himself never had any Hollywood dreams; he grew up in the suburbs of Boston and studied art at Colby College in rural Maine. But as Skinner’s impersonations of celebrities like Kris Jenner and Shawn Mendes cemented him as one Instagram’s preeminent comedians, LA was the place to be to sell the TV show he had written as his starring vehicle. (Skinner’s show, which is now called Overcompensating, will premiere on Amazon Prime this May. O’Connor is consulting on the marketing.)

Once in LA, it didn’t take long for O’Connor’s talents to get scouted as well. “When Ben got proper Hollywood managers they were like, ‘Well, Terry, you’re a creative director.’ It was one of those fake jobs that seemed so unattainable to me,” O’Connor says. He started working with a few small artists at the music label of one of the manager’s wives, while also taking odd gigs, like helping local real estate companies with social media. Then he met Charli XCX.

“It was our first Hollywood party and no one would talk to us, so we were standing awkwardly at the bar. Then we turned around and Charli’s standing right there,” he recalls. “That was the first friend we made.” At the time of their meeting, a few critically acclaimed mixtapes had turned Charli into a tastemaking cult favorite. Once again, O’Connor saw the potential for more. During a later hang, he recalls, “I was telling her my opinion on what she should do on TikTok. I was probably crossing some sort of social barrier, but that’s when we started working together because she wanted to try to figure it out as well.”

Charli saw the potential for more from O’Connor, too. He became one of her closest collaborators, shooting the bloody cover of Crash (Charli’s self-described “major-label sell-out album”) as well as Brat single artwork. He also helped with the strategy for all her social platforms and played a key role in Instagram-flooding activations like the Brat wall.“One question I get asked a lot is if I’m the brains behind Brat. I hate it, because Charli’s the brains behind Brat. I helped execute the vision,” he says. “What I’m good at is working between the label and the artist to make both parties happy, which was Charli’s innovation. It’s somewhat strange to have a random kid come in to work with the marketing and digital team, but that’s what she did — and then a lot of her peers started hiring me, too.”

Some of these collaborations are public: He’s been working with HAIM since 2022, most recently to recreate iconic Nicole Kidman and Kate Moss photos for the band’s new single artwork. But others are top secret. “I’m working with my bucket list [artist] right now, but I can’t say,” he teases. “All of my favorite artists, I’ve met or presently work with.”

“I’m able to see the best version of every person because I had to do that for myself when I came out of the closet.”

Just how public-facing he should be is something O’Connor grapples with as well. Last summer, he started developing a following of his own for his weekly “culture digest” TikToks in which he opines on topics like Luigi Mangione’s perp walk and Trump’s federal government slashes. The videos regularly rack up hundreds of thousands of likes. Yet as we amble down Orchard Street, where he’s being photographed in his Nike windbreaker with an oversized Balenciaga bag decked out in key chains, he playfully frets about sitting for our interview: “You’re going to ruin my mystique!”

Feeling torn between mainstream attention and freedom on the margins is, after all, kind of Charli XCX’s whole deal. Another thing they have in common: a porous boundary between their professional and personal lives. In XCX World, friends become collaborators and collaborators become friends. It’s not unusual for a day at work to feel like you’ve landed in the middle of a Boiler Room set. “She’s the friend who has the sparkle in her eye like, ‘Let’s get another.’ She’s exactly who you’d want to spend a night with,” O’Connor says. “I’ve always been inspired by the people I work with. I just get to bask in it.”