Jacob Webster sits down with theGrio to discuss his rise over the last four years as an in-demand celebrity photographer.
Each October, celebrities flood social media with elaborate costumes, recreations of pop-culture icons, and moments so dazzling that they turn Halloween into what feels like a virtual red-carpet event.
And somewhere behind those viral celeb Halloween looks—Doja Cat as Cynthia Doll, Serena Page and Kordell as Ms. B Haven and Mr. Freeze, Latto channeling Lil Kim—is Jacob Webster, the 27-year-old photographer turning the holiday into an art form.
“I love that,” Webster says of Page and Kordell’s viral 2025 Halloween looks as Ms. B Haven and Mr. Freeze from the campy 1997 film “Batman and Robin.” “Because they committed!”
A Maryland native now based in Los Angeles, Webster has become one of pop culture’s most in-demand celebrity photographers. Known for his glossy, hyper-stylized portraits and creative direction, he has worked with stars like Keke Palmer, Doja Cat, and Lori Harvey, helping to usher in a new era of Black visual storytelling.
“I do really appreciate that I’m in a space of, like, really amplifying Black voices and Black stories,” he said. “So the fact that people are looking forward to what I’m doing is even an honor in itself, and I think it says a lot about our creativity and our stories.”
Days after wrapping yet another triumphant season of bringing famous faces’ spooky dreams to life, Webster sat down with TheGrio to discuss how he has become the go-to photographer for celebrities.
“My ancestors are part of why I do what I do,” he explained. “In my creative journey and my photography, I feel like we all kind of hold a through line to people that came before us.”
Webster’s creative journey started when he was 14, shooting classmates after school in Silver Spring. Early on, he built buzz with reimagined photo shoots—Toni Braxton album covers, Disney princesses, even a live-action “Rugrats” series that went viral in 2018.
“That was my first time that my stuff blew up on Twitter,” he recalled.
Although inspired by some of the greats, like David LaChapelle and Annie Leibovitz, he didn’t want to build a career solely on recreating others’ ideas.
He added, “I wanted it to be like my own original idea.”
His breakout moment came in 2021 after college, when he left Maryland for Los Angeles the day after graduation with no clients and no plan beyond his faith and drive.
“I actually got a [tarot] reading done,” he admitted with a laugh. “The guy was like, do not leave L.A. until after Halloween.”
At the time, he was broke, homesick, and questioning whether to return home. But he stayed, and on Halloween that year, everything changed when none other than Doja Cat came calling.
“The day I [first] did Halloween was when I did Doja Cat as Cynthia Doll,” Webster recalled. “It was really full circle, because I did the ‘Rugrats’ … and I had the Cynthia doll Barbie in there.”
The photos went viral overnight, instantly putting the creative on the map. Since then, his name has become synonymous with celebrity imagery. Artists like Palmer now give him the reins on shoots.
“She’ll be like, ‘just do your thing, like, whatever you want to do. I’ll do it,’” he said, adding, “Now I’m starting to see that the more creative input you have as an artist, the better it comes out … There’s a certain synergy.”
But Webster’s approach isn’t just artistic—it’s strategic.
“I have a very strong strategy and strategic plan behind what I do,” he explained. “If I’m doing a shoot, I’m doing BTS of the glam, BTS of the scenery, an interview, filming on different formats. So no matter what I do, something’s got to stick.”
That balance of creativity and calculation has made him one of the defining visual voices of his generation.
“When people see me, I echo my message and my intentions,” he said. “I want to bring back strong imagery to pop culture. I work at the intersection of beauty, fashion, and culture … I inspire millennial creatives to find their voice through image and content creation.”
Asked about dream clients, Webster doesn’t hesitate: “Always Rihanna or Zendaya,” he said, already imagining the shoot.
“For Rihanna, I’d do ‘The Jetsons’ … and for Zendaya, ‘Bewitched.’ I can build a whole world around it.”
Still, at the heart of it all is legacy.
He said his ultimate goal is, “Always to, like I said, honor those that came before us, and to amplify Black stories and voices.”
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