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Jacob Webster sits down with theGrio to discuss his rise over the last four years as an in-demand celebrity photographer.\u00a0<\/p>\n
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.<\/p>\n
And somewhere behind those viral celeb Halloween looks\u2014Doja Cat as Cynthia Doll<\/a>, Serena Page and Kordell as Ms. B Haven and Mr. Freeze<\/a>, Latto channeling Lil Kim<\/a>\u2014is Jacob Webster<\/a>, the 27-year-old photographer turning the holiday into an art form.<\/p>\n \u201cI love that,\u201d Webster says of Page and Kordell\u2019s viral 2025 Halloween looks as Ms. B Haven and Mr. Freeze from the campy 1997 film \u201cBatman and Robin.\u201d \u201cBecause they committed!\u201d<\/p>\n A Maryland native now based in Los Angeles, Webster has become one of pop culture\u2019s 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.<\/p>\n \u201cI do really appreciate that I\u2019m in a space of, like, really amplifying Black voices and Black stories,\u201d he said. \u201cSo the fact that people are looking forward to what I\u2019m doing is even an honor in itself, and I think it says a lot about our creativity and our stories.\u201d<\/p>\n Days after wrapping yet another triumphant season of bringing famous faces\u2019 spooky dreams to life, Webster sat down with TheGrio to discuss how he has become the go-to photographer for celebrities.<\/p>\n \u201cMy ancestors are part of why I do what I do,\u201d he explained. \u201cIn my creative journey and my photography, I feel like we all kind of hold a through line to people that came before us.\u201d<\/p>\n Webster\u2019s creative journey started when he was 14, shooting classmates after school in Silver Spring. Early on, he built buzz with reimagined photo shoots\u2014Toni Braxton album covers, Disney princesses, even a live-action \u201cRugrats\u201d series that went viral in 2018.<\/p>\n \u201cThat was my first time that my stuff blew up on Twitter,\u201d he recalled.<\/p>\n Although inspired by some of the greats, like David LaChapelle and Annie Leibovitz, he didn\u2019t want to build a career solely on recreating others\u2019 ideas.<\/p>\n He added, \u201cI wanted it to be like my own original idea.\u201d<\/p>\n 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.<\/p>\n \u201cI actually got a [tarot] reading done,\u201d he admitted with a laugh. \u201cThe guy was like, do not leave L.A. until after Halloween.\u201d<\/p>\n 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.<\/p>\n \u201cThe day I [first] did Halloween was when I did Doja Cat as Cynthia Doll,\u201d Webster recalled. \u201cIt was really full circle, because I did the \u2018Rugrats\u2019 \u2026 and I had the Cynthia doll Barbie in there.\u201d<\/p>\n 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.<\/p>\n \u201cShe\u2019ll be like, \u2018just do your thing, like, whatever you want to do. I\u2019ll do it,\u2019\u201d he said, adding, \u201cNow I\u2019m starting to see that the more creative input you have as an artist, the better it comes out \u2026 There\u2019s a certain synergy.\u201d<\/p>\n But Webster\u2019s approach isn\u2019t just artistic\u2014it\u2019s strategic.<\/p>\n \u201cI have a very strong strategy and strategic plan behind what I do,\u201d he explained. \u201cIf I\u2019m doing a shoot, I\u2019m doing BTS of the glam, BTS of the scenery, an interview, filming on different formats. So no matter what I do, something\u2019s got to stick.\u201d<\/p>\n That balance of creativity and calculation has made him one of the defining visual voices of his generation.<\/p>\n \u201cWhen people see me, I echo my message and my intentions,\u201d he said. \u201cI want to bring back strong imagery to pop culture. I work at the intersection of beauty, fashion, and culture \u2026 I inspire millennial creatives to find their voice through image and content creation.\u201d<\/p>\n Asked about dream clients, Webster doesn\u2019t hesitate: \u201cAlways Rihanna or Zendaya,\u201d he said, already imagining the shoot.<\/p>\n \u201cFor Rihanna, I\u2019d do \u2018The Jetsons\u2019 \u2026 and for Zendaya, \u2018Bewitched.\u2019 I can build a whole world around it.\u201d<\/p>\n Still, at the heart of it all is legacy.<\/p>\n He said his ultimate goal is, \u201cAlways to, like I said, honor those that came before us, and to amplify Black stories and voices.\u201d<\/p>\n More must-reads:<\/strong><\/p>\n<\/div>\n