On her podcast “Going Rogue,” Jill Demling steps forward to honor the creativity, chaos, and connections that built a fashion legacy.
For over two decades, Jill Demling has cast the faces that defined a zeitgeist. She championed talents like Lady Gaga and Adele before the world caught on and helped orchestrate fashion’s most memorable editorial moments. Now, she’s revealing the stories that didn’t make it to print on “Going Rogue,” a weekly podcast that celebrates the photographers, editors, writers, and creatives who made those moments possible.
Demling’s career began at 23 when she landed a job as an assistant at Creative Artists Agency in Los Angeles. That’s where she learned how to handle pressure, or, in her words, “You either breathe, or you sweat a lot and have a panic attack.”
The lessons in interacting with Hollywood proved crucial when she moved to New York and joined American Vogue as Anna Wintour’s assistant in 1998. Within a year, Wintour promoted her to Entertainment Director—a leap that reflected her rare experience in both the fashion and celebrity worlds.
“You either breathe, or you sweat a lot and have a panic attack.”
Over the next 20 years, Demling booked over 200 American Vogue covers. She cast at least 11 covers a year and, in doing so, built a vast network of longtime collaborators, including fashion legend Grace Coddington and revered photographer Annie Leibovitz.
Wintour once said Demling had an “amazing sixth sense of what makes a Vogue story.” When Jennifer Hudson walked into a meeting for a planned inside feature in the “Power” issue (March 2007), Demling recalls telling Wintour, “We’ve got to try a cover—this is a star walking in.” At the time, Hudson was a rising star after being a finalist in American Idol. Hudson won a Golden Globe for “Dreamgirls” after landing the cover and before the issue came out. Breaking the thin, white mold most previous cover girls fit into, Hudson became a symbol of change and inclusivity in the fashion world.
“If I have the power to change someone’s career, let me do good with it,” says Demling.
Demling finds satisfaction in fighting for unexpected voices and watching them succeed. “If I have the power to change someone’s career, let me do good with it,” said Demling.
Demling’s American Vogue covers were cultural touchstones: Kirsten Dunst as Marie Antoinette, shot at Versaille (September 2006). Angelina Jolie flying her plane through a deserted airstrip (January 2007). Red-haired Rihanna in a skin-tight gown on the beach (April 2011).
Jill Demling photographed by Domen and Van de Velde.
In 2018, Demling’s time at American Vogue ended, but her influence in fashion media persisted. In 2019, she joined British Vogue under the new Editor in Chief who succeeded Alexander Schulman, her friend Edward Enninful. She cast historic cover stories like the September 2019 “Forces for Change” cover, highlighting 15 visionaries, including Greta Thunberg and Jane Fonda.
Her final project as British Vogue’s Entertainment Director was the March 2024 farewell issue for Enninful. The shoot gathered 40 former cover stars from his tenure, including Victoria Beckham, Serena Williams, Kate Moss, and Miley Cyrus. The biggest casting and highlight of her career, it took Demling three months to coordinate.
In 2019, Demling founded the Creative Casting Agency (CCA), which casts and consults for brands, social platforms, and digital media. She supports emerging talent and brings opportunities directly to them, giving her complete freedom to be “talent-first.”
Her work at CCA includes booking Doja Cat and Olivia Rodrigo for Vogue Singapore –their first Vogue covers. “That’s what I want to do. I want to be able to get younger talents on these magazines that I’ve always loved but haven’t been able to work with at the one magazine I was connected to,” she said.
Among many international magazines, Demling also casts for Vogue Hong Kong, Paper, CR Fashion Book, and Vogue Philippines, where she just booked a cover featuring Pom Klementieff skydiving–an idea she’d been pitching for months.
“I want to be able to get younger talents on these magazines that I’ve always loved but haven’t been able to work with at the one magazine I was connected to.”
Demling serves as Entertainment Director for Mission, where she recently cast Hari Nef, Towa Bird, and Grace Vandaarwal for covers. “No one else is creating art and, with it, changing people’s views or shining a light on those that need it most,” she said of Editor in Chief Karina Givargisoff.
In May 2025, she launched the “Going Rogue” podcast, a behind-the-scenes look at all the beautiful, creative chaos that goes into producing a magazine. So far, she’s featured hairstylist Orlando Pita, photographer Norman Jean Roy, writer Jonathan Van Meter, Leibovitz’s studio manager and agent Karen Mulligan, American Vogue editors Phyllis Posnick and Tonne Goodman, and Teen Vogue Editor in Chief Versha Sharma.
Those iconic covers are more than just visual touchstones; they are stories. Demling and her guests talk through Dunst’s over-dyed hair falling out during the Mary Antoinette cover, what it was like to fly with pilot Jolie, a wardrobe disaster at Rihanna’s shoot, and so much more.
Demling created the podcast to share these stories and reconnect with collaborators, herself, and the moments she was too busy to appreciate at the time. “You can never appreciate what you just did,” she said, because there’s always another month ahead to plan. She needed time “to have grown out of the things I was mad about or sad about and appreciate how lucky I am to have ever been part of that,” she said.
With “Going Rogue,” Demling finally gives those off-the-record moments the attention they always deserved. She proves that sometimes, the most impactful voices are behind the gloss.
Top image: Jill Demling with stylist Grace Coddington photo taken by Karen Mulligan. All imagery courtesy of Jill Demling.
