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Going Rogue: Daily Summaries Delivered
by Radio Free Rhinecliff
Welcome to the ultimate insider's guide to the world of fashion, celebrity, and media—straight from the heart of Vogue. I’m Jill Demling and for nearly two decades I was the Entertainment Director of Vogue. I've booked over 200 American Vogue covers, 30 covers for British Vogue, and more than 50 covers worldwide. That's nearly 300 covers that shaped pop culture, defined fashion, and captured the zeitgeist. But those perfect images? They're just the tip of the iceberg. "Going Rogue" is your backstage pass to the moments that never made it to print. The stories from the photographers who captured magic, the stylists who created iconic looks, and the writers who know every secret. You'll hear about the celebrities, the shoots that almost didn't happen, and the untold drama behind fashion's most memorable moments. Remember "The Devil Wears Prada"? That fictional 11-month snapshot? I was there for the real story—I even hired the person the book was based on and appear on page 21 of the book. But this isn't about one story. It's about hundreds of stories, from someone who was on the inside. This podcast is not an exposé, it's a celebration of the brilliant people behind the scenes that made all the famous moments possible at Vogue. It isn't just a podcast about fashion. It's about creativity, ambition, art, and the human stories behind the images that helped define a generation. We'll reveal how the talents behind these shoots got their start, and they'll share masterclass-level advice for a new generation of stylists, photographers, and creatives looking to make their mark. We're going behind the scenes of a world most people only glimpse through glossy pages and red carpet moments.
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- 6 days ago1h 46m
From House of Z to Gap Inc.: Zac Posen Goes Rogue
When Zac Posen’s company closed in 2019, he spent weeks sitting by the fire. He grieved in a way he never had before and watched social media fill with what felt like public epitaphs for a life he wasn’t done living. He had lost his staff, his archive and the rights to his own name. For the first time since he was 22, he stayed in one place long enough to watch the seasons change. Jill's known Zac for more than 20 years, from borrowing dresses out of his atelier to helping get Christina Ricci out of a corset at the Met. In this conversation she asks him what all of it taught him. They talk about growing up in a SoHo loft with no bedroom walls and a painter father whose studio took up half the space, being held back a year with dyslexia, and dropping out of school at 19 because opportunity wouldn’t wait. Zac opens up about the people-pleasing that made him “too good a partner” to everyone but himself, and about going back to the mannequin in his father’s studio when he had nowhere else to work. That quiet stretch led to a phone call nobody saw coming and to his job today running creative across Gap Inc. He talks about what it feels like to lead at that scale, and why the kid who was born to make things is still learning every day. To see the images from this episode, follow @goingrogue.podcast on IG. Follow on Instagram and Threads at @goingrogue.podcast and @jilldemling Follow on Bluesky Follow on TikTok Send us your questions or comments by calling us at 518-21-ROGUE Going Rogue is produced by Jill Demling and Maddie Kelly, who also serves as our social media director. Matty Rosenberg is the executive producer Be sure to follow Going Rogue on your favorite podcast platform. Going Rogue is part of the Radio Free Rhinecliff media network.
- Jun 12, 202654 min
Edward Enninful on Building EE72, Six Rihanna Covers, and Life After British Vogue
Jill sits down with Edward Enninful, the former British Vogue editor-in-chief who left the top of the masthead to build his own house. One year into EE72, the media and entertainment company he founded with his sister Akua, Enninful closes out 72 Magazine's first year with Rihanna on the cover, their sixth collaboration across W, British Vogue, and now 72. He and Jill trace their shared history from American Vogue in 2006 through the 40-icon British Vogue finale, then go deep on the new cover: the queen concept, photographer Szilveszter Makó's hand-painted backdrops, and why every Rihanna shoot happens overnight. Along the way: the '90s versus now, social media and the death of the curator, his Tate exhibition, advice for young creatives, and what he calls "the big flat," the collapse of silos between fashion, art, film, and music. Plus rogue rapid fire and a Prince versus Beyoncé question with only one possible answer. Follow on Instagram and Threads at @goingrogue.podcast and @jilldemling Follow on Bluesky Follow on TikTok Send us your questions or comments by calling us at 518-21-ROGUE Going Rogue is produced by Jill Demling and Maddie Kelly, who also serves as our social media director. Matty Rosenberg is the executive producer Be sure to follow Going Rogue on your favorite podcast platform. Going Rogue is part of the Radio Free Rhinecliff media network.
- May 1, 20261h 22m
"Channel Your Best Andrea Sachs": Six Real Assistants of Vogue
With The Devil Wears Prada 2 hitting theaters this week, Jill pulls together moments from six former guests who actually lived the job, assisting Anna Wintour, André Leon Talley, Tonne Goodman, and Vogue's other most demanding desks. Leslie Fremar (yes, the real Emily), Brian Coats, Gabriella Karefa-Johnson, Edward Barsamian, Andrew Bevan, and Karla Martínez de Salas on the 18 trunks through customs, the faxes, the $10 lunch budgets, the run-throughs, and the sink-or-swim moments that built six remarkable careers. What Andrea Sachs couldn't handle in a day, these six did for years. Follow on Instagram and Threads at @goingrogue.podcast and @jilldemling Follow on Bluesky Follow on TikTok Send us your questions or comments by calling us at 518-21-ROGUE Going Rogue is produced by Jill Demling and Maddie Kelly, who also serves as our social media director. Matty Rosenberg is the executive producer Be sure to follow Going Rogue on your favorite podcast platform. Going Rogue is part of the Radio Free Rhinecliff media network.
- Apr 24, 20261h 18m
The Devil Wears Prada: A Book, Two Movies, and Jill Demling
In a role reversal, Ned Martel takes the mic to interview Jill about her two decades at Vogue, timed to the release of The Devil Wears Prada 2. As the assistant who hired Lauren Weisberger, and the woman who turns up on page 21 of the novel, Jill has a firsthand stake in a story the culture keeps retelling. She walks Ned through the day the galley arrived, Anna's pivot from private hurt to public ownership of the movie, and her own running defense of the leather pants. From there the conversation opens into an oral history of the job. Jill describes Vogue in 1998: no iPhones, twenty-five handwritten phone messages waiting every morning, a diary read upside-down across the desk, and a telepathy with Anna so refined that hearing her own name was sometimes the whole question. She lays out the Monday fashion, Tuesday features, Thursday scheduling choreography, and the creative friction between Grace Coddington, Camilla Nickerson, and Anna that produced stories no other magazine could match. Jill and Ned trade stories about the September 2006 Marie Antoinette cover at Versailles, the La La Land campaign and the notes Anna accidentally sent to Damien Chazelle, the cautionary tale of The Shipping News, the Lady Gaga anniversary issue, and the Chanel sunglasses Jill hunted across every Four Seasons gift shop in the country. She reflects on what she inherited from Anna: efficiency, anticipation, and the refusal to take no for an answer. The episode closes with Anna's own going-away speech for Jill, read aloud for the first time. Send us your questions or comments by calling us at 518-21-ROGUE Going Rogue is produced by Jill Demling and Maddie Kelly, who also serves as our social media director. Matty Rosenberg is the executive producer Be sure to follow Going Rogue on your favorite podcast platform. Going Rogue is part of the Radio Free Rhinecliff media network.
- Mar 13, 20261h 20m
(From the archive) Celebrity Whisperer: Jonathan Van Meter pulls back the curtain on his extraordinary career interviewing Hollywood's elite.
(From the archive) Jill chats with legendary journalist Jonathan Van Meter, whose byline has graced the pages of Vogue, Vanity Fair, and The New York Times. Jonathan pulls back the curtain on his extraordinary career interviewing Hollywood's elite—from emotional exchanges with Angelina Jolie to unforgettable moments with Jennifer Aniston and Lady Gaga. From his humble beginnings studying theater to becoming the founding editor of Vibe magazine, Jonathan shares the pivotal moments that shaped his journalistic journey. Discover his secrets for creating the perfect interview environment, the challenges in profiling celebrities, and the decisions that led to his most powerful work. This episode offers a masterclass in profile writing and a behind-the-scenes look at the vulnerable moments that never make it to print Follow on Instagram and Threads at @goingrogue.podcast and @jilldemling Follow on Bluesky Follow on TikTok Send us your questions or comments by calling us at 518-21-ROGUE Going Rogue is produced by Jill Demling and Maddie Kelly, who also serves as our social media director. Matty Rosenberg is the executive producer Be sure to follow Going Rogue on your favorite podcast platform. Going Rogue is part of the Radio Free Rhinecliff media network.
- Mar 6, 20261h 17m
Priyanka Chopra Jonas on Bollywood, Hollywood, and the Long Road to Quantico
In the Season one finale of Going Rogue, Jill Demling is joined by co-host Edward Barsamian to talk with Priyanka Chopra Jonas during her press tour for The Bluff, discussing her "pirate core" fashion choices, including wearing a customized film breastplate on the red carpet. Priyanka reflects on learning confidence through her parents' emphasis on agency, her military-family upbringing, and experiences of racism while living in the U.S. as a teen before returning to India. She recounts entering Miss India at her brother's urging, winning Miss World, and building a major Bollywood career before moving to Hollywood at 30 and feeling forced to start from zero, resisting "diversity check" roles and landing Quantico. The conversation covers her relationship with Vogue, becoming the first Indian woman on American Vogue's cover, the bittersweet nature of being "first," and her evolving style, brand partnerships, motherhood, and legacy. Follow on Instagram and Threads at @goingrogue.podcast and @jilldemling Follow on Bluesky Follow on TikTok Send us your questions or comments by calling us at 518-21-ROGUE Going Rogue is produced by Jill Demling and Maddie Kelly, who also serves as our social media director. Matty Rosenberg is the executive producer Be sure to follow Going Rogue on your favorite podcast platform. Going Rogue is part of the Radio Free Rhinecliff media network.
- Feb 27, 20261h 27m
From Met Gala to Vogue: Edward Barsamian's Celebrity Fashion World (rerelease)
Jill re-releases a chat with her friend and colleague Edward Barsamian to explore his fascinating decade-long journey through fashion media. Edward shares stories from his impressive career path, starting as a style director at Vogue where he closely followed airport looks and red carpet appearances of stars like Amal Clooney and Zoe Kravitz, then moving into the digital world of celebrity fashion coverage. The conversation covers Edward's early Vogue years, his time at Gilt Group and The New York Times Style Magazine, and his return to Vogue in a major digital position. Edward recounts his experiences at glamorous events like the Golden Globes and Met Gala, where he interviewed celebrities and helped drive the digital transformation of fashion reporting. He reflects on the changing landscape of fashion media while sharing behind-the-scenes moments with high-profile figures including Kim Kardashian, Rihanna, and Kendall Jenner. Later, as Edward moved to Victoria Beckham, he opens up about the unique challenges of bringing a brand's voice to life across digital channels. This episode delivers practical career insights, observations on fashion's evolution, and solid advice for newcomers to the field. Perfect for fashion lovers and anyone interested in breaking into the industry. Follow on Instagram and Threads at @goingrogue.podcast and @jilldemling Follow on Bluesky Follow on TikTok Send us your questions or comments by calling us at 518-21-ROGUE Going Rogue is produced by Jill Demling and Maddie Kelly, who also serves as our social media director. Matty Rosenberg is the executive producer Be sure to follow Going Rogue on your favorite podcast platform. Going Rogue is part of the Radio Free Rhinecliff media network.
- Feb 20, 20262h 4m
Trading Places as Edward Barsamian Takes the Mic to Get Jill Demling to Spill
In this special episode of Going Rogue, the tables are turned as Edward Barsamian steps in as host, putting Jill in the guest seat for an unscripted conversation. The two first met on a Vogue shoot with Blake Lively in 2009 and worked together for six years at the magazine. Less than a year into launching Going Rogue, Jill steps away from behind the microphone to share her own story, from her unconventional path into fashion to her nearly two decades shaping celebrity culture at American Vogue. Jill traces her journey from a math major at Colgate who wore Betsy Johnson catsuits to upstate New York bars, to a temp worker in LA who accidentally wandered into Rob Reiner's private bathroom, to landing a dream job as Anna Wintour's assistant without knowing who Anna Wintour was. She reveals the strategic thinking behind cover selection, the delicate dance of negotiating with publicists and studios, and how she helped transform British Vogue into a global competitor during her collaboration with Edward Enninful. Beyond the glamour and legendary shoots at places like Versailles, Jill opens up about what inspired her to create a podcast, why she ultimately left Vogue after 19 years, and what excites her about working with independent publications, including Edward Enninful's EE72 and Carine Roitfeld's CR Fashion Book. It's a rare chance to hear the woman behind the microphone tell her own story. Follow on Instagram and Threads at @goingrogue.podcast and @jilldemling Follow on Bluesky Follow on TikTok Send us your questions or comments by calling us at 518-21-ROGUE Be sure to follow Going Rogue on your favorite podcast platform.
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About Going Rogue
Welcome to the ultimate insider's guide to the world of fashion, celebrity, and media—straight from the heart of Vogue. I’m Jill Demling and for nearly two decades I was the Entertainment Director of Vogue. I've booked over 200 American Vogue covers, 30 covers for British Vogue, and more than 50 covers worldwide. That's nearly 300 covers that shaped pop culture, defined fashion, and captured the zeitgeist. But those perfect images? They're just the tip of the iceberg. "Going Rogue" is your backstage pass to the moments that never made it to print. The stories from the photographers who captured magic, the stylists who created iconic looks, and the writers who know every secret. You'll hear about the celebrities, the shoots that almost didn't happen, and the untold drama behind fashion's most memorable moments. Remember "The Devil Wears Prada"? That fictional 11-month snapshot? I was there for the real story—I even hired the person the book was based on and appear on page 21 of the book. But this isn't about one story. It's about hundreds of stories, from someone who was on the inside. This podcast is not an exposé, it's a celebration of the brilliant people behind the scenes that made all the famous moments possible at Vogue. It isn't just a podcast about fashion. It's about creativity, ambition, art, and the human stories behind the images that helped define a generation. We'll reveal how the talents behind these shoots got their start, and they'll share masterclass-level advice for a new generation of stylists, photographers, and creatives looking to make their mark. We're going behind the scenes of a world most people only glimpse through glossy pages and red carpet moments.
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