Going Rogue Podcast By Radio Free Rhinecliff cover art

Going Rogue

Going Rogue

By: Radio Free Rhinecliff
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About this listen

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. Are you ready to go rogue with me?© 2025 Art Decorative Arts & Design
Episodes
  • The Versha Sharma Story Behind Teen Vogue's Evolution
    Jun 27 2025

    Jill sits down with Versha Sharma, Editor-in-Chief of Teen Vogue, for the story of her climb to EIC at one of America's most influential youth publications. Sharma has taken the baton and is continuing Teen Vogue's mission to be more than a glossy guide to prom dresses by expanding it into a powerful platform for political discourse, social justice advocacy, and inclusive storytelling.
    Drawing from her Louisiana upbringing as the daughter of Indian immigrants, Sharma opens up about dealing with feelings of otherness and isolation that ultimately fueled her passion for amplifying marginalized voices in the magazine. The conversation traces her path from political activism on Obama's 2008 campaign through her evolution into journalism, shaped by pivotal cultural moments during her college years.
    Sharma describes the strategic evolution she's guided at Teen Vogue, from embracing a digital-first model to prioritizing video content that resonates with Gen Z and millennial audiences. She describes the unique pressures of assuming leadership during the COVID-19 pandemic while navigating the social justice reckoning of 2020. The conversation highlights Teen Vogue's groundbreaking editorial choices under Sharma's guidance, from their powerful feature on Vivian Wilson, Elon Musk's transgender daughter, to their cover story on Representative Maxwell Frost, the first Gen Z member of Congress. These stories underscore the magazine's commitment to spotlighting young political voices and their role in driving societal transformation. Looking ahead, Sharma shares her vision for the magazine's evolution, from potential print revival to international growth.

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    43 mins
  • The Art of Fashion: Tonne Goodman's Vogue Legacy
    Jun 20 2025

    Jill talks with longtime Vogue colleague and renowned editor Tonne Goodman about her distinguished fashion career. Tonne shares her path from art school and early modeling to working with Calvin Klein before joining American Vogue, where she was mentored by the legendary Diana Vreeland. She recounts behind-the-scenes stories from high-profile celebrity shoots featuring stars like Angelina Jolie, Charlize Theron, and Britney Spears, and discusses her collaborations with top photographers including Mario Testino, Steven Meisel, Herb Ritts, and Annie Leibovitz. As they explore her career, Tonne emphasizes the collaborative spirit essential to successful fashion shoots and her diplomatic approach to managing complex productions. Drawing from her own experience as a former model, she reveals her fierce commitment to advocating for and protecting the talent she works with.

    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.

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    1 hr and 23 mins
  • The Woman Behind the Woman: Karen Mulligan's Story from Annie Leibovitz's Studio
    Jun 13 2025

    Jill sits down with her dear friend Karen Mulligan, the woman behind the legendary photographer Annie Leibovitz. Karen started as a production assistant at Annie's studio more than 25 years ago and worked her way up to become not only Annie's studio manager, but also her agent. Anyone who knows Karen knows she is Oz, making it all happen behind the curtain. It was on their first cover shoot together back in 2002 that Jill and Karen realized they had more in common than working long hours for two of the most influential women in the industry, and they have been best friends ever since.
    Karen reflects on her climb from entry-level production assistant to the wizard of Annie's studio, while she and Jill swap stories about the early days when a Rolodex was the closest thing to Google. She gives an insider's view of celebrity photo shoots, sharing raw stories of working with A-list talent like Angelina Jolie, Brad Pitt, Reese Witherspoon, and Joaquin Phoenix, revealing the mayhem that happens before those images reach magazine pages. From wrangling stubborn animals to coordinating shoots on active film sets while managing the inevitable crises of big budgets and bigger egos, Karen explains how problem-solving, adaptability, and finesse are essential. Listeners get rare insight into the controlled chaos that produces some of today's most recognizable imagery, told by the woman who has been orchestrating the magic from behind the scenes for decades.

    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.

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    1 hr and 27 mins
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