Going Rogue – Details, episodes & analysis

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

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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.

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? This podcast 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 creative people behind the scenes that made all the famous moments possible at Vogue

This isn't just a podcast about fashion. It's a podcast 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?

Follow on Instagram and Threads at @goingrogue.podcast and @jilldemling
Follow on Bluesky
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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.

Jill welcomes legendary Vogue editor Phyllis Posnick for an intimate conversation about her extraordinary career that helped define fashion photography for decades. Karen Mulligan— agent and long-time studio manager for Annie Leibovitz—joins the discussion, offering insights into the collaborative process between editors and photographers. From her Long Island beginnings to becoming one of the most influential editors at Vogue, Posnick shares intimate stories about her collaborations with photography giants Irving Penn, Helmut Newton, Annie Leibovitz, and Steven Klein. Discover the behind-the-scenes magic of her most memorable shoots, the creative problem-solving that saved seemingly impossible situations, and her unique methodology for blending high fashion with compelling visual narratives. Posnick also reflects on the invaluable mentorship she received from Anna Wintour and Alexander Lieberman while offering aspiring creatives her hard-earned wisdom about patience, thorough preparation, and the collaborative spirit essential to creating iconic fashion imagery. This episode is an expert tutorial in visual storytelling from one of the industry's most respected visionaries.

Follow on Instagram and Threads at @goingrogue.podcast and @jilldemling
Follow on Bluesky
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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.

Renowned photographer Norman Jean Roy opens up about his unconventional journey to success, revealing how a winding path through architecture, and professional baking ultimately led him back to the camera. Norman shares his perspective on overcoming the fear of failure, drawing from decades of photographing celebrities and models for Vogue and other publications. He explores the emotional depth required for powerful portrait photography and discusses how revisiting his own work with maturity has deepened his understanding of the human condition.
Norman also shares how a life-changing accident reignited his passion and pulled him back to photography. His story demonstrates that sometimes stepping away from your craft is exactly what's needed to rediscover why you fell in love with it in the first place.

Follow on Instagram and Threads at @goingrogue.podcast and @jilldemling
Follow on Bluesky
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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.

Jill chats with renowned hairstylist Orlando Pita to discuss his remarkable journey from self-taught Cuban immigrant to influential hair designer whose work has graced iconic Vogue covers and earned a place in the Smithsonian Design Triennial. Orlando opens up about his creative process and how his unconventional training freed him to innovate in hair styling, starting with cutting his family's hair and eventually working on high-profile shoots with Madonna, Beyoncé, and Lady Gaga.
They explore his pioneering approach to hair as visual art and examine the dynamics of collaborating with photographers and editors while navigating the shift from working with models to celebrity clients. Orlando shares stories from memorable shoots, including Madonna's 'Evita' Vogue cover and a unique collaboration with Irving Penn, while emphasizing how enthusiasm, gratitude, and continuous learning have driven his success. Orlando ends with some practical advice for aspiring hairstylists.

Follow on Instagram and Threads at @goingrogue.podcast and @jilldemling
Follow on Bluesky
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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.

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
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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.

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
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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.

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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Jill sits down with celebrity stylist Leslie Fremar for a look at her remarkable career journey, from her early days as Anna Wintour's assistant to independent celebrity styling. Leslie takes us back to what it was really like being an assistant in fashion's golden era with the countless behind-the-scenes challenges that shaped her resilience. She opens up about her styling philosophy centered on timeless, quality pieces, and pays tribute to her most influential mentors, both Anna Wintour and Vogue editor Tonne Goodman, whose guidance helped shape her approach to fashion and career. Leslie shares stories from her transition to independent celebrity styling, including memorable moments working with Charlize Theron and styling for major red carpet events. She doesn't shy away from discussing the industry's tough realities, from grueling photo shoots to navigating customs with designer pieces, while offering hard-earned career wisdom for aspiring stylists about the value of apprenticeships and staying true to your authentic vision.

Follow on Instagram and Threads at @goingrogue.podcast and @jilldemling
Follow on Bluesky
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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.

Jill catches up with Andrew Bevan, her former assistant at Vogue who's proven that being different is the quality that would define his career. The kid from Colorado who won best dressed in high school with a style he describes as "Gene Kelly meets Winona Ryder" has always been ahead of the trend, confident in his aesthetic even when others couldn't understand it. From aspiring Broadway star to Teen Vogue Style Director, Andrew opens up about his unconventional path through the fashion world, sharing incredible behind-the-scenes stories including booking cowboys, matadors and monks, oh my! Andrew unpacks his shift from handling the wildest requests as a Vogue assistant to carving out his freelance career in 2017, where he's now working with icons like Grace Coddington and legendary brands like Chanel.

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.