Going Rogue

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. Are you ready to go rogue with me?

Publisher

Radio Free Rhinecliff

Category

arts

Language

en

Explicit

No

First episode

14 May 2025

Latest episode

12 Jun 2026

Latest episodes

1 of 51 episodes have a transcript.

1. 

   12 Jun 2026TRANSCRIPT

   Edward Enninful on Building EE72, Six Rihanna Covers, and Life After British Vogue

   Host Jill Demling interviews former British Vogue editor Edward Enninful about building his new media company EE72 and their latest Rihanna cover.

2. 

   1 May 2026

   "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 (https://www.instagram.com/goingrogue.podcast/) and @jilldemling (https://www.instagram.com/jilldemling/) Follow on Bluesky (https://bsky.app/profile/goingroguepodcast.bsky.social) Follow on TikTok (https://www.tiktok.com/@going.rogue.pod?) 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.

3. 

   24 Apr 2026

   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.

Inside a recent episode

Edward Enninful on Building EE72, Six Rihanna Covers, and Life After British Vogue

Published 12 Jun 2026 · Transcript excerpt

[…] In the airmail piece, you said, I think people have underestimated me my whole career. I was always like, OK, I'll prove you wrong. What surprised you most about finally betting entirely on yourself? And does it feel different proving people wrong now than it did earlier? in your career? Starting, I was a little black kid that was trying to be a fashion director. So everyone was like, well, just give him a couple of years. And then I was like the only black stylist around. So it's always like, well, you know, that can't possibly last. And people have always underestimated me. When I took over the idea of 18, everyone's watched this and I had to prove people wrong. […]

Who has been a guest on Going Rogue

Names identified in recent episode analyses. Showing up to five guests.

• Edward Enninful
• Andrew Bevan
• Grace Coddington
• Phyllis Posnick
• Norman Jean Roy

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

4.9 / 5

31 ratings

Podcast Authority Score: 50 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

67

Social presence

0

YouTube

0

Engagement

85

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Questions about Going Rogue