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Jill Demling started her career assisting Kevin Huvane and Bryan Lourd at Creative Artists Agency in Los Angeles. At 24 years old, she moved across the country to work as one of Anna Wintour's two assistants. The job culminated in her being depicted in Lauren Weisberger's novel The Devil Wears Prada and being promoted to entertainment editor in 1999, which meant booking Vogue's covers for the next 18 years.

"There was nothing ever wrong with what we had to do, and I did worse at CAA. I put Kevin's coat on him," Demling told me in the latest episode of the Back Row podcast. Regarding the two Devil Wears Prada movies, she said, "She never yelled, and they got that right. She doesn't throw coats either. You might toss it onto something, not at someone. Everything's exaggerated."

When Demling started in the assistant role, Anna's kids Charlie and Bee were around 12 and 10 years old. Demling's tasks included reminding Charlie about his science papers, making sure Anna could get to all of Bee's basketball games, and organizing playdates. But she doesn't bristle at any of it. "This is a woman who is so passionate about what she does and is a passionate mother," she said. "She's trying to do it all and trying to be the best she can be and produce the best work she can, and she wants to surround herself with people who want to do the same."

Demling still works as a talent booker, for international editions of Vogue and other magazines. She just launched the second season of her podcast, Going Rogue, in which she interviews fashion world luminaries like Edward Enninful and Carine Roitfeld, and talks about her work. I had so much fun interviewing her on the podcast that I wanted to share a portion of our chat here in the newsletter. 

Ahead, Demling talks more about what assisting Anna in the late nineties was really like, how booking celebrities for magazine covers has changed, and, for Premium subscribers, how advertisers now effectively meddle with all of it. 

As a reminder, Premium subscribers get access to all Back Row podcast episodes along with the newsletter. Upgrade your subscription to access the bonus episode with Demling along with all paywalled podcasts.

And subscribe to the show in YouTube, Apple Podcasts, and Spotify for more interviews like this one.

You have a huge folder with you. That's a holdover from working for Anna?

Yes. You had to be prepared. There was no option not to be. One day she called me in and asked me to sit down. She goes, "So, who are we going to do for September?" I had my folder: "Well, this is coming out, and it's probably going to be nominated." "What about next September?" "Well, Nicole's doing a costume period piece." "The next September." "Well, they don't even know what films are being made." She goes, "Come back when you know."

After that, I knew every Broadway show, every major athlete. No one else came to meetings with anything but me, with my huge-ass folder.

What was a typical day like as her assistant?

Leslie Fremar, my junior then and now a big stylist, got in at 7 a.m. and got the fried egg sandwich on a toasted, buttered roll. I'd come in to a blinking answering machine with 20 messages, all from Anna. She had no computer, either. I'd type up her editor's letter and send it to her husband [David Shaffer]'s email so she'd have it at home, and she'd bring back a printed copy with edits instead of emailing me. 

This was pre-Starbucks. There was no Starbucks around there [at the old Condé Nast HQ at 350 Madison Avenue]. At 4 o’clock she always wanted her coffee milkshake, and we got that at Burger Heaven. It was so good, but it was like a thousand calories, made with coffee ice cream. When we moved to 4 Times Square, there was no Burger Heaven, and that’s when Starbucks came into the picture. She was a bit concerned that the Frappuccinos might not have the calories she needed. She needed that in the afternoon.

You said that Lauren Weisberger depicted you in her book, The Devil Wears Prada?

When Kate Betts went to Harper's Bazaar [replacing Liz Tilberis as editor-in-chief], she poached our entertainment editor. Anna came to me while I was answering her phone and said, "Do you want that job?" I said, "Sure." But I couldn't leave until there were two people in that office. So I'm booking covers, I'm still Anna's first assistant, and I'm interviewing people to replace me. I'd already convinced Leslie to take [my] job, so I had this spiel about working for Anna that I'm repeating to every candidate without stopping to breathe. Lauren was one of those people. She describes me as being anorexic, wearing leather pants and a half shirt. It was a Michael Kors sleeveless turtleneck sweater. She said it seemed like I was in a cult, with spinning pinwheel eyes, as I regurgitated this soliloquy about Anna Wintour, and that I didn't even really look at her. She's right, I didn't. Technically, Gisele plays me in the first movie.

It was demanding, working for Anna. Even her diary, they show it in the movie, but you don't even understand what that's like to be sitting down here and her standing with a ledge above you, pointing to a diary, "Mr. de la Renta here. I'll see Karl here." And it's upside down, and she's not saying the date or time. So it's memorizing, That's probably Wednesday, and that's probably 2:00. 

I was told you can't eat smelly food, so I had us on these protein shakes.

You wouldn't even get a salad from the famous Condé Nast cafeteria? 

Not if she was there. I'm answering phones the entire time. 

I still remember having a Sour Patch Kid in my mouth when she came around the corner early. I never did that again. 

Chewing gum is a known pet peeve of hers. You booked covers through the shift from models to celebrities. What did this look like, from your perspective at the time?

In 2001 I booked five celebrities. In 2002, 10. In 2003, 12 of 12. In 2004, 11 of 12. Julianne Moore was my January 2002 cover for The Shipping News, because Miramax told me it was going to be an Oscar film. Anna did not let it go for about 10 years. I'd say, "This film's probably going to be an Oscar film," and she'd go, "Oh, like The Shipping News, Jill?" 

Who was the ideal cover person for Anna at that time?

Nicole, Gwyneth. Renée Zellweger had a bunch. Nicole can wear the clothes. She appreciates fashion. 

Anna's favorite films are Moulin Rouge, The English Patient. Films that have fashion in them or are stylized, like Marie Antoinette. Or a musical, or something based on a famous novel.

Romantic comedies didn't get on the cover of Vogue for a while, and television didn't either. Jennifer Aniston only got a cover for The Good Girl. 

And you weren't doing as many pop stars. She did say in one interview that the Spice Girls was a cover she regretted.

Music was not Anna's thing. Beyoncé's first cover was 2009, and you know why she got it? I was at the movies on a Friday night and got a call that Katherine Heigl, who I'd booked for our "Shape" issue, was pulling out because her film moved. Two weeks before the shoot. I said, "If she pulls out, I'm never coming to her again for a cover, ever." It's Vogue, hello? They said no. I'm thinking, "Who else has a film? Beyoncé has Obsessed." That's the only reason.

It's crazy she got it for Obsessed and not "Single Ladies" or the album, I Am… Sasha Fierce, which came out in 2008.

It's kind of nuts, right? Maybe Anna was traumatized from the Spice Girls.

In 2015, Beyoncé did a Vogue cover without an interview, which was considered a big deal at the time.

She has photo approval.

When she did the cover for Obsessed too?

Not then. 

And Anna was okay with her approving the photos in 2015 and not doing an interview?

She's not okay with it, but listen, she's Beyoncé. Does she need Vogue, or does Vogue need her? I always ask, "Do you want me to say if she doesn't do an interview, she loses the cover?" Because I know she'll say, "Okay, bye." 

It's not a cover approval, so she doesn't get to choose the cover. Honestly, I never understood why talent can't see the pictures. Do we not want her to be happy with it? Do we want to deal with her trashing it?

I can't say [who this was], but someone's nipple was showing. They didn't want to ruin the dress with a bra and her team was promised it would be airbrushed. Once it's in print, it's there forever. If she had been able to see those images, she would've caught it.

Over time, celebrities got more say in their shoots. When did the advertisers become a bigger concern?

The biggest change, and it's so frustrating…