What makes a magazine cover iconic? As you can tell by the number of names on the header inside the glossy pages, each shoot is the lasting legacy of a visionary team of writers. But, one woman in particular has two decades of celebrity covers to thank for that have stood the test of time. Jill Demling began her career as Anna Wintour’s assistant at Vogue in 1998, only to find herself named entertainment editor in record time. Rising through the ranks to become Director of Entertainment, she hand-picked talent from around the world and gave them the much-deserved media spotlight, resulting in some memorable covers that defined things. Now as British Vogue’s Entertainment Director (yes, we’ll get to THAT Adele cover in a moment), as well as booking talent for Vogue editions around the world and juggling her own projects, we Had a million and one questions for her. Here’s how it all started….
Did you scrapp a lot when you were a kid? Where do you think your love for print media comes from?
It’s funny you ask, because growing up I used to cut pictures out of magazines and stick them all over my walls. Instead of Tiger Beat covers of Kirk Cameron, or any of the Coreys, I had runway images of Christy and Linda. I’m a big photo album person; I have two albums that Anna Wintour gave me when I was [my daughter] Story, which have his name engraved on the back. I’ve been ordering prints and sticking them in these books, with little messages, since she was born almost six years ago. I have similar photo albums from high school and college, and from studying abroad in Australia, which are covered by Toohey’s Red Beer labels!
You made your CAA debut in Los Angeles after college. Did you know at the time what kind of career you wanted to pursue?
I had no idea! I graduated from Colgate with a major in Studio Art and a minor in Mathematics. Every spring I applied for a summer internship at the Met, MoMA, Sotheby’s, Christies, and every major gallery in New York, and I was rejected each time. I took it as a sign and asked my father for a plane ticket to as far away as possible. I landed at John Wayne Airport in 1997 and finally found my way to Los Angeles. It was just me and BABS, i.e. the “bruised and battered Saab” my parents bought me in 1990 as a graduation present. Word to the wise, chants of hope don’t get an old stick-shift car up Mulholland Drive! While in Los Angeles, I started an internship for a production company called Original Film doing sound work on commercials. That is until one day I was controlling the crowds at the Hard Rock Cafe and I had to say [Mötley Crüe’s] Nikki Sixx to wait outside because we were filming… let’s just say I never worked as a PA again.
Ouch! What happened next ?
I quickly discovered The Freidman Agency, an entertainment temp agency, and they told me there was a vacancy at a talent agency where I would be buying gifts for clients. I knew I was good at buying stuff, so I made sure I got this job!
You started to vogue in ’98. Do you remember your first day as Anna Wintour’s assistant?
I moved to New York that summer and gave myself a few weeks to settle down. My little sister and her best friend were there, so I thought, “That’s great, I can share a summer sublet with them.” What I didn’t know was that it was going to be a room on 6th and Avenue C and I would be sleeping on a futon! I arrived around midnight on a Wednesday, had an interview with Anna on Friday and started working as first assistant the following Monday! I didn’t have time to think, let alone prepare. But I had been trained under [CAA leaders] Bryan Lourd and Kevin Huvane, so I knew I could handle it and I’m a quick study!
What were the springboards between assistant > entertainment editor > entertainment director? It looks like the trajectory of dreams…
Honestly, I think I skipped a few steps! I was Anna’s first assistant for only 18 months before I was directly promoted to entertainment editor. Don’t quote me on that, but I think I was the only assistant who went straight from her desk to the editor!
Before social media, how did you keep track of the moments and talents that would become huge?
Reading—reading all. I used to get all the trade magazines and newspapers: Variety, Hollywood Reporter, Rolling Stone, Billboard, The New York Times, The LA Times, Paper Magazine, New York Magazine, The Village Voice. No social media site will ever replace specialized newspapers and underground/indie magazines!
Did you keep all the covers you participated in?
I kept all the numbers vogue since June 1998. I actually had two copies of each issue; one set in my office and one set at home. When I left vogue, I realized there was no way to keep them all in a 1,000 square foot apartment with a dog and a toddler. I treasure my collection and always test my skills by thinking of a specific story and guessing the problem. I’m not wrong yet – Bobby Fischer’s skills!
Tell us some highlights of your work with British vogue during the last years?
Oh my God, there are so many! Let’s start by getting to work with a genius. Edward and I worked together for years at American vogue, and together we’ve created incredible stories, from the cover of Jennifer Hudson to a trip to Puerto Rico with crooner Bruno Mars. Our working relationship has resulted in a true friendship based on trust and collaboration. I am grateful every day to work for and with him. But if I had to choose one? Beyonce ! Fingers in the nose.
Adele’s recent cover has gone viral. What does it feel like when a cover goes viral like this?
Billie Eilish… Angelina… Beyoncé… Rihanna with TRUTH tattooed over her eyes… front line workers! I don’t mean to sound jaded, but with Edward, I’m more surprised when a cover is not it go viral.
Speaking of Adele, I read that she was someone you really pushed to feature early in her career. What’s in a certain talent that sets them apart as a future icon?
Absoutely! She came into my office and played me her debut album, and I knew right away that girl in a tracksuit with a messy pony was next. I used to say the world wouldn’t turn without real talent being discovered. I feel that the universe will make sure to shine a light on remarkable talent, and my job was to be open to any opportunity to meet that talent. Take every meeting with an open mind and, more importantly, an open heart.
Do you remember the first magazine cover that captured your imagination?
One cover that temporarily took my breath away was Edward Enninful’s “Apocalyptic Rihanna” shot by Steven Klein for W September 2016 issue. I vividly remember sitting at my desk at the time and immediately texting Edward and Amanda Silverman. I wrote something like “The most awesome cover I’ve ever seen in my life”. I am dead.’ Edward talked about his inspiration for this cover, imagining Rihanna as the last woman and warrior on earth. I’ve booked so many blankets in my 23 years at vogue that it would be impossible to choose my favorite, but the one that I have always loved so much is the Herb Ritts cover of Carmen Kass in a red piece on a boat from May 2001. When this was shot, I got my feet wet book celebrity covers, and celebrity covers would soon replace models. But I’ll never forget that cover. Herb was like no other!
You wear many hats, from running your business to working with Vogue Hong Kong and British vogue. Is there a normal daily routine for you?
I get up at 5am every day and most people I work with know this because they get my timestamped emails! I’ve always been a morning person – I had to be in the office at 6:45 when I worked as Anna’s assistant. For British Vogue, Vogue Hong Kong, Vogue Singapore, and Vogue Greece, I feel I need to be available to them, just as I am to my US-based clients. And I do more between 5 and 7 in the morning than I think most people do in their 9-5! Since I have a six-year-old who lives with me 50% of the time, waking up at 5 a.m. gives me a few hours before I have to take him to school. Otherwise, it’s all about the Tracey Anderson 6 a.m. class, and then I spend my day at my kitchen table zooming, pitching, wrapping up, researching, meeting, reading. And I love every minute.
Living in NYC, where do you like to go to stay inspired?
Between theatre, art, sport, the skyline, noise and crowded streets: it’s hard not to be inspired by living here!
How do you keep your ears to the ground on what’s going on and what’s cool these days?
Reading loads of online sites. I literally capture every profile I read and create sheets for my casting record. Many land in my
Folders “Excited About” or “New Faces”!
Back to the roots of scrapbooking! What are you most proud of in your career?
How I always fight for the underdog and never take ‘No’ for an answer.
Jill Demling and Billie Eilish (Courtesy)
What do you like best about the work you do?
I like people! And I like to see the result. Like when I support a young talent when he’s starting out and no one knows his name, and then you see him succeed and the whole world knows his name!
You always have more up your sleeve…can you give some clues about what you’re working on?
I certainly can’t share anything related to my editorial work, but I manage this amazing talent named Elladj Balde. He’s my one and only client and he’s about to EXPLODE. The world is about to know his name!
What is your goal for the rest of 2021?
To have more time for me and my daughter. I don’t think I’ve had a day off in 23 years!
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