Zibby is joined by the former deputy editor of Vanity Fair Dana Brown to talk about his debut memoir, Dilettante. The two discuss what they miss about the heyday of print magazines, the crazy true story of how Dana got his start at Condé Nast, and how working for the magazine helped him find where he belonged. Dana and Zibby also connect over the summer their times at VF overlapped and Dana shares what he’s currently reading.


Zibby Owens: Welcome, Dana. Thank you so much for coming on “Moms Don’t Have Time to Read Books” to discuss Dilettante: True Tales of Excess, Triumph, and Disaster.

Dana Brown: Thank you so much for having me.

Zibby: My pleasure. You may not know this, but the summer of my freshman year of college, I interned at Vanity Fair. It’s 1995. I remember you being there and running around the office. I was like, who is that guy?

Dana: That is so funny.

Zibby: You had just started the year before. When I saw your book come out, I was like, oh, my gosh, was that the guy who was Graydon Carter’s assistant when I was at Vanity Fair for that summer?

Dana: What a small world. Oh, my god, that’s amazing.

Zibby: I was part of the — every summer, they had this rotating . I got to go through every department.

Dana: No way. Let me ask you a question. Was it a good experience? Was it a valuable experience? Did you have fun?

Zibby: It was a good experience. It’s so funny, though, because you had a line in here that was exactly how I felt about it — wait, hold on, I want to find it — with there being no path to being an author. Let me see if I can find it. You said, “There wasn’t a lot of upward mobility at Vanity Fair. You were either an assistant or an editor of some sort, and there wasn’t much daylight in between. It was hard to make that leap to the next level, easy to get caught in the middle, and I hadn’t had the experience of working directly with a text editor like the other assistants or the foundation of an education and a degree in history or literature. The institutional knowledge I’d accrued was useful, and I was overflowing with it, but that wasn’t enough to carry me to the next level.”

Dana: That was the story of my life for almost a decade.

Zibby: I have a memoir that comes out very soon called Bookends: A Memoir of Love, Loss, and Literature. I have three pages all about my time at Vanity Fair and how I couldn’t get — after the first day there, I was like, okay, there is no path. I am filing author contracts. I am not going to be an author if I stay here.

Dana: That’s so funny. Listen, it was really true back then. I don’t know if it’s true anymore. That’s been such a huge shift in the business. The older people, and I’m including myself among this, we don’t know what’s going on with technology, and so we need these kids to tell us, to be like, no, no, no, you have to be on TikTok. We’re like, what’s TikTok?

Zibby: It’s so true. I remember — I don’t know, maybe you were at this meeting too. There was a big panel discussion on the internet and how it would affect magazines at Condé Nast.

Dana: Wow. I don’t remember this.

Zibby: Everyone was like, no, it’ll be fine. We don’t have to worry about it, but FYI, this is coming. I was sitting there in the boardroom being like, oh, yeah? Okay. Now there are basically no more magazines. It’s the saddest thing ever.

Dana: It decimated the magazine population in two decades. It’s so funny. There was a guy who was at VF for a little while named Toby Young who wrote that book about — did you have him —

Zibby: — So good. No, I didn’t have him on, but his book was amazing.

Dana: His book came out twenty years ago, I think, so it would make sense —

Zibby: — I read it. It was —

Dana: — How to Lose Friends and Alienate People.

Zibby: Yes, that was so funny.

Dana: He wrote a charticle in ’95 or ’96. Toby’s a great guy. He was really talented and ended up going back to the UK and becoming a pretty successful restaurant critic. He had done one of those little humorous charticles comparing the internet to the CB radio of the seventies and how it was basically the modern version of that. It was just totally taking the piss out of the internet. I look back at that now, and I’m like, oh, boy. We pissed off the internet, and it came after us and destroyed us.

Zibby: It was your fault, you and Toby Young taking down the magazine world. I read your book with so much interest from this particular vantage point, but I would’ve been interested in it regardless because you lived through — I left magazines after that one summer. You stayed and showed us what it was all like and all the twists and turns and even your in-depth description of how you even were plucked from obscurity to do this job in the first place. Can you tell listeners a little bit about how you were just at this industry hot spot?

Dana: Of course. It’s funny because I ran into somebody of my generation, and I guess your generation, who had been at Vanity Fair with me back then. They read the book. They’d known some of my backstory. She said to me, she was like, “Boy, when you told me you were writing a book, I was like, what’s he going to write about? What’s it going to be like? Nobody could’ve really told this story in the way that you did.” I was literally the only person that came in this way. I’ll try to be brief. I was a total screw-up as a kid.

Zibby: You don’t have to be brief. This is your episode. You do with this what you want.

Dana: By the way, thank god, because I’m terrible at being brief. I was twenty-one years old in the spring of 1994. I was working behind the bar of a restaurant called 44. I was mostly a barback. Occasionally, I was bartending. 44 was the media fashion hot spot, lunch and dinner and drink place. It was a restaurant in the lobby of the Royalton hotel on 44th Street right around the corner from Condé Nast’s building at 350 Madison. The owner of the restaurant was a guy named Brian McNally, who’s very good friends with Anna Wintour and Graydon Carter and Tina Brown. He was just part of that world as a restauranteur. He’d opened Odeon in the early eighties with his brother Keith, who also went on to fame and fortune in the restaurant business in New York. The Condé Nast editors would hire Brian and his staff to come and cater the parties and dinners that they would have at their houses and apartments. I was added to this crew just for Graydon’s for some reason. I was never trusted to go to the Anna Wintour or Tina Brown events.

For whatever reason, Graydon noticed me at these things and called Brian one day and said, “I want to interview that kid. I’m looking for a new assistant.” When Brian called me — I’d barely spoken to Brian. I was a nobody. He left a message on my answering machine at home and said, “Give me a call.” I was like, oh, my god, I’m fired. What did I do? There was no other reason why Brian would’ve called me at home. He called me and told me that Graydon Carter wanted to interview me. He had seen me working at these events and thought I looked like a hard worker and humble. I got this interview. It was kind of absurd. Again, I went to college for three weeks before realizing, oh, this is just a waste of time and money. I was really lost. I was playing music. I was playing in bands. I didn’t know what I was going to do with my life, the whole shape of my — I was twenty-one. I went on this interview. I didn’t know how to tie a tie. I had to have my brother tie a tie for me. I borrowed a suit from him. I got this job. I got this coveted job at Condé Nast and at Vanity Fair, which at the time — I don’t even know what to compare it to. Everyone wanted to be in the magazine business. It would be like going to work for —

Zibby: — Netflix or something.

Dana: Like Netflix or even Goldman. It was the place to be. It was the place to go craft a career. It was exciting. It was fun. It was glamorous. It was upscale. Magazine editors were really the important cultural figures in New York, if not the nation. They just held so much power. These little books that would arrive in the mail every month around the country and around the world were so important because it was the only link people had to culture in the outside world in this pre-internet age. You would go to this thing for everything.

Zibby: I love that you even have to explain this, by the way.

Dana: I know. It’s sort of sad, but I kind of feel like I do.

Zibby: No, you’re right. You do.

Dana: I talk to young friends. Most of them are adjacent to the business, and my nieces and nephews and stuff. They sort of get it, but not really. It’s just become a different thing. If you wanted to be in touch, you had a stack of monthly magazines either arriving or you went to a newsstand as if it was a bookstore. You would look around. Maybe you would bring thirty bucks with you. If you could afford that English magazine that cost $12 versus $3.99 — you would just walk out with your stack. It would sit next to your bed for a month until the next stack came. Then your apartment was littered with piles of magazines everywhere. It was a really exciting time for magazines.

Zibby: making people’s careers. When Vanity Fair would pick the new establishment or the Hollywood Issue or whatever and these ingénues would appear all Annie Leibovitz-ed out, that was life-changing.

Dana: You know, Zibby, it’s funny. Somebody reviewed my book in Canada. It was one of the first book reviews that came out, and so I was so excited to read it. He used the phrase — he said magazines made the weather. That’s exactly right. Magazines were everything. They made the weather. Whatever was going to happen in the next weeks or month, it was in these things. You could unlock it. It was sort of a journey to find yourself. What am I interested in? What are my likes? That was a big part of it. You know what I mean?

Zibby: Totally. Wait, go back for a second if you don’t mind. You wrote about your childhood and not really feeling like you fit in. Hold on, I wanted to read this one passage. You also talked about how you turned to books, but also turning to drinking, which, I have to say, is also in my book. “The second thing a sensitive, introspective, and lonely teenager discovers after books is drinking, quickly followed by drugs, which were harder to get your hands on than booze or a book. They don’t sell drugs at the library. Although, in the 1980s, they did sell drugs in Bryant Park right behind the New York Public Library, so you had to work your way up to that.” Tell me a little bit about growing up as a shy, quieter kid — you were the youngest of four — and feeling like you just kind of got lost. I feel like — this is totally not my place — you probably have some sort of learning disability because you’re obviously super bright.

Dana: You know, it’s funny you say that because I did — by the way, without going through therapy for years, I would’ve never stumbled on any of this stuff or been comfortable writing about it, trying to figure out my own head. I think it’s pretty common, actually, for kids to — what I discovered — yes, maybe I had ADHD, which wasn’t really a defined thing back then. They didn’t really know what it was. I don’t even know if my parents would’ve put me on Ritalin or whatever it is that everyone seems to be on now. I just couldn’t find my place in the world. I wasn’t good at anything. I wasn’t a really good athlete. I was terrible in school. I couldn’t draw. I could kind of play music passively, but not really. I really struggled to find my place in the world. That does, a lot of times, lead to this, I’m the shy guy at a party with my friends. I’m sitting in the corner. Okay, I’ll have a beer. Then it’s like, oh, okay, I can now talk to people. Then drugs make an appearance. I think this is an incredibly common trajectory for a lot of people. Unfortunately, a lot of times, this leads to a lot of issues. If you don’t figure it out and deal with it later in life, it really comes back to bite you and haunt you.

Weirdly, it sort of gave me a foundation of — I could drink when I was a kid. It really helped me at Vanity Fair because there was a lot of drinking. If you could keep up with the older folks, they were like, oh, wow. Crazy enough, I stumbled into the one business where it was going to help me, which is kind of absurd. It was kind of absurd. Again, twenty-one is really young. Twenty-one is really young when I walked into that place. As lost and out of place as I felt in the world, I felt that at Vanity Fair, too, when I started because I didn’t know how to do anything. I was really just an empty vessel. It became my place. It became the place where I found myself. It became the place where I began to discover things that I was good at. I had found a place where I fit in because it was full of weirdos. It wasn’t like going to work at a bank or a real estate agency. It was full of fashion weirdos and poetry weirdos and film nerds and pop culture geeks and music writers. It was like the island of misplaced toys. I really found myself fitting in there, which was kind of amazing. That’s a big part of the book. It’s this coming-of-age story and tale of finding yourself. Mine just happened to be at this magazine in the nineties. Of course, I ended up staying there for almost twenty-five years.

Zibby: Unbelievable. What do you think you’re good at now?

Dana: What do I think I’m good at now? Nothing, really. This is something I will, again, discuss with my therapist on Wednesday at noon. I don’t think I’m good at anything. No. You know what’s funny? I’d written before, little things for the magazine over the years. I’d never written a book before. I’d never written about myself at length like this. It was a similar process to — I really, really liked it. I really quickly found a writing voice. I’m really comfortable writing. You discover that’s what a writer is. A writer is someone who expresses themself in words because they can’t express themself in any other way. I’m going to pat myself on the back and say, you know, I think I am actually a pretty good writer. It is the medium where I’m most comfortable in, whether that’s a book — I write screenplays and television shows also. I feel really, really comfortable. It’s hard. I’m not always motivated, but I feel really comfortable sitting there with an open Word or Final Draft document just sitting there writing a scene or a chapter. I think I’m okay at that. By the way, this is progress in my life.

Zibby: It is progress. That’s great. Having gone on this journey with you, I feel proud that you’re able to even admit that.

Dana: That’s very kind of you.

Zibby: I often say that the thing that links writers the most, I feel like, is that everyone has this underlying anxiety disorder or something and this deep observation. It comes out, somehow, through the keys.

Dana: A hundred percent. It’s amazing to me. I really just discovered this about myself in the last three or four years. It’s never too late. It’s never late to figure this stuff out. I hate writing, but I love having written, and so I can put in the time doing it now. It’s sort of enjoyable.

Zibby: How are you in terms of keeping in touch with the Vanity Fair crew? How are they all still in your life, if at all? What are the relationships?

Dana: First of all, it’s so strange to have two years of our life, or two and a half years, taken away from us and not being in touch with these people. Although, then I realize I haven’t been in touch with family members and really close friends in two years. We’re a pretty tight group, actually. I’m still in touch with a lot of people. Part of the reason is, Graydon Carter went off and he started a digital magazine called Air Mail, which feels like Vanity Fair. It’s basically a digital version of his Vanity Fair in many ways. Although, I don’t think he has the budgets that he once had. There are a lot of Vanity Fair people that work there. I will occasionally write for them. I did a restaurant review for them a couple weeks ago. I got the copyedit back. I recognized a few of the things that the copyeditor suggested. I was like, I know exactly who did this. Tell him no. It’s a dear old friend of mine. Maybe you’ll appreciate this. It was changing any uses of the word “like” to “such as,” which is my one pet peeve in writing. I hate “such as” more than anything.

Zibby: I hate “such as” too because no one says it. No one says it.

Dana: It’s so antique. It just feels like you would see it in an old New Yorker or something. Anyway, but I knew exactly who copyedited it and sent a funny, nasty note. We’re very much in touch, a lot of us. People have gone on to do really interesting things.

Zibby: What restaurant did you review?

Dana: There was a pop-up of the famous restaurant from Copenhagen called Noma. There was a super expensive pop-up in Brooklyn for a week about three weeks ago or a month ago. I went and I did that. It was actually really fun. Reviewing restaurants is something I’ve always wanted to do, but it’s not the sort of thing that just lands on your lap. This sort of landed on my lap. I was like, yep, I’m in. I’ll do it.

Zibby: What do you think would’ve happened if Graydon hadn’t have picked you?

Dana: I think something would’ve come along. I really do. It’s funny. I’m not a believer in anything, really, but I do believe, a little bit, in fate. I think something would’ve come along. I don’t know what that would’ve been. I feel like in that era — maybe it’s different now. Maybe it’s the same. I think people did take — you hear these stories. I got hired at the whatever. I think people would take chances on people. Résumé and education aside, they would be like, this kid’s got — they’d be thinking like an old Preston Sturges movie or something. This kid’s got hustle. This kid’s got moxie. Bring him on board. I feel like there are versions of that story. I think something would’ve come along. God, I hope so. I’m sort of glad that I don’t have to live in that alternate universe because it could’ve gone really bad.

Zibby: Now that you’re an author too, what advice would you have for aspiring authors? Now you’ve gone through the process. By the way, I know Pamela Cannon well, who is your editor.

Dana: God bless Pam Cannon. She was a lifesaver. Honestly, this book would not have been readable without her. She really saved the day. Advice, first of all, find writers you love. I think that’s obvious. I think people who really like to read find that. They find that writer that just connects with them in some way, whether it’s the way they lay out a story, whether it’s the turn of phrase, whether it’s the use of language. Find writers you love. Really get to know the rhythm of writing. That helped me a lot. Obviously, I worked with a lot of writers. I was reading everything because you were always on the lookout for new, young writers. Find what really connects with you because I think that helps find your own voice when you sit down to write. God, it’s going to sound so cliché, but you’re going to fail a lot before you succeed. I know writers who have found their voice out of frustration because they were trying to fit their writing into a box that they thought would work in the marketplace. They were writing for this magazine, so they would sort of tone it down and do it in the style of that magazine. There’s something really freeing about finding your own voice and writing in your own style and writing in your own way that you can’t be afraid of. You have to embrace it because that’s the thing that’s you that you’re putting on the page. You need to sort of shut out the noise and just go for it. I think it’s really important to spend time getting to know writing, reading going to back to Joyce or whatever, and Hemmingway, but also modern, young writers. Understand, oh, I can be original. I can write in my own style in my own way. I can break rules. That’s really important because I think a lot of writers feel kind of stuck in little boxes. They’re forced on this one path. I don’t think there is one path. It’s not a one-size-fits-all kind of thing for writers.

Zibby: It’s so true. I know I experimented a lot with writing. A lot of writers can write in lots of styles. I’m like, I can write a first-person, present-tense, literary thing. I’m going to write a whole book like that, but that’s not really me. I can do it, but…

Dana: Again, I don’t know because I didn’t go to school for writing, but I’m sure they teach you everything. I’m sure they teach you every single style of writing. Do this from this character. Do this third-person. Do this whatever. It doesn’t necessarily make sense for you. When you sit to write a story, you need to write the way your mind is pulling you in. It’s really important to let go and let it just pull you and let it take you. You will know what that is and when it’s working because you will just be like, oh, my god, that’s great. Oh, my god, that’s great. Oh, my god, that’s great. You will not be able to stop once — it’s like a racetrack. You accidentally get in the right car. It’s fast. You’re like, whoa, I can’t believe I can go this fast.

Zibby: And that it could be more fun. It’s hard. It’s like wearing the wrong size shoes or something. You can do it, but it’s not going to feel good.

Dana: No. Exactly.

Zibby: You’ll get where you’re going.

Dana: You’ll get where you’re going, but you’re going to have blisters.

Zibby: Blisters. Amazing. What is your next writing project? Also, what are you reading right now?

Dana: What am I reading? I had so many amazing assistants over the years. They were all so much smarter than me and better writers than me, better everything. I used to hide behind their talent and pretend — I’d be like, do you mind writing this paragraph on this thing for the thing? An old assistant of mine, a guy named Julian Sancton, wrote a book. He’s going to kill me because I’m finally getting around to it about a year after it was published. It’s called Madhouse at the End of the Earth. It was this disaster of an Artic journey that these three guys took. I think it was in the late 1800s, so late nineteenth century. One of them was a con artist. One of them was a real explorer. I love contained stories. It all takes place in this one boat, for the most part. That’s a challenge as a writer, whether you’re writing for the screen or a book. You’re stuck in this one place. How do I pull the reader out of here at different points seamlessly? He does such a great job at that. I’ve been super into that book the past few weeks. Again, he’s going to kill me because it’s taken me a year to get to it. I think I’ve ignored his texts. Have you read it yet? Have you read it yet? Have you read it yet? I can soon be able to text him back and be like, yes.

Then I’m hunting around for the next book idea, which is a complete nightmare. Once you’ve written a memoir and if you’re somewhat successful, at least in getting your story down, you will have publishers knocking on your door being like, so what do you want to do next? If you’ve done the memoir already, you’re like, okay, I can’t go back there. What can I do nonfiction? What are people interested in? What are people talking about? I’m on the hunt for that. I’m not sure exactly what it is. I wrote a movie during COVID that I actually got to — I wrote and produced it. It is just about finished. I’m very excited about that. We’re probably going to try to take it to one of the festivals at the end of the summer. I’m writing another screenplay right now. Then the exciting news is that — I partly wrote this book because I was like, you know what, I want to make this into a TV show also because no one’s gotten magazines right on television. I just closed a deal with a production company to write the pilot for Dilettante. It’s an uphill battle, getting a series going, but I’m really excited. I’m going to write that pilot soon also. My Microsoft Word is going to get a break. My Final Draft Pro is going to be a little busy for the next few months. Screenwriting is so much fun. Again, that’s one of those things where until you find your voice and your style, it’s maddening. It’s frustrating. Then you find it. You can tell you’ve found it because people respond. Someone’s like, all right, yeah, I want to make this. You’re like, really? After my other ten sucked, this is finally — it really is just about understanding how it works and doing your research and reading others and watching movies. Once you find that style, it becomes exciting and fun. That’s it.

Zibby: Amazing. Congratulations. Very cool. Great seeing you after all these years.

Dana: I know. Zibby, thank you so much. It’s such a small world. It’s so nice hearing that. You were there, that was OJ. That summer, that was when the trial was going on, I think. Right before.

Zibby: I left before OJ because that was in —

Dana: — The fall. You’re right.

Zibby: I was whitewater rafting during the OJ thing, so sometime that summer.

Dana: Got it. Zibby, thank you so much. This was such a joy. I hope you have a lovely summer.

Zibby: Thank you. You too.

Dana: Take care. Bye.

Zibby: Take care. Buh-bye.


DILETTANTE by Dana Brown

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