Vanity Fair’s Michael Callahan on the ‘Killer Idea’ and Writing 6,000-Word Stories

'Lunch' with the author whose new book 'soaps up' Miss America

The joint was jumping at Michael’s today, where a scrum of paparazzi had their noses pressed against the glass in hopes of getting a better look at Quantico star Priyanka Chopra. Unfortunately for the shooters, the actress sat with her back to the window at Table One, alongside Elle magazine EIC Robbie Myers, who was hosting a table full of important-looking folks. Who says the power lunch is dead?

I was really looking forward to today’s lunch with author and magazine vet Michael Callahan, who I had gotten to know over Facebook through our mutual friend and fellow scribe Lisa DePaulo. We’re all part of this highly opinionated and lively group that obsessively weighs in on the important events of the day like what the hell were they talking about on the latest episode of Billions? I couldn’t wait to talk to Callahan about his new novel, The Night She Won Miss America (Houghton Miflin Harcourt), about a reluctant contestant who goes on to win the pageant and then vanishes. Based on a true story (more on that later), the book has garnered good notices from People and Town & Country. Callahan wrote a lengthy piece based on his book for the New York Post last Sunday.

Diane Clehane, Michael Callahan

While prepping for this interview, I came upon some clips where Callahan talked about spending his teenage years in northern Philadelphia devouring the sudsy novels he nabbed from his parents’ bookcase. The melodramatic novels of Irwin Shaw, Sidney Sheldon and Rona Jaffe as well as the mother of them all–Grace Metalious’ Peyton Place–all influenced his writing. I could relate.

I spent many an August afternoon on a lawn chair in my backyard on Long Island covered in Bain de Soleil reading those very same books. We even shared an obsession with Knots Landing–turns out neither one of us ever missed a Thursday night episode during its fourteen-year run on CBS. Clearly, he’s a man after my own heart.

Callahan’s first book, Searching for Grace Kelly, and his latest novel both take place in the 1950s, evoking deep nostalgia for a period when people actually dressed to go to out and a certain class of young women lived at the Barbizon in New York City. “There was a lot things wrong in mid-century America, but there’s something very alluring about the élan, panache and glamour of that time,” said Michael between bites of crab salad.

Having been on “the carousel of women’s magazines” that started at Mademoiselle, Callahan did stints at Redbook, Marie Claire and Cosmopolitan, where he worked for Kate White who I ‘Lunched’ with last month. When I asked why he was drawn to women’s magazines he told me, “There were more of them and more opportunities to be the man in pink there.” He went on to freelance for Seventeen during Atoosa Rubenstein’s reign. (Remember her?) “She was living in Trump Tower when she was the editor. She’s married to some hedge fund guy now.”

Houghton Miflin Harcourt

It was his former office mate Jonathan Van Meter who started him on the path to Vanity Fair. “Anna Wintour was hosting a book party for him at her home. It was the most intimidating thing I’d ever been to,” he said. “At the punch bowl, I met Vicky Ward, who was a contributing editor there and she said, ‘You should write for Vanity Fair.’ I said, ‘Why didn’t think of that?’” He laughed at the memory.

Realizing he would only have one chance to make a great first impression at the iconic title, Callahan recounted his strategy in formulating just the right pitch for Graydon Carter to greenlight. “I waited until I had a killer idea,” he said. “I didn’t want to go in with something that would wind up on the trash heap.” It was 2005 and Callahan considered what events might be reaching a 25th or 50th anniversary milestone and might be rife for the Vanity Fair treatment. Lo and behold, approaching was the 50th anniversary of the publication of Peyton Place. He pitched editor David Friend (an “old mensch” and a “great mind”) on doing a piece that would deconstruct the book and explore the “birth of the dirty novel” and was assigned to write a 6,000-word story.

Callahan, who lives in Philadelphia, went on contract at Vanity Fair in 2014 as a contributing editor and is still edited by Friend. I asked him why he thought Graydon has been left alone at Condé Nast while most other editors have either been shown the door or now have Anna Wintour regularly showing up at the offices. “Graydon is a formidable person and is a big presence in that company,” he said. “I have always been treated very well.” His latest piece for the magazine in the April issue is a profile of 91-year-old illustrator Robert McGuiness. He still pitches ideas but sometimes, “Graydon will call [David Friend] from the car with an idea and say, ‘Michael Callahan should do this.’”

Lest you think Callahan’s career has been one glossy town-car ride, think again. He got his start in publishing at Atlantic City magazine, where he shared an office above an old shoe store with Vogue’s Van Meter in the late eighties. “Believe it or not, a lot of big writers came out of there,” he said. “Atlantic City was a lot of fun then. Donald Trump wasn’t crazy at the time. Mike Tyson was fighting there, Madonna was there.”

Miss America 2017 Savvy Shields
Miss America Organization/Bruce V. Boyajian

@DianeClehane Diane Clehane is Adweek's weekly 'Lunch' columnist.