Jill Kargman: Odd Mom In

One Saturday night this past fall, a slew of Manhattan socials—Celerie Kemble and Marina Rust among them—went to the prom. Alighting from a fleet of Uber cars onto a dingy strip of Prospect Avenue in Brooklyn, guests in tuxedos and Jessica McClintock finery headed up a gilded double staircase into a magenta-lit ballroom festooned with hot-pink balloons and gold tinsel. Sporting wrist corsages and boutonnieres, they danced to a cover band and posed for photos under a white-latticed arch. It was the stuff a 17-year-old’s dreams are made of—the writer and social-circuit regular Jill Kargman’s 17-year-old dreams, to be precise. “This was the prom I never had,” says Kargman, who, having attended Taft, a New England boarding school, was deprived of that particular rite of passage. So she threw a prom of her own, a John Hughes black tie–themed dance to celebrate her 40th birthday and that of her husband, Harry.

The final scene from Pretty in Pink wasn’t the only fantasy Kargman would be living out that night. The evening also marked her public debut as a TV star. “The prom will be filmed for Jill’s new scripted comedy Odd Mom Out,” read the disclaimer in a follow-up e-mail to the invitation. “By attending…you consent to being filmed. So look fierce.”

Kargman is an Upper East Side mother of three—but she has never been a typical uptown lady. She is the author of five books, including Sometimes I Feel Like a Nut, a collection of essays. Odd Mom Out, which debuts in June and will be Bravo’s first scripted comedy, cashes in on her outlier status. Kargman plays Jill Weber, a Jewish native New Yorker who marries into a prominent WASP family. Weber, with her goth-chic wardrobe (not unlike Kargman’s own), tattoos (Kargman got two during an early midlife crisis), and her laissez-faire mothering skills, clashes with her glossy, wealthy sister-in-law Brooke (played by Saturday Night Live vet Abby Elliott), in particular, and the denizens of the 10021 ZIP code, in general. Kargman says she can relate to her character, though personally she has evolved. “I’m not so insecure about parenting now. I’ve found my groove,” she says over drinks at the restaurant Daniel a few nights after the prom. “But this is about someone who’s stressing and feeling like she’s doing everything wrong, which is the old me. I’m 40, and I don’t give a shit anymore.”

Tonight, Kargman is wearing a camel coat, a dark dress, and Chanel shoes; triple loops of Gara Danielle earrings sparkle on her ears, and Chanel and James de Givenchy rings, not to mention a bright pink gel manicure left over from her wild Brooklyn night, light up her fingers. She tells me that she never set out to create a sitcom. “I kind of stumbled toward this blindly.” In 2013, she had an idea for a morning talk show called Wake the Fuck Up and pitched it to Bravo. It didn’t pan out, but network execs Andy Cohen and Lara Spotts were so taken with Kargman that, after batting around ideas for a reality show (“I would never have a camera up my sphincter,” Kargman says), they arrived at a fictional (but reality-inflected) half-hour comedy satirizing the Upper East Side in all its glory and excess. Kargman not only stars in the project, she is also an executive producer and the series creator. “What we loved and were committed to was her perspective on that world,” says Spotts, Bravo’s senior vice president of development. “She’s the bottom of the one percent. It’s really funny to hear her talk about her financial struggles, when you’re like—hashtag, cry me a river—look at the apartment you live in!”

It’s not hard to understand what Bravo sees in her. Chatting with Kargman can feel like watching stand-up; she delivers line after line in her trademark neologese (“She has this whole other vocabulary—you need a glossary,” says Andy Fleming, one of the show’s directors). Upon receiving her cocktail, she eyes the garnish and asks, “Do I deep-throat the raspberry carcass?” Her initial reaction to her editor’s suggestion that she write a memoir, she recalls, was “Don’t you have to be gang-raped and have your limbs chopped off to write a memoir at 34?” Her bout with melanoma is summed up with “I had a tumor in my vag,” and the idea for her 2007 novel Momzillas, which provided fodder for Odd Mom Out, came to her “on the Godfather day of my period.”

Kargman has been honing her shtick since childhood. She grew up on Madison Avenue, the oldest of two (her brother, Will, an art consultant, is married to Drew Barrymore). When she was 9, her father, Arie, became president of Chanel USA, and she subsequently spent spring breaks in Paris, attending the Chanel runway show with her mom, Coco. (Kargman is quick to note, however, that she didn’t get a Chanel bag until she was 21: “Frances Stein, the accessories director, snuck me one. My parents were livid.”)

As a student at Taft, she was the quintessential theater geek (albeit one whose social life had revolved around late nights at the Palladium and Mars). “I think it was very important for her when we were growing up to have an outlet where she could let her freak flag fly,” says her longtime friend Trip Cullman, a theater director. Her less-than-preppy wardrobe always set her apart. “In 10th grade, late 1980s, she was wearing all black and a studded leather jacket,” says Lisa Turvey, a classmate from Taft. “Everybody else was wearing Patagonia jackets and those ugly L.L. Bean moccasins.”

Her mother, however, never saw her as a rebel. “Compared to the placid environment around her, she just stood out,” Coco says.

Kargman continued acting at Yale, starring in plays on a weekly basis and singing in the school’s New Blue a cappella group. (“Her performance of ‘I Will Survive’ was legendary,” says Cullman, a fellow Yale alum.) After graduating in three years with a B.A. in history of art, she took up writing, first for Interview and Style.com and then as a novelist. While not wholly autobiographical, her books have ruffled some feathers. “One thing that has plagued me is, people are like, ‘So-and-so is this character, and so-and-so is that one,’” she says. “Someone even went up to my dad and said, ‘Jill described our home—we have a Cy Twombly blackboard painting!’I was like, ‘A lot of people have Cy Twombly blackboard paintings. Don’t flatter yourself.’ Clichés exist for a reason. A lot of people were stewardesses and now live in triplexes on Park Avenue.”

No doubt, there will be similar speculation over Odd Mom Out, but Kargman isn’t concerned. Anyone who has spent two minutes with her knows she’s not one to filter for fear of offending. “Somehow, the way she swears is highbrow. I don’t know how she pulls it off,” says Spotts with a laugh, noting the show will have “no f-bombs, but a few ‘shit’s—and ‘pussy’ may be uttered. The really fun thing is when we have to go back to her and say that something she’s written won’t fly with Standards and Practices, she comes up with something 10 times more offensive that we can still put on the air.”

Though her family is surely used to Kargman and her antics, she admits that one plot line, involving anal sex and loosely inspired by her life, did give her husband pause. “I’m an ass virgin—we have not had anal sex,” she says. “Believe me, I’ve tried; but I cannot get it in!”

“Look, when you’re married to someone like Jill, you understand that person takes lots of risks,” Harry says. “You have to be confident to understand that she is going to be very raw. But hopefully, I’m a big enough person to not be rattled.” He was even okay with their children, Sadie, 11, Ivy, 8, and Fletcher, 7, appearing in the show’s pilot, though they were replaced by professional actors once the series was picked up, so as not to disrupt their school schedules. “I sat them down in our breakfast nook and told them,” recalls Kargman of, essentially, firing her children from the show. “I’d never had all three of them convulsively sobbing at one time. This is their college essay.”

But despite the inspired-by-real-life quality of Odd Mom Out, cowriters and executive producers Elisa Zuritsky and Julie Rottenberg stress that Kargman and Weber are not completely interchangeable. “The first few times we met Jill, we were like, ‘Wow, you look great! Are you going somewhere?’ Then we realized, she looks fantastic every day,” Zuritsky says. “That was one thing: Show Jill cannot be as fancy as real Jill.”

Not that Weber is a frump. On a crisp October day at Woodlawn Cemetery in the Bronx, where an episode in which Weber’s in-laws are vying for a particularly prestigious burial plot is being filmed, she’s decked out in a Ralph Lauren cricket sweater, a vintage skirt, and Chanel boots. Watching Kargman sing “Give My Regards to Broadway,” backed by three members of the Duke’s Men, a Yale a cappella group, and then break into a jig atop an actual grave, it’s clear that her two-decade hiatus from performing hasn’t diminished her ability to ham it up.

“I think of the show as a comedic version of a Dutch still life: It has all these beautiful, frothy things, but there’s a skull right in the middle,” says Kargman as she contemplates the dregs of her fancy pink cocktail. “A lot of people might define a life well lived by how much is in the bank. I feel like it’s how much you laugh.”

Hair by Edward Lampley for R+Co at D+V Management; makeup by ralph siciliano at D+V Management; photography assistant: Sean Lippy; fashion assistant: Dylan Hawkinson; special thanks to the Carlyle Hotel; Fashion: Kargman also wears AS29 earrings.