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America’s filthy funny girl is having the last laugh

Text by Horacio Silva
Portraits by Milan Zrnic
Styling by Andrew Vottero
Issue n° 13, Spring & Summer 2016

The comedy stylings of Whitney Cummings are not for the faint-hearted. A raconteur of disarming candour and eviscerating delivery, she gives incendiary stand-up performances that draw upon her own chequered personal relationships to pinpoint women’s experiences in the 21st century. The 33-year-old self-proclaimed “dirty comic” with the Ivy League education has turned her brand of risqué wit into TV gold: her sitcom 2 Broke Girls is currently in its fifth season, and she has a new show coming on HBO. Whitney’s success has been hard won — for every ratings winner, there’ve been several misfires. But her innate ability to capitalise on failure, pull herself up by the bra straps and bounce back again and again keeps the suits — and the suitors — coming back for more.

A fearless American stand-up comedian and writer whose potty-mouthed shtick suggests a Joan Rivers for the kale generation, Whitney Cummings is a broad with a broad, broad mind. Her rapier wit – “It’s the 21st century. I don’t need a big strong man to fight off a tiger; I need some geek who can get my naked photos off the cloud” – and plucky stage persona quickly earned her a reputation in her mid-20s as a name to watch and to drop. At just 28 she hit pay dirt with Love You, Mean It with Whitney Cummings, a one-hour cable talk show of her own, and two sitcoms on network television: Whitney, on NBC, in which she starred as the titular character and served as executive producer; and 2 Broke Girls, a high-rating millennial Laverne & Shirley-like series now in its fifth season on CBS, about a couple of hapless waitresses, which Whitney co-created with Michael Patrick King, the rainmaker behind Sex and the City.

“In this golden era for American female comedians, Whitney is on the new front of what is coming down the line,” King says. “Her material is a unique balance of celebration of success and self-deprecation. It really announces where a lot of women really are in the world.”

Maybe so, but America was not altogether ready for the Whitney Cummings blitz four years ago. Her eponymous sitcom was dropped after two seasons, as was her talk show, and the critics lambasted her as though she had been a heckler at a live show. She was by turns considered too loud, too crass, too populist, too skinny, too castrating. But with the recent release of I’m Your Girlfriend, her new HBO comedy special (a significant career milestone for American comedians that has showcased such greats as Richard Pryor, Chris Rock and Tracey Ullman, to name a few), and a slew of interesting new projects on the horizon, Whitney may end up having the last laugh.

I meet Whitney Cummings in early January at her home in Studio City, California, a gold statuette’s throw from Jared Leto’s house (and not far from where Miley Cyrus and Shia LaBeouf live). Dressed in Ash high-heeled sneakers, Rag & Bone stovepipe jeans, a Rails flannel shirt and a faux-punk sweater of unknown provenance that “is very expensive and made to look like shit”, a smiling Whitney greets me at the door with her two rescue dogs – Ramona, a 2-year-old pit bull, and 1-year-old Frankie, a Great Dane mix. Whitney looks slender and healthy, but she has yet to unpack from a recent trip, and the place is suffering from a residual Christmas hangover: the yuletide-themed novelty cushions and oversized tree have overstayed their welcome, the flowers are long dead, and there is enough loose glitter around the place to decorate a drag queen’s dressing room. “I used to really want to impress journalists and be perfect and funny, but that was before I got into intensive therapy,” Whitney, 33, offers as her disarming gambit, while lighting one of the rose Diptyque candles without which she claims not to be able to write or do much of anything.

The raw but refined interior – all polished concrete floors and reclaimed wood – is certainly an elegant study in haute sustainability, if a little indebted to the Belgian designer Axel Vervoordt, but it serves merely as a support act to the towering floor-to-ceiling windows that look out on a dramatically landscaped, grotto-like backyard, complete with a swimming pool that Whitney claims never to use. The low-to-the-ground furniture, rendered in luxe textures, naturally aged woods and muted colours – all from Environment, the purveyors of fashionably weathered design favoured by eco-conscious A-listers such as Leonardo DiCaprio – is inviting and handsome, as far as it goes.

Reclining on a cylinder chaise longue by WAKA WAKA, comedian Whitney Cummings is wearing a white merino wool jumper by A.P.C. and white jeans by ACNE STUDIOS.

“I bought this place from a gay architect with flawless taste, so I basically just had to turn on the TV when I moved in,” Whitney jokes. “As for art, I stopped buying it because I have such terrible instincts. About four years ago I purchased two giant works by James Georgopoulos, these gorgeous lacquered photos of guns from movies. But then a couple months later the massacre happened at the [Sandy Hook Elementary] school in Newtown, and I felt very uncomfortable having guns in my house as art. They just reminded me of innocent dead people, which was a bummer, obviously. So now I just put up stuff that makes me smile, like a dog in a wedding dress.”

The zen bungalow, with what Whitney refers to as “happy lights” strategically placed in every room to help mimic the serotonin-producing UV rays of sunlight, is certainly far removed from the dysfunctional house she grew up in Georgetown, Washington, DC, as the youngest of three children. Her mother, Patti, worked in public relations for Neiman Marcus, and her father, Eric, had a career in “venture capital” which is still a source of mystery to her. “I stopped asking questions about that part of the family narrative a long time ago!” she says. “‘Venture capitalist’ is a bit like ‘Instagram model’, isn’t it? As for my childhood, my parents divorced when I was 5, and I later went to a private school but got sent home with a letter pinned to my sweater saying that the tuition fees were overdue. We lived in a lot of debt and spent money on all the wrong things, like impressing people we didn’t even like. It was a very co-dependent household. For example, we had a lot of nice stuff in the fridge, but it was only for guests. My mom always drank nice enough white wine, so I thought we were fine, but she really just had an expensive drinking problem. A lot of families have that smoke-and-mirrors thing but there was just so much shadiness going on at home.”

In the past she has also talked about experimenting with drugs in her youth and running away from home to Rehoboth Beach in Delaware with her older sister, whom years later she helped deal with a heroin addiction. (Whitney has scrapped a film script she was writing about the misadventures of trying to get her sister clean. “Too much of a shit show,” she says of the doomed comedy.) Whitney says she got the debauchery out of her system early. She moved in with an aunt in Roanoke, Virginia, in her early teens and became a model student at school in Potomac, Maryland, earning a place at the prestigious University of Pennsylvania, one of America’s eight Ivy League institutions, in 2001. “I was not going to waste my opportunity,” Whitney says. “I was paying for part of the tuition” – her part-time work in her teens included modelling bridal and maternity wear at the local mall – “and when you actually see the bills you take your education a lot more seriously.”

Whitney graduated magna cum laude, taking three years instead of the usual four, with a degree in communications. “My plan was to become a journalist, or at the very least a muckraking documentary maker in the style of Michael Moore,” she says, laughing, “until I realised I had way too many opinions and couldn’t be objective.” She hightailed it to Los Angeles and landed a job on the Ashton Kutcher-produced MTV show Punk’d. It was there that the light bulb went off in her head. “It’s weird,” she says. “Someone suggested I try stand-up, and I said, ‘Sure.’ But it wasn’t like I really had a choice. I don’t think that anyone chooses to become a comedian. No one is like, Should I be a lawyer or a comedian? It’s more of a compulsion.”

Here and in the final image, Whitney is wearing a white wool T-shirt by CREATURES OF COMFORT.

Comedy also gave Whitney, who felt silenced as a child, a voice. “I think I always had a desperate need to be heard,” she says, “and I have always had an obsession with justice, which I think a lot of comedians do. A good comedian has to maintain a certain level of anger. You have to care enough to leave your house at 10pm and drive to some fucking comedy club, get your car dinged in the parking lot six times, and go onstage in front of 100 drunk people for 15 minutes for no money. You just have to really give a shit and maybe have an inflated sense of your effectiveness or reach to think that you are going to make any difference in the world.”

Whitney started off working two-bit comedy clubs, the odd sushi bar and bowling alley, and any venue with an open-mic night. Regular spots followed at the Comedy Store, the famous club in West Hollywood whose alumni include Steve Martin, Robin Williams and Roseanne Barr, and on popular late-night entertainment shows like Chelsea Lately with Chelsea Handler; so did a tour with Denis Leary. And among the Comedy Central Roast comedians, Whitney ranks alongside legends such as Kathy Griffin and Seth MacFarlane. (Her skewering of Donald Trump, Pamela Anderson and David Hasselhoff is the stuff of YouTube lore.) She signed with one of Hollywood’s “big three” entertainment agencies, Creative Artists Agency. After seven years on the circuit, Whitney caught a break when her agent told her Michael Patrick King was looking for a writing partner for a new sitcom he had in mind about two scrappy girls living in New York. CAA sent in a script she had recently completed about a young woman who attends AA meetings to impress her alcoholic boyfriend and ends up becoming an alcoholic in the process.

“I did a Scarlett O’Hara search for playwrights, bloggers, actors and comics,” King says, “and the script that stood out the most was Whitney’s. There was a line in it where some guy is trying to hit on the female character at a bar, and she just looks at him and says, ‘Unsubscribe,’ like she was deleting some spam email. I loved it. These were really insanely funny and hard-hitting jokes in an engaging voice.” Despite his instant rapport with Whitney, King had reservations about working with someone who he felt was just about to strike it big. “I walked her out and thought, I don’t know, she’s really talented and special but with that comes a lot of ego,” he remembers. For her part, Whitney (who was wearing $800 suede Louboutin wedges she had bought for the occasion out of the last $900 she had in the bank and planned to return afterwards) told King she didn’t think it would work out but asked him to send her the script once it was done so she could help to punch up some of the lines – for free! King had found his Scarlett. “I thought, Great, she hates herself just enough for this to be workable! And I was right: it was the best collaboration I have ever had with a writer.”

2 Broke Girls was an instant success, garnering an impressive average of 11.29 million viewers per episode over its first season. (Although it is averaging about half that figure halfway through its fifth season, partly because of an overall loss in viewership for traditional TV, 2 Broke Girls continues to dominate in key demographics, particularly women aged 24–39.) As the co-creator of the show, which has now been licensed to multiple stations and local affiliates around the States (this, in effect, is how the serious money in American television is made), Whitney stands to become extremely wealthy over the next few years, much like the producers and cast members of perennially popular shows such as Seinfeld and Friends. According to one magazine report – which Whitney disputes – she could earn as much as $45 million from 2 Broke Girls.

“Ha,” scoffs Whitney, who has a “Fuck Yoga, Make Money” sign on the desk of her home office. “My family saw that article, and now they treat me like an ATM!” But, she adds, with a serious note, “that figure is not true, and in any case, I have not gotten paid for the syndication rights, as that takes a long time. Money is still an ongoing problem because my family was financially irresponsible for so long, and I’m now paying for it. My parents had strokes without health insurance, for God’s sake!”

“My plan was to become a journalist, or at least a muckraking documentary maker, until I realised I had way too many opinions.”

2 Broke Girls was a bona fide ratings winner, but Whitney, in which the comedian played a version of herself who was in a live-in relationship with a dot-com millionaire she had no plans of marrying, left audiences cold. Whitney, who like her contemporaries Amy Schumer and Sarah Silverman portrays herself as being unapologetically promiscuous, became the target of rampant internet trolling (a lot of it by men, or at least users with men’s handles), and was blasted by the critics. One particularly acerbic review by Emily Nussbaum in The New Yorker soon after the show first aired in October 2011 called it a “terrible” show, “startlingly retro and cruel”, and dismissed its battle-of-the-sexes conceit as “off, airless – self-loathing disguised as self-assertion”.

Whitney has mixed feelings about the show’s demise. “Obviously it was emotionally very paralysing and traumatising,” she says. “But I also felt like it had run its course. Don’t forget we shot and aired 40 episodes, which is no small feat. But because of the punishing schedule, after a while you end up producing what I call ‘pencils down’ comedy. There simply isn’t enough time to write brilliant shows over such a long season. Part of the reason that I think British comedy shows are often so good is because they make, like, eight episodes at a time. They know when to say, ‘That’s a wrap.’”

Whitney says she had also outgrown the character she played in the show, who was based on her 25-year-old self. “I had made so much progress mentally,” she says. “Then I would have to go in there every day and regress to this person I was five years earlier. But it’s hard to have a show canned, and unlike what people think, it’s not made any better by having another show that’s successful. It’s not whack-a-mole! A show is a really big deal. You give it your entire life, heart and soul, time – there is no personal life, you have no social life, your health takes a hit. It’s an incredibly all-consuming experience.”

As anyone who knows Whitney will attest, she is constantly working on improving herself. For the past two years she has been trying to forgive the sins of her father and mother, scars from past relationships, and the psychological drubbing she got for Whitney with the help of eye movement desensitisation and reprocessing therapy. “In layman’s terms,” Whitney explains, “it’s essentially taking traumas from your childhood and reprogramming them so that similar circumstances don’t trigger distress. So if your parents, say, fought a lot over Christmas, and every time you are near a Christmas tree you get anxious, it’s because it’s been filed under ‘trauma’ in your brain. Neurology is kind of my little dorky hobby.”

Her clinical fixation now extends to her love life. “I’m dating a doctor and feel like I can no longer date anyone who isn’t in the medical field because of how obsessed I am,” she quips. Neurobiology is also feeding the myriad projects she currently has on the boil. (“Whitney has more career goals than anyone I’ve ever met,” says Michael Cox, the stand-up booker on The Tonight Show Starring Jimmy Fallon, who has hired her over the years. “Her drive is untouchable, yet her commitment to those around her is incredible.”)

I’m Your Girlfriend! – Whitney’s new hour-long HBO comedy special which debuted at the end of January and is now available on demand – is a hilarious remembrance of flings past in which she targets gender binaries and the essential neurological differences between women and men with the insight of a carnal, potty-mouthed Oliver Sacks. In one typical skit in the show, about birth control, sure, she takes a jab at the men she has brought home, but her knockout punches are saved for the cost of the pill and the ignominy of buying it in public. “Do you realise the morning-after pill is $49?” she asks the audience.

“I have never had sex with a guy and the next day thought, Yeah, that was worth 50 bucks. And it’s not just 50 bucks because you can’t only buy the morning-after pill or the cashier is going to think you’re a slut. So you buy a bunch of other products to hide it – you have to crowd it with Q-Tips and floss and a lot of other shit that you’re never going to use.”

For all her levity Whitney is, as The Atlantic recently reported, doing “comedy with a moral purpose”. And it’s not just talk. Recently, she took part in WomanCare Global’s Then Who Will? campaign with Jessica Biel to promote the benefits of sex education for children, currently a very divisive issue in the United States. “If you don’t tell them, then who will?” asked Whitney during an appearance on The Rachael Ray Show. “Kim Kardashian? Some porn star? Do you want Paris Hilton’s sex tape being your kid’s education?”

Whitney is now working on a film adaptation of the book The Female Brain by the American neuropsychiatrist Louanne Brizendine, which she is co-writing with Emmy-nominated writer and director Neal Brennan and directing herself. “It’s essentially about how our primordial neurology sabotages our everyday relationships,” Whitney explains. “Our reptilian brain has not caught up with modern times, so our survival instincts are at odds with our need and desire to feel safe and to love and be loved. It also explores the idea of how what annoys us today about our partner probably would have saved our lives 2,000 years ago.”

Then there is the pilot she is completing for HBO based on Are Men Necessary? When Sexes Collide, a collection of essays by Maureen Dowd, the redoubtable New York Times columnist, who told me she likens comedians such as Whitney (and her contemporaries Amy Schumer and Lena Dunham) who take on gender issues to “the soldiers who marched in front of Patton’s tank to check for buried explosives”. In the book Dowd ruminates on the changing playing field between the sexes now that traditional “masculine” pursuits are disappearing or becoming more gender-neutral and women are becoming more independent. Whitney – whom Dowd also called “talented, hard-working, generous, beautiful, smart, sexy, original and loyal” – says she can definitely relate to the thesis that successful women have a hard time finding guys. “Something happened when I got successful, or at least when other people ostensibly started thinking that I got successful,” Whitney says. “Guys started to get weird on me. It coincided with my turning 30, so I don’t know if it was that but I found myself really proud of achieving all my goals and living my dream but guys weren’t attracted to that part of me.”

It is an attitude on the part of men which makes no sense to her and which she will no doubt tackle head-on in the HBO pilot. In truth it makes about as much sense as a person with self-esteem issues submitting herself to constant judgment every time she steps out on a stage. Then again, Whitney is perfectly aware that becoming a comedian involves an element of mental illness. “I don’t want to over-pathologise myself,” she offers, “but it’s not a healthy vocation. It’s not healthy to feel the need to get up on stage every night and make people like you, to ask every 15 seconds, ‘Do you like me now? Do you like me now?’ It’s very masochistic. When people ask why there are so few female comedians, my only answer is that perhaps there are fewer female masochists.”