How New York’s Shock Jockette Got Supersized

It’s a few hours before the start of her WBLS radio show and Wendy Williams, who calls herself the Queen of Radio, is in tears. I can’t quite figure out why. We’re sitting in the eighth-floor lounge of the Times Square Marriott Marquis, deserted at this time of the morning, the way Wendy likes it. Just a minute ago, she was describing her big hair, her big green Gucci bag, her big jewelry, her big new breasts—with Wendy, who’s nearly six foot, everything has to be big. She seemed ebullient, celebratory. “I have arrived,” she was saying, and showed me a diamond-encrusted ring as big as a radish. “I’m beyond the velvet rope.”

It’s true. Wendy has definitely arrived. She is lately a dominant force in New York afternoon radio. Recently, she even snagged the No. 1 rating in the key 25-to-54-year-old demo, a feat she thought impossible. LiteFM, perennial king, is everyone’s office background. And Wendy’s not background. You have to listen to Wendy. She hardly plays music. She tells stories. She repeats gossip. She describes her own plastic surgery and gleefully critiques others’. (“Two baseballs on a stick” is her description of Whitney Houston’s results.) What won’t Wendy say? “Threesomes need to be talked about,” she declares. Once, she had Rick James on the phone when she discovered he was in the midst of a three-way. (“Is one of the girls wearing a strap-on?” Wendy wanted to know.) Another time, Whitney Houston phoned, “slumming” on radio, as Wendy says, to promote a CD. Wendy leaped: How did Whitney tell her daughter about her husband’s jail date? Whitney flipped, firing off expletives. “That interview was No. 19 on the E! Network’s 101 Most Shocking Moments,” says Wendy excitedly. “I beat out Richard Pryor setting himself on fire.”

And yet, as she sits on a cushiony hotel chair, fat, anomalous tears sweep across Wendy’s adorable, Botoxed face. She chases one with a fake cotton-candy-colored nail. It’s not an isolated outburst. Over a couple of hours, she wells up four, five times.

“Why the emotion?” I ask at one point, confused.

Wendy pauses, which is rare. “There are … wars in my head,” she confides.

“Radio wars?”

“Not so much,” she says. Wendy is 40 (though she doesn’t like to admit it) and has been in radio for two decades; radio she can handle.

“Then what?” I can’t imagine.

To her fans, she’s the black Howard Stern, uproarious, freewheeling, fearless; egging on Whitney, jumping in with Rick. Her show is syndicated in half a dozen markets. She’s coming out with a novel next June from Random House. If that’s not enough, there are Wendy’s two New York Times best sellers, including a tell-all memoir; a show on VH1; a CD produced for Virgin. All of it propelled by the outrageous and seemingly unflappable radio persona, the one she assumes every afternoon. “I stay true to the Wendy,” she assures me. “The craziness.” And yet in Wendy’s head, it turns out, there’s another persona—and another voice, a less brassy, less assertive one, impertinently trying to get out. This one is Wendy from Jersey, daughter of Tom and Shirley, middle-class schoolteachers who were sometimes disappointed by their talkative daughter. In the hotel lobby, Wendy tries to explain, “More was expected of my big sister than of me. And while she’s fabulous and she delivered all the goods, I ended up being fabulous, too, and delivering all the goods.”

Is it possible? The self-confident Queen of Radio is, after all these years, still desperate for her parents’ approval.

Wendy is determined to stay true to her over-the-top brand, to “the Wendy,” as she’s taken to saying. And yet she also wants it known that she still lives in Jersey, drives her son to school, attends his class trips; that she’s an eager-to-please suburban daughter determined to measure up to her parents’ exacting standards. “I’m still managing to be traditional,” Wendy quietly assures me. “You know, the kid, the husband, the house, the morals.”

It’s quite a conflict.

“Every day is a struggle to hold it all together,” she says and wipes a tear from the corner of her eye.

Inside her green Gucci bag, Wendy’s cell phone rings. She’s got to get to the studio. Wendy slides behind the wheel of her Mercedes, a $100,000 SUV as shiny as patent leather. Kevin Hunter, Wendy’s husband and manager, occupies the passenger seat, quietly taking phone calls. There’s traffic, and Wendy impatiently works the horn. She’s running behind, which she hates. (Once, traffic snarled in the Lincoln Tunnel; Wendy abandoned her car and walked to the studio.) Casually, Kevin mentions that it’s her production director’s birthday today, and maybe a lunch is in order. Suddenly, the well-behaved suburban daughter is nowhere to be found.

Williams with her parents: "She was always a success," says her dad, "in her own special way."Photo: Courtesy of Wendy Williams

Wendy shouts, “When people have birthdays, how does that affect my bottom line? I’m not Howard Stern. He can buy lunch every time there’s a birthday. We’re the little engine that could. The thing to do is to work hard so you’re here for your next fucking birthday.”

Wendy pulls up to the studio, turns the car over to Kevin, and a few minutes later slides into the big seat behind the microphone. She tells her production director preemptively, “I know it’s your birthday.” He’s sensed Wendy’s mood. That’s part of the job. “A bipolar day,” he says later. He’s not pushing anything.

It’s 2 p.m., time for “The Wendy Williams Experience,” as her show is called. Wendy leans into the mike. “Welcome to the mess,” Wendy tells her 781,000 New York–area listeners.

As a youngster, Wendy did not seem destined for success on the radio, or anywhere else. She grew up in Wayside, New Jersey, an upper-middle-class part of Ocean Township, one of four black students in her class, and one of the heaviest of any race. Wendy tried to follow her mother’s advice: yogurt, yogurt, yogurt! But by the sixth grade, she weighed 149 pounds. “That’s not a good look,” notes Wendy. A more serious infraction was that in a household of academic achievers, Wendy was a flop. Between them, Wendy’s parents have three master’s degrees. Her father, a junior-high-school principal, taught English literature at college. “My father is always quoting Shakespeare,” says Wendy. “I call it crazy, but in actuality, it’s intellectually just over my head.” Wendy’s media of preference were The Love Boat and The National Enquirer. She graduated 360th in a high-school class of 363. As she puts it, “There were three people academically stupider than me.”

These days, Wendy’s parents can’t remember anything negative about Wendy. “She was always a success,” says her father, though he delicately adds, “in her own special way.” To Wendy, it seemed different. “I was the thing that did not fit in my family,” she says. Especially in comparison with her perfect older sister, a soft-spoken, straight-A student (and a size 6!) who graduated law school the same year Wendy (barely) graduated high school. To Wendy, it seemed that her parents (and her older sister) walked around with one concern utmost in their minds: “What will become of Wendy?”

Fortunately, Wendy discovered that with a microphone in her hand, life improved. “The best thing that could have happened to me was I found that microphone,” she says. Her parents didn’t particularly like the idea: A D.J. was déclassé. But Wendy knew she was a gifted, entertaining talker, even if, for her parents, Wendy’s motoring mouth could seem excessive. (“I used to tell [her], ‘Wendy, shut up!’ ” says her father.)

Even as a child, Wendy had what she calls “futuristic vision,” an ability to plot the future, her future. She was the girl who walked around with a to-do list and a plan. “If you asked her twenty years ago what was her twenty-year plan, she had it,” says her best friend, Lisa Carnegie, whom she’s known all her life. In high school, she started to announce her younger brother’s Little League games, gleefully embarrassing him. By college—Northeastern University accepted her as “a wild card,” Wendy says—she’d turned to radio. Some afternoons, she caught the train from Boston to Grand Central just to listen to her favorite D.J.’s. In Boston, she got herself an internship at KISS 108. The job mainly involved placing contest sheets in front of Matt Siegel, known as Matty in the Morning. To get his attention, she tricked herself out in rhinestones, then sashayed into the studio when the mike was on. “Virtually everything in my life I have plotted on to get it,” she says. “Nothing has happened by fluke.” Siegel asked about the outfit. Wendy answered alluringly, “Dynasty,” referring to the TV show. Soon Siegel invited Wendy to review the evening’s television offerings on the air.

Her first real radio job was in St. Croix in the Virgin Islands, a good career move, though a lonely time. Next, she took a job in Washington, D.C., where she started to dabble in cocaine, a habit she took to New York at Hot 97, where she was a fixture by the mid-nineties.

New York, as she knew, was the place to be. “When you live in New York, you don’t give a fuck about what anybody else is doing,” she says. At Hot 97, her style gelled. Like everyone else, she’d started by playing music. The D.J. voice was smooth, easy, quiet-stormish. By the time she reached Hot 97, hip-hop was taking over popular culture, and with it a more raucous vibe, one that fit Wendy’s inclinations. Wendy told stories, happily gossiped about rap stars’ intimate lives. (Later, she’d interview Puffy’s baby’s mama; she’d ask Lil’ Kim about her nose job, Foxy Brown about her miscarriage.)

Meanwhile, she upgraded her exterior. “In my mind, I’ve always been fabulous,” she says. She’d long planned to be fabulous on the outside too. She’d grown up, as she puts it, “a fatty A-cup,” which wouldn’t do. “I want more. I want it bigger. I want it Wendy,” she says. (If she were a guy, Wendy figures, she’d have been a drag queen.) When she first got implants, she bounced excitedly up to her oldest friend Lisa. Lisa is naturally endowed. “Dammit, I need them bigger,” Lisa remembers her saying. She’s got D-cups now, though she wears a smaller bra for what she calls the “muffin breast” look, spillage over the edges.

Wendy had liposuction, too. She was sick of fighting chunkiness, even if it was celebrated. (On one song Tupac Shakur said of Wendy, “I’ll put Jenny Craig on your fat ass … Why you always wearing spandex?”)

While Wendy was at it, she rid herself of other excesses, like her first husband. She didn’t talk it out with him. Wendy was the woman with a plan—“to the nth degree,” as her sister says. After he left for work, she divided up their possessions and hired two moving vans and a locksmith. He’d figure it out.

For Wendy, everything was going well, and then in a moment it changed. In 1998, Hot 97 ignominiously booted her. There were reports that Wendy had been in a fistfight with another female D.J. (untrue, says Wendy). Certainly she had energized enemies. “Did Puffy have a hand in it? It is my belief,” she says. At Hot 97, Wendy liked to insinuate that certain rappers, despite their macho posturings, were gay. (Now she’s more subtle. Say a celebrity’s name. Then ask “How you doin’?” in a low, seductive voice. That’s the code.) Puffy was among those who came in for some innuendo. (So had Tupac.)

“Oh, yes, I was left on the side of the turnpike for roadkill,” she says. Wendy has no illusions about human nature. Most people, seeing a wreck, hold up their camera phone. “People rolled right past me, and I understood that,” Wendy says.

She limped out of New York and took a part-time assignment with Power 99 in Philadelphia. “I had no idea really what they did there,” she says. They knew her, though, which was not an advantage. Most (70 percent, according to one survey) hated her. Wendy has never minded being hated—a caller could say, as one did, “You look like a dude.” Wendy retorted, “But you’re listening.” Once they listened, Wendy had a knack for connecting. She offered up herself to her audience, shared every personal detail. By the time she left, listeners had cried with her through two miscarriages and the birth of a child.

By 2001, she’d helped Power 99 move from fourteenth to second place with 18-to-34-year-olds, and WBLS offered Wendy a chance to return to New York.

“I have arrived,” said Williams, showing me a diamond-encrusted ring as big as a radish. “I’m beyond the velvet rope.”

Wendy and Kevin, her second husband, scheduled a little business meeting. Kevin is a big, forceful man with a shaved head and a bunch of tattoos. Tom and Shirley had hoped for a college-educated fellow, a Carlton Banks type in khakis. Kevin had owned a hair salon, promoted parties. He wears to-the-knee basketball shorts; sometimes he addresses Wendy as Yo. But when he met Wendy, Kevin was, as a friend put it, “still hungry. He wanted to climb, to make it,” just like Wendy. He became Wendy’s manager.

About New York, though, Kevin hesitated. Philadelphia had been good to them.

“We’re fine right here,” said Kevin.

Wendy was earning $275,000 annually; she wanted more. “I’m ready to give New York another shot,” she said. At WBLS on Park Avenue South, Wendy’s studio is as glamorous as the inside of a UPS truck. The ceiling is low, the carpet stained, the plants fake. Wendy has a view of the East River, though she doesn’t look at it much. She focuses on her audience, the one she’s assembled in the studio: four black college girls who work as interns.

“Muses,” explains Wendy’s executive producer, Artie Evans, a former intern himself. They run for coffee and, sometimes, for Wendy’s hair clips, but mainly they stand in a clump against a wall. “When I look at you, give me a yay or a nay,” Wendy advises one intern. She wants to hear them—an oooh or a laugh, though not too much. Artie recalls his first attempt to talk to Wendy. “How are you?” he’d asked. Wendy rolled her eyes. “I don’t need no fucking mood check,” she told him. And so Artie has considerately issued guidelines to the interns. Don’t speak to Wendy unless spoken to. Don’t stare at Wendy when she’s on the mike, which makes her uncomfortable. In fact, don’t look Wendy in the eyes unless she looks at you.

Wendy is aware of her eccentricities. “Don’t make it sound so Michael Jackson,” is what she says. Doesn’t she deserve it? “It’s all on me,” Wendy points out. “At the end of the day, it’s not on anybody else.” It’s true. The show has a few standard segments, but it’s mostly unscripted; there are no show meetings. Much of it can seem unproduced. Occasionally there’s dead air. Wendy’s cell phone rings, twice during one show. (“Somebody’s calling who doesn’t know I’m Wendy Williams,” comments Wendy on-air.) Sometimes guests stop by. Sometimes Wendy lets Artie, a foot fetishist in addition to executive producer, suck their toes. Inevitably, she probes their sex lives (and eagerly awaits their departure so she can talk about them). The rapper Q-Tip is asked if he slept with Nicole Kidman. Porn star Jenna Jameson is asked if she prefers guys or girls. Singer Erykah Badu tells about her three boyfriends. Listeners, too, call or fax about their sex lives. One afternoon, Wendy takes up the matter of the listener with the fourteen-inch “Richard.” It’s perfect Wendy material, titillating and freakish, and Wendy ponders it with the utmost seriousness. “I couldn’t get soft and pink,” she decides. “I don’t want that tapping on my back every night.”

To keep the show working every afternoon, Wendy knows she has to keep her head tuned just right. Thus, the chorus of interns and their rules of conduct. There’s another crucial element. She must keep the wars in her head quiet, and so she must banish from her mind—“block out,” she says—the idea of her parents, the one she otherwise wants hovering over her life. If not, Wendy just might lapse. Instead of giddy, salacious Wendy with that ticklish low laugh, listeners might find well-behaved Wendy, devoted mom, steady wife, respectable daughter. Good life, but bad radio.

Her father, Tom, has appeared on Wendy’s show and talked about his novel. “I’d like to take the microphone myself,” he confesses. (Her sister wants anonymity—“Act like you don’t have a sister,” she told Wendy; but Wendy’s younger brother stopped by. He wanted to talk about early experiments bottling farts. Wendy sometimes shut off his mike.) “We are 100 percent behind her,” says mother Shirley, who’s read Wendy’s books, though Wendy refuses to discuss them with her. “We have had to broaden ourselves and have a more open mind,” says Shirley loyally.

Wendy’s parents live in Florida, where the show isn’t available. Recently, Wendy heard that her syndicators were working to get a Florida station onboard. “Oh boy, there goes the product,” she says.

One afternoon, Wendy sets her green Gucci bag next to the microphone and takes a call. She’s in a black Mossimo running suit, actually two; she had to buy two and extend the legs so they’d fit. The caller is a woman whose boyfriend married another woman because she couldn’t have children—“for convenience,” she says. He kept her on the side. Now, to the caller’s shock, she’s pregnant. Wendy may be the first person she’s told. “I just found out two hours ago,” she says, as if Wendy might keep the news to herself. For all the show’s “scandalosity,” as Wendy likes to say, listeners turn to Wendy for advice. “In my mind, Oprah is my big sister,” Wendy says. Wendy, though, is a sterner version. Empathy isn’t a given. Wendy’s outlook is more the unyielding self-improver. Teen pregnancy, for instance, is almost incomprehensible to her. “No baby was going to stand in my way,” Wendy says. Unintentionally pregnant (as an adult), Wendy chose an abortion.

Most of Wendy’s callers are women caught between a man’s actions and his promises. Wendy has been there. She may be steely in her determination, but she is at the same time ever vulnerable. And since with Wendy there’s no line between public and private, everyone knows. Kevin cheated on her while she was bloated and bedridden with their baby. Wendy has dealt with it. In part she understood; in part she wanted to kill him. (As an alternative, she hired a private detective.) “I have moved on,” she says. Wendy’s listeners often seem stuck. Many don’t have plans, except to wait it out.

When the caller asks if she should wait out her boyfriend’s marriage, Wendy almost can’t believe it. There’s a snarl in her voice. “He doesn’t want you,” she says. “He’s lying to you. Get your child support and go.”

Wendy’s harsh judgments aren’t reserved just for callers. On Wendy’s show, celebrities should behave responsibly, too. Wendy is a gossip and a moralist. That’s Wendy’s beef with Whitney, lately one of the show’s thematic backbones. Whitney is the un-Wendy. Wendy planned and plotted to get where she is. Whitney is the immensely talented woman who let her gifts dissipate. Wendy wants to be kind to Whitney, a sister in the struggle against drugs. Wendy has studied Being Bobby Brown, the reality-TV show about Whitney and her husband. “I like her,” Wendy offers tentatively about Whitney, but can’t pull it off. Wendy mentions Whitney’s round “crack belly,” imitates the sound of her getting high, and—this really gets to Wendy—notes Whitney “smoking [cigarettes] in the car with her kids.”

Wendy from Jersey—she lives near Montclair now—doesn’t smoke. She worries that her 5-year-old might not get into the right elementary school, and so reflect poorly on her parenting. Indeed, Wendy, despite the raunchy talk, is a purveyor of middle-class values, a sneaky vehicle for Tom and Shirley’s suburban virtues. She may bring the Wendy, but, really, she wants listeners to know she’s respectable. And they should be, too. No wonder Wendy leans into the mike at the end of a segment and dreamily says these words: “Finally maybe I can get a bit of what I deserve after a long hard career and finally get my parents’ approval.” She eyes an intern, who doesn’t know whether to laugh.

How New York’s Shock Jockette Got Supersized