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.)