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Wendy Williams Dishes the Dirt

Wendy Williams sat on a plush red sofa facing a trio of L.E.D. screens, each of which showed a man who was vying to enter her tumultuous, open-book life. It was a February episode of her syndicated talk show, and the segment, “Date Wendy,” was the culmination of a monthlong search. Williams had on a tousled blond wig, yellow sneakers, and a stretchy patterned dress. “My hands are sweaty,” she had confided earlier, during the daily monologue that she calls “Hot Topics.” Met with reassuring applause, she suddenly teared up, and, as a stagehand proffered a Wonder Woman tissue box, she confessed, “No, I’m teary because I can’t believe I have a show.”

“The Wendy Williams Show,” taped live in the Chelsea neighborhood of Manhattan, is in its twelfth season, an eternity in daytime years. It averages more than a million live viewers a day, with hundreds of thousands more catching up online. Its audience—“Wendy watchers,” in the show’s parlance—regards the fifty-six-year-old hostess as an ultra-fabulous, in-the-know gal pal. Williams came to prominence as a radio jock, and she has a talent for talking to millions of people (her viewership is mostly female, but she also has a big gay following) and making them feel like they’re on a dishy phone call with a friend. “Traditionally, for women at home, watching a daytime-TV show is ‘me time,’ ” Alexandra Jewett, a programming executive at Debmar-Mercury, the show’s production company, told me. “It’s a very intimate experience.”

For “Date Wendy,” hundreds of suitors had been narrowed down to three. On the air, Williams addressed Bachelor No. 1, a jazz musician named Julian: “What do you do in your down time?” “I like to make sure this body—this temple—is up to par, so I love to work out,” he said, earning a smile from the hostess. Bachelor No. 2 was Mike, a contractor from Maryland with a bald head and a glass of white wine. “What’s your idea of a fun date with me?” Williams asked. Mike suggested ringside seats at a Lamar Odom celebrity boxing match. Bachelor No. 3, Tyrone, was a sultry-eyed security guard nearly twenty years younger than Williams. “Age really don’t mean anything to me,” he assured her. “If our vibes can connect, we can connect.” The studio audience—usually a hundred and forty screaming fans but, these days, a dozen socially distanced staffers—oohed.

Watching from the wings, a handler asked me which guy I thought Williams would choose. I said Julian, who seemed age-appropriate and sincere. Tyrone was sexy but too young, and Mike had some slimy lines that smelled like trouble. (“If you’re feeling the fever, I’ve got the prescription.”) After a commercial break, Williams called for a drumroll and announced her choice: Surprise! It was Mike, who danced around pumping his fists. She said that she would call him later that night.

Williams is an anomaly on daytime television. Unlike her competitor Ellen DeGeneres, she’s not a standup comedian, and, unlike Kelly Ripa or the women of “The View,” she doesn’t have co-hosts. She’s her own sounding board, capable of filling endless time with off-the-cuff, bawdy talk, delivered in a Jersey accent. Her rambling spontaneity is an antidote to the cheery polish of the “Today” show; she’ll interrupt a celebrity tidbit to tell a story about her weekend, then lose her place. She barely uses a teleprompter and won’t wear an earpiece. Although her show features such daytime staples as interviews, shopping segments (“[email protected]”), and advice (“Ask Wendy”), its core is “Hot Topics,” ostensibly a gossip roundup but really a kind of free-associative performance art, in which Williams riffs on celebrity divorces, pop-star feuds, and “Real Housewives” antics. “Her talent is being Wendy,” the CNN anchor Don Lemon, who has guest-hosted the show, told me. “She has this degree of comfort on television, like she’s sitting in your living room talking to you.” The audience acts as her confidantes and her Greek chorus—or, in the case of “Date Wendy,” her wingmen. You don’t have to know the people she’s discussing to be engrossed by her chatty, opinionated commentary, which converts even operatic gossip into relatable mini-dramas. Assessing the news that Kim Kardashian was keeping a sixty-million-dollar mansion after her divorce from Kanye West, Williams shrugged and concluded, “It’s best for the kids. The kids know the house.”

Williams’s style, in contrast to her casual tone, is glam bordering on camp. Where other daytime shows favor beige couches and houseplants, her set is hues of lavender and champagne. She is five feet ten, and her outfits are drag-queen bold. She rotates through about a dozen wigs, since a thyroid condition stemming from Graves’ disease has thinned her hair. It also causes her already large eyes to pop, as if in mid-epiphany. In the past few years, her personal life has been supersized as well. Last year, she finalized her divorce from Kevin Hunter, her second husband and her manager, after he had a baby with a longtime mistress, capping off a series of dramas—stints in rehab, unplanned hiatuses—that spilled into the tabloids and, inevitably, onto her show. In January, Williams released a pair of autobiographical TV movies on Lifetime, one a dramatization and one a documentary, which recast her travails as a journey of self-empowerment. In “Wendy Williams: The Movie,” she was played by Ciera Payton; in “Wendy Williams: What a Mess!,” the real Williams lay on a daybed in her apartment, sobbing as she narrated the same events, with the viewer in the role of best friend. Together, the movies represented a brazen act of pop solipsism, with the raw fury of a breakup album.

When I asked Williams if, as the documentary title suggests, she considers herself a mess, she smirked and said, “Yes, but a well-put-together mess.” It was after the “Date Wendy” episode, and she was in her backstage office in a street wig, sitting on a leopard-print couch beneath a bedazzled swordfish that was made by a fan. (“They’re real Swarovski crystals!” she said.) The dating contest, she insisted, was not a stunt. “I studied the guys very closely,” she said, peeling off her false eyelashes. “I said, ‘I want to date for the potential of this becoming my boyfriend.’ ” She explained that her final choice was practical: Tyrone was too young, and Julian, the jazz man, would be on the road all the time. “How do I know that he’s in Turkey with a one-month residency and not screwing around?” she said. Mike runs his own successful business, “so we can both sit in first class, and we both know what fine dining is.” She added, “But that’s not what I want all the time. I like the cheesesteak from around the corner as well, and I like to eat it in bed.”

We took a black S.U.V. to her apartment, in the financial district: sleek black walls and crystal chandeliers, accented with colorful glass figurines, animal prints, and antique urns. “Chaka Khan did that for me for my fiftieth birthday,” she said, pointing to a painting depicting her and her ex-husband as a mermaid and a merman. Last spring, after her studio shut down because of the pandemic, Williams hosted “Wendy @ Home,” an abridged edition of her show, from her dining-room table, introducing viewers to her cats, Chitchat and Myway, and to her life-size Betty Boop statue with painted-on black skin. The results were so lo-fi absurd that John Oliver devoted a segment to the show on “Last Week Tonight,” calling it “an oasis of truth in a world full of lies.” He delighted in the “weirdly dominant manner” in which Williams ate a lamb chop. Nevertheless, Williams pulled the plug on the home edition after seven weeks, citing fatigue from Graves’ disease. But she told me that the experience had felt intrusive, even unsafe: “Anybody could be watching to case the joint.”

As we talked, she laid out supplies for a craft project: a tube of Krazy Glue, a glass case that was left over from a flower delivery, and four crystal cabinet knobs, souvenirs from the New Jersey house that she used to share with Hunter and their college-age son, Kevin, Jr. She wanted to attach the knobs to the bottom of the case as legs, place inside it a Supreme-branded wrench that her son had bought her, and display it as a design object. She took off her shoes and stuck out a bare foot, which, owing to lymphedema, had become swollen and gray, “like an elephant.” (She no longer wears heels, and her walk is a tentative shuffle.) She talked non-stop—about pandemic dating, about fans who make her hold their babies—in what felt like a seamless extension of her show. After a while, she returned to her Krazy Glue, which had hardened in the tube. “I’m not doing this tonight. I’m tired! ” she said. “How dare you, Krazy Glue?” Exasperated, she held up her half-finished objet d’art and said, “But you see where I’m going with this?”

Weeks later, Williams was in her makeup chair at 8 A.M., wearing a turban and a black robe. A television tuned to local news mumbled overhead, and her makeup artist, Merrell Hollis, dabbed at her cheeks. “Me and Jones had such a good time this weekend,” Williams said, recounting a girls’ day out with a former radio colleague (and onetime rival) known as Miss Jones. “Some people remember that we weren’t getting along, but we weren’t getting along because Kevin was, like, ‘Fuck her.’ When I opened the door, we had our masks on, but we hugged.”

“First, the dishwasher broke—now we have an insane boulder.”
Cartoon by Bruce Eric Kaplan

Hollis mm-hmmed as Williams explained that they had gone to two different steak houses: first to Peter Luger, in Brooklyn, then to the Strip House, in Manhattan. “That was the spot,” she said. “The men were everyplace. The ladies looked really beautiful. But we were definitely outnumbered. And all you smelled was garlic and money.” She assured Hollis that her salad, which she had Instagrammed, wasn’t only lettuce: “There was seafood, extra crumbles of blue cheese. We had so much food that we had bags and bags to take home—only for me to ask for the check and find out some man paid already.”

“Aw, ‘Sex and the City’!” Hollis cooed.

“My boobs looked really good,” Williams continued. “And we were home in time for the eleven-o’clock news.”

Hollis touched up some shiny spots. “What else happened over the weekend?” Williams asked herself, then gasped. “Nicki Minaj’s mother is suing!” It was a classic “Hot Topics” segue. On TV, Williams re-creates the laid-back rapport of a woman talking to her makeup artist. Watching her in the mirror, I realized that she was trying out material on Hollis, honing anecdotes and sharpening opinions.

“Mike is coming to town on Wednesday,” she said, as Hollis applied eyebrow pencil. It had been four weeks since “Date Wendy,” and she and Bachelor No. 2 were becoming an item. “Dr. Oz invited me for dinner, and so I text him back, ‘Can I bring a friend?’ So Thursday night is dinner at the Ozes, with all the kids running around. It’s a really beautiful scene. Plants. Servants. Not even housekeepers—servants, you know, with the clothes on. But all with a smile. And I didn’t tell Mike where we’re going.”

When Williams was done in makeup, she consulted with the rest of her glam squad, Jazmin Kelly (wigs) and Willie Sinclair III (wardrobe). Sinclair had pulled a pleated Kenzo dress and white Stan Smiths, an ensemble that he described as “very simple, very spring, very light.” Kelly, whom Williams called “an evil-brilliant wigologist,” had paired it with an “effortless” wavy do, dark with golden highlights. She told me that each day she imagined Williams’s look as that of a different character. Today’s was “a woman who shops at Bergdorf’s,” Kelly said. “She doesn’t have a job, and she’s fab. It’s the lady that lunches, dahling.”

Out on the set, three producers gathered for the daily “Hot Topics” briefing. “Boss is walking,” someone said, as Williams approached. She sat on a tufted purple chair, from which she presides each morning. “So, weekend talk,” a producer named Jennifer Brookman began. “I know you were with Miss Jones.”

“And that wasn’t just a salad full of lettuce,” Williams interjected. “That was a monstrosity.” David Perler, the showrunner, had new pictures of Mike to display. “The paparazzi was outside my house again today,” Williams said.

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