The Washington PostDemocracy Dies in Darkness

Wendy Williams made a lot of enemies in radio 20 years ago. Now she’s a daytime-television staple.

Wendy Williams answers questions before a live audience at The Fillmore in Silver Spring, Md., on July 31. Williams will celebrate her talk show's 10th season premiere on Sept. 10. (Marvin Joseph/The Washington Post)

When Wendy Williams unceremoniously left New York’s legendary Hot 97 radio station in 1998, it was under a cloud of drama. The shock jock had made some enemies of the very culture she was covering. Sean “Diddy” Combs — then known as Puff Daddy — whose songs ruled the airwaves, allegedly played a part in her dismissal. In some ways, she had become part of the music herself: Tupac Shakur’s “Why U Turn On Me?” crudely refers to Williams by name.

While that might have been the end of some people’s careers, Williams, 54, endures. Twenty years later, she is preparing to launch the 10th season of “The Wendy Williams Show,” her nationally syndicated daytime television talk show. Averaging more than 1.8 million viewers an episode last year, according to Nielsen, the former radio host is now interviewing some of the same stars — like Combs — who once entered her crosshairs.

It is an impressive display of staying power for the New Jersey native, whose brash takes on hip-hop culture and celebrity gossip lit up urban radio airwaves in New York and Philadelphia during the 1990s and early aughts.

Williams grew up middle class in Ocean Township, N.J., and began her on-air career early at Northeastern University’s on-campus radio station.

She’s talked about skipping class to intern with legendary Boston radio personality Matt Siegel and how she made $3.25 an hour at a radio station in St. Croix, Virgin Islands, the only on-air gig she could land straight out of college.

By 2008, the year that Lionsgate-owned media company Debmar-Mercury teamed up with Fox to put Williams on TV in a six-week summer trial run, she was the host of “The Wendy Williams Experience,” a syndicated radio show that reportedly reached more than 12 million listeners at its peak.

“I view her as one of the all-time great radio personalities — someone who essentially redefined the medium,” said Bill Stephney, a former Def Jam executive and Public Enemy producer, who also began his career in college radio.

Television executives say they were attracted to how outspoken Williams was and how her fans seemed to hang on her every word.

Ira Bernstein, co-president of Debmar-Mercury, remembers accompanying Williams to an early meeting at Fox and discovering firsthand — while walking just a few blocks — how popular she was.

“As we’re walking, literally cab drivers, doormen, Con-Ed workers were yelling ‘hi Wendy,’ ‘hi Wendy,’ ‘hey Wendy,’ and she would say ‘hi’ back,” Bernstein recalled. “She’s on the radio, and people are recognizing her.”

Still, that was in New York, where she was best known. A lot of people, including advertisers and station owners, were skeptical of her ability to appeal to wider television audiences, and even Bernstein admits it took a few seasons for Williams to find her footing.

But he said it was clear from the very first day of the test run that she had something special.

In the years since, Katie Couric, Harry Connick Jr., Anderson Cooper, Bethenny Frankel and Jeff Probst have all bid farewell to daytime talk shows, but Williams remains.

“Ten years later, we don’t really have too many skeptics left,” said Mort Marcus, also co-president of Debmar-Mercury. “She is really good at what she does.”

Even potential politicians have taken notice of her scope: It was Williams who landed the first nationally televised interview with Cynthia Nixon, the former “Sex and the City” star who announced her run for New York governor in March.

“We knew that by doing Wendy’s show — which reaches all corners of the state — we could get Cynthia in front of a diverse audience and introduce them to the real her,” Rebecca Katz, a senior strategist for Nixon’s campaign, said in an email.

“[Williams] pulls no punches and her audience trusts her,” Katz added.

Indeed, comedian Billy Eichner has called her “the only journalist I trust,” and used his own viral show, “Billy on the Street,” to prove her influence in his community. In one episode, Eichner walks through New York’s Chelsea neighborhood asking gay men if they care about HBO’s “Last Week Tonight” host John Oliver, who happens to be standing beside him.

“Who’s John Oliver?” one guy replies.

“Do you like Wendy Williams?” Eichner asks him, in response.

“I love Wendy Williams,” he says.

If "Ellen" is a dance party, "The Wendy Williams Show" is an actual party. Her co-hosts whoop during the theme song and try to pull off Williams's trademark greeting, which she developed in her radio days. The host narrows her eyes, opens her mouth slightly, placing her bottom lip into a sort-of downward curl and perches her hands in midair — like claws at ease — and asks, in a sultry voice, "How you doin'?"

There was plenty of “How you doin’?” happening at the Fillmore Silver Spring in July. Williams was in town kicking off a multicity tour to celebrate her show’s milestone season.

The crowd was primarily made up of black women who, like the woman they were there to see, were in full glam mode despite the heat. Inside, there were purple disco lights, pink chandeliers and “Glam Squad” staffers directing fans to free hair, makeup and nail stations as a DJ played thumping music.

Williams’s fans, to whom she refers to as her “co-hosts,” describe her as “real” and someone who says what other people won’t. She can be strikingly open about her personal life.

She’s confronted on-air rumors about the alleged infidelity of her husband, Kevin Hunter, who is her manager and an executive producer on the show (“You can believe what you want,” she told a TV audience before holding up her massive diamond wedding ring). And after fainting on-air last year, a terrifying incident that prompted her to take a three-week leave from the show, she opened up about her battle with Graves’ disease.

So when she took the stage in Maryland, Williams talked about her family foundation’s recently launched “Be Here” campaign, geared toward helping those struggling with substance abuse get treatment, a cause close to her heart. She struggled for years with a cocaine addiction and recently talked about her teenage son’s frightening run-in with synthetic marijuana three years ago.

But it wouldn’t be a Williams event without some entertaining straight-talk, so she took fans’ questions in a live version of the advice-driven “Ask Wendy.”

She offered an emphatic “no” to the 25-year-old man who wanted to know if he should introduce his boyfriend to his big Greek family after just three months of dating.

To the woman wondering if she should keep sleeping with her much younger brother’s friend, Williams said yes — but not to let him sleep over because she would fall in love with him.

“Thank you all for adoring the show,” Williams later told the crowd. “I’m as messy as you are, I always feel like you all know your own answers already.”

While Williams's success in radio is undeniable she was inducted into the National Radio Hall of Fame in 2009 her tenure is most remembered for her incendiary rhetoric. As an on-air personality, Williams earned the ire of many celebrities. Pop diva Mariah Carey immortalized Williams's in-your-face approach in her 2008 hit "Touch My Body" (" 'Cause they be all up in my business like a Wendy interview").

Her sudden exit from Hot 97 has long been the subject of hip-hop lore. A New York Magazine profile noted Williams “liked to insinuate that certain rappers, despite their macho posturings, were gay.” Shakur and Combs were both reported targets, as well as A Tribe Called Quest’s Q-Tip, who was the then-boyfriend of Williams’s Hot 97 colleague, Angie Martinez. Martinez wrote in her 2016 memoir “My Voice” that she nearly came to blows with Williams after Williams published a blind item in the ’90s suggesting Tip was one of the “men who like men.”

She had public fallouts with other peers, too, including her former protege, Charlamagne Tha God, who said in his 2017 book “Black Privilege” that he and Williams stopped speaking after a business dispute with her husband.

Williams’s successful TV series has consequently put her face-to-face with some of her former adversaries.

“It’s been a long time coming,” Combs told Williams after she welcomed him to the show in June 2017. “And I want to just tell you how proud I am of you because I don’t think you get enough credit for really being the first one to cover our culture — you know, the hip-hop culture and also hip-hop celebrities — and just understanding that it’s news.”

While her show and its marquee celebrity gossip segment, “Hot Topics,” almost never veer to the extremes of her radio days, having that open platform has sometimes gotten Williams in hot water.

In January, she drummed up controversy when she declared she was “sick of this Me Too movement” and said R&B singer R. Kelly, who for decades has been accused of sexual misconduct, “wasn’t a Me Too,” and that one of his alleged victims, a 14-year-old girl, “was there at his house, she let it go down.”

One of her most visible critics was activist Tarana Burke, who founded the “Me Too” movement in 2006.

“It is disgraceful that as wide as your audience is and as many young girls, many Black girls watch your show that you would openly victim blame like you did yesterday,” Burke tweeted. “You are the reason why we can’t make headway in our community around sexual assault.”

Asked if she felt her comments were more sympathetic to R. Kelly than his alleged victims, Williams echoed something she told viewers on her show.

“I feel like I know things about R. Kelly that he’s told me himself that I promised I would keep in confidence,” she said in a recent interview in Washington. “When I make a promise about keeping something in confidence, I do. And that’s that.”

Bernstein, reflecting on the show’s general willingness to tackle controversial subjects, said Williams “has never done anything that’s crossed a line for an advertiser or . . . the TV stations.”

“Nobody’s perfect, but she’s been pretty close to perfect now going on 10 years,” he added. “That’s pretty amazing for a shock jock that converted to TV.”

The ability to be unfazed by critics or critiques is one that makes Williams stand out.

“I’d never seen such a strong, unique, opinionated voice in a daytime host,” said “Wendy Williams Show” executive producer David Perler, who has previously worked with Rosie O’Donnell, Bonnie Hunt and Tony Danza.

“She’s not scared if someone comes on and says to her, ‘You said this about me,’ said Melissa Rivers, the daughter of the late comedian Joan Rivers, who was a frequent guest in the show’s early days. “[Williams] will be like ‘Yeah so, is it true?’ There’s a lack of pretense. You never feel like she’s sitting there going ‘I’m above you.’”

Williams’s colleagues say her knack for holding an audience’s attention while talking for long stretches is one of her biggest strengths — and sets hers apart from other talk shows that tend to have panels or field segments to fall back on.

As Williams tells it, that’s the crux of her show — just sitting there, talking to her fans. And she’s got a lot more of them these days.

“I’ve been being me all along, but the people watching now — they gave me a chance,” Williams said. “You need more than a year to grow on somebody, and it’s very intimate being invited into people’s homes everyday. Once that trust is built then you’re like that old friend. That’s the sweet spot.”

Taylor Telford contributed to this story.