The Misrepresentations of Wendy Williams’ Undeniable Legacy

Between the rise of the #FreeBritney movement and the plight of Star Trek’s recently departed Nichelle Nichols, the last two years have shined a spotlight on the complicated nature of conservatorships that shockingly often lacks oversight, given the level of power afforded. (A conservatorship is a legal arrangement in which an individual or group of people are given the authority to manage the welfare and finances of someone who is seen as unfit to care for themselves.)

After revelations about Britney Spears’ struggles in her 13-year conservatorship, the media industry and general public responded with outrage and reflection about their complicity. On a rundown of “Hot Topics” during a June 24, 2021 taping of The Wendy Williams Show, the eponymous host was discussing the disclosures that had come out of Britney Spears’ public testimony to the Los Angeles Court on her conservatorship. “The rehab that they forced her into,” Williams remarked, “the paparazzi was there every day.” Her tenor then subtly changes, a well-known calling card for longtime fans of her daytime program who are used to her abrupt tonal pivots. “How dare you, Mr. Spears. You had me fooled. And you, too. Mrs. Spears. Death, to all of them.”

The growing awareness of exploitative conservatorships seemed to indicate that their hold on troubled female stars would be under harsher scrutiny. But the uproar seems to have dissipated in the case of Wendy Williams, who was put under financial guardianship by Wells Fargo earlier this year. Compared to the frenzied focus on Williams’ personal life just a few years ago when her marriage dissolved, the response was muted in the mainstream. Where was the cavalry for one of the biggest names in daytime TV and radio history?

A genuine trailblazer in multiple media formats and the New Jersey stepchild of Howard Stern, Oprah Winfrey, and Joan Rivers, 58-year-old Williams’ imprint is found everywhere in pop culture. She is referenced in dozens of rap and R&B songs, including the seminal Mariah Carey line in “Touch My Body,” in which Carey croons, “’Cause they be all up in my business like a Wendy interview.” One of her wigs and a pink bedazzled Ask Wendy microphone, among other artifacts, are on view in the Smithsonian’s National Museum of American History television collection, positioning her alongside icons of American television such as Seinfeld, All In the Family, and Susan Lucci. In 2019, she received a star on the Hollywood Walk of Fame. One of the biggest personalities in radio, Charlamagne tha God, was mentored by Williams and co-hosted her radio show, The Wendy Williams Experience. “She taught me… you’re either going to be of the people, or of the industry,” Charlamagne told DJ Vlad in a 2015 interview. "When you’re of the people…You’re going to speak the views of the people. You’re not going to be afraid to express the regular opinion that any fan of this culture would.”

It was this precise commitment to “the people” that kept Williams' loyal audience watching. When she commented on Spears’ conservatorship in June, the live reaction was so visceral that Williams even shocked herself, gasping in astonishment alongside her studio audience. While Williams has established a legendary reputation as a prodigious agitator of celebrity life, the impetus for this reaction seemed to have a different inflection point: It was rare for Williams to admit she was wrong about anything. She had been party to many indefensible moments over her years at the helm of a syndicated daytime talk show, including a series of particularly contemptible remarks regarding R. Kelly’s survivors. However, Williams had recently come out of her own experience under the glaring eye of the paparazzi flash lens: In March of 2019, she revealed to her audience that she had been living in a sober house on the heels of her 21-year marriage being torn apart by infidelity and a child out of wedlock. Williams had gone from shaping the story to being the story.

Wendy calling for the death of Spears’ conservators and their enablers was scrubbed from future airings of the episode, but true to the immutable laws of the internet, the omission merely triggered the Streisand effect, entrenching it into the annals of lovingly curated compilations and meme collections. That instinct of fans to maintain stewardship over William’s best moments would serve them well: Currently, The Wendy Williams Show is no more. It ended while she was still on extended health leave since July 2021; as the program wrapped, so did its archives. Production and syndication company, Debmar-Mercury, swiftly decommissioned the show’s website, Instagram, and YouTube, to the fury of many longtime fans. Williams said she was not asked to contribute to the final episode, and disapproved of the unceremonious coda to her show’s 14-year run, but held no animosity towards the production team. While it may have been what best behooved the network to retain their production schedule, it was a complete misrendering of what made the show great; a collection of clips and moments in time devoid from the human touch that animated them.

Williams’ time as a radio shock jockette of The Dream Team with Dee Lee and Colby Colb in Philadelphia was groundbreaking. She created a uniquely intimate space among her listeners, shattering the artifice of entertainment by offering up the nooks and crannies of her own life—from her surgeries to her battles with addiction—in tandem with her ruminations on celebrity. Originally a 14th-place program among 18- to 34-year-olds, she connected with listeners about her struggles to conceive, grieving three miscarriages and a stillborn daughter before the birth of her son, Kevin Jr. Equal parts confession and sensation, the program moved up 12 places to become second in the market for its time slot. 

By the time Wendy returned to New York for The Wendy Williams Experience on WBLS in 2001, her craft was fully formed. She had also gone cold turkey from a cocaine addiction she had been hiding since her days as an undergraduate at Northeastern University. This is the period that is most often cited in reference to her tenure as the self-ascribed “Queen of Radio,” per the title of her 2004 tell-all book; she set the pace of media conversation in the proto-gossip blogger era. In 2003, the infamous Whitney Houston and Williams interview aired, giving many listeners their first peek at Houston outside of the clipped polish of her longstanding media training. It was a war of words between two Jersey girls:

Williams: [Mariah Carey] denied her breast implants. Do you deny yours?

Houston: Fuck no!

Williams: See, that’s my girl Whitney. I got ’em too. I mean, aren’t they the best?

Houston: I mean if you gonna, go for it, go for it. You know what I mean? 

Williams: Do you ever wish that you got him bigger?…they sit nice. They’re very well proportioned with you. It’s just that at one point when you lost so much weight, though, they did look like two baseballs on a stick. 

Houston: Yeah, they looked really weird. I’m sure that when you look in the mirror, you have some reservations about your looks too. [Hyena laugh] I’ve seen you, I know how you look.

Williams: ...what?

In 2007, Williams interviewed Kanye West after he stormed out of the VMAs. “Winning, Wendy, same thing, not too much difference,” West quipped. It was an acknowledgement that Williams had cemented her legacy as an antagonist of celebrities in a time when Black media was expected to celebrate Black excellence and admonish recriminations of beloved stars from mainstream press. 

When Williams got her deal to work on a daytime TV show in 2008, many doubted that she could transition her firmly Black—albeit suburban, as she is always quick to emphasize—vernacular to the screen. Fourteen years later, she has continued to prove them wrong, with 11 daytime Emmy nominations and nationwide syndication. 

On The Wendy Williams Show, Williams stepped into focus, gossiping about herself alongside her subjects. She discussed her life with her son, her weekend watches, and doled out advice in her “Ask Wendy” segment, generating a special bond with her audience. She was merely ratcheting up a level of intimacy that she had already built with her audience by turning her biggest insecurities—and her detractors’ most consistent insults—into a way to connect with her viewership. Call her “a man”? Tell that to anyone other than the Jersey girl who just paid for liposuction, breast implants, and a tummy tuck, and maybe you’ll find someone who cares more. She was free and open about paying to get the image she wanted in a pre-BBL era, when plastic surgery wasn’t nearly as sanctioned within the Black community; having dealt with fatphobia and bullying as a child—an experience she would elaborate on in her daytime show with her viral “Wendy Whaleiams” moment—she found power in transformation and shared that with her fans, reclaiming the “drag queen” label hurled at her as a point of ridicule with pride. 

Hate her or love her, it is nigh impossible to overstate Williams’ transformative imprint in the media space. She conceptualized a niche in Black media of a polyrhythmic parasocial relationship with celebrity; one that was equally fawning and reproachful. In a 2021 interview with the New Yorker, CUNY professor and historian Tanisha C. Ford likened Williams’ relationship with gossip to Howard Stern’s relationship to the “shock jock,” in that they provided analogous templates for their successors to emulate as the premier innovators of the style in their field. “So much of the way that YouTubers frame their gossip segments is based on Wendy Williams,” Ford pointed out, alluding to the cottage industry of “drama” channels and content creators such as reality TV vloggers. “Wendy created the model for how you spill tea. And she was doing this in the 90s.” 

Now, it’s hard to find a talk radio program without a gossip segment. Power 105.1’s The Breakfast Club has “The Rumor Report,” Hot 97 has “Flashing Lights.” Even Williams’ former nemesis Martinez admitted to Essence that she tuned into the talk show on occasion, observing that “[Wendy] has really mastered her lane. I find myself watching and laughing out loud. I don’t have any ill feelings toward her.” Much of the urban vlogosphere acknowledges their confessional style evolving from the popularity of Wendy Williams, with many of the popular channels faithfully following the ins and outs of her daytime show over the years for both commentary of pop culture as well as commentary over Wendy the person, even attending the show themselves. As Williams herself wrote in the opening line of her 2003 New York Times bestselling memoir, Wendy Got The Heat, “Bitches and niggas every day are practicing to do my shit.”

Even with the proliferation of tea-spilling, Williams was still the best at it. In a recent episode of Reality with The King, the host, Carlos King, an alum of The Real Housewives of Atlanta and reality TV producer, revealed in a conversation with Wendy Williams Show producer and sidekick Norman Baker that, when RHOA took a dip in ratings a few years ago, cast member Kenya Moore speculated that it was due to Wendy taking a hiatus from covering the show in her Monday rundown. “The power of her voice means a lot to people,” King elaborated. “It means a lot to the culture, and it means a lot to audiences.”

As a measure of comparison, fellow daytime pioneer Ellen DeGeneres was most recently afforded a season-long farewell after years of speculation about a hostile, racist, and abusive workplace environment; while she formally signed off in May of 2022, new episodes of the program with guest hosts will continue to air throughout the summer. 

Williams’ health struggles have been public for some time before her last appearance on set in July 2021. During the 2017 Halloween episode of The Wendy Williams Show, Williams passed out on live TV while dressed as the Statue of Liberty; in 2018, she was struggling with slurring her words, which she later attributed to painkillers she was taking for her fractured shoulder. She’s had to take several hiatuses due to flare ups from Graves’ disease and crippling lymphedema, and in September, she had a breakthrough case of COVID-19. But there seemed to be minimal plan to execute any sort of substantive roll-off or proper fanfare for Williams in absentia that would be befitting of her legacy or stature. In May 2022, a New York judge appointed a financial advisor to Williams after Wells Fargo had locked her out of her accounts under alleged suspicion of being either “incapacitated” or the “victim of undue influence and financial exploitation.” In response, Wendy accused her former manager, Bernie Young, of spending approximately $100,000 of her money to pursue financial guardianship despite her publicly severing ties.

In recent months, Wendy has done interviews with the press and been seen out and about in New York and Florida. In a Good Morning America appearance, she appeared bright-eyed and bushy tailed, but during a more recent TMZ on-camera conversation, she was vacant and disconnected, either unwilling or unable to follow a standard line of questioning. When prodded about the rumored podcast that Williams and her team planned to launch, her answers were rambling, stilted, and unfocused. YouTube comments sections filled with messages of heartbreak, grief, and confusion—fans, in true Wendy form, speculated whether her condition was due to her health issues, a relapse, or early-stage dementia. Most recently, reports have emerged of Williams announcing an unexpected third marriage to an NYPD officer; her agent, William Selby, clarified that “she is excited about a new relationship and probably got carried away in conversation.” 

Not all pop-culture consumers are empathetic to Williams’ recent hardships. There are some who have not been able to forgive Williams for her transgressions over the years, even going so far as to suggest that her health declined as karma for all of the reckless tête-à-têtes she’s provoked. A recent spat with beloved Instagram vegan persona Tabitha Brown led to many people believing that the media diva was bitter and projecting. It’s a common criticism leveled against her by detractors, who have had a strong distaste for her brash style of tell-all, stream-of-consciousness repartee at the expense of many celebrities’ personal lives. While there may be a strong temptation to frame this circumstance as Williams’ comeuppance, in reality, many radio legends who have been accused of comparable harms, if not greater, including Williams’ former mentee, Charlamagne, will still be revered for the work they have done in the media in the twilight of their careers. Williams deserves at least that much. Hate it or love it, her imitators could not succeed without her template.

Throughout Wendy Williams’ career, she has always been able to cut through the noise by managing to be a bolder, louder, and unrepentant than the average personality in her medium. It has been a successful road, if occasionally a lonely one punctuated by unforced errors. It has also placed her at a distinct disadvantage when she has run into misfortune. Williams allowed herself to be subject to public scrutiny by her audience, sharing her pain of discovering her husband’s infidelity while working on strict bed rest so that she could safely deliver her son to term. And she granted listeners license to call in and level transphobic insults without qualification, reasoning that she could connect with anyone as soon as she got them on the phone. She integrated her knack for banter with her willingness to stand at odds with the prized celebrity figures of the moment, even when it would come at her own expense. 

DeGeneres was able to close her program out on her terms, largely because while the reports that had come out from her program had been shocking, she had long presented an image of inoffensive, Louisiana charm that belied the inner workings of the studio; that was never a privilege that was going to be offered to a statuesque 5’11” Wendy Williams with a shameless New Jersey accent. As a large Black woman who seemed unafraid to be vocal when it suited her, Williams would never be perceived as anyone’s damsel in distress, despite her publicly sharing limited details of her toxic marriage over the years, which she later revealed was emotionally abusive. There is a collective instinct to protect an all-American girl like Britney Spears from mistreatment; that instinct could never be afforded to Williams, in part because she is perceived as culpable for the media ecosystem she participated in, but also because Black women as just not offered nearly as much sympathy in the greater racial calculus of whose humanity is more valuable. Williams even remarked on this herself on the May 13th, 2021 episode of The Wendy Williams Show, stating “19 years on TV doesn’t change your life, it exposes you for the person you really are;” at the time, Williams was dismissed as piling onto a longtime ratings competitor as opposed to acknowledging her own mistreatment.

Williams helped define the modern relationship between a radio host and its audience; the fruits of those decades of labor are assets that she is entitled to access and luxuriate in at her leisure. Any institutions or proxies seeking to restrict that should not be able use her recent health struggles or capitalize on her complex legacy to justify taking away her agency. As the case with Britney Spears has clearly shown, “concern” for someone’s best interests can quickly devolve into active harm by way of weaponized moral grandstanding—just take a look at how Spears’ current Instagram usage is being portrayed by the father of her children. “Either you are calling me crazy or the bravest woman you know,” Williams once quipped.

The fact that Williams has been reduced to advocating for herself in a series of disconcerting Instagram posts as she navigates her post-television life is an offense that is far beneath the heft and reach of her legacy. Fans should be able to support her next steps without financial interference and having to plead her case in the court of public opinion. The Wendy Williams Show may be over, but she will always be a Hot Topic—and absent direct access to Williams’ medical team, Wells Fargo’s determinations of mental aptitude are about as speculative as cryptocurrency and should not serve as a barometer as to her ability to access her money. A recent cover story by the Hollywood Reporter purports to paint the picture of a team working to protect Williams’ best interests as her health deteriorated behind the scenes, but curiously kept mention of her ongoing fight to access her finances to a minimum, despite the restrictions being predicated on her alleged wellness. Perhaps if Williams were unencumbered by financial strain, we would get less discombobulated messaging about her return to media and she would be allowed to rest and recuperate from whatever accumulated factors that have taken their toll on her day-to-day health. In this circumstance, we can minimize the chance of history repeating itself as we remain spectators to Williams’ next phase in life.

In the final episode of The Wendy Williams Show, guest host Sherri Shepherd gave Williams her flowers, effusing that “Wendy earned her title as the ‘Queen of All Media.’ If you think about it, Wendy Williams changed daytime talk with her unique take, her one-of-a-kind celebrity interviews, the signature ‘Ask Wendy’ segments and of course, y’all, her famous ‘How you doin’?’ Absolutely. And I wanna say, ‘Miss Wendy, you are an icon and you are loved by so many, so many.’” It is now the time to show that the statement was not made in vain, and that her contribution to the shift in media and pop culture—and the personal tax she paid for it—would not result in her being relegated to a social media joke in her twilight years, without the privacy, protection, and support that should be afforded to someone of her level of accomplishment. Offer Wendy Williams her just due; it is the least that she deserves.

Shamira Ibrahim is a Brooklyn-based culture writer by way of Harlem, Canada, and East Africa. She explores identity, cultural production, and technology as a critic, reporter, profile writer, and essayist.