Wendy Williams has always been a mess—but she usually was the first person to tell you as much. After all, who else but Wendy could executive produce her own Lifetime TV special, “Wendy Williams: What A Mess,” and follow that up with a movie dramatizing her struggles with addiction, a cheating husband, and all the public (sometimes literal) fallout in between?
Now, after an extended period out of the spotlight, a new two-part Lifetime documentary on Feb. 24 and Feb. 25 promises to take audiences behind the scenes and reveal exactly what has been ailing Wendy as she struggles to get back on her feet.
“I have no money,” Wendy is heard saying in the documentary, alluding to the rumors of her being in a financial guardianship. “And I’m going to tell you something, if if happens to me it can happen to you.”And just as quickly as a trailer for the doc went up, it was taken down. But the internet is forever and clips from the trailer have already been circulating in anticipation on X, formerly known as Twitter.
As much as her eponymous “The Wendy Williams Show” went out with a whimper—and Tamron Hall, Sherri Shepherd (as potentially the next Oprah) and Jennifer Hudson now vying for her target audience—the absence of Wendy’s directness has left a big hole in daytime TV and an even bigger hole in Black culture.
Make no mistake, Wendy’s larger-than-life personality was absolutely edited down and formatted to fit mainstream TV. Yet even as she balanced her newfound marketability against her past as a radio shock jock, she always kept Black culture a focal point of the day’s “hot topics,” and in many ways Black culture was better for it.
Yes, Wendy Williams could be the Queen of Messy but she was also the Queen of All Media, and in a time when celebrity beefs, breakups and bad boys all seem to be coming to light at once, It’s important to remember that Wendy tried to tell us at least more than a few times about the bad behavior that allegedly goes on behind the cameras.
Nicki Minaj As the Real #BigFoot Behind the Scenes
When the Bronx-born rapper Remy Ma infamously came for Nicki Minaj’s neck in the diss track “Shether,” hip-hop fans felt a mix of shock and confusion over the track. Some saw it as an already established rapper (Remy) attempting to stifle the career of the next generation (Minaj), but Wendy drew a very clear line in the sand and walked everyone through the moment.
“Why was Nicki targeted?” Wendy asked Remy about “Shether” on her show. In her response, Remy added to what many rappers have said about Minaj allegedly being a mean girl behind the scenes.
“That was a response,” said Remy. “She started it.” And it’s reminiscent of how Megan Thee Stallion’s recent “Hiss” diss was allegedly a response to Minaj attempting to stop her career, and the careers of other female rappers, behind the scenes.
Yet Wendy said it best when she pointed out that Megan Thee Stallion has three Grammy Awards and Minaj has none—despite being the Queen of Rap.
“You know how she earned them? By maybe being kind to the people around her.” Wendy also went in on Minaj’s marriage to Kenneth Petty and how much it has muddied her brand, but we will let Wendy break that down.
P. Diddy’s Alleged Power Trip, And Rap Behind The Scenes
When P. Diddy finally made it to Wendy Williams’ purple couch on the “The Wendy Williams Show,” the moment was years in the making. Wendy and Diddy alluded to their “history,” “forgiveness,” and now being able to have “grown” talk together on TV. But for those of us who remember Wendy Williams on the radio, she has been ringing the bell about Diddy’s alleged antics behind the scenes in rap for a long time.
Back when Charlamagne tha God was her radio co-host in 2009, Wendy invited former Bad Boy rapper Mark Curry on her show to talk about his book “Dancing with the Devil, How Puff Burned the Bad Boys of Hip-Hop.” The “devil” alluding to being Diddy, according to Curry.
“This a man that has a shadow of things that follow him, and it will rain on you too. So it’s really all about the dark cloud,” Curry told Wendy. Judging from the allegations alleged by P. Diddy’s longtime girlfriend Cassie Ventura, the clouds get darker.
However, Wendy was always shining a light on what goes on in some of rap’s darkest corners. Often to the detriment of her own safety, Wendy used her radio show to talk about women allegedly being passed around and abused in the music business. She was one of the first to call out R. Kelly’s relationship with an underage Aaliyah, and hinted at Russell Simmons alleged bad behavior behind the scenes.
Wendy was also infamously—albeit sometimes a tad homophobic—calling out rappers who were living a down low lifestyle and the detrimental effects it has had on some women. See Janet Jackson’s character story in Tyler Perry’s “For Colored Girls” for reference.
Bill Cosby as a Perpetrator
Out of all the Bill Cosby stories floating around from his days as Mr. JELL-O Pudding, Wendy perhaps had the best story. It was the early 1990s and early on in her radio career, Wendy did the morning gossip for her station. But when Cosby’s name came up more than a few times, he called her radio station and tried to have her fired.
Naturally, Wendy being the Queen of All Media, she took it as a compliment. “Of all the things in Dr. Cosby’s life that affect him, it’s calling little old Wendy?” Wendy recounted the story to Andy Cohen one night on “Watch What Happens Live.” “And all these years later, look at little old Wendy, and look at Cosby.”
Cosby infamously went to jail after being found guilty on three counts of sexual assault and after more than a dozen alleged rape allegations. And just as Cosby was getting ready to go to the clink in 2018, Wendy read him for filth in front of her studio audience at “The Wendy Williams Show.”
“You told Black boys: pull their pants up,” she said. “Well how about you pull your pants up?” she said.
Raging Against the Hollywood Machine
Whenever there is a Black woman with her own talk show, the comparisons to Oprah are seemingly inescapable. It’s not surprising: Oprah is a media juggernaut who has earned her billionaire status many times over—despite what some of her haters might think.
And yet as Wendy’s talk show grew in popularity, and the comparisons to Oprah began, she always maintained that she was “NoPrah.” It was a short and sweet dismissal of the comparisons between the two Black women, but if you read between the lines Wendy was also taking a stand against Hollywood.
After talking about celebrities all morning, Wendy made no secret that she usually goes back home (then New Jersey), “shuts the blinds,” and lives a normal life as a wife and mother.
“I’m just like you,” she often told her studio audience, and that was a big part of what made her so relatable. It was rare to see Wendy out rubbing elbows with the likes of Oprah, Ellen or any other associated Hollywood ilk because she knew that she would eventually have to talk about them on her show.
When it was revealed that Ellen DeGeneres’ show was not the happy place it portrayed itself to be, Wendy went in—despite appearing on her show and getting a frosty reception when she did.
“19 years on TV doesn’t change your life, it exposes you for the person that you really are,” said Wendy during her show’s Hot Topics segment. “I’m not sure all the guests were happy. I was a guest. I was unhappy. Just sayin’ [sic] and people called me out about it before I was able to say anything about it.”
Wendy also wasn’t afraid to dig into Hollywood’s golden couples, including, at the time, Will and Jada Pinkett Smith. On radio, Wendy spent several months talking about Will and Jada’s alleged alternative lifestyle, and Will eventually finally responded in a song.
In the 2005 track Mr. Niceguy, Smith famously rapped: “Wendy Williams, you don’t know me/I’m not your punchin’ bag, you gon’ blow me/Off, girl, better leave me alone/Before I buy your radio station and send you home.”
When it came to telling it like it is, before there was Tasha K, Shannon Sharpe, Jaguar Wright or a Hollywood Unlocked, Wendy was the original.
“These days people feel as if they have the right to information from celebrities, because if they can’t get that information from them directly, they can get it through social media anyway. But I haven’t changed. I consider myself the original,” Wendy told the New York Times in 2019. “I’ve been doing this for years and been vilified. Now everybody’s doing it.”
She added, “My approach has never been that I’m prying. If you’re a celebrity, and you invite me over for dinner, I’m not talking about that. But if I’m at a party, and you’re there with somebody other than your wife, I’m calling my Hot Topics. bureau to make sure we talk about that on the show.”
Of course Wendy had her own complicated relationship with celebrity as her star began to rise, and her life began to unravel with divorce, the loss of a parent and alleged addiction. But no one could deny her resume, and Black Twitter has been cheering louder and louder lately for the day she can return healthy and get back to her purple throne.
From bad boys—and girls—to the Hollywood elite, the list of hot topics Wendy was the first to speak truth on goes on and on. Yet in a year when it particularly seems like all the chickens are coming home to roost, we need Wendy’s sharp honesty more than ever to carve up the truth.
She’s an icon. She’s a legend. And after all this time away, she still is the moment.