The longer the Queen of All Media has been away from the spotlight to battle a dementia diagnosis, the more we realized she was right about a lot of things that were considered controversial during her time on radio and on her eponymous talk show, The Wendy Williams Show.
From closeted rappers and the politics of Hollywood to celebs behaving badly behind the scenes—including Nicki Minaj, Diddy, R.Kelly, Whitney and more—Wendy was among the first to let us know that all is not what it seems. And she mostly kept quiet about everything … mostly.
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Now with chatter circulating that there will reportedly be another installment of her controversial Lifetime docuseries, just as she celebrates her 60th birthday, we thought now would be the perfect time to recognize Wendy for all the hot tea she has poured for pop culture over the years.
Buckle up.
R.Kelly’s Controversies
When R. Kelly’s relationships with underage women were just a whisper in Black pop culture circles, Wendy Williams screamed it over the airwaves. After Vibe magazine published an alleged marriage certificate between a then-15-year-old Aaliyah and a 27-year-old Kelly, Williams took it a step further on her radio show and pointed out Kelly’s alleged penchant for younger women. Later, when the infamous R. Kelly tape dropped, Wendy wondered out loud who else has seen R. Kelly do something suspect and said nothing.
Diddy’s Dark Side
From her radio show to the TV, Wendy has always hinted at her “pissing a lot of people off” in the rap game for talking about what allegedly went down behind the scenes. The person she seemed to have pissed off the most was Diddy. When she finally got the Bad Boy mogul on her talk show, it was all “grown” smiles and respect. “Get into,” she urged the audience. Yet many of Wendy’s longtime fans remember a time when she talked about being treated like a pariah for talking about who Diddy really was behind the scenes.
Omarosa the Opportunist
We have to admit, it takes some serious guts to come on someone else’s talk show and try to insult them, but that’s exactly what Omarosa did just as Wendy was trying to get her talk show off the ground. In hindsight, the interview revealed that the former “The Apprentice” reality star was calculated about courting controversy—which could explain why she later joined Former President Trump’s administration to allegedly help Black people, and we all know how that turned out.
Politics of Hollywood
Wendy always made it clear that she was not willing to play the Hollywood game: she went home to her husband and son in New Jersey, and she said several times on the air how much she did not like to fraternize with celebrities. This came out the most whenever she was compared to Oprah. She said many times that she was “Noprah,” and liked to keep her distance from celebrities in case she needed to talk about them on Hot Topics. When that whole mess with Mo”Nique, Oprah, Tyler Perry and Lee Daniels popped off, she went absolutely in on everybody involved.
Kris Jenner Being a Mastermind
There is a reason Wendy Williams always referred to Kardashian mastermind Kris Jenner as “That Woman.” According to Wendy, Kris was the mastermind behind making Kim, Khloe and Kourtney Kardashian household names—which, according to Ray J, included brokering a deal for that alleged tape to get out to the public. However, as the years went on, Wendy seemed to gain a certain amount of respect for Kris and even began to applaud some of her alleged deals behind the scenes to keep the Kardashian’s in the limelight.
Ellen Being Mean Behind the Scenes
It’s rare that you can feel the tension between two people during an interview. Yet even the then-Queen of Nice, Ellen, couldn’t hide her distaste for Wendy Williams whenever she dropped by for an interview. Whoever set these interviews, surely it wasn’t Ellen’s idea, and she seemed intimidated by having a big talk show personality like Wendy on her show.
Whitney Houston’s Drug Struggles
In one of the most infamous interviews Wendy has ever done on radio, Wendy was one of the first interviewers ever to call Whitney Houston out over her drug use. Even Aretha Franklin thanked Wendy for confronting Houston about her drug use. The rest is pop culture history.
Nicki Minaj
Now that rapper Nicki Minaj has been outed as an alleged mean girl in the music industry, the many, many, many, times Wendy has gone out of her way to shade Minaj on her show makes sense.
Will Smith’s Extramarital Friendships
Will Smith knew Wendy Williams liked to talk about him, so much so that he even dissed her in a song, rapping: “Wendy Williams, you don’t know me/I’m not your punching bag, you gon’ blow me/Up, girl, better leave me alone/Before I buy your radio station and send you home.”
Well that didn’t stop Wendy from being shady on the radio or on her talk show when the topic of Will Smith and his alleged arrangement with Jada came up. Case and point above.
Beyoncé Being a Star
As Destiny’s Child became a household name, it became clear to fans that Beyoncé was being set up to go solo and become a star. Wendy said it out loud during this hilarious interview, and it rubbed them the wrong way. But was she wrong?
Kim Kardashian Seeking Attention
From her marriage to Kanye to her gratuitous naked photos, Wendy liked to clock Kim Kardashian’s at-times desperate seeming strategies to stay in the spotlight, and it was always an entertaining read.
Jennifer Lopez and Ben Affleck
Wendy always maintained that J.Lo should get back with Diddy. And yet, she revealed a side of J.Lo during one interview that told viewers that she was in love with actor Ben Affleck above all else. And she has maintained that Ben is her true love to this day.
Al Reynolds and Star Jones
“There’s certain people who knew all along what was going on,” said Wendy, referencing her days on the radio hinting that Reynolds was not straight. Years later on her talk show, Wendy was able to report on how much Star Jones knew about ex-husband Al Reynolds’ sexuality, and it was another case of Wendy being right all along.
Caitlyn Jenner
Before Bruce Jenner revealed themselves as Caitlyn Jenner, they were spotted multiple times in women’s clothing. Some accused Jenner of donning the clothing to generate ratings, however, Wendy all but confirmed that Jenner was transitioning.
Rappers in the Closet
On the radio, Wendy Williams became popular, and at time infamous, for talking about a number of rappers who were allegedly gay behind the scenes and would resort to violent in some instances to cover up their sexualities. She never named any names, but she used codes and suggestive references to wink to the audience that she knew something about a particular person. She explains it all above.
America Being in Trouble
There have been many jokes made about the moment Wendy Williams fainted on live TV while dressed as the Statue of Liberty on the Halloween episode of her talk show. On the internets, the clip has become a popular meme, but behind the scenes Wendy revealed it was the pinnacle of her pain as her marriage ended and her personal life began to unravel. For many viewers watching, the moment seemed to mirror the country’s feelings as Trump was headed to the Oval Office, and America, and Wendy, seemingly haven’t recovered since.
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