Top 10 Shadiest Wendy Williams Moments



Top 10 Shadiest Wendy Williams Moments

VOICE OVER: Rebecca Brayton WRITTEN BY: Emily Blair
Whether you agreed or not, the shadiest Wendy Williams moments had us all hooked. Our countdown includes insulting Beyoncé, Kylie's pregnancy, a small donation of $500,000, and more!

Top 10 Shadiest Wendy Williams Moments

Welcome to MsMojo, and today we’re counting down our picks for the Top 10 Shadiest Wendy Williams Moments.

For this list, we’ll be looking at moments when this talk show host gave some of her hottest takes on the latest celebrity gossip.

Is Wendy spot on or does she take things too far? Let us know in the comments!

#10: An Awkward Interview with Karrueche Tran

Over many episodes of her show, Wendy covered the long relationship between this “Claws” actress and Chris Brown, and wasn’t exactly nice in the ways she spoke about Tran. In multiple “Hot Topics” segments, Wendy victim-blamed Karreuche for staying with Brown for so long and even called her a “thot who was after a dollar” in a now deleted video. When Tran appeared on the show for an interview, things started smoothly enough with discussion of “Claws” and Tran’s dedication to body positivity. Unfortunately, Wendy clearly just wanted gossip on Chris Brown and relentlessly asked questions about him that made Tran visibly uncomfortable. Wendy even outright asked if she was abused, earning an awkward [“Huh?”] from Tran.

#9: Insulting Beyoncé

When discussing Beyoncé’s HBO documentary “Life Is But a Dream”, Wendy said she was such a big fan that she’d watch, even if she already knew everything that would be in it. Unfortunately, what seemed like a genuinely supportive and uplifting moment was ruined when the talk show host couldn’t help but include a mean little jab at Beyoncé’s expense. Wendy’s caveat for watching the documentary was getting past what she described as Beyonce’s poor speaking skills - going so far as to suggest that she sounded uneducated. Talk about rude and unnecessary.

#8: Calling John Legend Unsexy

When John Legend was named People Magazine’s Sexiest Man Alive in 2019, Wendy Williams did not agree in the slightest. She admitted he was cute, but thought he definitely was not fit for such a title. Doubling down on the shade, Wendy offers an alternative by bringing up an image of Jason Momoa to show her audience, prompting many audience members to cheer in agreement. While it’s unlikely the opinion of one person was a massive blow to John Legend’s self esteem, it still wasn’t a very nice thing for her to say. We’re pretty sure she wouldn’t have appreciated being in his shoes.

#7: No Sympathy for Meghan Markle

When Meghan Markle opened up about the anxiety that came with becoming part of the British royal family, Wendy Williams didn’t feel sorry for her in the least. Markle was having a difficult time adjusting to the constant scrutiny, as well as the scorn and ridicule from British tabloids. However, Wendy argued that she didn’t deserve sympathy, because she must have anticipated how the media would treat her. Wendy later says she likes Meghan and Harry but then manages to throw more shade right afterwards …

#6: Surgically Enhanced Shade

In 2013, Lil’ Kim got plastic surgery and Wendy Williams was not a fan. When the image of Lil’ Kim’s face appears on screen, Wendy almost chokes on her drink trying to contain her laughter. It’s really quite the dramatic response for a fairly unremarkable image. Wendy then goes on to say that the surgery makes her face look so tight it could be popped like a balloon. Williams claims to be on Lil Kim’s side, calling the media’s nasty coverage unfair, but continues to make snide comments … BEING the problem that she’s pretending to criticize.

#5: Kylie’s Pregnancy

While rumors were flying that Kylie Jenner was pregnant in 2017, Wendy Williams was already thinking about the potential baby’s future. Based on speculation that Kylie was acting as a surrogate for her sister Kim, Wendy seems relieved for the baby’s sake that this would mean the baby won’t be born with a thin upper lip like Kylie used to have. Dedicated fans of “The Wendy Williams Show” might notice some additional camera operator shade that the show is known for. Just as Wendy starts talking about Kylie’s thin lips, the camera cuts to an audience member who appears to have thin lips herself. Not even Wendy’s own audience is safe from the shade.

#4: Calling Madonna a “Grandma”

When Madonna began dating one of her much younger backup dancers, Ahlamalik Williams, Wendy Williams (no relation, as she’s quick to point out) thought something didn’t look right. She said that it was awkward that Madonna was dating someone just a few years older than her daughter Lourdes, calling the singer an “old grandma” at 61 years old. Wendy also went on to say, from one mature woman to another, that younger men like Ahlamalik are better suited for one night stands, not serious relationships. We’re not sure Madonna asked for your advice, Wendy.

#3: A “Fake as Hell” Injury

While practicing for a dance number on “Dancing with the Stars”, Christie Brinkley sustained a hard fall that resulted in a fractured wrist and shoulder. Her daughter Sailor stepped in to dance in her mother’s place in a move many saw as heartwarming. But Wendy Williams saw it as a straight up conspiracy. Watching the video of Brinkley injuring herself, Wendy explained her improbable theory that Brinkley faked the injury in order to boost her daughter’s modeling career. Brinkley was shocked by the accusation, especially because she’d been on “The Wendy Williams Show” before and considered the two friends.

#2: A Small Donation of $500,000

During the tragic and devastating Australian bushfires in 2019 and 2020, Australian couple Nicole Kidman and Keith Urban generously donated $500,000 to a wildfire relief fund. In response, all Wendy Williams had to say was “that’s it?”. She figured the donation, which she saw as a measly $250,000 each, was nothing in proportion to the couple’s large joint income, and that they, as Australians, should have donated much more. It’s bizarre to see anyone rationalize half a million dollars as a small donation, especially when it’s coming from one couple and not a big corporation. And no matter the amount, any donation is respectable if it’s for a good cause.

#1: The Shade that Launched an Infamous Feud

Wendy Williams has always been fixated on celebrity gossip, and early in her career her favorite celeb to talk about was Whitney Houston. Houston wasn’t the biggest fan of Wendy, but agreed to do an interview on her radio show in 2003. And after years of built up tension, this interview officially started the feud between Wendy and Whitney. They both acted hostile throughout the interview, but Wendy kept pressing for more information about Houston’s personal life, from her relationship to her drug habits. Houston blamed Wendy’s constant discussion of her for her defensive attitude. Whitney Houston later vowed to never appear on “The Wendy Williams Show”, and stuck to her word.