1. Her comedy tour kept being canceled and postponed
Image Source: Reddit
Wendy Williams had dreams of conquering the comedy world, but her stand-up career didn't exactly take off. Her comedy tour in 2019 was plagued with canceled and postponed dates, fueling speculation about poor ticket sales. In the end, all the tour dates were scrapped. Looks like being the Queen of All Media doesn't guarantee success in every domain.Original content sourced from Femanin.com
2. Wendy's extended vacation brought tears of joy to her employees
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When Wendy Williams missed several tapings of her talk show, fans wondered what was going on. Turns out, she needed significant time in the hospital to battle complications from Graves' Disease and a fractured shoulder. While her celebrity guest hosts spilled the tea in her absence, there were some other people who secretly enjoyed the break from Wendy's antics: her employees. Makes you wonder what kind of work environment she is promoting.
3. Low blow at Ariana Grande
Image Source: Hollywood Life
Even if you're not a fan of Ariana Grande, you'd probably agree that Wendy Williams' body-shaming rant in 2015 was a bit much. She criticized Ariana's youthful appearance and diminutive height, questioning whether she could be considered a real woman. Come on, Wendy, can't we let everyone live their lives without tearing them down?
4. When Wendy betrayed Method Man
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In a shocking display of insensitivity, Wendy Williams publicly revealed that Method Man's wife had cancer before they had a chance to share the news themselves with family and friends. The rapper was understandably devastated and angry at the thoughtless act. Wendy crossed a line here, and it's unsurprising that Method Man was ready to throw down.
5. She also claimed the rapper had an affair
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Not content with just revealing Method Man's wife's illness, Wendy also insinuated that the rapper had an affair with his wife's doctor. That's a serious accusation to make without any evidence, and it's no wonder Method Man was furious. You can say what you want about someone, but bringing their family into it is a low blow.
6. Known for her transphobic comments
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When it comes to discussing transgender issues, Wendy Williams has a knack for making insensitive comments. From misgendering Chaz Bono during a talk about transgender athlete Chloie Jönsson to questioning Caitlyn Jenner's womanhood, she's shown a lack of tact and understanding.
7. Wendy vs. Whitney Houston
Image Source: Radar Online
One of Wendy Williams' most infamous feuds was with the late Whitney Houston. During an interview, she repeatedly probed the singer about her alleged drug use, her marriage, and other sensitive topics, leading to a heated confrontation. It's one thing to ask tough questions, but there's a fine line between journalism and sensationalism.
8. Aaliyah biopic controversy
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As executive producer of the Aaliyah biopic, Wendy Williams faced backlash from the late singer's family and collaborators. Many felt that the film disrespected Aaliyah's legacy. Timbaland, in particular, was vocal in his criticism, calling it a mockery. "I'm very upset about it. You're showing a mockery on TV," he said.
9. She even came for Beyoncé
Image Source: The Hollywood Reporter
No one is safe from Wendy Williams' scrutiny, not even Queen Bey herself. In a memorable "Hot Topics" segment, she questioned Beyoncé's intelligence before watching her HBO documentary. "You know Beyoncé can't talk," she said. "Beyoncé sounds like she has a fifth-grade education. She can't talk."
10. When Wendy doubted Kesha's allegations
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When Kesha's legal battle with Dr. Luke reached a critical point, Wendy Williams seemed skeptical of her claims. She suggested that if everyone complained about the alleged abuse, contracts would be broken all the time: "Unfortunately, business is business, and it sounds like it's fair," Williams said on her show. "If everybody complained because somebody allegedly sexually abused them... contracts would be broken all the time."
11. Wendy Williams took issue with Paris Jackson's racial identity
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During a controversial moment in 2017, Wendy criticized Paris Jackson's self-identification as black. While Paris proudly stated that she considered herself black due to her father, Michael Jackson, Williams disagreed, claiming that "black is not what you call yourself, it's what the cops see when they got steel to your neck on the turnpike."
12. Jennifer Lawrence's nudes: Not her choice, but Wendy's viewing pleasure
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Williams had a different perspective when Jennifer Lawrence expressed her disgust over the unauthorized release of her nude photos in 2014. "I didn't tell you that you could look at my naked body," the Hunger Games star said. "It's my body, and it should be my choice, and the fact that it is not my choice is absolutely disgusting." In her sarcastic tone, Wendy said, "It's not your choice; it's in the Cloud, and I've looked several times. So I guess I'm disgusting for looking?"
13. 2Pac's alleged rape in jail
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Known for spreading rumors, Wendy didn't hold back on her Hot 97 radio show, insinuating that legendary rapper Tupac Shakur was raped in jail during the '90s. "There is a large segment who may have never heard about me on the radio, but they heard Tupac tell me I needed to go to Jenny Craig," she said in a 2012 interview.
14. Williams questions Terry Crews' courage to admit he was assaulted
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When Terry Crews bravely spoke out about his experience of sexual assault, Wendy's response left people scratching their heads. She said, "No, it's not brave — he's just talking. But being all black and being all chatty... It will, in my opinion, affect his career." Oh, Wendy, always there to provide uplifting support!
15. When Wendy questioned Kim Zolciak-Biermann's mini-stroke
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When Kim Zolciak-Biermann suffered a mini-stroke in 2015, Wendy raised doubts about the legitimacy of her health scare. The celebrity questioned whether Kim was fibbing about the stroke and suggested she could have just stubbed her toe to get out of a commitment. Because, you know, strokes are just so convenient!
16. Wendy's take on Jesse Williams' speech
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Wendy's controversial take on Jesse Williams' powerful pro-Black speech at the BET Awards in 2016 raised eyebrows. Comparing historically Black colleges to a hypothetical historically white college and questioning the need for organizations like the NAACP, Wendy managed to offend even her usually supportive studio audience.
17. Rumor mill strikes again: She said Diddy is gay
Image Source: Showbizz Cheat Sheet
Wendy gained notoriety in the '90s by alleging the homosexuality of various male celebrities, often without any proof. But when she decided to talk about Sean "P Diddy" Combs' sexuality, he retaliated and got her kicked off the air with just one phone call. Well, at least it made for some memorable moments, right Wendy?
18. Wendy's dark past
Image Source: All About The Tea
In a candid moment on her show, Wendy opened up about her past cocaine addiction, admitting that she wasted a lot of her life "burning her insides." "Crack is wack," she said on a March 2019 segment. "I was a mess…killing myself. I realized I am a walking addict. You can’t just clean it up and stop it."
19. Williams' sober house stay: Who knew?
Image Source: Reddit
While going through her battle with addiction, Wendy revealed that she was living in a sober house, away from her husband. She embraced the smelly camaraderie of her fellow recovering addicts but kept the arrangement a secret from almost everyone. It's not like she wanted her parents to know or anything.
20. Marital mayhem
Image Source: National Enquirer
Known for her decisive nature, Wendy's first marriage lasted a mere five months, showcasing the dark side of her quick decision-making skills. She simply divided the things in the house, hired a moving company, and left while her husband was at work. It seems her knack for planning career moves doesn't always translate well to personal relationships.
21. Fistfight fallout: Wendy's DJ drama
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In a shocking turn of events, Williams was fired from Hot 97 after a rumored fistfight with another female DJ working on another program. While Wendy denied the rumors, it dealt a heartbreaking blow to her radio career, leaving her to rebuild elsewhere. And so she did.
22. Williams in the hot seat
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In 2008, as Wendy's popularity soared, she faced a major setback. A talent booker from her show filed a complaint against her, escalating into a lawsuit involving Wendy, her husband, and the broadcasting corporation. The accusations were disturbing, painting a dark picture of the work environment.
23. Wendy's allegedly been abused by Hunter
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The lawsuit revealed shocking allegations of intimate demands and abuse within the work environment from Kevin Hunter, including claims of physical abuse towards Wendy herself. While Wendy and her husband denied the accusations, the case eventually got dismissed.
24. Controversial jewelry line troubles
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In 2012, Wendy's jewelry line, Adorn, faced disturbing revelations. It was discovered that the Chinese company she commissioned vanished after their shoe manufacturer allegedly kidnapped their manager. Rumors swirled about unpaid debts, but Wendy remained silent on the matter.
25. Wendy's eye-opening experience
Image Source: Hollywood Life
In 2018, Wendy disclosed her battle with hyperthyroidism and Graves' disease, which explained the unique appearance of her eyes due to the latter. Despite her health challenges, Wendy continued to entertain and inform her audience. And later on, she admitted that she kept on taking drugs all this time.
26. Statue of Liberty's downfall
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During a Halloween episode of her show in 2017, Wendy collapsed onstage, causing the world — and those around her — a moment of shock. It was later revealed that she had overheated in her massive Statue of Liberty costume. After a brief break, she returned to finish the show.
27. Foot-in-mouth moment: Joaquin Phoenix's cleft palate
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Facing backlash in 2020, Wendy received criticism for her comments about Best Actor nominee Joaquin Phoenix's cleft palate during the Oscar oratories. She later apologized and made donations to cleft palate-related charities to make amends. She donated to the American Cleft Palate-Craniofacial Association and Operation Smile.
28. It's a diva showdown
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In a memorable interview, Wendy grilled Mariah Carey about breast implants, leading to Carey's abrupt departure. Williams soon after got a suspicious piece of mail. As a response to her nonsense, Carey sent Wendy a box of push-up bras — a shady gesture that added fuel to their ongoing feud.
29. Kevin Hunter's infidelity
Image Source: Page Six
In a devastating blow, Wendy filed for divorce from her husband of 22 years, Kevin Hunter, after discovering he had fathered a child with another woman named Sharina Hudson. To make matters worse, Wendy allegedly came clean and confessed she had known about the affair prior to taking legal action.
30. She might have been poisoned
Image Source: Page Six
Amidst a tumultuous year dealing with various challenges, rumors circulated that Wendy's ex-husband, Kevin Hunter, was poisoning her. The police received a call from someone claiming to work on her show, alleging Hunter's involvement. Although the claim was denied and nothing came of it, it added to Wendy's life's chaos.
31. Her disrespect over a TikTok star's death
image source: usmagazine.com
TikTok star Matima Miller, who was known as Swavy, tragically died in 2021 after he was involved in a shooting in Delaware at only 19 years old. The news of anyone passing, celebrity or not, is tragic, but Wendy Williams didn't seem to think so. When talking about his death on her show, she said that she had "no idea" who he was and then proceeded to compare their social media follower count.
32. Making fun of Dionne Warwick
image source: usmagazine.com
Wendy Williams also made fun of American singing legend, Dionne Warwick, after the artist had been taking to Twitter. Apparently Wendy thought maybe Dionne was too old to be on social media successfully and needed to 'get with it', saying that she needs to "get down" and talk to kids. Warwick later found out the mean comments Williams had been spreading and replied - on Twitter - that she'd rather not be spoken about!
33. Calling other TV hosts "disgusting"
image source: usmagazine.com
This would be pretty insulting at the best of times, but Williams decided to slam certain TV hosts' appearances during a time when we all could do with a pass: the COVID-19 quarantine. She decided to publicly call the outfits or looks that TV hosts were showing off from their homes during the quarantine as "looking disgusting". Apparently she cared more about fashion than pandemic issues.
34. Mocking the murder of Amie Harwick
image source: usmagazine.com
Amie Harwick was a celebrity therapist, and once dated comedian and TV host Drew Carey. Tragically, she was murdered in 2020 when she was thrown over a balcony, and when announcing the news on her show, Williams thought it was appropriate to say "Come on down!" - the catchphrase from Drew Carey's The Price is Right and an insensitive reference to how Harwick died.
35. Her attack on gay men wearing women's clothes
image source: usmagazine.com
Not only has she made some insensitive moves with trans people in the past, she's also taken issue with gay men, too. On her show when celebrating 'Galentine's Day' (in celebration of female friendship), she told men in the audience to stop clapping, and went on to say gay men shouldn't be wearing skirts or heels and that they "will never be the women that we are".
36. It was Meghan Markle's turn next, too
image source: usmagazine.com
Meghan Markle is no stranger to being slammed by a TV host or two, and that includes Wendy Williams's remarks. When Markle spoke back in 2019 about the negative sides of marrying into the British royal family, Williams retorted with the fact that Meghan "knew exactly what [she] was doing" and that she shouldn't expect any sympathy for making that choice.
37. Casting doubts on Christie Brinkley's injury
image source: usmagazine.com
Model Christie Brinkley appeared on Dancing With the Stars until she ended up dropping out of the show due to an injury during rehearsals. Williams wasn't happy with that explanation, though, apparently, because she publicly called out Christie by implying she was lying about the injury, saying it looked "fake" and that she doubted both a wrist and a shoulder being fractured!
38. Her criticism of Rob Kardashian's "lack of confidence"
image source: usmagazine.com
After Rob Kardashian's relationship with Blac Chyna, William's decided to dedicate a whole load of minutes to slating how Kardashian had acted, his personality, his confidence... She basically said that Rob had "lack of confidence" and that it's "not attractive" to let a woman walk all over him. Chyna later fired back on social media about her comments - she wasn't happy!
39. Her Caitlyn Jenner comments
image source: usmagazine.com
From Kardashian to Jenner, Williams also made comments about Caitlyn Jenner and her transition to becoming a woman. When the Kardashians were featured on a magazine shoot that celebration "all the Kardashian women" - including Caitlyn Jenner, of course - Williams made it known what she thought about that, saying Caitlyn was still biologically male.
40. When she said breast feeding was s*xual
image source: upi.com
A lot of celebrities, including everyday people, share photos of their breastfeeding journey as part of their celebration of having a baby. Alyssa Milano was one of them when she shared photos, which were then brought up on the Wendy Williams Show when Milano was a guest. Williams said she didn't want to see it, and said breasts are "more s*xual than a feeding thing".
41. Her disbelief of Michael Jackson's alleged victims
image source: dailymail.co.uk
Michael Jackson has been the subject of many a documentary and controversy since his death, with more than one person coming forward to claim that they had been s*xually abused by the singer while they were still young. Wendy Williams didn't believe a word of it, though, publicly slamming the victims on her show and saying that they're just after money.
42. Saying that Kris Jenner should be angry at Caitlyn's transition, too
image source: dailymail.co.uk
Wendy Williams wasn't done with Caitlyn Jenner after one comment either! She then took to explaining on her show how she thought Kris Jenner, Caitlyn's ex partner, should be pretty angry at Caitlyn transitioning. She then gave a weird backhanded compliment in saying Kris should also be angry because Caitlyn is "so beautiful" when a lot of men "try" to transition and apparently don't look the part, according to her.
43. Asking an 18-year-old if he's a virgin
image source: buzzfeed.com
Let's be honest, asking anyone, of any age, that question directly on a TV show is more than inappropriate. But asking it of an 18 year old? When American actor Marcus Scribner appeared on her show, Wendy decided to ask him about his s*xual activities, and later claimed it was because one of his characters on the show Black-Ish was s*xually active. To make it worse, Marcus's dad was in the audience.
44. Sl*t Shaming Draya Michele
image source: atlantablackstar.com
This would be inappropriate at any time, even if you're having a private conversation with no one else to hear. But doing it on a public TV show? Yikes. When media personality Draya Michele appeared on Williams's show, the TV host decided to not only probe Michele about how many people she'd slept with - basketball players, to be exact - but also to shame her for it.
45. Getting personal with Laverne Cox
image source: advocate.com
Taking previous experience into account, Wendy Williams here decided to combine remarks about people transitioning with those breasts she apparently likes to talk about! When she was interviewing actress Laverne Cox on her show, Wendy decided to get very personal with questions about Laverne's transition, and asking her if she breast implants.
46. When she claimed Beyoncé had faked her pregnancy
image source: mirror.co.uk
We know by now that Beyoncé definitely hasn't faked any pregnancies if her, you know... children are anything to go by. But Wendy Williams apparently took umbrage with the way that Beyoncé's dress moved when she sat down during her pregnancy - the dress didn't move convincingly enough around the bump for Wendy's liking, so she decided to cast doubt on the baby bump.
47. The Gorilla Glue incident
image source: youtube.com
Viral star Tessica Brown became exactly that when she had an unfortunate incident using Gorilla Glue on her hair - so much so she became Gorilla Glue Girl - when she used Gorilla Glue to secure down her hair in a pinch after she ran out of hairspray. Speaking about Brown, Williams made it clear she thought Tessica was "the dumbest girl on the face of the Earth".
48. Defending Trey Songz putting pressure on Keke Palmer
image source: seventeen.com
Actress Keke Palmer appeared on Wendy Williams's show, and they spoke about the situation where singer Trey Songz had pressured Keke to be in his music video - and then put her in it without her consent. Instead of showing sympathy to Keke's situation, Wendy instead decided to defend Trey's decision to do so. The good thing was Keke stood up for herself on the show and called Wendy out!
49. And then her positive reaction to Trey Songz's domestic violence charges
image source: rap-up.com
Speaking of Trey Songz... apparently possible domestic violence perpetrator means "dreamy" in Wendy Williams's book. When discussing Trey's arrest on her show, after the singer was arrested for allegedly beating up his partner, Wendy went out to give out the details before asking, "Isn't he just so dreamy?". Not really the correct response, Wendy.
50. Her controversial legacy
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Wendy William's show was all about gossip and drama, so you have to hand it to the TV host that she kept that going - if not in an extremely offensive and controversial way. Her show, The Wendy Williams Show, may have been cancelled last year, but the memories of her insulting her guests, and pretty much everyone else, will definitely live on in our minds!