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From wildly awkward audience interactions to painfully personal interview questions, Wendy Williams delivered plenty of moments that left viewers squirming in their seats. Join us as we revisit the cringiest clips from “The Wendy Williams Show,” including viral missteps, tense celebrity exchanges, and comments that sparked major backlash. Which moment made you cringe the hardest?
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00:00Welcome to Ms. Mojo, and today we're counting down our picks for the most cringeworthy, awkward, or insensitive moments from
00:07The Wendy Williams Show that were just hard to watch.
00:11I was like, no, because I would have made a big deal. Like, if I farted, I would have definitely
00:15been the last, because farts are always funny.
00:18Number 20. Comments about HBCUs and the NAACP.
00:24In July 2016, during a Hot Topics segment, the subject was Jesse Williams' celebrated BET award speech, which he gave
00:33after receiving the Humanitarian Award at that year's ceremony.
00:37We've been floating this country on credit for centuries, yo. And we're done watching and waiting while this invention called
00:45whiteness uses and abuses us, burying black people out of sight and out of mind while extracting our culture, our
00:51dollars, our entertainment like oil.
00:53Wendy Williams called the speech very poignant, which was a fine start. But then she quickly pivoted.
01:00Williams questioned why historically black colleges and universities, as well as organizations like the NAACP, exist, asking rhetorically what the
01:10reaction would be to such an organization for white people.
01:13I would be really offended if there was a school that was known as an historically white college. We have
01:19historically black colleges. What if there was the end national organization for white people only?
01:28The studio went almost completely silent. Williams noticed, laughed nervously, and took the audience to task for leaving her out
01:37in the cold.
01:37Look, everybody's quiet. You're leaving me out here to hang to dry by myself. One wrong word, I know. I'm
01:47choosing my words carefully.
01:49Their silence had already said everything, but it was nothing compared to the online backlash that followed.
01:55Number 19, Marcus Scribner's sex life.
01:59Blackish was my first.
02:00And you were such a little, I mean, only because you booked it during puberty.
02:04Yeah.
02:04So we're used to him being short and young and stuff, and now all of a sudden he's 18 and
02:08manly and stuff.
02:09Yeah, it was a pretty nuts transition.
02:13Some interview questions are awkward. Some are inappropriate.
02:17And then there's whatever Wendy Williams decided to do during Marcus Scribner's guest appearance.
02:23Williams told the then 18-year-old blackish actor that she didn't want him dating,
02:28and then, without missing a beat, pivoted directly to asking about his sex life.
02:33Are you a virgin?
02:36Wendy trying to hit me with the difficult questions.
02:39You don't have to answer.
02:40All right, I'll leave it, I'll leave it a mystery for the audience to, uh, decide.
02:45Scribner handled it with good humor, joking that Williams was hitting him with the tough questions,
02:50but the combination of his age, the subject matter, and the casual way Williams went there
02:55made the whole exchange deeply uncomfortable to watch.
02:58The clip has since appeared repeatedly in online compilations of the most inappropriate celebrity interview questions,
03:04which is truly a hall of shame nobody wants to be inducted into.
03:08You are so cute. You're so adorable.
03:10Like, I don't want you to have a girlfriend. I don't want you to fall in love.
03:14I feel like you're the kind of guy you need to date around and date often, but don't be a
03:18dog.
03:19You know, be smart.
03:21If you need a palate cleanser after all that awkwardness, we've got you covered.
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03:30We got the drip, the sauce. We are the next generation.
03:33You know what's up? Let's get it.
03:36Number 18. Alyssa Milano pushes back on breastfeeding.
03:40Alyssa recently caused controversy because she was breastfeeding and put the picture on social media,
03:49and a lot of people thought that it was way too much.
03:52And that's not even a bad one.
03:54A discussion about breastfeeding became an unusually tense interview when Alyssa Milano appeared on the Wendy Williams show in January
04:012016.
04:02Williams said seeing women breastfeed in public made her uncomfortable and said she preferred to not see that.
04:09Milano immediately asked why, and Williams suggested she would breastfeed in a car instead.
04:15What about it? What about it upsets you?
04:18I don't need to see that.
04:19Why?
04:20Because I just don't want to.
04:23Would you eat under a blanket or would you?
04:25What I would do is I would go to the car.
04:28Milano pushed back, arguing that breasts are biologically meant to feed babies.
04:33But Williams maintained that breasts were sexual outside breastfeeding.
04:37Milano challenged that premise.
04:39And at one point, her argument drew applause from the studio audience.
04:43Breastfeeding is only a particular amount of time.
04:46The rest of your life, your breasts are sexual things.
04:49And I just don't...
04:51Yeah, but they weren't made.
04:52I mean, biologically, they're not made for sexual things.
04:55That's what we've done to them.
04:56They're the fun bags!
04:57Neither woman backed down.
04:59And the audience reaction only underscored the tension.
05:02For a daytime talk show interview, watching the guest calmly challenge the host's position
05:07made the exchange especially awkward.
05:10All over the world, there's a very village mentality where other women...
05:13I mean, you're lucky the baby's not here.
05:15I'd whip him out right here and beat him on your show.
05:20I can't! I can't!
05:22Number 17.
05:23Comments about Ariana Grande.
05:25And originally when she came out, even I subscribed to that like,
05:28uh-oh, Mariah, there's a younger version, you know, going on.
05:31But then after studying this girl longer, no, Mariah is a woman.
05:35Body commentary disguised as observation is still body commentary.
05:40And Ariana Grande's fan base made absolutely sure that point landed.
05:44During a Hot Topics segment, Wendy Williams took aim at the then 21-year-old pop star,
05:50saying Grande still looked like a child because of her small stature.
05:53You know, it's nice to look younger than you are, but when you look too young,
05:57and then you're short, she's only like 4 feet 11.
06:03Like, I don't look at her as like a woman.
06:06The backlash was immediate and massive.
06:09Hashtag cancel Wendy Williams began trending,
06:12with fans pushing for the show to be pulled entirely.
06:15Some called it body shaming.
06:16Others retaliated by targeting Williams' own appearance.
06:20When TMZ caught up with Williams outside the studio weeks later and asked about the campaign,
06:26she was completely unbothered, telling Grande's fans to shut up
06:29and declaring they were wasting their time because the show wasn't going anywhere.
06:33Our seventh season returns on January 4th, um, September 14th.
06:39So, for right now, they're wasting their breath.
06:43I am?
06:44For right now.
06:44No, they are.
06:45Number 16.
06:47Mocking Joaquin Phoenix's cleft lip.
06:49I think I've shared this with you before.
06:51Have I shared this with them before?
06:52I find him oddly attractive.
06:54Yes, I think so.
06:55Uh-huh.
06:55He played that Johnny Cash.
06:57It wasn't Reese who kept me.
06:59It was him.
06:59There's a version of this moment where Wendy Williams discusses Joaquin Phoenix's appearance,
07:04and it stays perfectly acceptable.
07:06That version did not air.
07:08During a Hot Topic segment in which she was actually discussing how attractive she found Phoenix,
07:12Williams made a gesture toward her own upper lip, mimicking the appearance of his cleft lip.
07:18When he shaves off his mustache, he's got a hairline fracture.
07:21He's got one of those, um, what do you call it?
07:23Cleft lip.
07:24Yep.
07:24Cleft palate.
07:25He's got this.
07:26Yep.
07:26He's got this.
07:27Uh-huh.
07:27No, I find it to be, I find it to be very attractive.
07:31The casual nature of it made things worse.
07:33She seemed almost unaware that the gesture read as mockery of a physical characteristic Phoenix
07:38was born with.
07:39The internet disagreed with her apparent obliviousness, and the backlash that followed was pointed
07:44and persistent.
07:45I think she was outright mocking him.
07:48I just think it was a bad decision in terms of how she physically did it.
07:54Williams later issued an apology, but the clip had already circulated widely enough that
07:59the damage was very much done.
08:01We're thinking about Beau today as he is in surgery.
08:03I want to apologize to the cleft community.
08:06Williams went on to say she was donating to two cleft lip organizations.
08:11Number 15, Laverne Cox interview.
08:14In June 2014, Laverne Cox appeared on the show to discuss Orange is the New Black and
08:19her experience as a transgender woman.
08:22Transgender people's experiences are really different.
08:23It's an individual experience, so there's no one, like, sort of blanket transgender experience.
08:28It's really about listening to individuals in terms of who they are and accepting people
08:32on their own terms.
08:33She was patient and thoughtful, explaining what it means to be transgender, and graciously
08:38fielding questions in what could have been a genuinely informative segment.
08:43Then Wendy Williams shifted gears entirely.
08:45She asked whether Cox had breast implants, and followed up by complimenting the appearance
08:50of her breasts.
08:59Cox, composed as ever, declined to discuss her surgeries, explaining with obvious restraint
09:05that she didn't want conversations about transgender identity reduced to discussions about bodies
09:11and medical procedures.
09:12It was a lesson in both grace and missed opportunity, and it made for a very awkward conversation.
09:18I've chosen not to talk about any of the stuff I've gotten done, because I think so often
09:22when trans people's experiences are talked about, we always, far too often focus on surgery
09:27and transition, so I don't talk about that.
09:28But I'm very happy with the situation.
09:31The situation?
09:32Number 14.
09:33Comments about Chloe Johnson and Chaz Bono.
09:36Chloe had her sexual reassignment surgery already, and that was back in 2006, and is legally
09:44recognized as a woman, but CrossFit won't allow her to compete as a female because they feel
09:50as though she has an unfair advantage.
09:52A 2014 discussion about transgender CrossFit athlete Chloe Johnson's bid to compete in the
09:58women's division became one of the show's most criticized segments.
10:02Joined by commentator TJ Partavilla and psychologist Dr. Jen Mann, Wendy Williams argued
10:09that Johnson had a, quote, unfair advantage, and suggested competition rules may need changing.
10:15And I happen to agree with those of you who said, yes, it is an unfair advantage.
10:19You know, I mean, and Lynn, we're going to come right to you, but since they're saying
10:23yes, I'm just going to tell you, I agree this is an unfair advantage.
10:26The discussion then shifted to Chaz Bono.
10:28Williams acknowledged Bono as a man, but then addressed him wrongly and suggested he wouldn't
10:34be as strong as someone assigned male at birth.
10:36You know, Chaz is a man now, but I bet you she still fights like a girl, like the rest
10:41of us, and she's not as strong as a man who was born a man.
10:45The remark drew significant condemnation from the public.
10:48Williams later tweeted an apology, describing herself as a longtime LGBTQ plus ally and pledging
10:55to become better educated on transgender issues.
10:58We went to wendyshow.com.
10:59We polled you 55% of you think it's unfair, but that is very close.
11:03There are a lot of you who think that it's absolutely fair that she should participate.
11:08Number 13, the Price is Right joke about a murder victim.
11:12Wendy Williams is under fire yet again for appearing to make a joke about the death of
11:18Drew Carey's ex-fiancee, Amy Harwick.
11:21In February 2020, Wendy Williams discussed the death of Amy Harwick, a therapist and former
11:27fiance of the Price is Right host, Drew Carey.
11:30Police said Harwick had died after falling from a third-floor balcony.
11:34While explaining the story, Williams acknowledged that Harwick had supposedly been pushed by another
11:39former partner of hers.
11:41She then invoked Carey's game show catchphrase while looking downward, as though following
11:46someone's fall.
11:47The audience groaned audibly.
11:49She was killed not by Drew, but by the ex-fiancee.
11:54Come on down!
11:56Williams seemed to clock immediately that the room had turned cold and moved on with the
12:01segment.
12:02Harwick's brother Chris publicly demanded an apology, noting his sister had devoted her
12:06career to supporting domestic violence victims and women's rights.
12:10Many viewers were quick to take to Twitter to call out Williams for her remarks.
12:14Number 12, Fartgate.
12:16In January 2020, Wendy Williams was discussing NFL player Odell Beckham Jr.
12:22when a distinctly fart-like sound came through her microphone as she leaned sideways in her
12:27chair.
12:28That cop wasn't playing that.
12:29I mean, you're lucky you only got battery.
12:33What if he filed for sexual assault?
12:36Viewers assumed it came from Williams, and the mystery became Fartgate.
12:40Later, Williams denied farting and said she had never done so on the show.
12:45I don't lean over like this to release a fart.
12:48I'm leaning over like this because it's comfortable.
12:50You know, if I sit like this all the time, you know, it's heavy on my spine.
12:54I don't have the back.
12:55I'm not trying to get the back.
12:57I like to release my hips and lean.
13:00She brought out a staff member who said an experiment involving a fish tank and an improper
13:04hose had produced the sputtering sound backstage.
13:07Then, in March 2021, another mishap followed.
13:12While discussing Kim Kardashian and Kanye West's divorce, Williams appeared to burp and fart
13:17simultaneously.
13:19It's a matter of time.
13:19She's not lonely.
13:21I apologize.
13:23I apologize.
13:24The audience erupted, and Williams apologized.
13:27In this case, however, the fish tank wasn't able to fall on its sword.
13:32Number 11.
13:33The infamous Omarosa interview.
13:35Back in 2008, during the show's original run, Omarosa came on to promote her book.
13:41The interview derailed before it really got started.
13:44This is not the time for you to look for your moment.
13:47I invited you here.
13:48Oh, I know how to find my moment.
13:49I understand.
13:50We're going to talk about the book.
13:52All right.
13:52Well, let's get to it, Wendy.
13:54Omarosa took issue with how Wendy Williams had introduced her.
13:57The digs escalated quickly, and things turned genuinely personal.
14:01When Williams picked up the book to show it to the camera, Omarosa snatched it right back.
14:07I'm seeing a softer side, and maybe you're evolving.
14:09I like that.
14:10Maybe you're evolving.
14:11No, this is the same Wendy.
14:13I'm just giving my opinion.
14:15Just my opinion.
14:16I see a little softer side.
14:18Maybe, you know, they're backing you up for the show.
14:20From there, both women went after each other's wigs, appearances, and personalities with the
14:26kind of precision that suggested this wasn't entirely spontaneous.
14:29I wanted to do that so that people would know about plastic surgery.
14:33You're very open.
14:33Yeah.
14:34But there are celebrities who are not.
14:35Yeah.
14:35Now, did you have a nose job?
14:37No.
14:37It looks like you had a nose job.
14:39No.
14:39Oh, okay.
14:40No, I mean, I just looked at before and I...
14:42The whole thing was a master class in barely contained chaos.
14:46After sparring for 10 minutes, Williams closed it out with the most pointed statement in
14:51daytime television history.
14:53It was truly iconic television.
14:56And I would suggest a wig that doesn't sit off my head three inches.
14:59That would be my suggestion.
15:02You know what, Omarosa?
15:04And on that note, thank you for coming on my show.
15:08Number 10.
15:09Don't touch the mic.
15:10Hey, hey, hey, hey, hey, hey, hey.
15:13Broadcasting 101, Northeastern University.
15:16They never lose control of your microphone.
15:18If there's one rule on The Wendy Williams Show, it's that you absolutely do not touch
15:22the microphone.
15:23The case of Wendy's microphone has become a bit of a running joke throughout the years,
15:27as Wendy often scolds anyone who tries to touch it during an interview.
15:31She'll typically draw it away from anyone else's grasp, give them a disappointed look,
15:35and verbally berate them in front of the audience.
15:38She'll also accuse mic grabbers of not being true fans of the show, because if they were,
15:42they would know not to touch the mic.
15:44Uh-uh.
15:48First time customer, I say.
15:50It's all done in good fun, of course.
15:51But it's also a little cringy seeing it be done time and time again.
15:55I'm your biggest fan.
15:56Where are you?
15:56And I'm not touching your microphone.
15:58No!
15:59Number 9.
16:00Ms. Melody Passed Away.
16:02These are grown women.
16:06With millions at their fingertips.
16:08Back in October 2018, Williams discussed a then-new feud between Cardi B and Nicki Minaj
16:14on her show.
16:14You know what I think?
16:16I don't even want them to do a collabo song together.
16:18You know what they need to do?
16:20Go on tour.
16:22During the monologue, she proclaims that they should go on tour with the likes of Remy Ma
16:26and Ms. Melody, an emcee who was associated with the 80s hip-hop group Boogie Down Productions.
16:31Unfortunately, Ms. Melody passed away in 2012 at the age of 43.
16:35Wendy Williams clearly did not know this.
16:38She is subsequently told by a producer and responds with a simple,
16:41aww, before moving on with her hypothetical tour lineup.
16:44Uh, Ms. Melody may have passed away, I think.
16:47Oh, she passed away?
16:49Aw.
16:50Mm.
16:51All right, MC Light.
16:55Number 8.
16:56Family Dynamics.
16:57If the show goes away, fine.
17:00You had nine years on TV.
17:02Now go count your money and count your blessings.
17:04Wendy Williams loves talking about the Kardashian family.
17:07It also seems like she can't keep up with the complicated family tree.
17:10In order to explain the family relations, Wendy brings out the Kardashian breakdown board.
17:15So if Rob and Chyna become engaged, then they will be, um...
17:20She explains that if Rob and Blac Chyna got married, and if Kylie and Tyga got married,
17:25then that would make Rob and Tyga in-laws.
17:27Not only that, but Kylie Jenner would both be an aunt and a stepmother to King Cairo,
17:32who is Blac Chyna and Tyga's child.
17:34It's enough to cause Wendy to stumble over her words and throw a pointer down in frustration.
17:38And, and then...
17:44Number 7.
17:45The Drea Michelle Interview.
17:47From Basketball Wives LA, please welcome a live hot topic, Drea Michelle.
17:52When it comes to awkward celebrity interviews, nothing beats the once concerning Drea Michelle.
17:57Michelle came to prominence in the early 2010s by starring in the VH1 reality series Basketball Wives LA.
18:03It's made abundantly clear that Williams doesn't much care for Michelle or her accomplishments,
18:08because she is horribly disrespectful throughout the entire interview.
18:12How many basketball players have you been with?
18:14I know that's, I know that's, if you don't watch the show, that seems like Wendy, you're crazy.
18:19But she's been, she, this girl has gotten around, and I appreciate you being honest about it.
18:24She brings up some awkward and personal questions,
18:27says really inappropriate things to the audience like,
18:29this girl has gotten around, and brings up wild rumors that Michelle has to awkwardly shut down.
18:34We expect our talk shows to be a little bit more professional than this.
18:38There were words on the show that you had been with three basketball players in one night.
18:42Like, passed around.
18:44Yeah, no, like, I would, I, you know, I would have millions, like, by now, you know,
18:49if I was doing crazy wild stuff like that.
18:52Number 6.
18:52An Older Spirit
18:53Here's a tip.
18:55If someone tells you their age, never say that they look older.
18:58During a question and answer segment, a woman named Jasmine approaches Wendy and tells her
19:02that she is 31 years old.
19:04Her problem is that she is constantly approached by older men.
19:07This doesn't seem to surprise Wendy, who tells Jasmine that she has an older spirit,
19:12and that she would not have guessed 31.
19:14In other words, Jasmine looks way older than 31.
19:17You have an older spirit.
19:19Yes.
19:20Okay, let me answer, please.
19:21I would not have guessed 31.
19:22That's not something you tell people, even if they're lying about their age.
19:26All Jasmine can do is laugh in embarrassment and claim that, yes, she is, in fact, 31.
19:31Yeesh.
19:32You know, you're 31.
19:33Get out here and have fun.
19:34Okay, very good.
19:35Yes.
19:35Yes.
19:37You never know.
19:37Number 5.
19:39Mispronouncing Dua Lipa
19:40While talking about the 2018 Billboard Music Awards,
19:43Williams hilariously mispronounces Dua Lipa's name as Dula Peep.
19:47What do you think about Dula Peep?
19:50Dua Lipa.
19:51Dua Lipa.
19:52Lloyd?
19:52Dua Lipa?
19:53I'm digging this and I'll tell you why.
19:55If you run a syndicated talk show, you should probably know how to pronounce the names of
19:59celebrities, especially celebrities as big as Dua Lipa.
20:03Yes, the mispronunciation was pretty funny, but it's also more than a little unprofessional.
20:07We'd understand if Dua Lipa is some up-and-coming SoundCloud artist that only the kids were
20:12talking about.
20:12But come on, this is Dua Lipa.
20:14I didn't like it for the Billboard.
20:16I don't like it.
20:17I like it for Ladies Who Lunch or something.
20:19She's had huge songs like New Rules and One Kiss.
20:22Shirley Williams, a woman who often covers pop culture, has heard her name in passing.
20:26Did you see all the surgery there last night?
20:28Oh my god.
20:29Police!
20:30You can't even talk about these girls behind their back anymore because their ears are there.
20:34Number 4.
20:35Singing Along with Fergie
20:36Please welcome to our show, Fergie!
20:38On October 2017, Wendy had Fergie on the show to talk about things like motherhood, her
20:44upcoming album, and her time with the iconic Black Eyed Peas.
20:47No disrespect to the peas, but I had never heard of them until Fergalicious entered the
20:53picture.
20:54And you were just this amazing girl with a whole bunch of rhythm, but you weren't trying hard
21:00to appropriate a culture.
21:02You were just doing your thing.
21:05And during one commercial break, Fergie gets together with Williams for a little sing-along.
21:10Well, we use that term very loosely.
21:12While Fergie is lip-syncing the lyrics to her hit song Glamorous, Williams sort of moves
21:16around looking confused and maybe a little panicked.
21:19She clearly does not know the words, and despite her best efforts, simply mouthing Glamorous
21:24a bunch of times is not enough to convince us.
21:27You're so much fun.
21:28Please only break the good show.
21:30You're so fun.
21:31Number 3.
21:32Dancing with Kiki Palmer
21:33She got me speechless.
21:36That never happens.
21:37While visiting the Wendy Williams show to talk and also promote her album, R&B artist Kiki
21:42Palmer decided to teach Williams some dance moves.
21:45They proceeded through a rather awkward dance tutorial, and following that, they danced to
21:50Palmer's song Dance Alone, or rather, they attempt to dance.
21:53So you want to start on the dance?
21:57Fine.
21:58Alright, what's the first thing that we do?
22:00Okay, the first thing is just like this.
22:02Your hands come like that, and your foot just comes right in front.
22:04Just like, yep, and back in place.
22:07Williams just cannot get the hang of the moves, or the pacing, so they have to awkwardly stop
22:11the music and start again.
22:13We don't expect Williams to be an amazing hoofer or anything, but this is one instance
22:17where the guest really should have danced alone.
22:19It's my girl, everybody!
22:22Kiki Palmer!
22:23Thank you so much for stopping me!
22:25Oh my gosh, babe!
22:25Number 2.
22:25Awkward and super personal audience question.
22:29As we've already seen from this list, Wendy Williams isn't exactly the greatest when it
22:33comes to audience interaction.
22:35In the middle of a monologue, Williams randomly asks the women in the audience to clap if they've
22:39ever been pregnant without knowing the baby's father.
22:42Has anyone in the audience ever been pregnant and not known who the father was?
22:46Clap.
22:46Clap.
22:48Unsurprisingly, no one claps.
22:50Also unsurprisingly, the question is met with audible groans from the audience, and
22:54you can even spot some people awkwardly looking around, laughing in embarrassment, and even
22:58rolling their eyes.
22:59This isn't really the type of question you ask an audience, and the audience rightfully
23:03is not having it.
23:05Number 1.
23:06Turn your phone off now.
23:07A cell phone interruption is an issue that all hosts, performers, and public speakers
23:12commonly deal with, and these professionals deal with the problem in different ways.
23:16The question is, should the host have talked about it?
23:19My answer is, yes.
23:24Of course.
23:25Wendy Williams went with a bizarre mixture of rudeness and politeness that had her audience
23:30confused.
23:31Somebody phone on?
23:32Yeah.
23:33Get out.
23:34Get out.
23:36Let's turn that phone off now.
23:37She initially yells at the person to get out, and while the audience laughs at first, they
23:42soon grow incredibly silent when they realize that Williams is serious.
23:45As further contemplation and some disapproving O's from the audience, Williams changes tactics
23:51and goes the polite route.
23:52It is a confounding rollercoaster of emotions, and it all goes down in 30 wacky and incredibly
23:58awkward seconds.
23:59I was being overdramatic, but kindly please turn your phone off.
24:06Which Wendy Williams moment had you reaching for a pillow to scream into?
24:10Let us know in the comments.
24:15Let us know in the comments.
24:16Let us know in the comments.
24:16Let us know in the comments.