5 Times Wendy Williams Made Her Talk Show Guests Feel Uncomfortable

Wendy Williams had a long run with her eponymous talk show that ran for 14 years, during which she interviewed countless celebrity guests such as Joe Manganiello and Jennifer Lopez. "The Wendy Williams Show" had a segment called "Hot Topics" which was a breakdown of the latest gossip, with much shade thrown by the host. While her verbal barbs have probably riled up many stars, she shared with Time back in 2015, "Kim [Kardashian] has a really good sense of humor. She knows who she is, she knows what she puts out there. She is not one for her feathers to be ruffled." Williams added, "I come with strong opinions, but strong opinions are what drive the show."

Still, talking about celebrities while they're not there and having them on the show is completely different. Williams is known for her blunt mannerisms and there have been many times she has pushed her guests to the brink of cringe-level. Some moments are simply uncomfortable to watch, while others are downright rude. We're here to break down every moment the talk show host has gone a bit too far.

Alyssa Milano is a proud breastfeeder and she's not afraid to show it. In 2014, she shared a sweet snap of her breastfeeding her daughter with a quote by Milan Kundera that read, "Ah, the joy of suckling! She lovingly watched the fishlike motions of the toothless mouth and she imagined that with her milk there flowed into her little son her deepest thoughts, concepts, and dreams." That wasn't the only breastfeeding pic she shared, and when she was a guest on "The Wendy Williams Show" in 2016, the host had something to say about it (via ABC News.) "I don't need to see that — I just don't want to. I would go to the car," Wendy Williams. After Milano expressed shock at that, Williams countered with, "Breastfeeding is only a particular amount of time. The rest of your life, your breasts are sexual things." The "Charmed" star quipped back with, "You're lucky the baby's not here! I'd whip 'em out right here and feed [her] on the show."

Milano later shared with HuffPost Live (via The Wrap), "It's so crazy to me how the mentality is so archaic, and people are just not comfortable with women breastfeeding. Obviously, it's because we've sexualized breasts to the point that people can't see past them being breasts."

Draya Michele stirred up drama in "Basketball Wives LA" for four years but she found herself in the hot seat when she visited "The Wendy Williams Show" in 2011. In a video captured by YouTube content creator StephCharlo, Wendy Williams didn't waste any time digging into the reality star's past and bluntly asked her, "Did you strip?" Michele wasn't bothered and stated that she did in the past, but when Williams grilled her about how many men she had slept with, things got awkward. "There were words on the show that you had been with three basketball players in one night," the talk show host said at one point, which earned her a side-eye from Michele. "I would have millions, like, by now if I was doing crazy wild stuff like that," Michele shot back.

Years later, amid Williams' health issues, Michele returned the shade with an Instagram Story that read, "Hope @wendyshow starts to feel better again soon. We didn't have the best interaction but I understand the nature of your job I have always respected it even though it didn't respect me" (via Atlanta Black Star). She then cheekily offered to guest host while Williams was out of commission.

Many know Laverne Cox as one of the stars of "Orange Is the New Black" and an openly transgender woman. As reported by The Advocate, while Cox was on Wendy Williams' show in 2014, she was asked to describe what being transgender was, to which she replied, "Transgender ... very basically means that the gender you identify as is different than the one you are assigned at birth. Very simple." Williams in her abrupt fashion then asked the actor, "You've got breast implants?" Cox refused to answer the question so as not to focus primarily on trans people having surgeries. "I don't talk about that, but I'm very happy with the situation," she stated.

The same year, Williams was blasted for an offensive remark about Caitlyn Jenner on her show, per The Wrap. While she initially praised the Olympic winner for being able to be herself, Williams then told the audience, "He at least waited for his kids to grow up, so he doesn't have to go to PTA meetings with a shaved Adam's apple, and a blowout, and pink nails, and a cigarette. You know what I'm saying?" The president of GLAAD, Sarah Kate Ellis, called Williams' comment "ludicrous."

Wendy Williams is no stranger to digging deep with her talk show guests but she was downright inappropriate with Marcus Scriber, who was 18 years old when he appeared on "The Wendy Williams Show" (via còi cọc on YouTube). After evading her questions about his dating life, saying "It's complicated," she slammed him with, "Are you a virgin?" The audience was visibly surprised and Scribner looked downright shocked. "Wendy trying to hit me with the difficult questions," he answered. "I'll leave it a mystery for the audience to decide," The "Black-ish" star added.

Suffice it to say, many slammed Williams for her treatment of Scribner. "Poor guy! This was s***ty of her, that question was invasive at best or sexual harassment at worst. He handled this so beautifully, [it's] nice to see a young person with such situational awareness, restraint, poise, and media savvy ... And with his Dad standing right there, too!" a fan wrote on Reddit. "Props to him for thinking on his feet in such a rude and sociopathic situation," another replied.

In 2017, Keke Palmer posted a series of videos shared by Beyond the Media during which she put Trey Songz on blast for filming her for a music video without her consent. Palmer claimed that she felt pressured multiple times to appear in the video for "Pick Up The Phone" so much that she had to hide in the closet while waiting for a car. After Songz assured her she wouldn't be filmed, the "True Jackson, VP" star found herself in the video.

During her show, Wendy Williams defended Songz by questioning Palmer's involvement in the video, insinuating that the actor knew that the music video was being filmed and should have just left if she didn't want to be there, per The Wendy Archive. "You sound crazy girl, talking about you hid in a closet," Williams declared. Following the diss, Palmer went on "The Wendy Williams Show" to tell the host, "I will say, Wendy, I would have loved to turn on your show and [see] you be a little bit more compassionate and a little less accusatory." When Williams again took to Songz's defense and asked her why she didn't leave, Palmer told her, "Because I was nervous! ... Think about your first time that you were in a situation where someone challenged you sexually." Although the conversation was tense, the two left with an understanding of each other, and many fans applauded Palmer for taking Williams to task for blindly taking Songz's side.