Tea, Shade & Everything in Between: Every Time Andy Cohen Asked the Questions All of Us Were Thinking

Andy Cohen is known for getting up close and personal with celebs on his show, Watch What Happens Live

Andy Cohen, Laverne Cox, Tituss Burgess
Photo: Charles Sykes/Bravo/NBCU Photo Bank via Getty

On top of being the King of All Things Bravo, Andy Cohen is the also the King of the Uncomfortable Question. From the moment a celebrity guest sits down in the Watch What Happens Live clubhouse, it’s assumed they’ll be spilling every drop of tea in their pot. Seriously, nothing is off-limits for Cohen, and he manages to trap celebs in a truly genius way: a game called “Plead the Fifth.”

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Cohen tells his guests upfront that he’ll be asking them three juicy questions, but only lets them off the hook for one if they choose to plead the fifth. From forcing celebrities to talk about their famous feuds to asking Mike Tyson what an ear tastes like, Cohen asks the questions all of us were thinking.

When he asked Wendy Williams if she had met her ex’s mistress and their baby.

While playing a game of “Plead the Fifth,” Cohen brought up Williams’ split from Kevin Hunter, whom she divorced after 21 years of marriage when she learned that he cheated on her and fathered a child with his mistress. Cohen asked: “How would you describe your relationship with the other woman and are you behind the Ferrari repo?” (The question was in reference to tabloid reports that Williams had a Ferrari Hunter allegedly bought his mistress repossessed.)

Williams played coy, saying she didn’t know anything about the Ferrari, but Cohen pressed her: “How would you describe your relationship with that woman?” Williams exclaimed, “I don’t know these people. I don’t know the baby, I don’t know the woman. I don’t know who Kevin became, I don’t know who I am!” She playfully added, “Get out of here, Andy!”

When Shaquille O’Neal declared that he would not be pleading the fifth, so Cohen turned around and asked, “Shaq, your shoe size is 23. How big is your d—?”

And O’Neal responded with, “Let me show you …” and Put. His. Shoe. Against. His. Leg. You know, for reference.

When he asked Kourtney Kardashian — in front of her sister Khloé — if she would have stayed with Tristan Thompson post-cheating scandal.

After a long pause, the eldest Kardashian sister responded, “I think I would!” Her sister Kim Kardashian West added, “Well, you stuck with Scott [Disick] through a lot …” Kourtney explained, “Yeah, and I think that when you have a family, like, you do everything you can for your family.”

When he asked Nicki Minaj who the best-endowed man in the music industry was.

The question even took Minaj by surprise before she gave a diplomatic answer about having had a boyfriend for 10 years and therefore not being *ahem* acquainted with many industry men.

When he asked Kim Kardashian West if her mother, Kris Jenner, would ever reconcile with Caitlyn Jenner.

Kardashian West was super open with her answer, but that doesn’t mean that anyone expected Cohen to ask her! Kardashian West replied, “I would say two. Two percent, and those are Kendall and Kylie. All fair, I think.”

When he literally asked Mike Tyson what an ear tastes like.

We’re sure Mike Tyson has heard his share of ear-biting jokes, but Cohen really went there when he asked the boxer, “What does an ear taste like?” Totally cringe-worthy, but Tyson was at least a good sport when he replied, “Well, that depends. Depends on what ear that you bite.”

When he asked Mariah Carey to say three nice things about Eminem.

And she responded by being ever-so-clever and complimenting M&M’s candy. The songstress had an infamous feud with the rapper that resulted in her song, “Obsessed,” and a diss track from Eminem.

And he wasn’t shy about asking her about her alleged breakup agreement, either.

When the Elusive Chanteuse broke up with billionaire fiancé James Packer in 2016, there were rumors floating around that she and Packer had a “$50 million breakup agreement,” which resulted in a multi-million dollar settlement. Cohen asked Carey: “Why would there be a breakup agreement and are you working on a breakup agreement?” He wouldn’t let her get off easy and continued to ask her despite her clear attempts to dodge the question.

When he asked Oprah if she had ever taken a dip in the “lady pond.”

To be fair, Cohen has since said that he regrets asking her that question. He told Access, “I asked her — not even during ‘Plead the Fifth’ — I asked her if she had swum in the lady pond, so to speak … The second after I said it, I kind of regretted it.” Oprah said that she had not, in fact, taken a dip in the lady pond, and Andy was mortified.

When he asked Nick Lachey what the best part about no longer having Joe Simpson for a father-in-law was.

Lachey, who had previously been married to Jessica Simpson, said that it would have to be “not having to play grab-ass under the table on Easter Sunday.”

When he asked Demi Lovato why she unfollowed Selena Gomez.

At the time it was suspected that Gomez’s friendship with Taylor Swift had something to do with the unfollow, and Lovato told Cohen, “I think it’s just one of those things where people change and people grow apart.”

When he asked Lindsay Lohan about her list of conquests allegedly taken from a diary she kept while in rehab.

At the time, a list had been published that allegedly belonged to Lohan that listed all of the men she had slept with — including some famous names. Cohen really went there with this one during “Plead the Fifth,” asking: “Recently, an alleged list of your alleged former conquests was leaked or published. A few of the names on the list were, like, Ashton Kutcher, Orlando Bloom, Zac Efron, James Franco, Justin Timberlake … Will you confirm having trysted — ” But before he could finish the question, Lindsay interrupted with, “I cannot confirm or deny.” Instead of letting it go, he pushed her to confirm two of the names on the list. That’s when Lindsay tried to plead the fifth again before saying, “That was actually my fifth stay in L.A. at Betty Ford and someone, when I was moving, must have taken a photo of it. So that’s a really personal thing, and it’s really unfortunate …”

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Celebs be warned! When you step into The Clubhouse, everything — and we mean everything — is fair game.

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