What Andy Cohen Has Said About Most Challenging ‘Watch What Happens Live’ Guests

After more than 15 years on air, Andy Cohen has been candid about some of the most challenging guests he’s had on Watch What Happens Live.

Most recently, in January 2026, Cohen made headlines when he shared he didn’t have any intention of inviting former Biggest Loser trainer Jillian Michaels back to the clubhouse.

“I don’t think there’s a market for that,” Cohen told Entertainment Weekly at the time, regarding the odds of Michaels returning to the show. “By the way, I don’t think she would come.”

While recalling Michaels’ 2013 appearance on his late night show, Cohen added, “She was furious. I should watch it back, if I cared. I don’t see what she was upset about.” (Luxury Handbag Shopping reached out to Michaels for comment.)

Years before, Cohen shared that Vanderpump Rules alums Lala Kent and James Kennedy’s expletive-filled appearance on WWHL was also one that goes down in infamy.

Scroll down to see more of the infamous guests on WWHL:

Jillian Michaels

During her one and only appearance on WWHL in 2013, Jillian Michaels’ notable moments included addressing some of the mistakes people make while working out and giving a thumbs up when The Real Housewives of Beverly Hills alum Brandi Glanville called in to say she would like to “swim in the lady pond” with her, per Entertainment Weekly. Michaels also participated in Andy Cohen’s “shotski” alongside The Big Bang Theory’s Melissa Rauch.

“[Jillian] left and she was screaming at my staff,” Cohen alleged to the outlet in 2026, noting he didn’t know what upset her so much. “And if you scream at my staff, that’s kind of it for me.”

Michaels, meanwhile, shared in a 2019 interview with Luxury Handbag Shopping that she was “exhausted” while filming WWHL after doing press all day and recently battling the stomach flu when Cohen brought out the shotski.

“So he was explaining [the shotski] to me and I was a little bit out of it and I nodded like, ‘Yeah I got it. So you drink the shot or whatever,’” she told Us at the time. “He turns around again over his shoulder and looks at me and goes, ‘Do … you … understand?’”

She continued, “And this was before the show started. And it’s live! So you can’t leave. … At the end of it, I was like, ‘I gotta tell you, that was a truly hideous experience. Like in all the years I’ve been doing this, nothing like this has ever happened.’”

Lala Kent and James Kennedy

When Vanderpump Rules alums Lala Kent and James Kennedy appeared on WWHL in 2015, Andy Cohen recalled that he “yelled at them the whole time” for their cursing.

“They were like, ‘Oh, we are sorry. We are sorry. OK, OK, OK,’” Cohen recalled to Bravo at the time about their reactions to his yelling. “You know what, here’s the thing. I was really excited about having them on the show, especially James because he’s been so entertaining on Vanderpump Rules this season. And he was really excited about being on.”

He continued, “The bummer is that I talked to him before the show, and he said, ‘I’m so excited about being on the show. I didn’t sleep last night. I’m so excited.’ And then, it was just gross. They didn’t stop cursing, and I was really irritated. The viewers hated it. They were cursing so much, whoever our censor is, they’re very liberal, and every time you say a curse word, they block out the sentence before, the sentence after, so it’s like the whole episode was on mute. And it was very irritating. And it just left a really bad taste in my mouth.”

Cohen noted that Lisa Vanderpump sent him a message that night asking what happened, to which he replied, “Let me put it this way. They made Jax [Taylor] and Kristen [Doute] look like Michelle and Barack Obama.”

When asked whether Kent and Kennedy would ever be “allowed back” on WWHL, he replied, “No.” He noted that the twosome did apologize to him after the show. (Kent and Kennedy, who have been open about struggles with substance abuse and were drinking at the time of the appearance, have since both appeared on Cohen’s late night show.)

Years later, Kent reflected back on her appearance in her 2021 memoir, Give Them LaLa, writing, “I wrote a heartfelt note to [Cohen and Vanderpump] both. Lisa immediately forgave me … but Andy was still very upset, and I wasn’t sure he’d ever warm back up to me.”

Amber Rose

While appearing on the Rachael Ray Show in 2016, Andy Cohen was asked who has been his “least favorite guest” on WWHL.

“OK, I will say that Amber Rose came on and she didn’t want to answer any of the questions that I was asking her. And she was wearing sunglasses and she said on the air, she goes, ‘Am I your worst guest ever?’” Cohen shared. “I go, ‘You are in the running right now, you really are.’”

He continued, “But I have to say, I really liked her a lot and after the show, we had a laugh about it and I was like, ‘That really didn’t work great.’”

Debra Winger

When Andy Cohen was asked to name his worst WWHL guest ever during an audience Q&A at a For Your Consideration Emmys event in 2019, a fan suggested Debra Winger’s appearance the year before.

“Oh my God, it was bad,” Cohen agreed, per Bravo. “I almost can’t talk about it.”

Cohen noted that he was not expecting the way Winger’s appearance went. “You know what’s weird about Debra Winger? We really did connect, and during the commercial break, she kept saying, ‘You know, you’re like my Jewish little brother. I feel connected to you,'” he shared. “But then when the camera came on, she wasn’t having me.”

Cohen went on to recall one moment with Winger, when she played a round of Plead the Fifth.

“I asked her to rate her onscreen kisses in order, like [John] Travolta, Richard Gere, and [Robert] Redford. I mean, that’s a fair question,” he said. “She was like, ‘Would you remember if you did those 30 years ago?’ I was like, yeah! … 50 years ago! Yeah, I would! Call me crazy! If I was a female lead in An Officer and a Gentleman.”