Andy Cohen Reveals His Biggest WWHL Regret, Favorite Guest

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Andy Cohen reflected on his biggest regret and his favorite guest ahead of the 15th anniversary of Watch What Happens Live.

As he also addressed his drama with Madonna, 65, looked back on the drunken appearances of Regina King, 53, and Jackée Harry, 67, and gushed over his friendship with Anderson Cooper, 57, Andy, 56, said his 2013 episode with Oprah Winfrey, 70, was among his most memorable moments on the late-night talk show.

“This was a huge moment for me and for the show,” Andy told Entertainment Tonight on June 28. “I’m such a fan of Oprah.”

As fans might remember, Andy asked Oprah if she’s “taken a dip in the lady pond” on the episode.

“That’s probably one of my few regrets,” Andy admitted. “It meant so much to me that Oprah Winfrey did the show. It’s gone brilliantly and I turn around and ask her if she’s [ever] had sex with a woman. I mean, couldn’t I leave it alone?”

After questioning Oprah about her sexuality, and having her reply, “No, no I have not. Thank you,” Andy said the former talk show host was “super cool” and “not awkward” before noting that she apparently didn’t know what his question meant.

“Gayle King told me later that week that Oprah didn’t know what I meant by ‘the lady pond,’” Andy shared. “I thought I explained it pretty well there, but listen, I was so grateful that Oprah did the show and I still am. That remains, I think, my favorite episode.”

As for his favorite guest, Andy named Patti LuPone, 75.

“I mean, Patti LuPone has no F’s to give so she is the perfect clubhouse guest. She’s been here many times,” he stated, looking back on a 2017 episode in which Patti shaded the singer as a “movie killer.”

“This clip got me in a lot of trouble with Madonna, who called me a ‘troublemaking queen’ from the stage of her Celebration Tour. [She] said, ‘You need to stop talking crap about me on your show,’” Andy recalled. “Now the truth is, it wasn’t me talking crap about her. It was people like Patti LuPone — who I also love, by the way.”

While Andy sent Madonna a reel of “all the nice things we said” on other episodes, it wasn’t quite enough to get her to appear on WWHL.

Although Andy would love to one day welcome Madonna to his show, he sees the project as a success regardless.

“The secret to the success of Watch What Happens Live, I think, is spontaneity, authenticity, fun, humor, me going there and people never knowing what’s gonna happen,” he explained. “People let their guard down here. It’s also live, we’re on at night, we serve alcohol. It’s so small in here that it’s deceptive, like, people don’t realize they’re actually on television.”

On one particular episode in 2011, Andy said Regina and Jackée got “sauced.”

“They were smashed in the green room and they were more smashed the longer we went on,” Andy shared. “I was wondering if it was too messy and then I realized, ‘Oh, wait, people on Twitter are loving this’ and it became a really, really historic episode.”

Moving on to his years-long relationship with Anderson Cooper, 57, Andy said their friendship “means a lot.”

“We’ve gotten so much closer over the past 15 years. We’ve been on tour together, we co-host New Year’s Eve together, we’ve been through a lot and being dads together has been a great joy in our lives,” he gushed, giving a nod to his son Benjamin, 5, and daughter Lucy, 2, and Anderson’s sons Wyatt, 4, and Sebastian, 2.

“Being a dad has totally changed how I approach work, too. I come, I do my thing, I go home to the kids and I love bringing them here,” he noted.

Meanwhile, at the time of the 2009 debut of WWHL, things were much different.

“I used to go out every night until all hours after the show, and now I really stay home,” he revealed. “I go home and kiss my kids goodnight while they’re sleeping and I can’t wait to see them in the morning. My life has totally changed and I wouldn’t have imagined this for myself 15 years ago.”

“The next chapter of life is really all about the kids,” he added. “And keeping this show going and keeping the [Real Housewives] as fresh as we can.”