Oprah reveals the ‘inappropriate question’ she once asked that still makes her ‘cringe’

Oprah Winfrey
Photo credit Getty Images
By , Audacy

Oprah Winfrey is all about “aha moments,” but it’s an “oh no” one that has her looking back in shame.

The 67-year-old has conducted thousands of interviews, but there’s one in particular that still haunts her for asking an “inappropriate” question.

Oprah brought up the topic while appearing on Rob Lowe’s podcast “Literally!" which is available to listen on the Audacy app.

“Oh, Burt Reynolds!” the OWN maven said. “Oh, gosh! I have a Burt Reynolds story.”

In actuality, the interview wasn’t with Reynolds, but with his "Smokey and the Bandit" costar, and girlfriend at the time, Sally Field.

"My big mistake: I asked her, 'Does Burt sleep with his toupee on?'" Oprah recounted to Lowe. "I even say now, I cringe to even think that I asked that question. But I asked it because the producers are like, 'You have to ask, you have to ask, you have to ask. That's what everybody wants to know.'”

Things with Field went downhill fast.

She continued: "And so I asked it, and she went cold on me. She shut down, and I could not get in again."

Lowe, who worked with Field on the ABC series “Brothers & Sisters,” shared his own history with the actress.

“She’s one of the most amazing actors I’ve ever known, but when Sally goes cold, it’s like Khrushchev in the Cold War. She will bury you,” Lowe noted.

But Oprah said Field was fully in her right for the response and took complete responsibility for the extremely awkward moment.

“It was like, ‘Whoa, Sally went cold on me on live TV,'” she said. “I deserved it, I deserved it, I deserved it, ’cause that is such an inappropriate question.”

While that may not be Oprah’s proudest moment, her recent bombshell interview with Meghan Markle and Prince Harry definitely left quite the impression on the world.

“I had no idea that it would have the reverberating impact that it has had and continues to have,” Oprah recently said of the royal sit-down.

“I did a lot of preparation for that. It was really important to me that what we put out there in the world was put out into the world at the time that everybody could see it and that things didn’t leak and things weren’t misconstrued before the actual interview happened.”

For more enlightening interviews, listen to “Literally! with Rob Lowe” on the Audcacy app.

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