Oprah Winfrey reveals the one 'inappropriate' question she regrets asking to this day

Oprah Winfrey is touted as one of the best interviewers out there, ran the highest-rated talk show, and has been often dubbed the "Queen of All Media." However, there was one mistake in her highly successful career that haunts her even today.

In a recent appearance on Rob Lowe's "Literally!" podcast on Wednesday, Winfrey looked back on the one question that she regrets asking. The talk show host revealed that she made the mistake years ago during a sit-down interview with actress Sally Field.

The interview was going smoothly, but at one point, Winfrey asked the Academy-award winner a personal question about Burt Reynolds, whom the actress used to date in the late 70s.

"I asked her, 'Does Burt sleep with his toupee on?'" Winfrey recalled.

"I even say now, I cringe to even think that I asked that question," she admitted.

"This is when I was younger and I was not living from the point of view of the surrogate," Winfrey explained, adding that she "did feel a responsibility" at the time to ask Field about Reynolds as she was facing pressure from the producers.

"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," she said. However, Field did not like the question as Winfrey had expected, and the rest of the interview went downhill.

"She went cold on me. She shut down and I could not get in again. I could not," Winfrey said. Lowe also added: "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."

Winfrey admitted that the question about Reynolds, who passed away in 2018 at the age of 82, was likely a step too far.

"It was like, 'Whoa, Sally went cold on me on live TV.' I deserved it, I deserved it, I deserved it, 'cause that is such an inappropriate question," she confessed.

Lowe added with a laugh that he still wants to know the answer to that question, to which Oprah said: "She certainly didn't answer it. And then it didn't matter what else I said."

The 67-year-old had previously also spoken about the awkward question, admitting in an interview with Today's Billy Bush in 2005, "It was a bad question. I wouldn't do it today."