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Oprah’s ‘Big Mistake’ from Her Decades-Long Career Still Haunts Her  Jordan Strauss/Invision/AP
Jordan Strauss/Invision/AP

Poised, pioneering, and powerful, Oprah Winfrey seems like she could do no wrong. But even the indomitable TV host has made a few flubs over the course of her multidecade career and innumerable celebrity interviews.

The 67-year-old TV legend revealed her “big mistake” during an interview with Rob Lowe on his podcast Literally! with Rob Lowe. During the interview, Oprah discussed her interview with actress Sally Field in the late ’70s. Everything was going fine– until the one question Oprah asked Sally Fields about her partner Burt Reynolds.

Here’s What Happened When Oprah ask Sally Field About Burt Reynold’s Toupee

“This is when I was younger and I was not living from the point of view of the surrogate,” Winfrey told the 57-year-old Oscar-winning actor, adding that she “did feel a responsibility” to ask Field about Burt Reynolds, her co-star in ’70s movies like Smokey and the Bandit and boyfriend of five years.

“My big mistake: I asked her, ‘Does Burt sleep with his toupee on?’” the talk show host admitted. “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.’ And so I asked it, and she went cold on me. She shut down, and I could not get in again.”

Lowe, who has his own experience working with Field on the ABC drama series Brothers & Sisters. “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,” he sympathized.

But Oprah knew she was in the wrong for going so personal.  “It was like, ‘Whoa, Sally went cold on me on live TV,’” the television mogul remembered. “I deserved it, I deserved it, I deserved it, ’cause that is such an inappropriate question.”

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Sally Fields & Burt Reynolds

In case you need a refresher on Fields and Reynold’s relationship. In an interview with The New York Times, Fields revealed that their relationship was  “not without loving and caring, but really complicated and hurtful to me.”

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But when 82-year-old Reynolds died in September 2018, Fields was flooded with feelings and nostalgia…There are times in your life that are so indelible, they never fade away. They stay alive, even forty years later.”

Watch: Who Is Oprah Winfrey’s Mysterious Long Time Partner?

A lover, fighter, and freelance writer, María Cristina hunts down buzzworthy stories by day and trains to be a championship kickboxer by night. As a full-time digital nomad, she's lived everywhere from Chicago to Mexico City to Medellín to Bali -- but Austin, Texas will always be home.
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