Oprah Winfrey Reveals the One Celebrity Interview That Went Very, Very Wrong: ‘I Deserved it’

As someone who interviews celebrities as part of my job, I can honestly say that asking the right questions is key. One wrong move and an interview—that may have been running smoothly—can quickly switch directions. And apparently, even Oprah Winfrey has run into this problem on occasion. 

Earlier this week, the television mogul paid a visit to Rob Lowe's Literally podcast, where she opened up about one interview in particular that turned out to be a “flub.” The conversation in question was with actress Sally Field, during which Winfrey asked about her on-screen co-star and off-screen boyfriend, Burt Reynolds. 

“Oh, gosh! I have a Burt Reynolds story,” Winfrey told Lowe during the episode before revealing her “big mistake” which still affects her to this day.

“My big mistake: I asked her, ‘Does Burt sleep with his toupee on?'” she continued. “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.” Yikes. 

The 57-year-old Parks and Rec star, who has a close working relationship with Field, told Winfrey he wasn’t surprised that she shut down after that question. He said, “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.” 

Luckily, the OWN creator learned from her mistake and takes total accountability. She added, “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.”

Hey, mistakes happen to the best of us.

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