Oprah Winfrey opens up about ‘big’ interview faux pas: ‘I cringe to even think that I asked that question’

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Kelly Rissman

US News Reporter

Oprah Winfrey is known around the world for her interview skills, but even she can remember one question she regrets asking.

The TV icon recounted the moment during a conversation with Rob Lowe for the latest episode of the actor’s podcast Literally! With Rob Lowe.

The interview took place earlier in Winfrey’s career, when she interviewed Sally Field.

Winfrey, who felt a responsibility to “ask the questions the viewer wanted”, brought up Burt Reynolds, Field’s Smokey and the Bandit co-star and former partner. The pair dated for several years in the late Seventies.

“I asked her, ‘Does Burt sleep with his toupee on?’” Winfrey told Lowe, to which he exclaimed: “O-M-G.”

“I even say now – I cringe to even think that I asked that question,” she added. “But I asked it because the producers were like, ‘You have to ask, you have to ask, you have to ask, that’s what everybody wants to know.”

Field, according to Winfrey, then “shut down” and the interviewer “could not get in again”.

“I deserved it,” Winfrey added. “Because that is such an inappropriate question.”

Things between Winfrey and Field eventually worked out: Winfrey interviewed the actor again in 2012 during a revealing conversation on her cable channel, the Oprah Winfrey Network.