Oprah Winfrey reveals the one interview moment that still makes her cringe to this day

The TV icon spoke with Rob Lowe about the worst questions she's asked a guest

Oprah Winfrey recalled the one moment from her decades of interviewing celebrities that still makes her cringe to this day. 

The 67-year-old television icon has interviewed almost every celebrity and major public figure under the sun throughout her long and storied career in show business. Most recently, she made headlines for explosive tell-all interviews with people like Elliot Page as well as Meghan Markle and Prince Harry

However, speaking as a guest on Rob Lowe’s "Literally" podcast Wednesday, Winfrey revealed that there is one interview in which she feels she really dropped the ball, noting that the memory still haunts her to this day. 

Oprah told her story after Lowe lamented the fact that late-night talk show hosts today focus too much on getting stars to play fun, silly games rather than getting to know them or their craft. He used the late Burt Reynolds as an example of someone fascinating that late-night hosts could get to know, prompting Winfrey to chime in with her own story about the man. 

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Oprah Winfrey revealed the interview that makes her ‘cringe’ to this day. 

Oprah Winfrey revealed the interview that makes her ‘cringe’ to this day.  (Getty Images)

"Oh, Burt Reynolds!" she interjected (via E! News). "Oh, gosh! I have a Burt Reynolds story."

That’s when she launched into a story about interviewing Reynolds’ "Smokey and the Bandit" co-star and real-life girlfriend at the time, Sally Field. Winfrey noted that she was pressured to ask a question that she now considers one of her career's earliest and greatest flubs. 

"My big mistake: I asked her, 'Does Burt sleep with his toupee on?'" the OWN mogul explained to her shocked host. "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.'"

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

Lowe, who had his own experience working with Field on the 2006 ABC drama "Brothers & Sisters," noted that he’s familiar with the otherwise "amazing" celebrity’s cold shoulder. 

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"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," he joked. "She will bury you." 

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Winfrey made sure to note that no one should be upset at Field over the awkward TV moment. She admits that she takes full responsibility for asking an "inappropriate question" and concluded that she "deserved" every bit of Field’s coldness on the day.