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Oprah Winfrey reveals her one celeb interview mistake that still makes her ‘cringe’: “So I asked…”

Oprah Winfrey says she deserves the cold shoulder from a Hollywood icon over an 'inappropriate' question that still makes her cringe

Oprah Winfrey has conducted thousands of interviews over her legendary career, but there’s one moment that still makes her ‘cringe.’ During a candid conversation on Rob Lowe’s ‘Literally podcast,’ Winfrey opened up about a past blunder that she now deeply regrets. The revelation came after Lowe expressed his agitation with modern late-night talk shows prioritizing silly games over deep conversations. This nudged Winfrey to recall an unforgettable mishap involving Hollywood icon Sally Field. "Oh, Burt Reynolds!" Oprah exclaimed before having a sudden realization. "Oh, gosh! I have a Burt Reynolds story." She revealed that when she was younger, she had the opportunity to interview Field, who famously dated Reynolds for years.

However, instead of focusing on her career, Winfrey made the mistake of asking a question that immediately soured the conversation. She revealed, "My big mistake: I asked her, 'Does Burt sleep with his toupee on?' 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."

As per E! News, Lowe, who worked with Field on ‘ Brothers & Sisters,’ affirmed Winfrey’s description of the actress. Lowe noted, "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 later confessed, "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. I wouldn't do it today." But this isn’t the only interview Winfrey now looks back on with regret. A resurfaced 1986 interview with Cindy Crawford has gone viral for all the wrong reasons. Crawford, who was just 20 years old at the time, appeared on her show alongside her modeling agent, John Casablancas.

As per Decider, during the segment, Winfrey immediately commented on her body, saying, “Did she always have this body? Stand up just a moment, now this is what I call a body. So did you have to groom her? Or did she always have this body? This is unbelievable.” Crawford visibly uncomfortable, complied with the request nervously. Looking back at the moment decades later, Crawford expressed, “I was like the chattel or a child, to be seen and not heard. When you look at it through today’s eyes, Oprah’s like, ‘Stand up and show me your body. Show us why you’re worthy of being here,' In the moment I didn’t recognize it and watching it back I was like, ‘Oh my gosh, that was so not okay really.’ Especially from Oprah!”

She further spilled the beans, “She asked me what my measurements were and asked me to stand up. And I stand up and she was like comparing herself to this little girl.” Following Crawford’s comments, the interview was quietly removed from Oprah's YouTube channel, sparking speculation that the talk show host wanted to distance herself from the controversy.