Oprah Winfrey Admits This Celebrity Interview Makes Her 'Cringe'

Oprah Winfrey has had countless interviews with famous celebrities over the years. From sitting down with well-known musicians to British royalty, the media mogul is no stranger to making headlines for her bombshells discussions.

Though there are likely hundreds of interviews Oprah prides herself on, there’s one that is anything but her favorite as it still haunts her to this day.

Oprah Winfrey has interviewed almost every celebrity under the sun 

Throughout her long and storied career in show business, Winfrey has interviewed a plethora of celebrities and public figures.

From Prince Harry and Meghan Markle to Michael Jackson, Oprah has sat down with hundreds of A-listers over the years to discuss some hard-hitting topics fans have wanted answers to.

While there’s likely a long list of interviews Oprah enjoyed from start to finish, not every discussion she’s had has been a breeze.

In fact, there’s one interview, in particular, that was so cringeworthy that she gets uncomfortable just thinking about it.

Oprah Winfrey wishes she could do one awkward celebrity interview over

On May 12, Oprah appeared on an episode of Rob Lowe’s Literally podcast, where she revealed the one awkward interview she conducted years ago that still makes her cringe today.

The conversation began with Lowe mentioning that he isn’t a fan of current late-night talk show hosts centering their programs around the guests playing silly games rather than getting to know them or their craft.

He then used the late Burt Reynolds as an example of someone who made it easy for talk show hosts to get to know as he would just sit down and tell stories. 

This prompted Oprah to share her own story about the legendary actor.

“Oh, Burt Reynolds!” she interjected (per E! News). “Oh, gosh! I have a Burt Reynolds story.”

She then launched into the story of when she interviewed Reynold’s Smokey and the Bandit co-star Sally Fields back in the day.

Oprah shared that she was pressured to ask Fields a very personal question about Reynolds, which she not only considers one of her greatest flubs but the biggest mistake of her career.

“My big mistake: I asked her, ‘Does Burt sleep with his toupee on?’” Oprah recalled to Lowe. “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.’”

She continued, “And so I asked it, and she went cold on me. She shut down, and I could not get in again.”

Oprah takes full responsibility for the cringe-worthy TV moment

After hearing the OWN mogul’s cringe-worthy story, Lowe was empathetic and shared his own experience of getting the cold shoulder from Fields, whom he worked alongside on the 2006 ABC drama 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,” the 9-1-1: Lone Star actor quipped. “She will bury you.”

In Fields’ defense, Oprah admitted that she was wrong to ask the question, noting that she shouldn’t have brought up that particular subject matter.

“It was like, ‘Whoa, Sally went cold on me on live TV,’” she said. “I deserved it, I deserved it, I deserved it, ’cause that is such an inappropriate question.”

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