Oprah Winfrey Admits This Celebrity Interview Makes Her ‘Cringe’

Oprah Winfrey has interviewed countless celebrities over the years. From sitting down with well-known musicians to her conversations with Prince Harry and Meghan Markle, the media mogul is no stranger to making headlines for her bombshell discussions.

Though Oprah has done dozens of notable interviews, there’s one that is anything but her favorite as it still haunts her to this day.

Oprah Winfrey
Oprah Winfrey during 2020 Global Citizen Prize Awards Special | Global Citizen Prize/Getty Images for Global Citizen

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 hard-hitting topics.

RELATED: Oprah Says Meghan Markle Texted Her’ Intention’ Prior to CBS Interview

Though she’s conducted plenty of interviews over the years, not every discussion 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. “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 Field back in the day.

Burt Reynolds and Sall Fields
Black and white photo of Burt Reynolds and Sally Field in ‘Smokey and the Bandit III’ |
Bettmann/ Getty Images

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Oprah shared that she was pressured to ask Field a very personal question about Reynolds. She not only considers it 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. He shared his own experience of getting the cold shoulder from Field, 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 Field’s 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.”