Oprah Winfrey on the Question She Asked Sally Field About Burt Reynolds That Makes Her 'Cringe' Today

"I even say now, I cringe to even think that I asked that question," Oprah Winfrey said on the Literally! with Rob Lowe podcast

oprah, sally field, burt reynolds
Oprah; Sally Field and Burt Reynolds. Photo: Bertrand Rindoff Petroff/Getty Images; Ron Galella Collection via Getty Images

Oprah Winfrey says there's one interview question that still haunts her.

Winfrey, 67, appeared as a guest on Rob Lowe's Literally! podcast on Wednesday, where she looked back on asking actress Sally Field an uncomfortable question about the now 74-year-old's former partner Burt Reynolds during a sit-down years ago.

"This is when I was younger and I was not living from the point of view of the surrogate," Winfrey explained to Lowe, 57, adding that she "did feel a responsibility" at the time to ask Field about Reynolds. (The pair dated for several years in the late 70s; Reynolds died in September 2018 at the age of 82.)

"I asked her, 'Does Burt sleep with his toupee on?' " Winfrey recalled.

As Lowe expressed his shock at Winfrey's question, the Wrinkle in Time actress admitted, "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,' " added Winfrey. "And so I asked it and she went cold on me. She shut down and I could not get in again. I could not."

Lowe then gave his own two cents on Field, having worked with the famed actress on the ABC family drama series 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," said Lowe. "She will bury you."

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Winfrey again reiterated that the question about Reynolds' hair was likely a step too far. "It was like, 'Whoa, Sally went cold on me on live TV,' " she told Lowe. "I deserved it, I deserved it, I deserved it, 'cause that is such an inappropriate question."

"Meanwhile I still want to know," Lowe said with a laugh.

"She certainly didn't answer it. And then it didn't matter what else I said," Winfrey said.

Winfrey previously reflected on asking Field the pointed question back in 2005 during a wide-ranging interview with Today's Billy Bush.

"It was a bad question," Winfrey said. "I wouldn't do it today."

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