The 67-year-old television icon was a guest on Rob Lowe's "Literally" podcast on Wednesday, May 12, where she revealed one question from a celebrity interview she conducted many years ago that still haunts her to this day.
Her story was spurred by Lowe mentioning he gets annoyed by the fact that current late-night talk shows are so focused around the guests playing silly games, and that he wishes they would go back to a time when a fascinating celebrity, such as Burt Reynolds, would just sit down and tell stories.
"Oh, Burt Reynolds!" Winfrey replied fondly before she suddenly experienced a light-bulb moment. "Oh, gosh! I have a Burt Reynolds story." She prefaced it by saying her memory was in the category "of flubs in the world."
Winfrey went on to explain that the incident happened when she was much younger and interviewing Sally Field, who not only shared the screen with Reynolds in such projects as "Smokey and the Bandit" but also dated the late screen legend in real life for a number of years.
"My big mistake: I asked her, 'Does Burt sleep with his toupee on?'" the OWN mogul recalled to a stunned 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."
Lowe was certainly empathetic and shared his own experience from working with the 74-year-old Oscar winner during their time on ABC's "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 57-year-old "Wayne's World" actor quipped. "She will bury you."
For her part, Winfrey was quick to admit she shouldn't have broached that particular subject matter. "It was like, 'Whoa, Sally went cold on me on live TV,'" the "Wrinkle in Time" performer said. "I deserved it, I deserved it, I deserved it, 'cause that is such an inappropriate question."
This isn't the first time the TV superstar has discussed the challenging exchange. During a 2005 Today show interview looking back on her career, Winfrey brought up her query to Sally and referred to it as "awful."
She added back then, "I wouldn't do it today." Talk about a hair-owing experience.