Over the course of her long and illustrious career as a talk show host, Oprah Winfrey has interviewed pretty much every celebrity, politician, and high-profile figure, getting them to open up to her about their private lives. But she recently confessed that there's still one question she asked that haunts her all these years later.
Oprah appeared on Rob Lowe's Literally! podcast this week, revealing that even she makes professional mistakes from time to time. Lowe brought up how he wishes late-night hosts would stop playing games with their guests and get back to letting interesting people, like Burt Reynolds, tell stories, at which point Oprah interjected, “Oh, gosh! I have a Burt Reynolds story.” She explained that when she was younger she interviewed Sally Field, who starred alongside Reynolds in a handful of 70s films like Smokey and the Bandit and dated the actor for five years. “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,” the TV icon confessed. “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.”
Lowe was sympathetic to Oprah's blunder, recounting his own experience working with Fields on the show 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. She will bury you,” he said. But the OWN founder admitted she shouldn't have gone there. “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.”
In a 2018 interview with the New York Times about her memoir, In Pieces, Fields confessed that her relationship with the late actor was “not without loving and caring, but really complicated and hurtful to me,” later telling NPR, “we were a perfect match of flaws.” But upon learning of Reynolds death in September of that year, she told the Times, she was “flooded with feelings and nostalgia...There are times in your life that are so indelible, they never fade away. They stay alive, even forty years later.”
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