Oprah Winfrey Reveals Which Interview Moment Makes Her Cringe to This Day

Oprah Winfrey has done countless high-profile interviews throughout her career, and she's now revealed which one makes her cringe to this day. On Wednesday, the iconic TV host sat down with actor Rob Lowe on his podcast, Literally, and revealed that her biggest interview regret was from a conversation about late Hollywood legend Burt Reynolds. "Oh, Burt Reynolds!" she interjected when Lowe brought up the actor. "Oh, gosh! I have a Burt Reynolds story."

Winfrey explained that she once interviewed Sally Field, who co-starred in Smokey and the Bandit with Reynolds and also dated him around the same time. "My big mistake: I asked her, 'Does Burt sleep with his toupee on?'" Winfrey revealed, shocking 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.'"

The media mogul continued, "And so I asked it, and she went cold on me. She shut down, and I could not get in again." Lowe comforted her by explaining that he could relate, as he also encountered Field's cold-shoulder when they pair worked together 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," he quipped. "She will bury you."

Winfrey then clarified that Field deserves no criticism whatsoever for the awkward moment. She admits to taking full responsibility for the "inappropriate question." The TV icon also stated that she believes she "deserved" the cold response she got.


Earlier this year, Winfrey took part in another memorable interview, sitting down with Prince Harry and Meghan Markle for a candid conversation about their experience with the Royal Family over the past few years. During the interview, Markle dropped a number of bombshell comments and allegations, such as that there were Royal family conversations about what color of skin their baby, Archie, would have, prior to his birth. The interview had made a number of headlines, and it likely not one Oprah will look back on with regret.