Oprah Reveals Her Biggest Interview Mistake Ever

Oprah Winfrey is known for (among other things) being one of the most iconic interviewers ever. Over the years, the TV mogul sat down with celebrities like Michael Jackson, Whitney Houston, Tom Cruise, Rihanna, Kim Kardashian, and more recently, Prince Harry and Meghan Markle. During her interviews, Oprah is able to swiftly handle sensitive topics and tough questions, with her guests revealing things we never thought we would hear before. However, it seems like this wasn't always the case for the popular interviewer.

Speaking with Rob Lowe on the "Literally!" podcast, Oprah revealed that she once made a huge interview mistake that still makes her "cringe." On the May 13 episode, Oprah and the host complained about how late-night shows' interviews don't have much substance anymore, and rather focus on celebrity guests playing silly games. Then, Lowe mentioned Burt Reynolds, which seemed to trigger Oprah.

"Oh, Burt Reynolds!" she said (via E! News). "Oh, gosh! I have a Burt Reynolds story."

Many years ago, Oprah Winfrey interviewed actor Sally Field, who dated Burt Reynolds and starred with him on the 1977 film "Smokey and the Bandit." During the interview, however, Oprah asked Field a very personal question ... and she didn't appreciate it.

"My big mistake: I asked her, 'Does Burt sleep with his toupee on?'" Oprah told Rob Lowe on his podcast (via E! News). "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.'"

So, after Oprah asked the salacious question, Field was completely turned off. "She went cold on me. She shut down, and I could not get in again." Lowe, who's very familiar with Field, said her reaction was to be expected. "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 said. "She will bury you."

Oprah definitely learned from her mistake and admitted that the question was totally uncalled for. "I deserved it, I deserved it, I deserved it, 'cause that is such an inappropriate question," she said.