Oprah Winfrey reveals her biggest celebrity-interview 'flub' was an 'inappropriate' question she asked Sally Field that still makes her 'cringe' to this day

·3 min read
Oprah Winfrey reveals her biggest celebrity-interview 'flub' was an 'inappropriate' question she asked Sally Field that still makes her 'cringe' to this day
FILE - In this March 13, 2018, file photo, actress Oprah Winfrey poses for photographers upon arrival at the premiere of the film "A Wrinkle In Time" in London. Winfrey announced Wednesday, May 20, 2020 that her Oprah Winfrey Charitable Foundation will donate money to organizations dedicated to helping undeserved communities in Chicago; Nashville, Tennessee; Milwaukee, Wisconsin; and Kosciusko, Mississippi, where she was born. (Photo by Joel C Ryan/Invision/AP, File)
Oprah Winfrey. Associated Press
  • Winfrey said she once interviewed Sally Field and asked about her former flame, Burt Reynolds.

  • "My big mistake: I asked her, 'Does Burt sleep with his toupee on?'" Winfrey said.

  • "Sally went cold on me - on live TV," she told Rob Lowe on his podcast.

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Even though Oprah Winfrey is widely considered one of the greatest interviewers in broadcast history, she can definitely admit when she's messed up in the past.

While speaking to Rob Lowe for his podcast, "Literally! With Rob Lowe," Winfrey opened up about the time she went too far while interviewing the Oscar winner Sally Field.

"Of flubs in the world, this was when I was younger and not living from the point of view of the surrogate, but I did feel a responsibility to ask the questions people wanted," Winfrey began. "And Sally Field was on. My big mistake: I asked her, 'Does Burt sleep with his toupee on?'"

The "Burt" she's referring to is the late legendary actor Burt Reynolds. He and Field dated on and off through the late 1970s after the two starred in the hit movie, "Smokey and the Bandit."

Reynolds, who was a sex symbol in those days, was known to wear a hairpiece (though he never admitted it until much later in his life).

burt reynolds and sally field in smokey and the bandit
Burt Reynolds and Sally Field in "Smokey and the Bandit." Universal Pictures

The result of Winfrey's question: "Sally went cold on me - 0n live TV," she said.

"I cringe to even think that I asked that question, but I asked because the producers are like, 'You have to ask! You have to ask! You have to ask! That's what everybody wants to know,'" Winfrey told Lowe. "So I asked it, and she went cold on me. She shut down, and I could not get in again."

Lowe, who worked alongside Field on the series "Brothers and Sisters," agreed during their conversation that you don't want to get on Field's bad side.

"When Sally goes cold, it's like Khrushchev in the Cold War," Lowe said. "She will bury you."

"I deserved it," Winfrey said. "'Cause that is such an inappropriate question."

sally field gidget
Sally Field. YouTube screencap

In 2015, Reynolds told Vanity Fair that Field was the "love of my life."

Still, in her 2018 memoir, "In Pieces," released 12 days after Reynolds died, Field detailed her rocky relationship with Reynolds, which began in 1977.

"By the time we met, the weight of his stardom had become a way for Burt to control everyone around him, and from the moment I walked through the door, it was a way to control me. We were a perfect match of flaws," she wrote.

"Blindly I fell into a rut that had long ago formed in my road, a pre-programmed behavior as if in some past I had pledged a soul-binding commitment to this man."

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