In 1988, less than two years into her syndicated talk show’s run, Oprah Winfrey scored the interview of a lifetime. Oscar-winning actress Elizabeth Taylor agreed to sit down with Winfrey on her daytime chatfest. The two women were set up on cozy armchairs at the Hotel Bel-Air, but the comfort stopped there. According to Oprah.com, Taylor gave Winfrey a last-minute stipulation. The “Cleopatra” star, who was between marriages at the time, specified that Winfrey couldn’t ask her anything about her relationships. Winfrey was caught off guard by the request and later said of the stipulation, “That’s kind of hard to do when you’re Elizabeth Taylor and you’ve been married seven times.”
During the interview, Taylor didn’t give Winfrey much of anything. Her responses were short, there were awkward silences, and Winfrey was even given a terse “None of your business” as an answer to one of her questions, via The New Yorker. At one point, Winfrey found herself blurting out an uncharacteristic nervous retort at her guest. “You’re so revealing — you just tell everything! I declare, you’ve got to stop talking so much, Ms. Taylor!” she said.
Winfrey later revealed that Taylor apologized for the interview and explained that she’d been in a lot of hip and back pain that day. But that didn’t make the rewatch any easier for her. Via The New Yorker, Winfrey has called the conversation “the worst interview of my life.”