Oprah Winfrey has recalled how the late Barbara Walters “swooped in” to take her interview with Monica Lewinsky in 1999.
Walters’s famous conversation with Bill Clinton’s former intern-turned-lover remains one of the most-watched television interviews in history. Airing on ABC's 20/20, the discussion marked Lewinsky’s first televised interview following the Clinton-Lewinsky scandal, which had captivated and polarized the nation.
Before that iconic interview took place, Winfrey was originally slated to have the televised conversation with Monica Lewinsky.
In the new ABC documentary Barbara Walters: Tell Me Everything, premiering Monday on Hulu, Winfrey shares the story behind why her interview with Lewinsky was ultimately canceled.
“We have an agreement with Monica Lewinsky’s team,” Winfrey explained. “And then Barbara swooped in and said to Monica Lewinsky: ‘I can give you a better deal. I can not only do a Barbara Walters primetime special, but I can offer you Nightline. I can offer you Good Morning America.”
“And I just had The Oprah [Winfrey] Show,” she continued. “So I didn’t like that.”
However, Winfrey hinted that she wasn’t surprised by the fact that the famous interview went to Walters instead of her.
“Because Barbara had been number one, she had been it, she had been the madame for so long, that she saw that as her rightful place in the space,” the talk show host added. “And if there was something that deserved a special one-on-one interview, I think she felt like she was the one who was supposed to have it.”
According to Winfrey, “9.9 times out of 10,” Walters would get that interview.
The interviewer’s two-hour chat with Lewinsky broke TV records, drawing more than 75 million viewers across the U.S.

Walters went on to form a friendship with Lewinsky, who was also featured in the new ABC documentary. During a 1999 interview with TV Guide, Walters said that if she’d had the chance, she would have told Lewinsky to end her relationship with Clinton much earlier than she ultimately did.
“I would have tried to tell her that this was a relationship that had no future,” she said. “But have you ever tried to stop a daughter when she is in love from doing anything? It’s very hard.”
Elsewhere in Barbara Walters: Tell Me Everything, Winfrey opened up about what she learned from Walters, who managed a busy career while raising her only child, Jacqueline.
Winfrey claimed Walters has a “complex” and “charged” relationship with Jacqueline, and that’s one of the reasons why Winfrey herself “never had children.”
“You are a pioneer in your field, and you are trying to break the mold for yourself and for women who are going to follow you,” she added. “And something’s going to have to give for that. And that’s why I didn’t have children. I knew I could not do both well.”
Winfrey also acknowledged how Walters shaped the entertainment industry for female TV hosts everywhere.
“I think she knew, after a time, that what she had done helped open the door for women like myself and every other woman who crossed the threshold,” she said.
Barbara Walters: Tell Me Everything includes audio from Walters’s early interviews. She passed away in 2022 at the age of 93. The documentary will be available for streaming on Hulu starting June 23.
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