Barbara Walters Once Named Her Worst Interview Guest Ever

Barbara Walters was, without a doubt, one of the most tenacious journalists to ever live. The inimitable broadcaster broke the glass ceiling in the previously male-dominated field thanks to her impeccable talent in writing and interviewing. "She was an early ballbuster, and I mean that in the nicest possible way," journalist Katie Couric said of the late television personality, per Vanity Fair. "She rattled a lot of cages before women were even allowed into the zoo."

Over the course of her 50-year career, Walters sat opposite celebrities, politicians, royals, and other controversial personalities to coax answers out of them regarding pressing issues. One of her most famous interviews was with former White House intern Monica Lewinsky, which reportedly drew nearly 50 million viewers, according to The New York Times. Walters put her in the hot seat, interrogating Lewinsky about her sex scandal with former president Bill Clinton. "You showed the president your thong underwear. Where did you get the nerve? I mean, who does that?" Walters asked (via The Hollywood Reporter). "Where was your self-respect, where was your self-esteem?"

Every "Barbara Walters Special" was gripping, to say the least, but there was one interview that challenged her because the interviewee was, in her words, "boring."

According to Barbara Walters, interviewing actor Warren Beatty was quite the challenge. She even went as far as to describe him as "boring" because of the way he answered her questions. In an appearance on "The Tonight Show Starring Jimmy Fallon," Walters recalled the time Beatty proved to be difficult.

"You know who I think the most boring interviewee is? And I've told him this so this is... The most boring interviewee is Warren Beatty," she mused. "I'll give you an example. It takes forever. You say to him, 'What's the title of your new movie?' and he goes, 'Uhh... Let me think... The title...' Who cares!" Walters doubled down on this statement in an interview with the Toronto Star in 2010. When asked what the worst interview in her life was, she answered Warren Beatty, point blank. "It was like pulling teeth, she told the publication. "I'd ask him, 'How are you?' and he'd say, 'That's a very hard question.'"

Beatty, for his part, admitted to feeling "insulted" by Walters. In a 2017 profile on Esquire, he said that the interview only went south because of Walters' choice of questions, and not because he was "boring."

Some of Barbara Walters' interviews were considered failures because of the interviewee, but some were because of the questions she asked them. She particularly regretted her interview with Ricky Martin in 2000, when she coerced him to discuss his sexuality. At the time, the singer identified as straight.

"In 2000, I pushed Ricky Martin very hard to admit if he was gay or not, and the way he refused to do it made everyone decide that he was," Walters shared with the Toronto Star in 2010. "A lot of people say that destroyed his career, and when I think back on it now I feel it was an inappropriate question."

Martin later admitted that the interview had a negative impact on his mental health. During that time, he was still confused as to what his sexuality was, telling People in 2021 that he was dating "lots of women." And so, when he sat opposite Walters, he was pretty much blindsided. "When she dropped the question, I felt violated because I was just not ready to come out. I was very afraid," Martin confessed. "There's a little PTSD with that."