Barbara Walters’ memorable interviews: The late journalist brought Oprah Winfrey to tears

Barbara Walters died on Friday at age 93, but her brilliance and tenacity in many of her iconic interviews will live on.

The legendary journalist sat down with an impressive array of entertainment industry stars and world leaders in her career, which reached all the way back to the 1950s.

Walters managed to get to the heart of interview subjects known for being on the other end of the questions, including Oprah Winfrey, and she conducted major interviews with major figures including Fidel Castro and the Shah of Iran.

But the pathbreaker also developed a reputation for asking unnecessarily probing questions and ignoring the feeling of her guests in some of her more infamous sit-downs.

Legend: Barbara Walters had a string of iconic interviews throughout her decades long career with politicians and entertainment stars. The journalist, who died on Friday at age 93, is seen with Oprah Winfrey in 2006

One of Walters’ most acclaimed interviews was with Winfrey, who had conducted more than her share of memorable interviews prior to the 2010 meeting.

The veteran interview probed Winfrey about rumors that she was a lesbian that had dogged her for years, which clearly annoyed the television host. 

After Walters asked Winfrey about the rumors, she emphatically denied them.

‘I’m not a lesbian. I’m not even kind of a lesbian,’ she said. ‘And the reason why it irritates me is because it means that somebody must think I’m lying. That’s number one. Number two: why would you want to hide it? That is not the way I run my life.’

Winfrey even shed some tears in the chat after Walters asked her about her longtime friend Gayle King.

‘She is the mother I never had. She is the sister everybody would want. She is the friend that everybody deserves,’ Oprah gushed. ‘I don’t know a better person.’

Opening up: During a 2010 interview with Winfrey, Walters quizzed her about lesbian rumors and got her to tear up while serenading her friend Gayle King; pictured in 1998

Opening up: During a 2010 interview with Winfrey, Walters quizzed her about lesbian rumors and got her to tear up while serenading her friend Gayle King; pictured in 1998

But Walters’ prying questions weren’t always appreciated by her guests, and some found them to be sexist and misogynistic at times.

Brooke Shields spoke with Walters during a famous 1981 interview that saw the veteran journalist ask the young teenager to parade her body and figure for her viewers.

‘She asked me what my measurements were and asked me to stand up,’ Shields recalled in November while appearing on The Drew Barrymore Show.

‘And I stand up, and she was like comparing herself to this little girl. And I thought, “This isn’t right. I don’t understand what this is.”‘

She added that she ‘just behaved and just smiled,’ but she ‘felt so taken advantage of in so many ways.’

Last year, Shields said the interview — which was taped shortly after her famous Calvin Klein Jeans ads debuted — was ‘practically criminal’ and ‘not journalism’ during an appearance on the Armchair Expert podcast last year.

However, in her interview with Barrymore, Shields also had kind words to say about Walters’ status in the world of journalism, even if she didn’t believe she was given a fair shake. 

Invasive: Brooke Shields has a less positive experience. She complained years later about how Walters asked for her measurements when she was a teen in 1981 and had her stand up to show off her figure; seen in 2016 in NYC

Invasive: Brooke Shields has a less positive experience. She complained years later about how Walters asked for her measurements when she was a teen in 1981 and had her stand up to show off her figure; seen in 2016 in NYC

Bad feeling: 'I thought, "This isn’t right. I don’t understand what this is."' Shields added that she 'just behaved and just smiled,' but she 'felt so taken advantage of in so many ways'

Bad feeling: ‘I thought, “This isn’t right. I don’t understand what this is.”‘ Shields added that she ‘just behaved and just smiled,’ but she ‘felt so taken advantage of in so many ways’

Too soon: In a 2000 interview, Walters pushed Ricky Martin to say if he was gay or not, but he later said he felt 'violated' over the questioning. He later came out in 2010; seen on The View in 2011

Too soon: In a 2000 interview, Walters pushed Ricky Martin to say if he was gay or not, but he later said he felt ‘violated’ over the questioning. He later came out in 2010; seen on The View in 2011

Ricky Martin had a similarly awkward interview with Walters in 2000, when she repeatedly asked him about his sexuality in the face of rumors that he was gay, which he eventually confirmed by coming out in 2010.

Coming out in 2000 meant drastically different prospects for the singer and actor, but Walters pushed him for an answer anyway to the personal question.

‘I think that sexuality is something that each individual should deal with in their own way, and that’s all I have to say about that,’ the Latin singer replied.

But the View co-host wouldn’t let up.

‘You know, you could stop these rumors. You could say, as many artists have, “Yes, I am gay,” or you could say, “No, I’m not.”‘

Last year, Martin told People that he ‘felt violated’ after Walters asked about his sexuality because he was ‘just not ready to come out’ at the time.

World leaders: Walters famously traveled to Cuba to interview Fidel Castro, who let her hold his gun while he drove her around the island in his Jeep. After their interview, he made her a grilled cheese sandwich

World leaders: Walters famously traveled to Cuba to interview Fidel Castro, who let her hold his gun while he drove her around the island in his Jeep. After their interview, he made her a grilled cheese sandwich

Among the 20/20 co-hosts most famous interviews with world leaders was her 1977 interview with Fidel Castro in Cuba.

In addition to the occasionally testy conversation, Walters described how Castro drove her around Cuba in a Jeep. She even had to carry his gun when they forded streams to keep it from getting wet on the floor.

After the sit-down, which wrapped up around 1 a.m., Castro concluded by making Walters a grilled cheese sandwich from his kitchen, according to Harper’s Bazaar. 

The two would have several other interviews in subsequent years. 

Digging deep: Walters got Mike Tyson's then-wife Robin Givens to confess about his physical abuse in 1988. She filed for divorce a month after the admission

Digging deep: Walters got Mike Tyson’s then-wife Robin Givens to confess about his physical abuse in 1988. She filed for divorce a month after the admission

Walters showed off her ability to get extraordinary confessions out of her guests during a 1988 interview with Mike Tyson and his then-wife Robin Givens.

She shook up the conversation when she asked Givens: ‘Does he hit you?’

Givens paused, before replying, ‘He shakes, he pushes, he swings. Sometimes I think he’s trying to scare me… Just recently, I’ve become afraid.’

Tyson was stone-faced during the confession, but after the interview was concluded he ‘flew into a rage and threw a chair,’ according to ABC News.

Given subsequently filed to divorce Tyson just a month after the interview. 

Fighting back: Amy Schumer didn't appreciate Walters' questions about faked orgasms and tried to turn the tables with the same question; seen in 2015

Fighting back: Amy Schumer didn’t appreciate Walters’ questions about faked orgasms and tried to turn the tables with the same question; seen in 2015

Walters’ pushy questions didn’t go as well in a 2015 interview with comedian Amy Schumer, when she asked the comic if she ever ‘fakes orgasms.’

Unfazed, she turned the tables on Walters and asked her, ‘Have you ever faked it?’

‘I’m not gonna tell you,’ Walters replied, adding that it was, ‘Because I have this image of myself as being dignified and so on.’

But Schumer said she also saw herself as being ‘dignified,’ and noted a recent conference she participated in advocating for new gun safety legislation. 

‘I have to tell you that doing an interview with you is not exactly like interviewing Henry Kissinger,’ Walters snapped back. 

Leading ladies: Among Walters' most popular interviews was a series of chats with Hollywood legend Katharine Hepburn, the first of which occurred in 1981. She was mocked for asking the actress what kind of 'tree' she was; seen in 1987

Leading ladies: Among Walters’ most popular interviews was a series of chats with Hollywood legend Katharine Hepburn, the first of which occurred in 1981. She was mocked for asking the actress what kind of ‘tree’ she was; seen in 1987

Among Walters’ most popular interviews was a series of chats with Hollywood legend Katharine Hepburn, the first of which occurred in 1981.

During that first conversation, Hepburn noted that she felt ‘very strong’ at that point in her life and career, before comparing herself to a tree, which inspired one of Walters’ most mocked questions.

‘What kind of a tree are you? If you think you’re a tree now,’ she asked.

Despite the absurdity of the query, Hepburn played along.

‘I hope I’m not an elm with Dutch elm disease, because then I’m withering,’ she replied with a laugh. ‘Everybody would like to be an oak tree. That’s very strong, very pretty.’

Start of a beautiful friendship: Hepburn was game and said she didn't want to be 'an elm with Dutch elm disease, because then I'm withering'; seen in 1981

Start of a beautiful friendship: Hepburn was game and said she didn’t want to be ‘an elm with Dutch elm disease, because then I’m withering’; seen in 1981

Walters’ death was announced on Friday night by ABC News.

Disney CEO Bob Iger shared the news in a tweet in which he called her a ‘pioneer.’

‘Barbara was a true legend, a pioneer not just for women in journalism but for journalism itself,’ he wrote. ‘She was a one-of-a-kind reporter who landed many of the most important interviews of our time, from heads of state to the biggest celebrities and sports icons.’

‘I had the pleasure of calling Barbara a colleague for more than three decades, but more importantly, I was able to call her a dear friend. She will be missed by all of us at The Walt Disney Company, and we send our deepest condolences to her daughter, Jacqueline,’ Iger said in a statement Friday.

Her cause of death was not immediately released. 

The journalist began her career way back in the 1950s, and she became the first female network news anchor in 1976.

Her final on-air interview was with then presidential candidate Donald Trump in 2015, though she subsequently kept a low profile in her final years. 



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