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By DEIRDRE DURKAN-SIMONDS FOR DAILYMAIL.COM
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Barbara Walters was famous for asking provocative questions to some of the world’s most fascinating subjects from Monica Lewinsky and Elizabeth Taylor to Fidel Castro.
Although she made a name for herself with her bold and probing interview style, the legendary broadcast journalist, who passed away at age 93 in 2022, often, pushed it too far with her guests.
In a trailer for Hulu’s upcoming documentary, which chronicles the highs and lows of her illustrious career, the TV personality can be seen cruelly confronting Taylor Swift on her love life, taking a swipe at Donald Trump and driving Oprah Winfrey to tears.
Back in 2014, Walters grilled the pop star, then 25, on her failed romances as she mused that as she has become ‘more famous so have the boyfriends.’
‘Her hits chronicle high-profile relationships that blossom, wither, die, and then get turned into song lyrics,’ Walters said as a montage of photos with Swift and some of her exes, including Harry Styles, Jake Gyllenhaal, Joe Jonas, John Mayer, appeared.
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Barbara Walters famously grilled Taylor Swift on her failed romances as she mused that as she has become ‘more famous so have the boyfriends’
While referring to the Grammy winner’s highly autobiographical songwriting style, Walters brazenly asked the singer how she ever intends ‘to find anybody’ to date.
Earlier in the interview, Swift acknowledged the double standard in how people view it to be ‘brave’ when male musicians share their emotion, but ‘if a woman shares her experience in writing she’s oversharing… or she might be crazy.’
The Cruel Summer hitmaker also reflected on the long-running joke that people who date her should ‘watch out [or] she’ll write a song about you.’
When Walters quipped there may be some truth to that one, Swift quickly slammed the ‘old’ joke, which she said came ‘from a place of such sexism.’
The remarks were made during ABC’s Barbara Walters Presents: The 10 Most Fascinating People of 2014.
The Tell Me Everything documentary also highlighted Walters fearlessly going toe to toe with Trump as she claimed people don’t see him ‘show any humility’ and asking Courtney Love if she had ‘ever done drugs in front’ of her child.
‘She asked the question that nobody else had asked,’ Oprah Winfrey recalled. ‘And asked it in a way that always hit a nerve.’
In 1988, Walters caused Winfrey to cry after asking if she wished she had been born white.
While referring to the Grammy winner’s highly autobiographical songwriting style, Walters brazenly asked the singer how she ever intends ‘to find anybody’ to date
The Tell Me Everything documentary also highlighted Walters fearlessly going toe to toe with Trump as she claimed people don’t see him ‘show any humility’
‘She asked the question that nobody else had asked,’ Oprah Winfrey recalled. ‘And asked it in a way that always hit a nerve’
During the interview, Winfrey hesitantly answered that she did wish she was white when ‘growing up in Mississippi.’
‘In my mind then white kids were loved more,’ she explained. ‘Their parents were nicer to them and, so, I wanted that kind of life.’
Other standout moments in the trailer included showing resurfaced footage of her telling the Kardashians sisters point-blank that they have no talent, pressing Barbra Streisand on why she never had her ‘nose fixed’ and asking Martha Stewart why ‘so many people hate’ her.
‘No one ever got out totally unscathed,’ journalist Cynthia McFadden said of Walters‘ unflinching interview style.
Disney CEO Bob Iger also praised her for foreseeing ‘that celebrities are news.’
Barbara Walters Tell Me Everything is set to premiere at the Tribeca Film Festival on June 12 and will hit Hulu on June 23.
