Barbara Walters Grills Taylor Swift On Love Life In Explosive Hulu Documentary

Barbara Walters is once again making headlines, this time posthumously, as Hulu prepares to release a no-holds-barred documentary chronicling the legendary broadcaster’s jaw-dropping career.

The late trailblazer, who passed away in 2022 at age 93, was renowned for her fearless, often polarizing interview style.

And in the new trailer for "The Barbara Walters Effect," viewers get a taste of just how bold and, at times, brutal, her questions could be.

In one especially tense clip, obtained by PEOPLE, Walters grills a then-25-year-old Taylor Swift on her love life.

With photos of Swift and her famous exes, including Harry Styles, Jake Gyllenhaal, and John Mayer, flashing across the screen, Walters deadpans, “As you’ve become more famous, so have the boyfriends.”

She then goes for the jugular, asking how Swift ever expects “to find anybody” to date with her track record of heartbreak ballads.

The "Love Story" singer, known for weaving personal experience into her music, didn’t take the jab lightly. “That’s an old joke,” she replied sharply, calling out the sexist undertone. “It comes from a place of such sexism.”

Earlier in the same interview, Swift acknowledged the frustrating double standard that plagues women in music. “If a man writes about his feelings, he's brave. If a woman does it, she's oversharing or ‘crazy,’” she said.

The documentary doesn’t stop at Swift.

It also revisits the moment Walters left Oprah Winfrey in tears during a painfully personal interview, as well as her infamous confrontation with Donald Trump, in which she accused him of lacking humility.

In a 1990 interview on ABC's "20/20," Walters confronted the current President of the United States about his public persona, particularly his perceived lack of humility.

She pointedly asked, "With all of the publicity, and with the way that you have answered, there are people who say, 'Why won't he show some humility?'"

Another clip features Walters questioning Courtney Love about doing drugs in front of her child, a moment still debated to this day.

During this conversation, Walters directly questioned Love about her past drug use, including whether she had ever used drugs in front of her daughter, Frances Bean Cobain. This line of questioning was part of Walters' signature probing style, aiming to delve deep into her subjects' personal lives.

Some viewers felt that Walters' questions were invasive, while others saw them as a bold attempt to hold public figures accountable for their actions, especially concerning sensitive topics like parenting and substance abuse.

And one of Barbara Walters’ most unforgettable interviews came in 1980, when she sat down with former President Richard Nixon and asked a question that stunned viewers: “Do you ever deeply regret that you didn’t just burn the tapes?”

Walters was referring to the infamous Watergate tapes, the secret White House recordings that ultimately led to Nixon’s resignation in 1974.

The directness of her question caught Nixon off guard, prompting a rare moment of reflection. After a pause, he admitted, “Yes, I think so. I think it was a mistake.”

That clip, along with many more, will be revisited in the upcoming documentary.

Barbara Walters died on December 30, 2022, at the age of 93.

According to her longtime publicist, Cindi Berger, the legendary journalist passed away peacefully at her home in New York, surrounded by loved ones. Walters had largely stayed out of the spotlight in her later years as she reportedly faced ongoing health challenges.

A true pioneer in broadcast journalism, Walters broke barriers as the first woman to co-anchor an evening news program and went on to co-create the long-running talk show "The View." Following news of her passing, tributes poured in across social media, with fans, colleagues, and celebrities remembering her trailblazing career, sharp interviewing style, and enduring impact on the industry.

"Barbara Walters: Tell Me Everything" premieres on Hulu on June 23.