Barbara Walters’ Friends Reveal Her Biggest Regrets, Private Struggles and Greatest Triumphs (Exclusive)

When most people think about Barbara Walters, they probably recall the older version of the trailblazing journalist: her signature blonde bouffant, her political debates with colleagues on The View or her famous sit-down TV interviews during which she sat across from celebrities and occasionally made them cry.

But the new documentary Barbara Walters Tell Me Everything (Hulu, June 23) explores a much deeper — and occasionally darker — side of Walters. It examines her rise to the top as the first female co-anchor in nightly network news, and looks at the sexism she faced along the way and how her home life suffered as she fully dedicated herself to her career.

“Her road to success was paved with potholes and peril and naysayers,” says her longtime friend and current ABC News senior executive producer David Sloan in this week’s PEOPLE cover story. He stayed in Walters’ life until she disappeared from the spotlight in 2019, as she privately battled dementia before her death in 2022 at age 93.

Despite Walters’ incredible success, she was painfully insecure, her friends and colleagues agree, and was especially down on herself about her looks: In the documentary, Katie Couric recalls her saying, “Oh, we’re so alike: Neither of us is that attractive.”

The insecurity likely stemmed from Walters’ unsettled childhood.

She was raised in Boston with a showman father who ran a nightclub, where she got to meet stars like Frank Sinatra. But when the nightclub went belly up, the family lost everything they owned, and Walters had to go to work to support her parents and older sister, Jaqueline, who was developmentally challenged.

“She took that responsibility very seriously,” her friend, former NBC correspondent Cynthia McFadden says of Walters becoming the sole breadwinner, first as a writer for the Today Show, where she eventually appeared on televised segments.

In 1976, ABC hired her as the network’s first female nightly news co-anchor, opposite Harry Reasoner. In many ways, it was a dream job that no woman had ever done before. In reality, it was horrible. She endured endless bullying from the old boys’ club, who hated sharing the spotlight with a woman.

“Harry was downright rude to her,” says McFadden. The film shows other male colleagues icing her out. “I would walk into that studio, and Harry would be sitting with the stagehands, and they’d all crack jokes and ignore me. No one would talk to me. There was not a woman on the staff,” Walters recalls in resurfaced commentary, also calling it “the most painful period in my life.”

Despite the sexist forces working against her, Walters proved to be a formidable interviewer and was given her own specials, beginning in 1976.

“She asked the questions that nobody else asked,” says Oprah Winfrey in the film. Of course, that wasn’t always a welcome thing.

“Some of her interviews haven’t aged well,” McFadden says of her invasive questions with a laugh, while Midler agrees that “sometimes she got under people’s skin.” In her very first special, taped in 1976, Walters asked Barbra Streisand, “Why didn’t you have your nose fixed?”

In another interview, she asked Vladimir Putin if he’d “ever ordered anyone killed.” She once looked Martha Stewart square in the eyes and said, “Martha, why do so many people hate you?” When Martha replied that everyone had people that both loved and hated them, she said, “No, not everyone has people that hate them.”

In 2014, she told the Kardashians, who were then rising reality stars, “You don’t act, you don’t sing, you don’t dance, you don’t have any — forgive me — talent.” Taylor Swift became visibly agitated with her when Walters asked her about deterring suitors because she might write songs about them. Says McFadden: “No one got out of a Barbara interview unscathed.”

For more on Barbara Walters, pick up the newest issue of PEOPLE, on stands Friday

Those who knew her best say she was just doing her job. “You’ve never seen someone more prepared,” says Sloan of Walters repeatedly going over her questions, written on index cards.

“And she really changed the way people ask questions. Can you imagine sitting opposite Chris Christie, the then-governor of New Jersey, who was running for President, and saying, ‘Aren’t you too fat to be President?’ But these were the things that the people watching at home on their sofas really wanted to know.” 

Barbara Walters Tell Me Everything will debut on Hulu on June 23.