Two and a half years after Barbara Walters’ death, those who knew the legendary broadcast journalist best are reflecting on her enduring legacy.

PEOPLE has an exclusive first look at the trailer for the upcoming documentary Barbara Walters Tell Me Everything, which offers a revealing look at Walters’ decades-spanning career and her experiences as a woman navigating a male-dominated industry. Through raw footage and interviews with some of her most notable friends and colleagues, the documentary celebrates her profound impact and doesn’t shy away from the darker aspects of her life.

As Billie Eilish’s “Bad Guy” plays in the background, the trailer — which opens with a clip from Walters’ interview with the Menendez brothers, where she firmly challenges their claim of being “normal kids” — showcases footage from some of her most compelling and unforgettable sit-downs. Whether she was asking Taylor Swift how she plans “to find anybody” romantically, or telling the Kardashian family they “don’t have any talent,” Walters was an unpredictable force.

“No one ever got out totally unscathed,” Cynthia McFadden, Walters’ former ABC News colleague, says in the trailer. “She asked the question that nobody else had asked,” Oprah Winfrey adds, followed by a clip of her crying in response to Walters’ probing. “And asked it in a way that always hit a nerve.” 

Walters herself acknowledged that it wasn’t her appearance that opened doors for her in television: “I was never beautiful,” she says in a recording featured in the trailer. “If I had been a dog, I mean maybe they wouldn’t have put me on television, but I mean, nobody ever put me on because I was beautiful or glamorous.”

Those closest to her — and those who looked up to her — agree her true power lay in her journalistic instincts. “She was fearless,” Bette Midler says. “And sometimes she got under people’s skin.” Katie Couric adds, “She could talk to anyone. About anything.”

The trailer also revisits some of her most boldly unfiltered moments — asking Courtney Love if she used drugs in front of her children, Barbra Streisand why she never got her nose fixed and Richard Nixon whether he regretted not burning the Watergate tapes. Walters never shied away from challenging the powerful, as shown in her interviews with now President Donald Trump, as she calls out his lack of humility, and Martha Stewart, whom she asks why everybody hates her.

“You’re surrounded by beautiful flowers, the lighting is perfect and then suddenly she would just throw a hardball out of nowhere,” Andy Cohen recalls. Disney CEO Bob Iger adds, “She had a vision that celebrities are news, and she turned out to be right. They were newsmakers.” 

Of course, her interviews also showed her passion and wit — she swatted away a makeup artist mid-interview because she cared more about substance than looking shiny and innocently flirted with Clint Eastwood, sparking laughs.

“Whether it was her looks or her voice, or just the fact that she was a woman, there were people that just didn’t believe in her and she loved proving them wrong,” Iger reflects. “Her job was the love of her life.”

Barbara Walters Tell Me Everything premieres Monday, June 23, on Hulu following its world premiere at the 2025 Tribeca Festival on Thursday, June 12