Barbara Walters’ Most Memorable Interviews, Including Her ‘Mistake’ of Asking One Star ‘What Kind of Tree Would You Be?’

Throughout her prolific career as a journalist, Barbara Walters was known for fearlessly asking the questions that were on everyone’s mind.

The legendary broadcaster died on Friday at the age of 93 and was remembered for her unique ability to draw confessions, tears and insights from her subjects. As former Walt Disney Company CEO Robert Iger (who worked with Walters during her many years at ABC) put it: “She was a one-of-a-kind reporter who landed many of the most important interviews of our time, from heads of state and leaders of regimes to the biggest celebrities and sports icons.

From Fidel Castro to Elizabeth Taylor, her subjects ran the gamut of why they captured the world’s attention — but Walters’ signature interview style remained incisive and impressive for decades.

Below, look back on the conversations that help define the late newscaster’s legacy.

Virginia Sherwood/Disney General Entertainment Content via Getty Monica Lewinsky

In what still remains one of the most-watched interviews ever to be televised, Monica Lewinsky told her story to Walters in 1999. The two of them discussed then-President Bill Clinton’s affair with Lewinsky at length, and Walters never shied away from addressing the details of the provocative controversy.

After nearly 90 minutes of probing about Hillary Clinton, Linda Tripp and the Lewinsky’s infamous blue dress, Walters ended the interview with two intense kicker questions: Was Lewinsky still in love with Clinton, and what did she plan to tell her future children about the scandal?

“Sometimes I have warm feelings, sometimes I’m proud of him still, and sometimes I hate his guts and he makes me sick,” Lewinsky acknowledged.

As for the second question? “Mommy made a big mistake.”

President Richard Nixon (center) visits Berlin. Wolfgang Kunz/ullstein bild via Getty Images Richard Nixon

Walters interviewed nearly every U.S. President since Richard Nixon (neither Joe Biden nor Donald Trump were interviewed during their terms), but few of these conversations are as well-remembered as her 1980 conversation with POTUS 37.

Walters lobbed several hardballs at Nixon during his first network interview since leaving the White House following the Watergate scandal. In the final minute of their chat, she spared no pleasantries by asking, “Are you sorry you didn’t burn the tapes?” In 2000, the renowned journalist called Nixon’s answer that he “probably should have” the “great climax” of her interview.

Mike Tyson & Robin Givens

In 1988, Walters sat down with Mike Tyson and his then-wife Robin Givens to discuss the alleged violence in their relationship. Walters pressed Givens and Tyson about why they remained together — and whether he was abusing the actress.

Though neither explicitly admitted nor denied the accusations, Givens came a telling answer: “I think for the first time I can understand abused women…you know, you say, ‘Why do you stay in there?’ Well, number one, you love the person, and number two, you get accustomed to being treated poorly. So every day, behavior that you would normally not accept becomes everyday behavior.”

A week after the interview, Givens filed for divorce.

Christopher Polk/NBCU Photo Bank/NBCUniversal Hugh Jackman

Hugh Jackman and Walters shared a comically intimate moment in the early aughts. During a performance of The Boy from Oz, Jackman brought the famed journalist and Matt Damon up on stage for a bit of improvised patter. Nearly two decades later in October 2022, Jackman recalled the moment in an interview with Variety: “I brought up Barbara Walters and Matt Damon, and made Matt Damon give Barbara Walters a lap dance, which turned into me giving Matt Damon a lap dance.”

But Jackman’s most recent mention of the moment wasn’t the first time it was revealed to the public. In fact, The Greatest Showman actor and Walters reenacted the hysterical moment after reminiscing about it on camera during an interview. When Walters said she had not received a lap dance since the on-stage gag, she asked Jackman if he would “like to do it now.” He responded that he “would do it any time.” Cue the lap dance!

Katharine Hepburn

As a widely respected journalist, few doubted Walters’ ability to ask the right questions. But critics and fans alike had a lot to say about the veteran journalist’s conversation with Katharine Hepburn in 1981. When the actress compared herself to a tree, Walters pushed to learn which specific type she meant, an inquiry for which she was continuously mocked.

In 2006, Walters addressed the comment in a special titled 30 Mistakes in 30 Years. She begins with No. 30: “And it’s a big one. Never ask anyone what kind of tree they want to be…”

The episode then shows the video of her speaking to Hepburn — who saids she’d like to be an oak tree — and a clip of longtime Tonight Show host Johnny Carson bringing it up in 1983 with his own riff that he’d choose to “be a tumbleweed.”

“For the record, I would someday also like to be an oak growing tall in the forest right next to Katharine Hepburn, or drifting along as a tumbling tumbleweed with Johnny,” Walters quipped.

Christopher Reeve

In Barbara Walters: Her Story, the television mainstay spoke about her 1995 conversation with Superman star Christopher Reeve after he was paralyzed in a horseback riding accident. She called it “one of the most moving interviews I ever did.”

When Walters asked Reeve what would happen if he could never walk again, he answered, “Then I won’t walk again … either you do or you don’t. See, it’s like a game of cards, and if you think the game is worthwhile then you just play the hand you’re dealt. Sometimes you get a lot of face cards, sometimes you don’t. But I think the game’s worthwhile, I really do.”

V. Stiviano

In the wake of Los Angeles Clippers owner Donald Sterling’s career-ending racism scandal, Walters interviewed both his wife, Shelly Sterling, and his mistress, V. Stiviano, for 20/20.

Stiviano told Walters she liked to be called “Mr. Sterling’s right-hand arm man.” She explained, “I’m his confidant, his best friend, his silly rabbit. … I joke around and I make him laugh. I do things that some people find very silly.”

Elizabeth Taylor

When Walters spoke and Elizabeth Taylor and her sixth husband John Warner in 1977, Warner voiced his concerns about how the actress needed to “take care of herself” and “ought to eat a few more vegetables and a little more orange juice for breakfast.”

Walters memorably asked Taylor if she was worried about putting on weight, questioning, “Does it matter to you?” Responded Taylor, “No it doesn’t. ‘Cause I’m so happy and I enjoy eating and I like to cook.”

Walters followed up, “You wouldn’t care if you got fat?”

“I am fat!” exclaimed Taylor.

Henry Kissinger

As Walters reminisced in 2000 about her many interviews with Henry Kissinger, she shared a funny recollection from before the U.S. Secretary of State was married: “I remember saying to him, ‘You know you’re the newest sex symbol of Washington. … How do you feel about it?’ And he said, ‘I love it. Now when I bore people, they think it’s their fault.'”

The journalist also told a story from when she and Kissinger journeyed to his small hometown in Germany. He told Walters about how much he loved soccer, but had been excluded from games because he was Jewish. Thinking they wouldn’t be noticed, the two of them went to watch a game play out, only to witness a remarkable reaction. Walters recalled, “We walked in — unannounced, we thought — to the soccer game, and he was recognized. And the soccer team stopped, and everyone in the stadium stood up.”

Fidel Castro

One of Walters’ most controversial specials ever was her week in Cuba with Fidel Castro. The dictator historically escorted Walters and her crew across the Bay of Pigs — making them the first Americans to traverse the inlet in 16 years since America’s failed 1961 invasion.

“The word charismatic was made for him. You would have liked him, I would have liked him,” she told ABC’s Byron Pitts in 2016, nearly 40 years after she met Castro in 1977. “Then you had to stop and say, ‘Just a minute.’ You know, this is a man who does not believe in freedom of the press, does not believe in democracy as we know democracy, had political prisoners. But when you were with him, he was forceful, charming, forthcoming.”

Anwar Sadat and Menachem Begin

One major standout in Walters’ legacy will forever be her joint interview with Israeli Prime Minister Menachem Begin and Egyptian President Anwar Sadat in 1977, the first time the two political enemies ever sat down together and spoke.

The story of how the interview came to be shows not only Walters’ tenacity as a journalist, but also her ability to ingratiate herself to her subjects. After a lengthy journey to the Middle East, Walters said she only expected to sit down with the two leaders individually. But Begin surprised her when he said that he’d convinced Sadat to be interviewed together “for the sake of our friend Barbara.”

At one point during the trio’s discussion, Walters tried to open their minds to the possibility of “a ray of light … some concession … down the road.” Sadat responded, “You are always like this, Barbara,” which caused all three to share in a rare moment of loud, mutual laughter and appreciation.

Clint Eastwood

In Barbara Walters: Her Story, the newscaster admitted to getting a little flustered during a 1982 interview with Clint Eastwood, on whom she “had the biggest crush.” She conceded that when he started to flirt with her, she “fell apart.”

In the clip, the two joked about how they might fare in a relationship, with Walters saying, “You would drive me nuts and I would drive you crazy.” Eastwood countered they “could try it and see if it worked out,” prompting a laugh from Walters and her crew to “stop and reload” the film in their cameras, presumably so she could take a moment to compose herself.

Sean Connery. Bob Penn/Sygma/Sygma via Getty Images Sean Connery

In 1987, Walters called out Sean Connery for claiming it was “not the worst thing to slap a woman now and then.”

When Connery confirmed his opinion hadn’t changed, Walters demanded he answer what could ever merit slapping a woman, to which he replied “[when one has] tried everything else.”

The actor went on to say that women “can’t leave it alone … they want to have the last word. And you give them the last word, but they’re not happy with the last word, they want to say it again and get into a really provocative situation.” He added, “Then, I think it’s absolutely right.”

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Mark David Chapman

“I have interviewed a lot of alleged and convicted killers,” Walters explained during Her Story. “Probably none as hated as Mark David Chapman, who killed John Lennon.”

The special then showed the 1992 moment when Walters sat down with Chapman and asked why he murdered the musician — “I thought by killing him I would acquire his fame” — and prompted him to retell the moment he fired the shots.

The Menendez Brothers

Though she was consistently professional, Walters wasn’t always stoic. She did not seem impressed when she interviewed the Menendez brothers in 1996, later describing them as two people who had “killed their parents and then wanted us to feel sorry for them because they were orphans.”

In particular, Walters challenged Erik Menendez’s claim that he was “just a normal kid.”

“Oh, Erik!” she said. “You’re a normal kid who killed your parents!”

Betty Ford

In 2014, Walters remembered her 1977 meeting the “obviously inebriated” First Lady Betty Ford, who struggled to speak clearly as the women toured the White House. “Some years later she went into rehab herself, became sober and founded the Betty Ford Clinic,” Walters said. “A wonderful legacy.”