Barbara Walters' 9 most iconic questions from grilling OJ's lawyer Robert Kardashian to fiery Vladim

AS a trailblazer in broadcast journalism, Barbara Walters wasn’t shy when it came to asking tough questions to the most high-profile figures.

In a legendary career spanning more than five decades, Walters interviewed pop culture icons - from celebrities to politicians and several others in between.

Known for often landing the “first interview,” Walters pulled no punches in her direct yet oftentimes controversial line of questioning.

Walters became the first female anchor on an evening news program in 1976 when she joined ABC News.

Three years later, she co-hosted 20/20 and would launch The View in 1997.

She retired from the program in 2014 but remained an executive producer and still continued to do some interviews and specials for ABC News.

ROBERT KARDASHIAN

In 1996, two years after the brutal murders of Nicole Brown Simpson and Ron Goldman, Walters sat down with OJ Simpson’s friend and defense attorney, Robert Kardashian.

Following Simpson’s controversial not guilty verdict, Walters asked Kardashian - father of Kourtney, Kim, and Khloe - a question burning on the minds of millions.

“Do you think OJ Simpson is guilty?” Walters asked.

Through her uncanny way of getting people to let their guard down, Kardashian was able to express his true feelings at the moment.

“I have doubts,” he said.

JOHN WAYNE

Western star John Wayne was in the hot seat when he spoke with Walters in 1979.

The newswoman put him on the spot about supposed sexist comments he had made in the past about men and dominance.

“Do you think men should be the dominant figure in a relationship still?” she asked.

“Well, if this country had stayed the way it was, and if we hadn’t made it so tough for a family to keep up their type of living [that] their wives had to go to work, I would think it would be more pleasant,” Wayne said.

He added: “I think it'd be more pleasant for the lady as well.”

However, later in the interview, Wayne alluded to a higher power either a man or a woman, giving audiences a rare look into the actor's more thoughtful side.

MONICA LEWINSKY

An estimated 74million viewers sat down to watch Walters interview Monica Lewinsky following the highly-publicized sex scandal between then-President Bill Clinton and the White House intern.

Lewinsky broke her longtime silence to speak with Walters on 20/20 on March 4, 1999.

With a simple “Describe yourself,” Walters was able to get Lewinsky, who was ostracized in the public, to open up.

“I think I’m a - I’m very loving. I’m very loyal. I think I’m intelligent,” Lewinsky answered with a nervous laugh. “I think I certainly feel that I have been misportrayed in the last year.”

Walters also asked: “What will you tell your children when you have them?”

Lewinsky replied: “Mommy made a big mistake.”

Walters was quick to respond: “And that is the understatement of the year.”

Lewinsky also used the time to apologize to the Clinton family, especially Hillary and Chelsea.

VLADIMIR PUTIN

Walters cut to the chase when she spoke with the Russian president in November 2001.

It marked the first time President Putin was interviewed by an American journalist since the terrorist attacks on September 11.

“Have you ever ordered anyone killed?” she asked bluntly.

Through a translator, Putin simply answered “Nyet” - Russian for “No.”

HILLARY CLINTON

During her annual Most Fascinating People in 2012, Walters asked Hillary Clinton about her future plans after it was announced that she was stepping down as United States Secretary of State.

While others expected Clinton to ride off into the sunset, Walters wasn’t so sure.

She asked Clinton what would convince her to start a second presidential run in 2016 after losing the Democratic nomination to Barack Obama in 2008.

Clinton answered: “You know, that’s all hypothetical because right now I have no intention of running.”

However, Clinton would eventually run in 2016, claiming the Democratic nomination before losing to Republican opponent Donald Trump.

SHAH MOHAMMAD REZA PAHLAVI

Two years before he was overthrown, Walters interviewed the Shah at his palace in Iran in 1977.

Mohammad Reza described himself as a “progressive” Shah, giving women equal rights, and supporting women’s right to vote and freely choose their profession.

However, when Walters asked him “Do you think women can rule?” the Shah was hesitant.

He said women lacked men’s intelligence and abilities but his wife, Farah Diba, shockingly resisted his point.

“I don’t think you really believe that,” said Diba. “But what have men done to the world, really?”

KATHARINE HEPBURN

A comically offbeat moment with actress Katharine Hepburn in 1981 showed Walters’ ability to spin questions on a dime.

During the interview, Hepburn mentioned to Walters that she sees herself as a tree.

Without missing a beat, the iconic “What kind of tree are you, if you think you’re a tree?” question was asked.

Hepburn, who was equally quick-witted, understood the line of questioning and said she’d be an oak.

MIKE TYSON

In a controversial interview with boxing champ Mike Tyson and his then-wife Robin Givens, Walters asked point blank if the rumors of Tyson’s alleged abuse were true.

“Does he hit you?” Walters asked in the tense interview.

“He shakes. He pushes, he swings. Sometimes I think he’s trying to scare me. There were times when it happened when I thought I could, after, handle it, you know,” Givens answered.

“And just recently, I’ve become afraid. I mean, very, very much afraid.”

A week after the interview, Givens filed for divorce.

ROBERT AND MICHELLE SMITHDAS

Not every person Walters interviewed was an A-List celebrity or head of state.

In 1998, she sat down with Robert and Michelle Smithdas, a married couple who were both blind and deaf.

Walters asked Robert to describe his wife despite never actually seeing her before.

“First of all, she is petite and rather delicate, very delicate bone structure.”

She turned to Michelle to ask her the poignant question: “Do you think [being blind and deaf] happened to you for a reason?”

JiveVlog