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Barbara Walters’s Biggest Interviews, From Castro to Bieber (Video)

After 52 years interrogating world leaders and megawatt entertainers, the groundbreaking newswoman will reportedly retire next year. A look back at her biggest and best interviews.

She’s interviewed every U.S. president and first lady since Richard and Pat Nixon, countless world leaders, a constellation of Hollywood stars, and even the Kardashians. So when reports surfaced this week that Barbara Walters is planning to retire in May 2014 we couldn’t help but look back at her landmark career. (Walters herself hasn’t confirmed or denied the news.)

From Castro to Bieber, here are some of the newswoman’s most impressive—and entertaining—career highlights.

Fidel Castro (1977)

It took two years for Walters to land an interview with Cuban dictator Fidel Castro in 1977, a year in which his country had held 11 Americans hostage. But when he finally did sit down, Castro not only answered almost all of Walters’s questions, which included interrogations on the subjects of Communism, his own death, and the U.S. embargo, in an unprecedented move, but also aired all five hours of the sitdown on Cuban television. It was the first time an interview with an American journalist ever aired in the country—even though many portions didn’t flatter the leader.

Anwar Sadat and Menachem Begin (1977)

One of Walters’s biggest scoops came in 1977 when she convinced Egyptian president Anwar Sadat and Israeli Prime Minister Menachem Begin to sit down for their first joint interview during one of the most tumultuous times in their countries’ relationship. It wasn’t just a major TV interview, but a historic moment. There’s no video of the interview available online, but in this clip Walters chronicles the riveting story behind how the whole thing came to be.

Katharine Hepburn (1981)

Walters’s interview style is legendary, throwing her subjects off guard with intensely researched, pointed inquisitions mixed with abstract questions. The notorious pinnacle of Babs’s abstractness, without a doubt, was the befuddling question in her 1981 interview with actress Katharine Hepburn: “What kind of a tree are you, if you think you’re a tree?” Walters later called the moment one of her greatest mistakes. But once the late-night hosts laid off the ridiculousness of the question, it settled into an endearing, iconic TV moment—and not so much a gaffe.

Muammar Gaddafi (1989)

The United States broke off diplomatic relations with Libya before Walters traveled there to interview its leader, Muammar Gaddafi. At the time, the despot was considered one of the world’s most dangerous terrorists. Walters’s conversation with the man Libyans referred to simply as “The Leader” tackled his views of Americans, Americans’ views of him, and his involvement with international terrorism. Throughout the entire discussion, Gaddafi almost never looked Walters directly in the eye.

Michael Jackson (1997)

Whenever Michael Jackson sits for a TV interview, the result is a captivating concoction of circus-strange, heartbreaking, hilarious, and ceaselessly interesting. That was true of Walters’s 1997 conversation with the King of Pop, which covered the role of paparazzi in his life and his reaction to the death of Princess Diana. The most haunting quote, now that we know how Jackson died, comes in his anecdote about how he learned of Diana’s death: “I woke up, and my doctor [emphasis ours] gave me the news.”

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Monica Lewinsky (1999)

Walters’s interview with Monica Lewinksy in 1999 was the very definition of a blockbuster—it was seen by a record 74 million viewers. The exchange that had America buzzing: Walters asks Lewinsky, “What will you tell your children when you have them?” She replies, “Mommy made a big mistake,” after which Walters looks to the camera and says, “And that is the understatement of the year.”

Vladimir Putin (2001)

Walters introduced Americans to the largely enigmatic Vladimir Putin, who, though he was one of the world’s most powerful leaders, was barely known in the U.S. when he was elected Russian president in 2000. Walters grilled him about his reported involvement with the KGB, his steely personality, and even whether he ever ordered anyone killed.

Anna Wintour (2006)

Was Vogue editor Anna Wintour the inspiration for the harrowing Miranda Priestly in the book and film The Devil Wears Prada? That question provided the impetus for Walters to finally sit down with the notoriously interview-shy fashion overlord in 2006. It was a rare interview, and a candid one. Wintour revealed that she’s had the same short bob haircut since she was 15, she expects her employees to uphold a standard of fashion at her magazine, and, yes, she may have inspired Meryl Streep’s character in Prada: “If Meryl seemed somewhat strong, I respect that.”

Hugo Chavez (2007)

In 2007, Walters interviewed Hugo Chavez, the controversial—and recently deceased—president of Venezuela. It was Chavez’s first interview with an American journalist since the leader attacked President Bush, calling him “the devil,” at the United Nations the year before. Bluntly, she told him Americans consider him an enemy, and asked what he thinks about that perception.

Justin Bieber (2010)

He was the biggest pop star in the world. He taught her how to Dougie.

Bashar al-Assad (2012)

As it still does, the bloodshed in Syria and the failings of its tyrannical leader Bashar al-Assad dominated headlines in 2012. It was an impressive get, then, when Walters managed to sit down with Assad at the height of the conflict, his first American interview since the Syrian uprising began. The interview with the dictator covered his unlikely rise to power, his reputation as a tyrant, and the torture of his citizens. Assad’s baffling denial of the charges: “There was no command to kill or be brutal.”

The Broken Child in All of Us

Sure, we will remember and cherish Walters’s vanguard contributions to journalism, nation-altering scoops, and breathtaking insights into the world’s most powerful and exciting minds. But we will also remember all those times she made people cry. And there were so, so many times.