Barbara Walters' 5 Most Memorable Interviews (Video)

From making Oprah Winfrey cry to getting Monica Lewinsky to admit she made "a big mistake," THR looks back on the television journalist's best on-camera moments.
Ruven Afandor
Barbara Walters

After making news for 53 years and sitting down with everyone from top entertainment personalities like Oprah Winfrey to dictators such as Fidel Castro, Barbara Walters' list of interview subjects is unmatched.

Her professional career took off when she became the first female co-host of NBC's Today show in the 1960s and soared even higher when she landed the role of the first female co-anchor on a nightly newscast on ABC in the 1980s.

As the television news personality retires from her on-air work on The View and ABC News this week, The Hollywood Reporter recalls five of her most memorable interviews.

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1. Oprah Winfrey

In December 2010, Oprah -- in a rare occurrence -- answered questions instead of asking them, during a three-hour ABC special with Walters. In the revealing interview, Oprah addressed lesbian rumors and even cried as she talked about her relationship with best friend Gayle King. "She is the mother I never had. She is the sister everybody would want. She is the friend that everybody deserves," she said. "I don't know a better person."

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2. Monica Lewinsky

When the former White House intern sat down with Walters in 1999 a record 74 million viewers tuned in. Walters helped to humanize Lewinsky as she shed light on her affair with former President Bill Clinton. At the end of the interview, she asked Lewinsky, "What will you tell your children when you have them?" to which Lewinsky replied: "Mommy made a big mistake." Walters added, "And that is the understatement of the year."

VIDEO: 'The View' Co-Hosts Reunite, Reminisce With Barbara Walters

3. Michael Jackson

As expected, there wasn't a dull moment in the King of Pop's interview with Walters in 1997. He addressed the deaths of Princess Diana, who was a fan of his, and Mother Teresa, as well as his potentially psychic abilities. Walters also got the singer to open up about his struggles with the press. "The tabloid, the paparazzi — I've been living all my life like that, hiding and getting away," said a distressed Jackson. "You feel like you're in prison."

4. Vladimir Putin

Walters has her fair share of interviews with powerful leaders, including Russia's Vladimir Putin in 2011. Shortly after being elected president in 2000, Walters peppered the enigmatic leader with questions about his involvement with the KGB, his childhood and whether he had ever ordered anyone killed. He talked about the difficulty that comes with being characterized by the mass media, the love he received from his parents, and the influence of literature and movies on his life.

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5. Anna Wintour

It's no secret that fashion editor Anna Wintour was the inspiration for the character Miranda Priestly in the book-turned-movie The Devil Wears Prada. In 2006, the same year as the film's debut, Walters asked Wintour about her take on the portrayal. "I was 100 percent behind it," she replied. "I'm a very decisive person... so if Meryl [Streep, who played Miranda] seemed somewhat strong, I respect that." She also discussed how the mood of the country is reflected in fashion and how Vogue captures such trends.