Fidel Castro (1977)
Walters worked two years to land an sitdown with the famously press-shy Cuban dictator and the interview did not disappoint. Castro appears to be in a near-bemused state at the beginning of the interview but quickly gets serious once Walters starts grilling him on the future of Communism, the contentious relations between U.S. and Cuba and, daringly, the Cuban dictator's own mortality. When Cuban television aired the entire five hours of their interview in primetime, it broke all ratings records.
Katharine Hepburn (1981)
Walters has always kept her interviews engaging by throwing the occasional bizarre query into the mix with her well-researched questions, but she almost went to far with the Oscar-winning Hepburn. Midway into their spirited conversation, Babs asked, out of the blue, "What kind of a tree are you, if you think you're a tree?" Hepburn looked taken aback, but admitted that she would probably be an oak. Walters later said the tree question was one of her biggest career regrets, but the program was still one of the most revealing interviews of Hepburn's career.
Mike Tyson and Robin Givens (1988)
The public had already heard rumours of problems in the marriage between the brutish boxer and his petite TV actress, but Walters brought them into sharp focus. Viewed today, it's a strange interview. Tyson looks on without expression and says almost nothing; Givens describes her husband as "manic depressive" and describes married life with him as "torture, pure hell, worse than anything I could possibly imagine." Walters, wisely, does not address the hearsay accusations and stays at a respectable distance throughout the chat. Less than a month later, Givens would file for divorce.
Michael Jackson (1997)
Jackson wide-eyed and more than a little weird in this extended interview with Walters, who noticeably toned down her usual pitbull approach in her conversation with the King of Pop. For most of the interview, Walters talks to Jackson as though he were a small child, and in that manner elicits a haunting portrait of a tortured soul both freakishly famous and painfully shy at the same time. Jackson discusses his extreme distaste for the paparazzi, at the time still in its fledgling phase, and it's chilling to watch him reveal how he learned of the death of Princess Diana: "I woke up and my doctor gave me the news."
Monica Lewinsky (1999)
When former White House intern Monica Lewinsky finally decided to speak to the American public–after allegations of her torrid affair with sitting president Bill Clinton came to light and nearly derailed his presidency–she trusted Walters. More than 75-million people watched the ABC interview was pretty much boilerplate territory for both parties, until near the very end, when Walters asked Lewinsky: "What will you tell your children when you have them?" Lewinsky's response: "Mommy made a big mistake." At which point Walters took a short half-beat break, and then turned to the camera and said, "And that is the understatement of the year." Ka-zing!