When it’s a matter of iconic television interviews, Barbara Walters is standing in a league by herself. She wasn’t just asking questions—she was creating cultural moments. She was grilling presidents, celebrity-scandal-ridden celebrities, and Hollywood celebrities on the hot seat, having conversations that became events the whole world talked about.
Her guest list spanned decades, continents, and front pages, and every sit-down shared the same equilibrium of preparation, curiosity, and fearlessness. Below are 12 of her most renowned interviews, unveiled at number 12 for maximum suspense.
12. V. Stiviano & Shelly Sterling (2014)
Following Donald Sterling’s lifetime suspension from the NBA for racist remarks, Walters pulled off the impossible: an interview with both Sterling’s girlfriend, V. Stiviano, and his wife, Shelly. It was awkward, tense, and compelling—proving that Walters could still land the big exclusives in her Golden years on TV.
11. Patrick Swayze (2009)
Walters interviewed Swayze when he was battling cancer, and the result was tragic. He spoke openly of personal tragedy and sickness, and Walters allowed silences to ring as loudly as responses. It was a lesson in emotional hearing mastery.
10. Arnold Schwarzenegger (2000)
Walters saw Schwarzenegger’s political potential before he was California’s governor. Her questions cut through the Hollywood bravado and went straight to his ambitions, catching him at a pivot point before his next performance began.
9. Monica Lewinsky (1999)
This was the interview everybody had been clamoring for since the Clinton scandal, and Walters got it. She did not pull any punches with the tough questions, famously asking Lewinsky about her self-respect and self-worth. The interview was one of Walters’ most notorious moments.
8. Courtney Love (1997)
Walters grilled Love on it all—from drug use in front of her child (no) to blaming herself for Kurt Cobain’s death (yes). She was a tough but empathetic interviewer, permitting space for vulnerability without excusing her guest.
7. The 10 Most Fascinating People (1993)
What started with Hillary Clinton in the first edition became an annual television tradition. Walters’ “Most Fascinating People” special became a portrait of the most newsmaking personalities and figures of each year.
6. Mike Tyson & Robin Givens (1988)
In a now-legendary interview, Walters queried Givens why on earth she loved Tyson, and Givens provided her with a blunt—and disastrous—description of his temper and instability. The interview aired on the night before they divorced, making it as salacious as anything that transpired in the ring.
5. Sean Connery (1987)
Walters fought with Connery over his defending slapping women. He did not budge, and Walters held his ground. It was stiff, straightforward, and utterly unflinching.
4. Katharine Hepburn (1981)
The “tree” question remains in popular culture lore. Hepburn posed it to herself, and Walters played along—resulting in one of those bizarre, ad-lib TV moments only she could make memorable.
3. Menachem Begin & Anwar Sadat (1977)
Convincing the Israeli Prime Minister and Egyptian President to sit at the same table on television was not an easy task. Begin is reputed to have convinced Sadat to do so “for the sake of our friend Barbara.” It was diplomacy, television, and history all in one.
2. Fidel Castro (1977)
After years of dogged persistence, Walters finally managed to get Castro to consent to an interview. She provoked him on press freedom as he smoked his cigar—a photo that is still one of her classics.
1. Barbra Streisand (1976)
The first-ever “Barbara Walters Special” included Streisand, along with President Jimmy Carter and First Lady Rosalynn Carter. Walters proved she could mix politics and entertainment, and millions watched.
Barbara Walters was not only interviewing—she was redefining what was possible in an interview. Her thorough background work, nerve, and persistence opened doors for future generations of journalists, particularly women, to reach higher, dig deeper, and ask the questions nobody else would dare. There may never be another Barbara Walters, but these interviews are a testament to the unparalleled strength she had behind the camera.