10 Amazing Barbara Walters Interviews

Say what you will about Barbara Walters, but you can never question her staying power. Walters announced her retirement (to come in 2014) on Monday’s episode of The View, which likely means that we can expect to have a year of memories from the woman who has been interviewing the biggest names in the world for over 50 years. While speaking on her future plans, Walters said that she hoped she had “inspired other women to make television in front or behind the cameras as a career”.

As a writin’ woman, even if I have not always respected her blunt approach, I honor Walters in this moment with some of her very best – be it most interesting, hardest, scariest or saddest – interviews of all-time.

1. Oprah Winfrey There are very few people who can sit down with Oprah Winfrey and make her cry. It is nice to see the tables turn every so often, and Walters certainly did just that when she interviewed Winfrey at the end of 2010. Walters asked about everything we always wondered: Winfrey’s relationship with Stedman Graham, her relationship with Gayle King, her choice to not have children, her seeming inexhaustibility.

In my opinion, though Winfrey is relatively open about her dieting and fluctuating weight, the most important quip from the interview comes from their discussion about weight. “I will never diet again. [I am more] than my thighs.”

2. Monica Lewinsky Everyone in the world may know of this interview because of this moment:

Walters: What will you tell your children, when you have them? Lewinsky: Mommy made a big mistake. Walters: You can say that again.

But Walters asks a question that I truly believe sets her apart from plenty of other journalists. Walters gives Lewinsky a chance to “describe herself” for once, and then follows it up with the acknowledgment that she was unable to speak for so long, so she gives her the chance to say whatever she would like. Lewinsky uses that to apologize to Chelsea and Hillary Clinton, classily, though admittedly a little unbelievably.

3. Fidel Castro Walters had interviewed Castro before, but 25 years later, the two reunited in a fierce interview about everything from Cuban constitution to whether or not Castro was married. Sitting down with a notorious man like Castro should intimidate a person, but Walters speaks to him with the same calm and sass as she has when interviewing the Kardashian family.

Walters: Do you allow demonstrations at all? Castro: Here we don’t have them. Walters: But do you allow them? Castro: Here, we don’t have them. Why would we need to prevent anything that doesn’t happen at all? Walters: But you don’t let it happen! Maybe people might want to protest!

I don’t know, arguing with a President? Bold.

4. Lucille Ball Anyone who has ever sat down for a conversation with Ball, I will forever envy. Walters spent an afternoon with Ball and her second husband and asked her hard hitting questions about everything, but namely Desi Arnaz. It is hard to hear Ball’s vibrancy dwindled down to a fierce honesty when speaking of a couple that the world holds so dear in our hearts. Walters breaks down any form of privacy and asks Ball about Arnaz–in front of her husband. 

Walters: You had the success. The marriage looked perfect. It was everything, and then it fell apart. Ball: That was his problem. Walters: And I heard you were devastated. Ball: I couldn’t understand anymore than–for the same reason you’re asking the question. Walters: I think people still don’t understand it. Ball: I don’t either.

5. Hillary Clinton Walters has interviewed Clinton a million times, but my favorite moment between Walters and Clinton comes when, instead of asking Clinton about Benghazi, Walters pushes the former First Lady to run for President. 

Walters: What would it take to convince you to run in 2016? Clinton: You know, that’s all hypothetical because right now I have no intention of running.

Walters does not let the issue go, and I certainly hope that Clinton hasn’t either.

6. Katharine Hepburn

If you ever get the opportunity to sit down with a powerhouse of a famous actress like Katharine Hepburn, do not ask her what kind of a tree she would be. Walters has long been mocked for asking Hepburn the tree question, but when I finally watched the interview myself, I was impressed with the lack of awkwardness. It’s not so bad, you guys! What kind of tree would you be? Hepburn classily answers that she hopes she would be an oak tree. “Very strong, and very pretty.” 

7. Ellen DeGeneres “I think it was the first time I realized what kind of power humor has.” Walters hit the nail on the head with DeGeneres’ route to becoming a comedian. She did it to make her mom laugh, and for those of us who know DeGeneres, and her show, we all know how much she loves her mother.

Walters is capable at times of softly asking about basically anyone’s life, but when it comes to sexual abuse, especially with someone we all care about, someone we all love so much, it becomes a tough subject. When Walters asks DeGeneres about her former sexual abuse by a man her mother was married to, she remains calm, classy and respectful–three conditions that are hard to remain within when asking something so personal.

8. Michael Jackson Delicately and un-assumedly questioning Michael Jackson, one of the strangest and most interesting people in our nation’s history, about his relationship to Princess Diana took guts. Though I must admit here that I am a huge Jackson fan and I feel that Walters speaks down to him more than necessary, I still appreciate her dauntlessness when it came down to asking the hard-hitting Jackson related questions about Princess Diana, his children, the paparazzi.

Walters: The way you dress, the way you look–invites attention. The whole appearance as you grew up was larger than life. More extreme. You don’t think that calls the paparazzi to you? Jackson: No, no, no. Maybe I like to live that way, I like to dress that way. I don’t want paparazzi, really, but if they come? Be kind. Write the kind thing to write. Walters: Michael, is it the press’ role to be kind? Jackson: To be kind? Walters: Because the press also sometimes has to look into things, to be tough. You can’t always be kind. Jackson: (laughs) What you saw happen to Lady Diana? You tell me.

She pulls out a Jackson we did not often see: a real one.

9. Bobby and Whitney Whitney Houston, may she rest in peace, was a very controversial character, but nothing made her more controversial than her relationship with Bobby Brown. Walters interviewed both of them, as Houston held their six month old baby girl, shortly after their marriage. Though her interview was mostly focused on Houston and her career, she wasted no time in (relatively condescendingly) addressing Brown’s fidelity issues. 

10. The Kardashians Walters introduces the family by saying that there had been quite a bit of outrage over the girls being called a few of the “Most Fascinating People” of the year. If I have learned one thing in the entertainment world, it is that the Kardashians are truly a hot topic. Anytime I casually mention Kim’s name as a term of endearment, there is outrage from everyone. I like Kim, what of it?! Alright, anyway, this interview is pretty straightforward, but Walters immediately touches on the good stuff: Kim’s sex tape, Khloe’s drunk driving and “ugly duckling” status, and of course Kim’s 72 day marriage.

The whole interview is great, in my opinion, though it doesn’t take much to get the Kardashians to talk about themselves.

We look forward to one more year of these interviews, Walters. Happy (future) retirement!

Featured image via E!, Lewinsky image via zimbio, Katharine images via thegloss.