When I tell people what I do, one of the questions I’m regularly asked is about my worst interview, about the celebrity who was nastiest to me. That is actually the second most popular question I get (according to my completely unscientific study) right after who is the biggest celebrity I’ve interviewed.

I never quite know how to answer either of these questions, but for different reasons. The biggest celebrity question is easy – I reply that it depends on how you define celebrity. Depending on who you are and when you’re asking the answer changes completely.

The answer about the worst interview isn’t hard, but it is different, because the assumption is wrong. Asking about the worst interview and the nastiest celebrity is really asking two different questions and assumes the stereotypical notions of celebrity are real and that a celebrity would come out during a junket interview, when they are actively trying to entice people to like them and support their film, and be awful to people who can help them. I really haven’t had the latter experience. People have better and worse days, but never has anyone been horrible to me.

But, a worst interview? Of course, I’ve had a worst interview, but it’s just the worst because it’s the most disappointing, the one to which I was most looking forward but that didn’t go as I planned. There was no rudeness, no anger – I asked a question inelegantly, it was heard slightly differently than I anticipated, and things began on the wrong foot. It is exceptionally hard to recover in a four minute interview when it starts badly. Check it out below.

So, there it is, Robert Redford, a man who not coincidentally may be my answer when I’m asked about the biggest celebrity I’ve interviewed. That interview breaks my heart. I love Robert Redford. “Butch Cassidy and the Sundance Kid” is one of my favorite films, as is “The Sting.” I think the man is an absolute genius, both in front of and behind the camera. It is an interview that I wanted to go brilliantly, one where I wanted to hit it off with the interviewee and really feel that instant connection. That didn’t happen.

Actually, rewatching the interview, I do nothing but gain more respect for Redford. I understand exactly how he heard my question, and it’s a fair interpretation. The question is about the ’60s counterculture, the fight against the Vietnam War, and the way he shows the outgrowth of a sect of that movement later. I called it a “hard” look at the counterculture and say that he doesn’t always show it in a positive light. He drew a distinction between a “critical” look and a “hard” one, and bristled a little at the way I put my question.

The answer made—makes—complete sense. The interview is fine. I just wish it had gone down differently, that I had done my job better.

The bristling, however slight it may have been, kills me. More than two years later, I still wish I had that question back. It is one that keeps me up at night. Maybe if I had just said “x.” Maybe if I told him about my love for the Sundance Kid. Maybe if I had done anything else.

Maybe, one day, I’ll get another chance.

photo credit: Sony Pictures Classics