Terry Gross is the best interviewer in English with a regular show in any medium, and has been for decades. I’d even even be willing to proclaim her best of all time, if you only count people with long-running interview shows. (There are some documentary filmmakers who are great interviewers, etc., but only publish occasional niche work.)
She is invariably respectful, even of complete asshats. She prepares well for every interview, listens to her guests, asks good starting questions and insightful follow-up questions, and gets people to open up about topics they don’t usually discuss. She knows she has a wide audience and makes sure guests explain things in an accessible way. She doesn’t throw softballs at people, but she also isn’t aggressively confrontational. It’s clear that her goal is always to understand where someone is coming from give them space to explain their point of view in their own words, rather than trying to win an argument, score cheap points, or kiss ass.
As a result, she usually has very good guests, from a wide variety of backgrounds, talking about a wide variety of topics.
Pick anyone going on a book (or whatever) interview circuit and listen to / watch 4 or 5 of their interviews back to back. The Fresh Air interview turns out best almost every time. Usually it’s not even close. Other interviewers try to tell the guest’s story for them, or are trying to push the guest into one identity bucket or another, or have a point they want to make and won’t listen, or haven’t prepared and have no idea about the guest’s field or background.
I'd put Bob Edwards (former Morning Edition anchor, now on SirriusXM) in there as well.
Paul Kennedy, CBC, Ideas isn't strictly an interview programme, but it's exceedingly good long-form, and intelligent.
I'm surprised I'm not coming up with any British / BBC interviewers, though there can be good programming there as well, at times.
Brooke Gladstone and Bob Edwards of On the Media also make my list. Their subject range from friendly to collegial (other people in the media industry), to hostile. It's possible to tell the dynamic, but the demeanor is always professional.
I am quite the fan of Gross, and she's grown on me over the years.
As a 20+ year listener of NPR (and Terry Gross), I always thought Gross was the best interviewer without a doubt. About 2 years ago, I stumbled upon a Howard Stern interview and was blown away. Never thought much of the shock-jock before, but you should check out his interview with Letterman from last week.
She is invariably respectful, even of complete asshats. She prepares well for every interview, listens to her guests, asks good starting questions and insightful follow-up questions, and gets people to open up about topics they don’t usually discuss. She knows she has a wide audience and makes sure guests explain things in an accessible way. She doesn’t throw softballs at people, but she also isn’t aggressively confrontational. It’s clear that her goal is always to understand where someone is coming from give them space to explain their point of view in their own words, rather than trying to win an argument, score cheap points, or kiss ass.
As a result, she usually has very good guests, from a wide variety of backgrounds, talking about a wide variety of topics.
Pick anyone going on a book (or whatever) interview circuit and listen to / watch 4 or 5 of their interviews back to back. The Fresh Air interview turns out best almost every time. Usually it’s not even close. Other interviewers try to tell the guest’s story for them, or are trying to push the guest into one identity bucket or another, or have a point they want to make and won’t listen, or haven’t prepared and have no idea about the guest’s field or background.