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“You can ask questions about their childhood and find out, were they sick, were they well?” she says. “Just all those things that create who you are.”

Were they outgoing or inhibited?

Were they good in school, and did they like school?

What were their parents like, and where were they from?

How were they parented?

Did they like to read?

Did they go to the movies?

What were the first records they bought?

In a powerful interview with comedian Tracy Morgan, Terry dug down to the roots of a troubled adolescence that nurtured Morgan’s latent creativity. Notice how she framed her questions without judgment but without hesitation.

GROSS: So I just wanted to get back to your childhood a little bit. When your father died of AIDS when you were in high school, you dropped out of high school, and you needed money. So you say you started selling marijuana and then eventually started selling crack.

MORGAN: Yeah.

GROSS: But—so I’m wondering. Did you take Al Pacino’s advice from Scarface—don’t get high on your own supply?

MORGAN: No, I never did drugs. My drug of choice was beer, was liquor. As far as narcotics, no. I would smoke weed and drink beer like any other—like Michael Phelps do that. But I never did no narcotics—never. My father had died from that. So I already knew better. You know, I’m a very smart person. I was able to see that. As a child, I was able to know that I wanted a better life.

GROSS: You say that it was helpful to you as a comic to sell crack because of all the characters that you met. What do you mean?

MORGAN: Well, it wasn’t helpful for me to sell crack, especially to my old community, and it still bothers me today, but it’s something that I did. It was survival. Now I’m living. Now I don’t have to do any of that stuff. I’m a grown man now, but when I did, I wasn’t good at it. So I had my fledging attempt at being a drug dealer.

GROSS: So, tell me really, how did you feel when you were selling crack, knowing that you were selling a drug that destroys lives?

MORGAN: I was a kid. I had no fear. I was crazy, and when you don’t have fear, you’re crazy.

Terry’s questions penetrate gently but insistently. She is interested in creative tension, setback, and adversity, but she does not try to embarrass or trip up her guests. Her voice is warm and her listening accommodates the ranges of emotion she encounters:

“I’m not looking to shame somebody. I’m not looking to have them say anything that’s going to keep them awake at night, regretting that they said it. I’m not looking to have them say something that’s going to end up with their mother or their child or their best friend hating them for saying it.”

Terry Gross prefers to let her guests take the lead when questions get personal and the emotions get rough: “I don’t just sit down and ask people about their sexual orientation or their religion or their fear of death, unless it comes up organically in some way through their work or through something that they said.”

That’s where empathy plays a vital role. “I try to imagine what is it like to be that person,” Terry explains. “What might they have been feeling when they did this or experienced this? And is there anything like that in my life, not because I want to talk with them about my life, but because I want to be able to understand it in a way that might make sense to me.”

When Terry interviewed renowned author Maurice Sendak, her empathetic questioning produced a remarkable moment.

Sendak, the beloved children’s author of Where the Wild Things Are and other books, was a famously complex character. He could translate dark reality into a playful children’s adventure. An avowed atheist, he was introspective and deeply creative. He came out as gay late in life. In September 2011, as the New England fall was setting in, Sendak spoke with Terry by phone. He was eighty-three and in failing health. His partner was gone, and loneliness was his companion. But Sendak had just published Bumble-Ardy, a book about a pig who, on his ninth birthday, throws himself his first birthday party. The story is a fable about growing up and staying young, about celebration and convention, about love and forgiveness. Terry had interviewed Sendak many times before. They’d known one another for years. He trusted her. You can hear the affection in her voice.

She congratulates him on the book and asks simply:

How have you been?

Sendak sounds fatigued and resigned.

“It’s been a rough time,” he admits. He’s gotten “quite old.” He is still working but it doesn’t matter if he ever publishes again. What time he has left is “for me and me alone.” Sendak speaks about the death of his publisher and his publisher’s wife. “My tears flow,” he says. “I am having to deal with that and it’s very, very hard.”

There can be art in a question. Terry’s next one paints with a deft stroke. Having heard Sendak’s loneliness, feeling his mortality, she asks:

Are you at the point where you feel like you’ve outlived a lot of people who you loved?

“Yes. Of course,” he answers. “And since I don’t believe in another world, in another life, that this is it. And when they die they are out of my life. They’re gone forever. Blank. Blank. Blank.”

Terry acknowledges the thought: “Having friends die tests our faith.” She knows Sendak does not believe in God and rejects religion. Still, she wonders whether he feels any spirituality as he considers his own death.

Is your atheism staying strong?

“Yes. I’m not unhappy about becoming old,” he says. “I’m not unhappy about what must be. It makes me cry only when I see my friends go before me and life is emptied.” He reflects on the hundred-year-old maple trees just outside his window. “I can see how beautiful they are. I can take time to see how beautiful they are. It is a blessing to get old.”

As Terry thanks Sendak, thinking she is bringing the interview to a close, the conversation takes its most interesting turn. She hears more than his words. She picks up on his tone of voice, the way he paces his thoughts. She hovers on the moment.

GROSS: Well, I’m really glad we got the chance to speak because when I heard you had a book coming out I thought what a good excuse … to call up Maurice Sendak and have a chat.

SENDAK: Yes, that’s what we always do, isn’t it?

GROSS: Yeah. It is.

SENDAK: That’s what we’ve always done.

GROSS: It is.

SENDAK: Thank God we’re still around to do it.

GROSS: Yes.

SENDAK: And almost certainly, I’ll go before you go, so I won’t have to miss you.

GROSS: Oh, God what a …

SENDAK: And I don’t know whether I’ll do another book or not. I might. It doesn’t matter. I’m a happy old man. But I will cry my way all the way to the grave.

GROSS: Well, I’m so glad you have a new book. I’m really glad we had a chance to talk.

SENDAK: I am too.

GROSS: And I wish you all good things.

SENDAK: I wish you all good things. Live your life, live your life, live your life.

Nearly poetic, Sendak spoke from his most solitary place, staring directly at the mortality that we are all destined to confront. Terry told me it was one of the most emotional interviews she has ever done.