Paul Holdengräber *95, left, founder and director of “Live from The New York Public Library,” interviews drag queen RuPaul.
Sarah Stacke/The New York Public Library
A master of the interview talks to everyone from boxer Mike Tyson to biologist E.O. Wilson

Paul Holdengräber *95 once spent his days discussing comparative literature in front of a classroom of students at the University of Miami and Williams College. But for the last 10 years, he has chatted before an audience of 500 with some of the world’s most interesting people — from hip-hop artist Jay Z to writer Cheryl Strayed, from magician David Blaine to biologist E.O. Wilson — as founder and director of “Live from The New York Public Library.”

“The great moments are when something happens and both people are sort of baffled,” Holdengräber says. Case in point: his interview last spring with drag queen RuPaul, which began with a wary RuPaul clearly uninterested in being in the interviewee’s seat and ended with the two in an impromptu dance after RuPaul propositioned Holdengräber and received a gracious rejection.

On stage, armed with weeks of research and literary quotations that he sprinkles into the conversation, Holdengräber is highly engaged with his guests and clearly takes pleasure in the process. He credits his years at Princeton, where he earned a Ph.D. in comparative literature, with teaching him “infinite curiosity.”

His upbringing was a training ground for his current work, he says. His Viennese parents escaped from Hitler’s Europe to Haiti, where they met. Holdengräber spent his early years in Mexico, then in various European countries before the family settled in Belgium when he was about 9. His father encouraged both vigorous discussion and hitchhiking, and Holdengräber’s teenage jaunts through Europe and America taught him how to talk with whoever was behind the wheel.

“It’s wonderful being interviewed by him. It’s exhilarating,” says Adam Phillips, a British psychoanalyst who has held a series of conversations with Holdengräber. “It is genuine performance art and it is genuinely intimate, and every conversation feels new and intriguing.”For his part, Holdengräber often leaves the stage wondering whether the conversation worked: “I have a maddening sense of what the perfect conversation would be, but it always eludes me.”

Paul Holdengräber *95 On Some of His Most Memorable Interviews

Boxer Mike Tyson: “This was one of the most extraordinary conversations. He both listened very carefully and responded with great candor and intelligence and feeling. My mother had me ask what it feels like to be hit so hard in the head. He said, ‘What I did for a living is what you try to avoid your whole life.’”

Poet W.S. Merwin ’48: “The interview with then-poet laureate W.S. Merwin was deeply moving. When he came on stage, I felt guilty. I said, ‘I don’t read enough poetry.’ He said, ‘Don’t read poetry. Read poems.’ To my mind, that was very liberating.”

Musician Patti Smith: “One of the most glorious moments I’ve had was interviewing Patti Smith. I’ve lived my life backward in so many ways. In the middle of my life I discovered Patti Smith through her writing, which is highly poetic, and then I listened to her music.”