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Stephanie Nakasian: Paying Tribute To Billie Holiday

In the mid-1980s, Stephanie Nakasian was working as a consultant on the New York Stock Exchange when she decided to quit her job and come out to her parents -- as a jazz singer.

"I was really happy with it, and everything was going well, but some piece of my life was missing," Nakasian says. "I had some friends who had said, 'No, you're really an artist,' and I said, 'No, I'm really a businessperson. Can't you see I'm wearing a three-piece suit and carrying a briefcase?' And they said, 'No, I think you're really an artist in your core.' So I decided to try it and sing and meet people, and next thing you know, I'm tossing [Wall Street] away."

Nakasian, who has recorded seven albums, including Thrush Hour: A Study of the Great Ladies of Jazz and The Classic Songs of Billie Holiday, tells host Terry Gross that it took her parents a while to accept her new career.

"I bought a house at one point," she says. "And I think there was that feeling of, 'Okay, this can be [good].' And I think they saw at that moment that it was actually a way of life that I could sustain."

Nakasian got her big break soon after she quit Wall Street, when she began touring as a backup singer with seven-time Grammy winner Jon Hendricks. In an interview with Gross, Nakasian describes what it was like to sing with Hendricks on the jazz song "Jumping at the Woodside."

"My job was just to go "Jump jump jump jump jump," and in the beginning I said, 'This is ridiculous; this is one note,' " she says. "And then I realized I'm really learning how to place the rhythm in these nice punctuated -- I call them 'flicks.' Like flicking a note without it being harsh and heavy. And I just stood next to him and sang that line, and with him, and in doing that, I kind of got it."

After touring with Hendricks, Nakasian settled down in Charlottesville, Va. She teaches music lessons, travels on the jazz circuit and records albums both as a leader and with her partner, the jazz pianist Hod O'Brien.

Interview Highlights

On why she wanted to record an album of Billie Holliday songs

"Well, I've been teaching my students about the classics of jazz for years. Billie was one that I had not kind of delved into, and I was approached by a record label to do Billie Holliday -- especially the early [recordings]. This is an early 1935 recording which is now 75 years since, so it made sense to do this and try it, and I love the feeling of it. It's very perky and happy. It's some of the more obscure music, which I always love. And I just love doing it. So I decided to try to channel her and get more Billie into my singing, as well. That's part of the reason to do it."

On how much she wanted to emulate Billie Holliday and how much she wanted to emulate herself

"I think as an artist, we always want to develop our own expression. And I found in the last 20 years that my students don't know a lot of this music. So I've been trying to get into some of the older singers and present that to my students.

"My approach has always been, with these tributes, not to mimic or imitate, but try to put myself into and do kind of a half-and-half -- which is tricky, but my goal is to become a better singer and a fuller singer based in the history of it. So Billie taught me a lot as we listen to phrasing ... she has this gentle thrusting, the way she bends the notes -- so all of that is a teaching tool for others and for me, and I also got more of her style into my own singing, so it was beneficial on both sides."

Copyright 2022 Fresh Air. To see more, visit Fresh Air.