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Jim Jarmusch (left) and Tom Waits in 1985.
Jim Jarmusch (left) and Tom Waits in 1985.Deborah Feingold

Madonna looks like she has been sucking on that red lollipop all day, her hair teased to 1980s perfection and her right arm lined with black bangles. She peers into the camera as if she’s about to wink, already aware that she’ll soon be one of the most famous pop stars in the world.

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An early portrait of Madonna on the cusp of fame in 1982, it’s also a testament to photographer Deborah Feingold’s finely tuned sense of her subjects and the qualities that make them special. That picture is one of several iconic images that make up Feingold’s new book, “Music,” her first-ever anthology, with an introduction by music journalist Anthony DeCurtis.

“It all started in Boston,” says Feingold, who grew up in Cranston, R.I., and graduated from Emerson College before moving to New York in 1976. “This started out as a hobby, and I did something that I loved. What you see is what I saw, and in this day and age, what you see is what a team decided for you to see.”

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Working for publications as varied as Musician (a long-gone magazine out of Gloucester) and Rolling Stone, Feingold trained her camera on the likes of Mick Jagger, Tina Turner, Prince, Billy Joel, Yoko Ono, Chet Baker, Judy Collins, James Brown, and the list goes on.

Ahead of Damiani publishing her book on Sept. 30, plus an in-store signing at Porter Square Books in Cambridge on Sept. 25, Feingold took us behind the scenes of some of the images.

Billy Joel in 1982.
Billy Joel in 1982. Deborah Feingold

Q. What’s a photo that you really had to work hard to capture?

A. Tom Waits and Jim Jarmusch. If you look at the film from that shoot, all they did was change positions — one sat on the top, one sat on the bottom. Their faces never changed. They basically wouldn’t talk to me. That photo reflects my experience as well: When the [expletive] is this going to end? Two rolls of film of that. And I’m not sure why there’s a 10-dollar bill in the edge of the frame. Maybe I was paying them to do something. “Could you just move a little bit?” (Laughs.)

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Q. How much do you like to know about a subject before a shoot?

A. I will research a subject if I’m doing a book cover [she shot the cover of then-Senator Barack Obama’s “The Audacity of Hope”], but what’s the point? They just want you to come in, take the photo, and get the hell out of there. I really feel that I worked in a way that was different from others. A lot of people in this field were journalists. You can see from my photographs that I wasn’t a journalist. I used to say that if I had shot war, the war would have ended by the time I composed the shot. My friends and my daughter do not like me to photograph them, because I’m too slow. I don’t overshoot. People with digital [cameras] shoot so much because it’s free and fast. I still shoot like I can’t afford the film. It’s a discipline.

Madonna in 1982.
Madonna in 1982.Deborah Feingold

Q. Your photos of Madonna took on a life of their own.

A. I have no explanation for that. It was a 20-minute shoot in my apartment that was so tiny that all my furniture folded up against the wall, including the bed, table, and chairs. I was all set up. I had one assistant. She came with Liz Rosenberg, who remained her publicist. Her makeup was ready to go. I had a bowl of lollipops, Tootsie Rolls, and bubble gum. I probably didn’t get paid or have a budget; hence a bowl of lollipops and bubble gum. Everything was very simple. I shot four rolls of film, and for every frame she changed it up. It was like a dance, and I was a good follower. I had the skill, but she led. Twenty minutes later, she knew we had finished, and she left. She was a working girl, I was there to work, and that’s what you see.

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Q. The book covers a range of genres, but what kind of music do you prefer?

A. I grew up with [’50s music], stuff like Bobby Darin and Ricky Nelson. I had a big love for the Shangri-Las. I love soul music. By the time I was living in Boston, I used to go to the Sugar Shack to hear Ashford & Simpson and Bill Withers. I used to go to Paul’s Mall and the Jazz Workshop. Meeting jazz musicians was a whole other lifestyle I didn’t know anything about.

Q. One of your first assignments was to shoot Chet Baker. What do you remember about that day?

A. I was offered the opportunity to photograph Chet for his record label. The photo shoot was at a third party’s apartment on the Upper West Side. You could hear a pin drop. I kind of placed him in different areas of the house. I even have pictures of him in the bathroom. I’m sure there was minimal conversation, which he seemed very happy with. People do remark about that image because [he died when] he went out a window. So it’s a little haunting.

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Q. What about that photo of Sinéad O’Connor?

Sinéad O’Connor in 1990.
Sinéad O’Connor in 1990.Deborah Feingold

A. That was shot in Montreal. That’s about 15 minutes after my assistant said, “Oops, I forgot the cord to the strobe.” That was me saying to myself, and I quote, “Take a breath.” I had shot Sinéad once before for Rolling Stone and got a really beautiful portrait of her. Rapport is very important, and I’ve just had my assistant tell me that we can’t light this shoot in a dark hotel room, and I can’t lose it. I’ve got to act like nothing is wrong. Remember: This is not digital. It’s not easy to shoot in low light. So that’s a shot that never, ever would have happened if it had not been for a mistake. That’s why I love mistakes. You keep it moving.

From left: Joe Perry and Steven Tyler in 1985.
From left: Joe Perry and Steven Tyler in 1985.Deborah Feingold
Prince in 1980.
Prince in 1980.Deborah Feingold
Keith Richards in 2000.
Keith Richards in 2000.Deborah Feingold
Chet Baker in 1977.
Chet Baker in 1977.Deborah Feingold

Interview was condensed and edited. James Reed can be reached at james.reed@globe.com. Follow him on Twitter @GlobeJamesReed.