I’ve always been attracted to the melancholy—in art, in music, in life. It’s probably not a trait I’d have chosen, but it’s one I’m stuck with, and one I long ago learned not just to accept, but to embrace. From the time I was a little girl, I found that the happy-go-lucky aspects of life that other kids seemed to like (you know, like the circus) just didn’t do it for me. I always preferred a little angst with my entertainment. Sure, I liked to play with my friends, but I clearly remember preferring the company of the sage old ladies in my ‘hood to that of the girls my age.

There they’d be—Debbie, Linda, MaryAnne, and the other eight-year-olds on my block—roller-skating or jumping rope or playing tag in the street. And there I’d be, sometimes playing with them, but often sitting with Minnie, Sarah, Bessie, Mrs. Liebowitz, and the other 70-year-olds, sipping tea and listening to them reminisce about the dancehalls of their youths and their long-dead husbands, my eyes filling with tears as I nodded along and patted their hands in empathy, the youngest member, by six decades, of this inner-city kaffeeklatsch.

Whatever the early loss—or buried trauma or gene mutation—that made me gravitate as a child toward sad songs, it also propelled me into the music industry, in which I would build my career, and drew me to the musicians themselves, particularly the vagabond mystics, panhandling guttersnipes, and bohemian troubadours who populated (or so I thought) Greenwich Village and the Haight, and who suffered, it seemed, for their art.

Why was it that I was drawn to melancholy sounds, from the plaintive wails of a lost puppy to the mournful distant whistle of an evening train, and sad songs and melodies— from Pete Seeger’s wistful “Where Have All the Flowers Gone?” to Phil Ochs’ malaise-filled “There But for Fortune” to the Marmalade’s self-pitying “Reflections of My Life” to Dion’s elegiac “Abraham, Martin and John”? At five years old, I was both excited and a little frightened by the opening notes of Jimi Hendrix’s version of “All Along the Watchtower”, which I found at once beautiful and menacing, and Cream’s “White Room”, which made me think the boogieman was around the corner. At seven, I’d run upstairs and into my mother’s safe arms whenever my older brother played Norman Greenbaum’s creepy but compelling “Spirit in the Sky.” At eight, it was the guitar riff in T. Rex’s “Bang a Gong (Get It On)” that weirded me out. And at 10, it was Lou Reed’s “Walk on the Wild Side” that made me want to know all about this place called New York City and prompted me to ask my very old-fashioned mother what “giving head” meant.

As a kid, I envied my friends, who were happy to go to the circus, able to just enjoy the trapeze artists and the cotton candy, not worried about whether the clowns missed their parents or whether the elephants were sad because they had to stand alone for hours in trailers. At the same time, I knew there was more to life, and I knew there was something behind the scenes, behind the curtain—just like on Let’s Make a Deal. One day, I would know what was behind that curtain, and maybe, I’d even be there behind that curtain with those musicians and artists to whom I was so drawn.

The fact that I was a good girl and an A-student carried a lot of weight when I was caught sneaking Buried Alive, Myra Friedman’s biography of Janis Joplin, out of the library when I was in fourth grade, sandwiching it between my math and religion textbooks, poring over the sordid details of Pearl’s lonely childhood and her heroin death, wishing that I could have helped her. I was somehow able to filter out the stuff I didn’t know about and knew that I shouldn’t know about yet, like sex and drugs, but I couldn’t let go of the rock ‘n’ roll. Of course, my having that book didn’t go over big with the nuns, but my mother told them that her daughter was a good girl and they should be proud of the fact that I had compassion for others.

She was right, I did have compassion. I had it in droves. When the Nitty Gritty Dirt Band released “Mr. Bojangles” a year or two earlier, I took it to heart. I wondered if there really had been such a man, and if his dog had really died. I didn’t just listen to the song as a singable little reverie the way—I assumed, at least—everyone else did. No, I pictured poor Mr. Bojangles in his worn-out shoes, grieving for his dog after 20 years. I wondered what kind of dog it was, how the dog died, if he felt any pain, and how Mr. Bojangles found out about his dog’s death. Of course, Mr. Bojangles didn’t keep me from riding my bike or playing dodge ball with my friends. But he always had a tiny secret place in my heart, along with the circus clowns, and the elephants, and the old widows on my block. Still, I kept my “condition”—this attraction-cum-aversion to the sad, the downtrodden, the imperfect, sometimes even the archaic—a secret. How could I articulate it, after all, when I couldn’t quite put my finger on it?

It wasn’t until about 10 years ago, during a serendipitous phone call with a total stranger, that I discovered my “condition” wasn’t the byproduct of a buried trauma or gene mutation. In fact, it’s not a condition at all—it’s an aesthetic. It’s a way of looking at the world which, though melancholy, is not necessarily pessimistic. It’s an aesthetic that permeates rock ‘n’ roll, blues, most forms of jazz and folk, and many genres of art and literature. It’s the very essence of punk, at the core of film noir, at the heart of the Beat Generation.

I remember the exact moment that I found out that, not only was I not alone, but I was in great company—the company of many, if not most, of my musical, literary, and artistic heroes.

By that time, I’d been working for nearly a decade with Rick Danko—ironically, one of the few great musicians I’ve ever encountered who was known for his jovial demeanor. I was on the phone with a TV producer named Chris, setting up an appearance for Rick, when our conversation meandered to random music and art. Chris and I clicked immediately; we talked about everyone from Poe to Frida Kahlo to the Velvet Underground to Gram Parsons to Edith Piaf.