Memory Lane: How Madonna’s “Immaculate Collection” Changed My Life

I graduated from stories-on-tape on the first night of Chanukah in 1995, when my sister gave me my first real album—Madonna’s The Immaculate Collection on cassette. I was 10, and at 14 years my senior, my sister was part of the Madonna generation, but this wasn’t something I registered until much later.

Getting your first album—your first encounter with musical pop culture—has to be one of the most definitive moments in a girl’s childhood. For me, the Madonna cassette represented a new grown-up connection to my sister. Everything before—games, stuffed animals, books—had marked the differences between us. While I couldn’t wear the same clothes and makeup as her, I could at least now listen to her music.That album quickly became an obsession. My favorite song was “Vogue,” which I’d dance and sing along to, impatiently rewinding the tape over and over again. With “Holiday,” I’d imagine I was a pretty 20-something getting ready for a night out. And then there was “Crazy For You,” a slow ballad that made me feel sad, even though I didn’t know why.

At the time, I was a misplaced city girl living in what I deemed Hicksville, USA. I’d been born in New York and had grown up in Manhattan until I was eight. Then, on a whim, my parents decided to open a bed-and-breakfast in Massachusetts. A self-righteous and defiant urbanite, I wanted nothing to do with country life, and I made sure everyone knew it. I rebelled against my parents by affecting annoying and snobbish behavior. In school, I became known as the different girl who, when she wasn’t wearing bell bottoms and poodle skirts, dressed exclusively in clothes from the Gap. (Material girl, much?) I craved sushi in a town where you had to drive 45 minutes to get some.

And I also listened to Madonna.

I didn’t even realize this was another thing that made me different until one day in art class. We were making clay candle holders, and some of my classmates at the table began talking about music. That’s when Todd Enniss turned to me and asked, “Leo, what kind of music do you listen to?”

“Oh … well, I like Madonna.”

“Madonna!” Todd shouted. “She’s SICK!”

The entire class fell silent for a few seconds, all eyes on me, then dissolved into laughter. My cheeks reddened.

“She is not,” I tried to counter. “Madonna is an important pop culture icon,” I said, reciting words I’d heard from my sister, no doubt the teachings of whatever postmodern theorist she’d read in college.

But there was no winning this one. My class thought Madonna was a dirty, sinful character. Everyone hated her and hated those who listened to her.

After this incident, I looked more into Madonna. I knew that her thing was “being sexy,” but aside from that, I didn’t understand that much about her image, and it bothered me that, apparently, Todd Enniss did. For sure, her songs, especially some of the more sultry ones, did arouse a sexual curiosity in me, but one I only equated with feelings of being a woman and not a girl.

I surreptitiously began watching MTV, catching her videos or interviews whenever I could. Watching the channel, I came to understand, had to be a secret from my parents. I got my secret music video screenings down to a science—MTV was channel 28, and Nickelodeon was 27. I kept my thumb poised on the remote control so that when mom or dad’s footsteps sounded, wholesomeness was just a click away.

As I began increasing my exposure to pop music, I added more and more to my collection of cassettes—next was Mariah Carey’s Music Box followed by Ace of Base. When my 12th birthday came around, my parents bought me a boom box with a CD player, and my sister again bought albums to go with it—this time a starter collection of artists I had to be educated in—Liz Phair, Nirvana, The Cardigans, Bjork. For my first CD purchase, I bought the disc version of The Immaculate Collection, knowing somehow that the tape would be something I’d want to keep around for a long time and preserve as best I could.

It’s now the only cassette I own.