15 Women Reveal Their Madonna “Life Moments”

Madonna, in her crown. (Graphic: Helen Jane Hearn/TueNight.com)

Where were you when Madonna told you to Express Yourself? Had you been living in a Material World? Cherish-ing your boy toy? Desperately seeking a place to Vogue? We asked our contributors and friends for those moments in time when Madge was the backdrop to their lives — the soundtrack, the fashion, the filmic inspiration and even a dinner party companion.


I tried out for Drill Team in junior high to the song “Borderline.” I didn’t like Madonna. I had no desire to try out for drill team. I had no dance skills. The only way you were allowed to try out for drill team, however, was as a four-person squad. So I was drafted by three of my friends to complete theirs. We practiced relentlessly (six times counts as relentless when you’re 13). When the time came to perform and the play button on the boom box was hit, Ms. Carter gave us the head bob that said “YOU’RE ON!” I thought we actually had a shot. Twenty seconds later, I managed to crush the dreams of three very angry girls. I will never forget Kristen Hunter screaming across the locker room, “YOU’VE RUINED DRILL TEAM FOR US ALL, JIFFY. I WILL NEVER, NEVER FORGIVE YOU.” And all I could think of were the “Borderline” lyrics running through my head…”just try to understand, I’ve given all I can, ‘cause you got the best of me.” But apparently the best of me is not called by the spirit of the dance — and no amount of Madonna will change that.

Jiffy Iuen, Founder, Frank Collective

Fingerless lace gloves & lingerie

A group of my friends got together at our buddy Sue’s house, but her little sister and friends were hanging out there as well. They all wore lace gloves, bustiers, black leather bracelets and lots and lots of crosses. We were horrified but strangely attracted. I don’t think I’d ever seen anyone “dress up” as their favorite singer before, unless you counted leather-fringed moccasins and Indian prints.

Annette Earling, graphic designer

Desperately Seeking Susan

Summer, 1985. I’m 16, stranded in the netherworld where Queens melts imperceptibly into Long Island. It’s all bland split-levels and lawns fading in the summer heat. But look west at night, and a shimmering glow fills the horizon: Manhattan, so close you could touch it and yet a wholly separate, elusive universe of dangerous cool. Back then, Hell’s Kitchen was decades away from being littered with trendy restaurants. It was just littered with litter. And sex shops. And edgy dive bars nothing like the strategically designed “edgy dive bars” you’ll find in New York today. It was grubby, scary and utterly fascinating to a teenager who’d never taken a risk. That’s when I saw her, bigger than life on a screen at the shopping mall multiplex. Madonna, fearlessly treading through the very neighborhoods I wanted so badly to explore. She washed her face at a sink in a Port Authority bathroom as if this intimidating place was her own home. Could I ever be that confident? By summer’s end, I’d begun sneaking into the city on Friday nights, spending my babysitting money on overpriced drinks at Palladium in my mesh tank top with a floppy black bow tied through my excessively hair-sprayed hair. I didn’t have Madonna’s confidence yet, but I’d discovered how good it feels to be afraid and go dancing anyway.

Melissa Rayworth, freelance writer/editor, melissarayworth.tumblr.com

“Like a Virgin”

I watched a lot of MTV, including Madge bringing the house down in a wedding dress at the 1985 Video Music Awards when I was far too young to have the foggiest idea what was going on (though I loved it anyway). I’d strut around the neighborhood, introduce myself to other kids as Madonna and offer to sing my hit song “Loch Ovirgin,” which I assumed was the tale of me and my beloved having good clean fun in Scotland.

Lauren Oster, Writer, laurenoster.com

Listening to “Like a Virgin” and my mom asking me if I knew what a virgin was.

Jessica W., digital strategist

The Virgin Tour

Madonna taught me how to negotiate under fire. I wore a “The Virgin Tour” T-shirt to high school in suburban Atlanta (I was in 9th grade). The principal thought I needed to be sent home, but I negotiated putting masking tape over the word “virgin” and not wearing it to school again. I was allowed to finish the day.

Laura Loving, Artist, StudioLauraLoving.com

The Virgin Tour, May 28th, 1985, Pittsburgh Civic Arena, was my first concert ever! I was six years old and went with my older sisters. I wore an amazing blue suede short-sleeve shirt with a red bedazzled overlay (you had to see it to really grasp the awesomeness) and white lace gloves. We drove there in their friend’s convertible with the top down. I thought I was the coolest girl in the whole world because I was the only kid I knew allowed to go to the concert. I obviously didn’t understand really anything about what Madonna sang about, but I loved everything about her then and I love everything about her now.
Sloane Davidson, Founder, Farsight Media Consulting and Dinner Mode


“Papa Don’t Preach”

I’d just graduated from high school. A few weeks after I heard “Papa Don’t Preach” for the first time, I stood up to my strong, stern father with the words “I may be young at heart, but I know what I’m saying” still echoing in my head. Finding my backbone would change the course of my life by helping me believe in myself even when authority figures didn’t.

Suzan Bond, Writer, Suzan Bond

“Like a Prayer”

I was cripplingly uncool in middle school and would seize on any opportunity to improve my social status. Somehow I convinced three of the popular girls in my 7th grade class that I had an “in” with Star Search. We planned to appear on the show and perform “Like a Prayer,” dressed in full-on Madge-esque costumes. (Naturally, I would be the lead singer.) We rehearsed at recess and lunchtime. They weren’t exactly kind to me, but the specter of fame swirled around our practice sessions. By the end of the week, when I couldn’t produce definitive proof of our impending celebrity, they returned to their cliquey ways and I went back to eating alone in the library, reading VC Andrews and rewinding “Like a Prayer” over and over on my Sony Walkman.

Sara Gilliam, Founder, PunchDrunkVillage

Dick Tracy

 I spent my junior year in Paris studying at the Sorbonne. It was the ’90s, so, of course, like all good liberal arts majors at the time, I was way into cinema studies. The only assignment I had to do for this class was write a critical theory paper about a film. (Junior years abroad: What fantastic bullshit!) I never actually went to class. Instead, I spent my days nursing a $30/day caffe creme habit at (the original and sadly long gone) Cafe Costes, where I handwrote a 10-page essay in mediocre French about Dick Tracy. Thank you, Georgetown, you dope, for giving me three college credits for a lot of drivel about the use of primary colors in a horrid Madonna movie.

Pavia Rosati, Founder, Fathom


In college, my friend Tom and I used to go out dancing all the time. He loved Madonna, but the song Vogue pissed him off because he didn’t find it very danceable without doing stupid vogue-ing moves. When it would come on, we’d always stop dancing and then we’d go somewhere with a good sight line and gossip about who we thought were good or bad dancers. Good times.

Amy Vernon, Co-founder, Predictable.ly

Truth or Dare

 While living in Lancaster, Pa., my friend Regan and I HAD to see Truth or Dare, but it wasn’t showing in our smallish town. No Netflix! No Internet! So we drove to a suburban Philadelphia mall one Saturday to see it, and we were not disappointed. (Also including a bonus trip to IKEA.)

Diane Otter, Editor


It was 1992, and I was editing at Entertainment Weekly. When a review copy of Madonna’s erotic coffee-table book Sex came in, a small group of us stole away to a senior editor’s office and paged through it as if we’d just smuggled in contraband. We couldn’t quite believe what she was about to release to the world — a book filled with soft and hardcore Steven Meisel images featuring herself, writing as the character “Mistress Dita,” along with special guest stars including Isabella Rossellini, Naomi Campbell and Vanilla Ice. As my coworkers and I huddled around the aluminum-covered pages and debated whether it was art or straight porn, there was one thing I could be sure of: Nothing in J-school had prepared me for this.

Beth Arky, Freelance writer

“Ray of Light”

1998, singing this irresistible tune with my sons, ages six and eight, in the car at the top of our lungs.

Amy Barr, Writer/Mom, tuenight.com

The Confessions Tour

In June of 2006 I attended the Madison Square Garden Confessions Tour concert with my best friend, Toby. We were in our early 30s at the time and had been best friends since fate made us college roommates (where a big part of our bonding was over our mutual love of Madonna). As college freshmen, Toby and I had gone to the Girlie Show Tour in 1993 (my first Madonna show), and now we were roommates again, this time in NYC instead of Ann Arbor. The Confessions Tour was different from The Girlie Show, in part because I remember Madonna sitting down with a guitar for one of the numbers and making a joking apology for not being a better guitar player but saying she was learning to play because at her age “[she] couldn’t run around the stage the whole time anymore.” I remember thinking, “Wow, that’s a really frank and surprising comment for her to make about aging.” And I was pleased, being in my 30s, to think that Madonna was going to show us how to get older and adapt and continue to kick ass. Sigh. I feel like that tour was the last time she seemed like someone who was showing me the way to be the best, most fearless version of myself. Present-day Madonna is more of a cautionary tale. Coda: Toby and I remain great friends who now live with our respective spouses and children, handle aging with a normal degree of equanimity, and we often reminisce about the Madonna we used to love.

Amanda Clayman, Financial Therapist, www.amandaclayman.com

Real-Life Madonna

I was at a pretty hip dinner party in New York, feeling not quite hip myself, when I spotted two beautiful children sitting on the couch by themselves looking bored. I caught the eye of a person I thought was their mother to get the nod of yes-I-see-you-it’s-fine approval and started chatting with them. They were both about the age of my older daughter, charming and very smart. They told jokes and we laughed together while we waited for dinner to be ready. At one point, I asked about their mother and they pointed to a blonde woman with her back to me — not the woman I nodded to, who I realized now must be a babysitter. The call for dinner came, and being a mom, I brought them to a nearby sink to wash their hands. As I lifted up the boy to reach the water, I suddenly realized why their names, Mercy and David, had sounded vaguely familiar to me. I was horrified to realize I was holding Madonna’s child in my arms. My heart was pounding as I put him back down and hustled the two of them back to their sitter and mother.

At the end of the night, I mustered my courage and approached Madonna, my girlhood idol. I tapped her on the arm. “Your children are so smart and funny and charming. They are an absolute delight,” I said to her in one long breath. She smiled at me and raised an eyebrow. “They’d better be!” And I loved Madonna as a mom.

Adrianna Dufay, TueNight.com

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