Susan Choi
The Virgin Tour, 1985
They were both paragons of style, Madonna and my boyfriend’s Guess? Jeans–clad mother, although I’d already perceived Madonna’s style was more within reach. Yeah, I too had four inches of rubber bangles on each arm that summer, like some kind of cultural rash. My boyfriend and I desperately pursued every stripe of carnality we could think of in his postmodern bedroom—his house had been designed by his mother—while MTV blared as our “cover.” I remember “Borderline” and “Lucky Star” as an endless atmosphere for our efforts.
At the end of that summer, I ordered him to deflower me, so that I wouldn’t have to live with the shame of starting high school a virgin. We crossed the borderline between summer and fall, between innocence and experience, with what we imagined was great dignity. Then one day his mother opened the door. Madonna was on MTV. Under our blanket, we—well. She had come to empty his wastebasket. “You shouldn’t leave your French letters in the garbage, bunny,” she admonished. “After a while, they’ll smell.” The video ended, the door clicked shut again.
Elizabeth Wurtzel
“Who’s That Girl?” Tour, 1987
Madonna’s greatest talent is being herself. But during that awful summer of Reaganomics and shoulder pads, she was not a very good version of herself. The joke answer to the tour name was, Who cares? The Madonna adorableness—those fleshy arms she held up to the air dryer in Desperately Seeking Susan—had turned into big, bad muscle. Her spiky platinum “punky” hair made her look more like a socialite at Mortimer’s. And me, I was 19 going on 20, working for a paper in Dallas and trying very hard to be me, whoever that was. It wasn’t working out that well, either. I was absolutely manic—it later become apparent that this was clinically true—and drinking too much. Still, somehow, work got done, I got done, and as it turned out, Madonna made it back from a bad-hair life.
Michael Musto
Blonde Ambition Tour, 1990
By the time the tour hit Nassau Coliseum, I was living and breathing Madonna so voraciously I had even paid to see Dick Tracy. The city was in a slump under Dinkins, but the clubs were gleeful and almost reckless because it seemed as if no one was watching. But Madonna was watching, and brazenly tapping into the gender play and ritualized showing off. We all wanted a piece of her, like the stage-storming fan who was dragged away by security as Madonna sang “Keep people together.” Oh, good, I thought, one less fan to compete with.
Rick Marin
The Girlie Show Tour, 1993
For a newly single and struggling writer, Madonna meant easy money for infotainment stories, and easy access to a rival hackette also hot on the trail of the Immaterial Girl. When the Sex book came out, we huddled in a “confessional” viewing booth in the old Brentano’s on Fifth Avenue and were, like most viewers, unshocked. The dungeon-themed book party at Industria was the beginning of the end of the meatpacking district, a louche pastiche paving the way for Pastis. Robin Leach pronounced it “quite tame.” Likewise the Girlie Show’s burlesque, which the hackette and I fled for my neighborhood version, Billy’s Topless. We drowned our professional self-pity in irony, Beck’s, and bed—too shamed the morning after ever to speak again.
Laurie Gwen Shapiro
Drowned World Tour, 2001
I smiled cautiously from the sidelines of a Hamptons Film Festival party as the thrumming “Ray of Light” began to play. The sight before me was almost too much to bear: a rapturous pre-9/11 group sway. I had a husband in an Australian grad school, but now the world’s most adorable filmmaker indicated by a slight tilt of his head that I should join in. We clasped hands, acknowledging the raw connection. But I heard more than I wanted as Madonna held up a mirror to her life. At song’s end, I dashed to the rest room, splashed water on my face, and speed-dialed Melbourne. I wanted my husband home and I wanted to have a baby.