In the early 1980s, I found myself on a double bill with a rising singer I’d never heard of; her name was Madonna. My Motown cover band had equal billing, but that clearly eluded Madonna’s team, who saw the downtown club gig as a showcase for her and her alone. Madonna sound-checked with such elaborate precision that my band never got to do so; by the time she was obsessively through with the mic, the doors were opening to the public and we were fucked. What’s more, after our performance, Madonna’s manager didn’t want us greeting guests in the joint dressing room, because the apparently demure Madge was getting ready for her set and didn’t want to change in front of strangers. I demanded my rights, while thinking, “This creature isn’t going anywhere.” I should have realized then that it was just this kind of aggressive tunnel vision that would rocket her to the pantheon.
Madonna was suddenly everywhere on the club scene, but her first single, the 1982 ditty “Everybody,” was so insistently whiny, I still wasn’t convinced she had a snowball’s chance. But she made it, with artfully done videos, rampant sexuality, and an ability to charm people’s pants off with feisty frankness. She even tried Hollywood, bombing out with stuff like the screwball comedy Who’s That Girl? while never letting people see her sweat. By 1987, I was hooked, so I went to see Madonna promote the movie outside a theater in Times Square, where she told the assembled throngs, “Shut up, so I can talk.” The steely determination was impressive.
She struck up a sensational gal-pal relationship with lesbian comic Sandra Bernhard, indulging in all sorts of innuendo that got the media and public panting. The two stars were at the center of 1989’s “Don’t Bungle the Jungle” — a BAM benefit for the Brazilian rainforest — where their sardonic antics upstaged ecological issues. After Madonna rattled off some rainforest facts, Sandra moaned, “Who the fuck do you think you are, Tracy Chapman?” “No,” replied Madonna. “I’m not working at a convenience store. But I do like to sneak off to a 7-Eleven at night for some jawbreakers.” “The bitch is cold,” Sandra interjected. “Funky cold Medina.” They launched into a version of “I Got You Babe,” and the comic sang, “I know we don’t have a cock, but at least I’m sure of all the things we got.” “Don’t believe the stories,” urged Madonna as the show wound down. “Believe the stories,” implored Sandra.
When I interviewed Sandra for my Voice column, she claimed their lesbian shenanigans were just shtick and people should relax about it. “I mean, God, you know, Madonna is a raging lesbian!” she said, eyes rolling. “I mean why don’t they take it really literally!” But when Madonna was spotted wildly making out with Sandra’s ex-girlfriend Ingrid Casares, I took the denials with a grain of potpourri.
By this point, I started feeling that Madonna was omnisexual, devouring whoever looks appealing at the moment, like someone shopping with a full pack of credit cards. I also sensed that she could leave her partner behind at a moment’s notice if they no longer suited her vision. In 1990, Madonna dated smoldering, bisexual model/ex-hustler Tony Ward, who later told me how their six-month relationship had ignited. They were on a night out together when the singer bristled that he wasn’t paying enough attention to her, so she impulsively put her cigarette out on his back. He started to be more attentive.
In 1991, the endlessly enjoyable doc Truth or Dare showed Madonna getting burned by the straightest partner ever: Warren Beatty. Their pairing couldn’t last, since she only existed when there were cameras in her face (or other body parts), and he positively withered under the glare, alarmed by the attention. The movie now comes off as one of the original reality shows, complete with staged moments; but still, Madonna centers it with her wicked wit and prayer circles. Rarely has self-adoration seemed so charming. (For more on Madonna: Truth or Dare, which begins a one-week revival run at Metrograph on Friday, see Melissa Anderson’s column, below.)
And then she went and dated cheesy rapper Vanilla Ice! I was simultaneously horrified and jealous. But she regained hormonal cred with her Sex book, which used gay models, locales, and themes — as well as some occasional straight ones — for a calculatedly racy romp that sold out instantly. It was basically the adult-entertainment version of Truth or Dare. At the book party, I wore a pope outfit with a pendant consisting of a ripped-up photo of fiery singer Sinéad O’Connor. (On SNL, Sinéad had ripped up a photo of the pope; Madonna would later go on the same show to satirically rip a picture of scandalous adulterer Joey Buttafuoco.) “Look, Madonna, Michael Musto’s dressed like the pope,” said the superstar’s bemused publicist, Liz Rosenberg, at the Industria Superstudio bash. Madonna flashed an appreciative smile, and that awful double-bill experience instantly melted for me. I even forgot the delicious irony surrounding the fact that the woman who didn’t want to change in front of an audience had by now made the world her gynecologist, as they liked to say on Absolutely Fabulous. But I still didn’t seize the chance to start a conversation; keeping some mystery about Madonna seemed like a novel idea.
In the Voice, I posed for a parody of Madonna’s naked-hitchhiking shot from the book. As I stood, tucked, in heels and wig, on a chilly New Jersey street, cops pulled up and threatened action. We showed them the Sex book, they flipped through the pages with eyes aglow, and then they left, smiling. I guess I was starting to develop my own steely determination — just as Madonna was flashing more humanity. I wrote a cover story for the angry gay magazine OutWeek, praising her for shining a spotlight on the LGBT community and upping our value in the world’s eye. Her devotion was not the full-throttle activism of Lady Gaga years later; this was a different time, when a mere image or remark could send shock waves. But Madonna could be glamorously silly, too: At her 1995 “Bedtime Story” party at Webster Hall, Madonna slinked out in silky sleepwear to read from the children’s book Miss Spider’s Tea Party. The event was shot for MTV, and I was interviewed on camera — in jammies — established as an awestruck follower of the woman who’d once dissed me.
As the years passed, Madonna strove to stay relevant while refusing to budge from dance/pop. In 2001, she defended Eminem’s homophobic raps by saying he was merely “stirring things up.” In 2003, she kissed Britney Spears at the VMAs, and, unlike her Sandra shtick, this clearly was a stunt, and not one done with any artistry or appeal. But Madonna was making a fortune on tour — even as, the whole time, she never stopped trying to become an Oscar winner. At a 2009 dinner for Pedro Almodóvar, I saw her snuggle up to the Spanish director and try to get him to use her in a movie. Pedro didn’t bite, but I know enough about Madonna by now to realize that she should probably start rehearsing some kind of acceptance speech. Shut up, so she can talk.