Madonna (Rewind): Music as Sex and Sex as Power in the Reign of the Queen of Pop

Madonna always knew her life would be art. She rose through the late 70s New York scene reinventing pop iconography and feminism alike. But whether it was Toronto police threatening her for indecency, her short-fuse husband, Hollywood bros exploiting her charisma, or far worse, Madonna learned quick: the world doesn’t know what to do with a truly free woman. To view the full list of contributors, see the show notes at ⁠www.disgracelandpod.com⁠ https://disgracelandpod.com/. This episode was originally published on October 22, 2019. To see the full list of contributors, see the show notes at ⁠⁠⁠⁠⁠www.disgracelandpod.com⁠⁠⁠⁠⁠ https://cms.megaphone.fm/organizations/c83125d2-8508-11ed-bd28-ff0aff7ee233/podcasts/efca2ef8-85f9-11ed-8fe3-bb208936046f/episodes/29bc673e-85fa-11ed-9d9c-cffe44583488/www.disgracelandpod.com. To listen to Disgraceland ad free and get access to a monthly exclusive episode, weekly bonus content and more, become a Disgraceland All Access member at ⁠⁠⁠⁠⁠disgracelandpod.com/membership⁠⁠⁠⁠⁠ https://disgracelandpod.com/membership. Sign up for our newsletter and get the inside dirt on events, merch and other awesomeness - ⁠⁠⁠⁠⁠GET THE NEWSLETTER⁠⁠⁠⁠⁠ https://mailchi.mp/doubleelvis/disgraceland-email-newsletter Follow Jake and DISGRACELAND: ⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ https://www.instagram.com/disgracelandpod/ ⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠ https://www.youtube.com/@disgracelandpod ⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠ https://twitter.com/disgracelandpod (formerly Twitter) ⁠⁠⁠⁠⁠Facebook Fan Group⁠⁠⁠⁠⁠ https://www.facebook.com/groups/491024204626127/ ⁠⁠⁠⁠⁠TikTok https://tiktok.com/disgracelandpod See omnystudio.com/listener https://omnystudio.com/listener for privacy information.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:13Speaker 00

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• 0:44Speaker 01

  Sponsored by GSK, the makers of Extenture. Depamocumab ULAA. If your asthma keeps interrupting, it may be time to try something else. Extenture is an ultra-long-acting prescription maintenance treatment for severe asthma, eosinophilic type, ages 12 and older. It isn't for sudden breathing problems. Extenture is the first and only add-on treatment that can help deliver protection from asthma attacks with two doses a year. Just one dose every six months. That's a lot of time for everything in between. Serious allergic reactions can occur. Get help right away for swelling of face, mouth, tongue, or trouble breathing. Don't change or stop medicines, including steroids, unless told by your doctor. Report if you have a parasitic infection, common cold, sinus infection, inflammation

• 1:29Speaker 01

  in the nose, flu or flu-like symptoms, joint pain, or sore throat may occur. Carry on with fewer attacks and ask your doctor about Extenture. Learn more at extenture.com or call 1-833-393-3678.

• 1:44Jake Brennan?

  All right, guys, welcome into another rewind episode of DisgraceLand. We're getting into the archive with Madonna this week. This episode was originally released back in 2019, if you can believe that. That is just wild to me. October 22, 2019. A lot of you might not know this based on my, the way I portray my tastes here in DisgraceLand. I come from the world of punk and hardcore, but I've got some pretty well-rounded tastes like most of you as well. Big Madonna fan, always have been. Huge part of my childhood. If you grew up as a kid in the 1980s and 1990s, she was impossible to escape, and I always loved her vibe.

• 2:26Jake Brennan?

  And when I got into the research for Madonna, I grew to love her even more because I never truly knew the history of Madonna in downtown New York in the late 70s and early 80s. And I just found it fascinating that she was running around the same clubs with Sade and Beastie Boys and Keith Haring, and just an amazing time. And I hope, I hope we captured it. We did justice to that era in this episode. I had a lot of fun doing the music for our little homage to "Borderline," which you'll hear in here as well. So check this out, I hope you dig it. Madonna's obviously been in the news lately. She always finds herself in the news. I just heard my kids come home, so that's news to me.

• 3:11Jake Brennan?

  I'm gonna get running. I hope you dig this episode. Give me a call, 617-906-66638. Voicemail and text at disgracelandpod on the socials, [email protected], and let me know what you think. DisgraceLand is a production of Double Elvis.

• 3:28Jake Brennan?

  A quick warning for those affected by depictions of physical and sexual abuse. This episode details both.

• 3:44Jake Brennan?

  The stories about Madonna are insane. She's one of the most daring, explosive artists of all time. She was raped at an early age. She was targeted by the Vatican for her performances. And nearly arrested in front of 50,000 people for simulating masturbation. She repeatedly pushed herself through her art, using it as a weapon to fight off abusive directors, to overcome overbearing producers, to outrun breathless paparazzi, and to outlast A-list significant others. Madonna obliterated mainstream attitudes about sex, refused to be slut-shamed, and pushed herself creatively right up to the limits of the law.

• 4:24Jake Brennan?

  She was a megawatt star who would not be dimmed, not by critics, not by knife-wielding maniacs, and certainly not by hot-headed machismo narcissists. Along the way, she made great music, some of the greatest pop music ever made. That music I played you at the top of the show, that wasn't great music. That was a preset loop from my Mellotron called "Mellow Push Push MK1." I played you that loop because I can't afford the rights to "Mickey" by Tony Basil. And why would I play you that specific slice of choreographed cheerleader cheese? Could I afford it? Because that was the number-one song in America on December 16, 1982.

• 5:08Jake Brennan?

  And that was the day Madonna took the stage for the first time at New York City's dance interior and began to slowly but powerfully push herself into American consciousness. A small step that would lead to scandal, controversy, intense expression, and icon status. On this episode, sex, controversy, rape, cheerleader cheese, and Madonna. I'm Jake Brennan, and this is DisgraceLand.

• 6:01Jake Brennan?

  The video is grainy, so poor that it immediately smacks of surveillance footage. Madonna, 19 years old, is lying on the floor of a downtown diner. She's just been raped. She's sobbing, mumbling, frantic, scared, and nonsensical. She can taste fear in her mouth, adrenaline. Her right breast is exposed. She's wearing all white, stretch pants, and an oversized men's button-down shirt that she borrowed from her boyfriend, who is comforting her. He just made the scene. Around him, the number of restaurant onlookers grows to a small gaggle. They're no doubt hardened by their city, but not so jaded that a freshly raped teenage girl lying on the floor doesn't warrant a curious second look.

• 6:44Jake Brennan?

  Madonna cries, Madonna moans, Madonna writhes on the sticky tile floor. Her boyfriend swears revenge.

• 6:52Jake Brennan?

  It's a scene, one of the many urban storms that swell up daily in Manhattan, stirred by violence, stifled by cynicism. Madonna is in a familiar position, the center of the storm. A position she seeks, a position she craves, a position she pushes herself into, even in this moment, not as a raped woman, but as an actress playing a raped woman.

• 7:16Jake Brennan?

  The part was her first from the independent film "A Certain Sacrifice," shot guerrilla style around the city across 1979 and 1980. Three years before Madonna would become a star, and decades before Madonna would confirm to Harper's Bazaar that in her first year in New York, she was raped for real, held with a knife to her throat on a steaming-hot Manhattan roof, and forced into performing fellatio. Most rape victims would understandably not want to relive their trauma on film a mere year later. But for a hungry artist like Madonna, this was an opportunity. An opportunity for real expression, real art, transcendence.

• 7:56Jake Brennan?

  An opportunity to express herself, push past her own limits, and achieve true artistry. To stand out as the undeniable force of nature she knew she was, which she knew the world would see too, someday.

• 8:11Jake Brennan?

  New York City, Madonna's New York City in the late 70s and early 80s, was a beautiful mess. Reggie Jackson, Jimmy Breslin, garbage strikes, the Son of Sam, the Bronx on Fire, punk rock, street art invading highbrow galleries, the advent of hip-hop, and cheap rents.

• 8:29Jake Brennan?

  It all felt like an explosion of creativity, a place and a time where culture-shifting music and art was conceived, and Madonna was there and affected by all of it. Blondie, Basquiat, Keith Haring, Fab Five Freddy, Andy Warhol, and more. Not to mention countless punk rock and dance club kids moving to the rhythm of New York's pulsing crime, grime, and electricity. It shaped Madonna, fueled Madonna. In a way, it made Madonna. New York City doesn't quit, ever. It pushes itself into every pore of your being until you become it, are expelled by it, or killed by it. The city treated Madonna-Louise Chaconi no different. The roots of Madonna's creativity and virgin horror ethos were well-established before

• 9:13Jake Brennan?

  she made it to Manhattan from suburban Detroit in 1978, growing up working-class Catholic in Rochester, Michigan. But New York City and its merry-go-round of creative characters helped Madonna turn her essence into the iconic image that turned the world on. And New York City at the time was one big come-on. How far could you push it? It was a place where one day you were just another face in the crowd at Max's Kansas City or CBGB's, and with the right timing, be discovered, made famous, a lucky star, seemingly overnight.

• 9:46Jake Brennan?

  At least that's how it seemed for those who knew Madonna at the time. But stardom doesn't happen overnight for anyone. It's a combination of hustle, timing, and expression. Three things Madonna was a no-shot supply of, not to mention talent.

• 10:03Jake Brennan?

  The Clash were onstage at Bonds International Casino. In between songs, Joe Strummer was chastising the Times Square crowd for the less-than-warm welcome they'd given the opening act, Grandmaster Flash and the Furious Five. It was a rock and roll crowd, and Flash, to them anyways, scratching records with a suede kangol on under his headphones, absent any live instruments onstage, might as well have been an alien. Joe Strummer, the Clash frontman, wasn't having it. Madonna and the crowd that night thought Joe was decidedly more attractive when he was angry than when he was strumming, but still, nowhere near as attractive as Clash bassist Paul Simonin, who'd let Madonna and her two friends sneak in through the stage door, just as he'd done for countless other seemingly anonymous fans who'd shown up

• 10:48Jake Brennan?

  without a ticket. The Clash were in the middle of the now-famous seventeen-night run at Bonds, a stretch that started out as eight shows, but after greedy promoters oversold the venue, the band had righteously agreed to keep playing shows until every ticket was honored for their fans. It resulted in a month-long residency with a mind-boggling run of openers, including The Dead Kennedys, Kraut, The Fall, Bad Brains, and Lee Scratch Perry. The Clash's generous attitude toward their fans extended beyond ticket holders to the point of just letting in whoever showed up. Madonna didn't have a ticket, but she pushed her way in. When she made the scene, she took note of the frumpy yet devastatingly cool Jean-Michel

• 11:31Jake Brennan?

  Basciat, the visionary iconoclastic street artist who was in the midst of becoming one of the most sought-after gallery artists in the world. A year later, with this star in even more intense ascent, he and Madonna would move in together. Eventually, he'd get strung out on heroin. Most people in her position, a 25-year-old struggling to make her own ascent through the downtown art and music scene while dating one of the youngest, coolest, most talented rising visual artists at the time, would have held on, tried to make the relationship work out, junk or no junk. But not Madonna. Drugs weren't her scene, so Jean-Michel Basciat was out. Madonna dumped, pushed on.

• 12:13Jake Brennan?

  Madonna was disciplined, hungry, some would say desperate, but that rap was ridiculous at best, sexist at worst. One man's discipline is another man's desperation. If Madonna were a man, would her career origins be seen as desperate? Probably not. She saw what she wanted, and there was nothing, there was no one who was gonna hold her back from her goal of becoming a singing sensation and then an actress, a modern Marilyn Monroe by way of downtown chic, but, you know, who could actually act. Her ambition, off-putting as it was to powerful men in the music business at the time, was part of her charm to the legions of young women who would constitute her early fanbase. By the time Madonna recorded her first singles, "Everybody" and "Burning Up," she was equally

• 12:58Jake Brennan?

  entrenched in downtown punk and dance club culture, two scenes that took themselves a little too seriously, but Madonna seemed to treat it all with the mischievous wink and nod of a free-spirited Catholic girl next door. To those just outside her orbit, fans in particular, it seemed like Madonna was always in on a joke that you'd never quite get, but that compelled you to wanna know more about her. With an armful of rubber bracelets, cross necklaces, and mesh halfshoes, she exuded mischief, sensuality, and sex. She wasn't the most beautiful girl in the club, but she was by far the most interesting. She wasn't the stunning Debbie Harry, the suicide blonde crushing studded hearts from

• 13:39Jake Brennan?

  the stage at Seabees, and she wasn't the beautiful beyond compare Shah D, slinging drinks from the bar at Danceteria and frightening young, lovestruck, post-punk adolescents into awkward silence. She was Madonna, and she was on to something else. Her style was her own, leather and lace fashion manifest as the virgin whore dichotomy she playfully tinkered with, part vintage punk, part Catholic schoolgirl in trouble, and perhaps more important, she flaunted her vulnerability. She willfully exposed her round belly, treated it as an asset as opposed to a physical liability at a time when male record executives expected female singing stars, at least the ones who they wanted to top the charts, to be the perfect image of femininity.

• 14:23Jake Brennan?

  Rail thin, perfect in body and in manners. If Madonna's imperfect looks didn't betray her outsider status, then her accent certainly did. It was bridge-and-tunnel Betty Boop by way of Midwestern adolescence. It was decidedly uncool, not of New York, non-regional, its own thing. As a result, it was a thing that, along with her humor and confidence in her looks, turned most men on, and this outsider status made her supremely relatable to teenage girls and marginalized gay kids. Madonna immersed herself in the growing dance club scene of the early 80s in Manhattan. In club culture, a culture that celebrated and flaunted sex was as big an influence

• 15:06Jake Brennan?

  on Madonna as downtown punk. Her sexuality was hers to play with, and she was unafraid to share it with the world. All of this is on display in her first single to hit the Billboard U.S. Top Ten, "Borderline." It's hard for me to explain the greatness and appeal of Madonna's "Borderline." The opening notes on the electric piano got me every time I hear them. It's a simple, childlike sound and melancholic melody that looks back to the 70s, and then the beat comes in, and all of a sudden, you're in a new decade, onto something fresh, fully committed to the promise of the unknown. The feeling is similar to the beginnings of any great relationship.

• 15:50Jake Brennan?

  You feel comfortable and safe, while at the same time excited about where it's all going. The single was Madonna's first big come-on. Her flirtatious glance across the bar, her nonchalant bump on the dance floor. It was electric, the casual touch from her hand, pushing it, the whisper in your ear, "Keep pushing it," the mischievous laugh, heart-melting, the smile, the pout, the abandon, the control, a total turn-on. Madonna had made a pass at America, and America was smitten.

• 16:42Speaker 03

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• 17:11Speaker 01

  Sponsored by GSK, the makers of Extenture, Depamocumab ULAA. If your asthma keeps interrupting, it may be time to try something else. Extenture is an ultra-long-acting prescription maintenance treatment for severe asthma, eosinophilic type, ages 12 and older. It isn't for sudden breathing problems. Extenture is the first and only add-on treatment that can help deliver protection from asthma attacks with two doses a year, just one dose every six months. That's a lot of time for everything in between. Serious allergic reactions can occur. Get help right away for swelling of face, mouth, tongue, or trouble breathing. Don't change or stop medicines, including steroids, unless told by your doctor.

• 17:52Speaker 01

  Report if you have a parasitic infection, common cold, sinus infection, inflammation in the nose, flu or fluke-like symptoms, joint pain or sore throat may occur. Carry on with fewer attacks, and ask your doctor about Extenture. Learn more at extenture.com or call 1-833-393-3678.

• 18:17Jake Brennan?

  Sean Penn wasn't fucking around. He was gonna shoot him down. Paparazzi, parasites, vultures circling their Malibu home on his and Madonna's wedding day. The shotgun was missing in the house, Sean was manic, Madonna was laughing. As usual, it was all a joke. Annoying, yes, a possible harbinger of what her life would become, an endless test of her so far bottomless appetite for attention, but in the moment, pretty damn funny, and if she were being honest with herself, totally exciting. Sean didn't see it that way, because Sean saw everything through the gaze of a serious-minded artist. He was just her type, currently taking his at bat as one of those next Brando, next Pacino types to come along every decade or so.

• 19:02Jake Brennan?

  To him, the helicopters were a big fucking problem. They were the kind of problem only a power couple as rich and famous as he and Madonna could even have. The helicopters would drown out the sound of the ceremony, making it impossible to hear, which was the reason everyone was there in the first place, to hear Sean and Madonna proclaim their deep love for one another. It was the reason she found it funny, and the reason he couldn't stand it, and at least in that way, they balanced each other's intensity. Plus, Sean got word that the choppers were freaking out the guests, especially Martin Sheen, who was rumored to be flashing back into intense paranoia, back to his days in the Philippines when he was filming Apocalypse Now, experiencing a very real alcoholic meltdown

• 19:44Jake Brennan?

  and using it as fuel for his performance on a set drowning in cocaine, LSD, and machismo, sharing prop helicopters with Filipino military while dodging revolutionary guerrillas. Turned on and tuned way the fuck out. Sheen had replaced Harvey Keitel, who, according to manic director Francis Ford Coppola, didn't have the acting chops, so Martin Sheen poured himself into the role and ended up having a heart attack on set for his efforts, and at the moment, in Sean Penn's backyard, it looked like he might be having another one. Either that, or like he might snap, like an actual shell-shocked Vietnam vet, instead of the actor who famously played one in the epic war film.

• 20:26Jake Brennan?

  Additionally, Martin Sheen's sons Charlie Sheen and Emilio Estevez looked bored. So did Tom Cruise, and so did Andy Warhol. But Andy always looked bored, and to him, Charlie, Emilio, and Tom looked good enough to keep his mind occupied while Sean and Madonna sorted out the helicopter thing. Where the fuck was the shotgun? Sean gave up and settled on dispatching a friend to etch into the sand on the beach below his home in giant 25-foot letters, "Fuck you", as a silent scream at the vulture photographers circling above. Madonna laughed. She looked great in all white with her black top hat. "What the hell was all that about?", Andy Warhol wondered. Warhol was insightful about celebrity, in this case, as he was in all cases.

• 21:10Jake Brennan?

  "What the hell was all that about?" is exactly what America would be saying about the marriage that began that day, until the day it dissolved, inevitably, like the grains of sand that made up the giant "fuck you" on the beach. But for the four years in between, Sean and Madonna's marriage was a straight-up tidal wave. Madonna, for her part, entered into it with clear eyes about their chances. She understood that when two like-minded, volatile artists got together, that they could either spur each other to greatness or flame out in epic fashion.

• 21:42Jake Brennan?

  A year after the big "fuck you" in the sand, they were on the island in Macau, filming a movie together, Shanghai Surprise. As Madonna suspected, their union had become a nonstop test of endurance against a swarm of paparazzi. When Sean was arrested on the island for dangling a photographer over a balcony, she wasn't surprised. She might have even liked it a little. She was surprised, however, to learn Sean had escaped from an unlocked jail cell and high-tailed it to Hong Kong on the first ferry he could find. The entire troubled production fled Macau, and they were able to keep the incident out of the papers. But Sean Penn would not get less volatile when they were back home.

• 22:24Jake Brennan?

  If the Penn Shikoni marriage was meant to push two artists to new heights, the fiasco and bombing of Shanghai Surprise was a loss on Sean Penn's turf. The movie biz. Madonna, the musician, she was in the middle of an unprecedented creative high. With "Borderline", she had crossed the threshold into stardom. But when her second album, "Like a Virgin", dropped in 1984, she became a true pop icon. The in-on-the-joke "virgin whore" act she had developed in the ripe dance and punk scenes of New York resonated across the globe. And it didn't come easy. Madonna had a stare-down veteran hitmaker, Nile Rodgers, who was producing the album. He didn't believe in the song, thought it was a novelty bit. Madonna held firm.

• 23:08Jake Brennan?

  She was undaunted by the more experienced, more successful man sitting in the producer's chair, and she insisted on recording the track. It goes without saying whose instincts were right. The artist had a vision, a vision her producer at the time couldn't see. She was rewarded for her commitment, as was Rodgers, who eventually bought in and produced a tight-sounding monster. "Like a Virgin" became a massive smash. Madonna's first number-one hit, followed immediately by "Material Girl", "Angel", "Into the Groove", "Dress You Up", all cracking the Billboard Top 5. Every single, over half of the nine-track album, was a stone-cold hit. Madonna had pushed herself in the mainstream American consciousness.

• 23:53Jake Brennan?

  She was a megawatt star, and nothing was going to dim her shine. Not even leaked nude photos from her days as a model back in New York, struggling to make it. When the pictures were leaked to Playboy without her approval in 1985, she refused to be shamed. Unlike Sean Penn, Madonna could handle the exposure. No shame, no pain. Virgin, whore, what's the difference? In the end, we all sink beneath the sun. Madonna pushed on. She owned Live Aid, performing alongside titans of the music industry at the time, from Eric Clapton and Mick Jagger to Patti LaBelle and Tina Turner, in front of a live audience of 100,000 and a global simulcast audience of 1.9 billion, nearly 40% of the Earth's population.

• 24:38Jake Brennan?

  And she crushed it. Her movie career took off with the success of "Desperately Seeking Susan", and her third album, "True Blue", dedicated to Sean Penn, cemented her status as the queen of pop, selling 25 million records around the world. But all this glory brought even more attention. She and Sean had driven each other to new extremes, and among the two stars at the time, it was Madonna who truly transcended from the top of her craft to global icon. They inevitably, but amicably divorced in 1989. And with the '90s on the horizon, Madonna was freer than ever to push cultural and sexual boundaries right up to the limits of the law.

• 25:19Speaker 04

  We'll be right back after this word, word, word.

• 25:23Speaker 03

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• 25:54Speaker 01

  Sponsored by GSK, the makers of Extenture, Depamocumab ULAA. If your asthma keeps interrupting, it may be time to try something else. Extenture is an ultra-long-acting prescription-maintenance treatment for severe asthma, eosinophilic type, ages 12 and older. It isn't for sudden breathing problems. Extenture is the first and only add-on treatment that can help deliver protection from asthma attacks with two doses a year. Just one dose every six months. That's a lot of time for everything in between. Serious allergic reactions can occur. Get help right away for swelling of face, mouth, tongue, or trouble breathing. Don't change or stop medicines, including steroids, unless told by your doctor. Report if you have a parasitic infection.

• 26:37Speaker 01

  Common cold, sinus infection, inflammation in the nose, flu or fluke-like symptoms, joint pain or sore throat may occur. Carry on with fewer attacks, and ask your doctor about Extenture. Learn more at extenture.com or call 1-833-393-3678.

• 26:55Jake Brennan?

  The after-party was lame. It was always lame. Besides, by Madonna's estimation, who had time to party? Which megastar performer, which singers are actually partying after putting on a show on the scale of Madonna's Blonde Ambition Tour? Madonna, playing multiple characters throughout the course of her setlist, diva, showgirl, and of course, both the virgin and the whore. Numerous complicated set changes, an Ayn Rand fountainhead-looking Metropolis set, a cabaret set, a religious set, an Art Deco set, and a Dick Tracy set dedicated to promoting her new film with her new boyfriend, the incorrigible Warren Beatty. There were stage costumes designed by Jean-Paul Gaultier, a 10-piece band, eight dancers,

• 27:37Jake Brennan?

  a film crew, a production staff of 100, 18 tractor trailers, a giant 747 plane to haul all of the equipment around, and a private jet to get her the fuck out of there after the show. But no, the damn after-party. Prince, Michael Jackson, Elton John, even Mick Jagger and the Rolling Stones, Madonna didn't understand. First of all, how do singers do it? Sit there in a cramped, barely furnished room in the bowels of a cold stadium, covered in sweat, your adrenaline pulsing through your body, your brain on overdrive, your vocal cords strained, and carry on conversations about nothing with famous people you don't know but who act as if you're lifelong friends, when really, all you want to do is compare

• 28:21Jake Brennan?

  show notes with your dancers and your band and celebrate the Herculean task you all just pulled off, staging a highly complex, physically demanding, emotionally draining show in front of 30,000 people. But no, the after-party.

• 28:38Jake Brennan?

  L.A. was the worst, for obvious reasons. The biggest starfuckers on the planet are stars themselves. Madonna thought it was silly, the Hollywood ass-grabbing. But Warren Beatty took it seriously. This was, after all, his town. He'd been on the A-list for 25 years, a career player in Hollywoodland. The social conventions of celebrity, the clubbiness of it, the premium on privacy and appearances, the coded do's and don'ts, they were all just sacred cows for the slaughter to Madonna. But from Beatty's perspective, they were to be taken seriously as rites of passage into his inner sanctum. Al Pacino, Lionel Richie, Chuck Kong, Mandy Patinkin, Olivia Newton-John, Martin Scorsese,

• 29:23Jake Brennan?

  they were all there with her backstage. And so was Kevin Costner, who despite his A-list blockbuster status at the time in 1990, was awkward as fuck when he met Madonna. He told her in all earnestness that her show was "neat", like he'd just seen Annie Hall for the first time before coming to the show that night, but didn't get the joke. Neat went out, I would say, at the turn of the century. Madonna was repulsed by Costner's lameness, and as soon as he split, she turned to her friends in pantomime vomiting to express her displeasure with the star. Neat. Beatty was not pleased. But the jam backstage was no surprise. Neither were the jam stadiums. Madonna was one of the biggest attractions in the world.

• 30:07Jake Brennan?

  The production, the creativity, and the performances, the whole show was novel for the time. It was a hot ticket, selling nearly half a million seats in the first two hours after they went on sale, and eventually grossing $60 million. And it wasn't without controversy. The show was a full-on theatrical production exploring Catholic sexuality. Onstage, the grueling craft work took its toll, and mid-tour shows had to be canceled so Madonna's throat could recover. Offstage, Catholic watchdog groups across the U.S. and Europe protested the subject matter. And when the Blonde Ambition Tour hit Italy, the Vatican threatened to outright ban Madonna from performing.

• 30:48Jake Brennan?

  But in 1990, for Madonna, nothing was more controversial than her show in Toronto.

• 30:56Jake Brennan?

  Madonna was sleepwalking through Where's the Party onstage at the Skydome. Fifty-three thousand people, more if you counted the mouth-breathing Canadian Mounties on hand to bust Madonna if she went ahead with her performance of Like a Virgin, where she had been infamously simulating masturbation as part of her dance routine. The song was coming up next. It was all Madonna could think about.

• 31:19Jake Brennan?

  When she got the news backstage before the set that she was being arrested if she went ahead with the performance, she was immediately defiant. "I'm not changing my fucking show," were her exact words. Her defiance quickly turned to exuberance. The thrill of the arrest was downright exhilarating, as was the prospect of the ensuing publicity shitstorm where she'd get hauled in for public masturbation, or indecency, or whatever charge the Mounties threw at her. She refused to be humiliated and shamed. Despite the smooth talk from Madonna's management, authorities weren't budging. Madonna's camp threatened to cancel the show. The Mounties held firm. She touches herself, she goes to jail. Backstage, the tension and excitement was palpable.

• 32:02Jake Brennan?

  Nikki Harris, a dancer in the show, told Madonna, "The cops meant business," and that "They arrested Bobby Brown for fucking onstage." Madonna lit up. "Did they?" And then slyly answered, "I hope he's in jail when I get there."

• 32:18Jake Brennan?

  And with that, Madonna defiantly walks onstage. Sitting on the plush, red-velvet-covered bed, center stage in a gold bustier, black fishnets and high heels. Gone is the belly from her borderline days. Her body is taut, fit, muscular, a dancer's body, a result of the grueling physical demands of the four-month, three-continent, ten-country tour. The drums percuss their way into the beginning of her most identifiable song, Like a Virgin, but they're slower, more sensual. The feel of the live version of the song is significantly different than the single version. The tempo is down, less playful, more seductive. The

• 32:59Jake Brennan?

  dance on the bed is all upper body, a Middle Eastern-influenced siren call in the flesh. Arms extended, slithering to the beat like cobras, and then Madonna turns to face the crowd and begins to slowly sing the words. The crowd immediately freaks out. Her serpentine arms continue to wade through the stage lights above her. The drums kick in. Madonna rolls onto her back, spreads her long legs, revealing her gold panty-clag crotch, and comes to her knees on the bed. She grinds her hips into an imaginary lover beneath her, pushing it. The song continues through the chorus, back to the verse, and when she hits the second chorus, she does another spread eagle and more grinding, more intense this time, pushing it, harder, hotter.

• 33:45Jake Brennan?

  Madonna leans into the ride, straddling her imaginary lover, teasing. Her hand begins to rub her belly, slowly inching down her navel, closer to the crotch. She moans the vocal refrain, slides her hand back down her belly again, this time even closer, closer to her crotch, pushing it, dominating her audience of thousands, a baseball stadium jammed with horny-inspired fans and a small handful of conservative, soul-crushing Canadian Mounties.

• 34:16Jake Brennan?

  The song hits the bridge and Madonna falls onto her back on the bed. Two dancers at her side caress her arms and back. She rises up onto her feet onstage and begins massaging her Jean-Paul Gaultier-coned breasts, and falls into the arms of her two dancers, who take her. She rise beneath them, still singing, not missing a beat. They mouth her nipples, palm her vagina. The song's tempo picks up. Madonna's hand grabs her crotch. She's on her back, thrusting her hips up. It's more than sex. It's violence. It's inspired. It's nasty. Madonna rolls over onto her stomach on the bed and begins frantically dry-humping, banging her head and her blonde hair up and down and up and down and up and down,

• 34:58Jake Brennan?

  her healed feet outstretched like a V. The crowd is freaking out, in full throat, screaming, cheering, panting right there alongside her with every thrust until the music finally comes down. Post-climax, post-coitus.

• 35:16Jake Brennan?

  The show could have ended right there. Madonna's performance of Like a Virgin, under threat of censorship from Canadian Mounties, was so inspired that there was no need to finish the set, but of course, she did. And in the end, there was no arrest. The authorities, perhaps sensing a potential riot, backed down. And Madonna had once again used her art to win out in the end.

• 35:53Jake Brennan?

  Vanilla Ice took Madonna from behind. It was staged, but so what? It was hot, as was Madonna wrapped in two other women, all curves, buzz cuts and tattoos, with a knife to her crotch. Or Madonna alone in a leather blindfold, studded lingerie with exposed nipple cutouts, a riding crop between her teeth and hand between her legs, mesmerizing in kinky black and white. This was Madonna's idea of a coffee table book. SEX, all caps. It was to be a literary and visual companion to her fifth album, Erotica. SEX would sell out its first edition within a few days, but even as America shelled out money to peep Madonna's erotic fantasies with one hand, it slapped her wrist with

• 36:38Jake Brennan?

  the other. Madonna's pushing of the envelope, her virgin horror image, had always attracted intense criticism, but after SEX, the criticism reached a new level. Critics who had once praised her pushing boundaries now trashed her work, casting her as a try-hard slut. Time Magazine predicted, "It'll be the first aluminum-covered soft porn book ever to grace the remainder bin," but they were wrong, of course. Today, SEX is one of the most in-demand, out-of-print books in the world, but the prudish backlash of the early 90s was real. As a result of the hypocritical controversy, Erotica would be Madonna's first record since 1983 with no number-one hits. With all the noise, the Times seemed right for focusing fully on her acting career.

• 37:24Jake Brennan?

  As an actor, Madonna, despite her more-than-capable turns in desperately seeking Susan in The League of Their Own alongside Rosanna Arquette and Tom Hanks, respectively, critics never considered Madonna a serious actor. Madonna wasn't supposed to act. She wasn't supposed to write books. She wasn't supposed to push boundaries on film. She was supposed to make records and videos to show off her belly above a boy toy belt buckle, and tour and make the power players in the music industry more and more money every time she got a creative itch to scratch, so long as it was the right itch. She was supposed to inspire critics to write lofty, over-intellectualized reviews and long-form think pieces dissecting the motive and meaning behind her lyrics and her evolving

• 38:06Jake Brennan?

  image. She wasn't supposed to make movies. Look what happened to Elvis. Singles, records, tours, that's where it was at. Everything else was just noise, overexposure. But Madonna would not be put in a box. She knew she had the goods for the screen, and she wasn't going to let self-important critics or the showbiz patriarchal power-starter dictator creative station. The reviews for Body of Evidence, the 1993 crime drama Madonna starred in alongside Willem Dafoe, were vicious. To follow it up, Madonna chose to go deeper, darker, agreeing to co-produce and star in notoriously tough and controversial director Abel Ferrara's Dangerous Game, opposite Harvey Keitel.

• 38:48Jake Brennan?

  The story tracks a famously uncompromising director, played by Keitel, who must cast a commercial starlet, played by Madonna, in order to get his film financed. Meta enough for you yet? It gets better. There was one more turn of the screw. The film, inside the film's lead, is played by James Russo, a real-life good friend of Madonna's ex-husband, Sean Penn. The project with Ferrara, Keitel and Russo was a snake pit of masculinity. The production, an underground dogfight that Madonna pushed herself into the middle of to answer her critics. And the results: electric, thrilling, transcendent.

• 39:26Jake Brennan?

  As a director, Abel Ferrara believed in breaking down his actors, berating them on set, forcing them through take after take to act in mentally and physically challenging situations, humiliating them when necessary, all in an effort to strip the actors of any contrived stage artifice and to hopefully bring raw emotion to their performances. The idea was that once they had been so beaten down, they'd forget they were actually acting. Ferrara's method was one that Harvey Keitel and James Russo bought into wholeheartedly. Nothing was out of bounds. Improvised lines thrown out to push the actors, mainly the female lead on the set, the only one on set, by the way, who was an actual A-list celebrity, Madonna, were meant to not only sting, but to break her.

• 40:10Jake Brennan?

  Russo's character calls her a cunt. He goes on to say, "She's a fucking horn. She can't act." Keitel calls her a "commercial piece of shit." Those last two daggers were meant to cut deep, given that they were essentially more concise, more profane versions of the criticism that the press had been hurling at Madonna on a regular basis. The situation was beyond intense, horrific in some ways. The line between art and real life was being obliterated. Madonna grew paranoid, anxious, tense, insecure. Violence was imbued into the nature of every shoot. Volatility was heavy in each direction. The insults from Keitel, Russo, Ferrara continued. This was not what Madonna had signed up for.

• 40:52Jake Brennan?

  The attacks would not let up. She felt humiliated. The shame, that feeling was familiar, reminded her of something she did not want to be reminded of. She could taste the fear in her mouth, the adrenaline. She felt violated, scared. She questioned herself. She blamed herself. She tried to play it cool, pull the act off, but it was too much, too intense, and she was afraid, afraid that her worst nightmare was happening all over again. The assailant kicked the door open. It happened so fast that she didn't have time to react. "Take your clothes off," he shouted. She stood, stunned. He forced her to the ground. Her body was so stiff that he couldn't make it happen. Even forcibly, he couldn't get

• 41:34Jake Brennan?

  it in, so he lost it. And the insults continued. He called her a disgusting lesbian, a stupid dyke, a pathetic piece of shit, and claimed that if he couldn't get it in her pussy, he was gonna make her suck it.

• 41:50Jake Brennan?

  When it was over, she remembered the choking feeling, gagging on it, and then being dragged over to the side of the roof by her hair and the feeling of the knife against her throat. She heard the rapist say that he didn't know if he should slit her throat or push her off the building.

• 42:08Jake Brennan?

  That's what Madonna's character said, anyway. That's how she detailed her rape to Harvey Keitel's character in the film and in real life, on set, answering her co-stars and directors off-screen abuse and creative taunting by digging deep into her past, into her own real-life rape, detailing the most traumatic event of her life, pushing herself deeper and deeper to deliver a tour de force of an acting performance that is the best reason to revisit the movie today. Only a year later, Quentin Tarantino would unveil Pulp Fiction and eat Abel Ferrara's lunch as Hollywood's go-to celluloid provocateur. But the boys' club running the set of Dangerous Game thought they were truly cutting-edge badasses and blamed Madonna for the movie not working. And they were wrong.

• 42:53Jake Brennan?

  Even mainstream gatekeepers, Siskel and Ebert, in their two-thumbs-down review called out the movie's blatant misogyny against Madonna. It wasn't subtle. A film about a film by a provocative director made by a provocative director, where the story dead-ends into all the men, calling the female lead a bad actress. A female lead played by the heavily criticized Madonna, insulting her on and off-screen as harshly as possible, just to see if they could break her. Most people would have buckled in the situation, broke. Madonna dug in. She pushed. She triumphed. She lived to tell. Dangerous Game didn't work as a movie when it came out, but 26 years later, it holds

• 43:34Jake Brennan?

  up in another way, as an accidental documentary about how Madonna is an unbreakable force of nature. Throughout the entirety of her career, men thought they could control her: rapists, record producers, A-list movie star boyfriends, directors drunk on their own testosterone, and especially the critics. But there is no controlling a true artist. Especially one as true-blue as Madonna. Underestimate Madonna, and you invite your own disgrace.

• 44:04Jake Brennan?

  I'm Jake Brennan, and this is DisgraceLand. DisgraceLand was created by yours truly and is produced in partnership with Double Elvis. Credits for this episode can be found on the show notes page at disgracelandpod.com. If you're listening as a DisgraceLand All-Access member, thank you for supporting the show. We really appreciate it. And if not, you can become a member right now by going to disgracelandpod.com/membership. Members can listen to every episode of DisgraceLand ad-free, plus you'll get one brand-new, exclusive

• 44:49Jake Brennan?

  episode every month, weekly unscripted bonus episodes, special audio collections, and early access to merchandise and events. Visit disgracelandpod.com/membership for details. Rate and review the show and follow us on Instagram, TikTok, Twitter, and Facebook @disgracelandpod, and on YouTube at youtube.com-at-disgracelandpod. Rock-a'roll.

• 45:12Speaker 05

  He's a bad, bad man.

• 45:16Jake Brennan?

  All right, guys, thanks for checking out this episode of DisgraceLand, the special archive episode on Madonna. Hope you dug it. Hit us up, 617-906-6638. Voicemail and text at disgracelandpod. On the socials, [email protected]. Let us know your thoughts on Madonna in DisgraceLand.

• 45:35Speaker 00

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• 46:05Jake Brennan?

  Hey, guys, time to dust off your detective skills while unwinding in the Caribbean on Virgin Voyages' second true crime voyage. It's back by popular demand, this five-night, adults-only escape sets sail March 20, 2027, to Grand Turk in the beach club at Bimini. The difference between this year and last will be that I will be on the cruise this year, along with Zeph, and he and I will be taping a live version of DisgraceLand along with podcast hosts from Exactly Right's Buried Bones, podcast of the year award winners Wyscrack, and other fan favorites. Get on this cruise with us, guys, and enjoy live podcast recordings, behind-the-scenes storytelling, exclusive meet-and-greets, and immersive true crime programming throughout this one-of-a-kind voyage.

• 46:50Jake Brennan?

  Head over to www.virginvoyages.com/truecrime to secure your spot.

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