George Michael: Lewd Acts, Guilt, and Freedom

Summary

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DISGRACELAND – "George Michael: Lewd Acts, Guilt, and Freedom"

Host: Jake Brennan
Date: March 18, 2025
Production: Double Elvis Productions

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Episode Overview

This episode of DISGRACELAND dives into the tumultuous life of George Michael—pop superstar, sex symbol, and icon for both his music and his tabloid scandals. Brennan explores the dualities that defined Michael’s existence: public adoration versus private shame, sexual liberation versus secrecy, and creative genius versus destructive compulsion. This is a story not just about music, but about the tangled intersections of fame, identity, repression, addiction, and the true price of freedom.

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Key Themes & Discussion Points

Setting the Stage: MTV, Sex, and Image (03:15–07:00)

• The 1980s music scene, dominated by sexually charged imagery, set the backdrop for George Michael’s rise. Brennan places Michael among the era’s “horniest” stars, even outpacing Prince and Madonna.

  "No artist on MTV right now in the late 1980s is hornier than George Michael."
  — Jake Brennan [04:10]

• Michael’s debut solo single “I Want Your Sex” is described as both a bold statement and a PR problem amidst the AIDS epidemic; Michael tries (unsuccessfully) to pitch it as an anthem for monogamy.

  “George counters with the explanation that the song 'I Want Your Sex' is not about casual sex but monogamous sex, all while the AIDS epidemic rages on in the background.”
  — Jake Brennan [05:49]

• Backlash from media, radio bans, and the BBC refusing to air the video before 9 pm only fueled the song’s—and his album’s—success.

Behind the Image: Shame, Kink, and Secrecy (07:15–12:10)

• George Michael's discomfort with his own image and sexuality is highlighted. Despite worldwide desire, he struggled deeply with self-acceptance and internalized shame, rooted in his upbringing.

  "Guilt, as George himself once said, was a massive turn on. Guilt got him off."
  — Jake Brennan [10:28]

• Brennan describes Michael’s early experiences with “cottaging” (cruising for anonymous sex in public places), the exhilarating danger of being caught, and the lengths to which Michael went to hide his sexuality from the public and his family.

• The all-consuming effect of secrecy and the corrosive impact of hiding from not just loved ones, but millions of fans, is underscored.

  “If you’ve ever had to hide who you really are from someone you know, it can be isolating. For George Michael...he was hiding himself from millions of adoring fans.”
  — Jake Brennan [11:09]

Love and Devastation: The Anselmo Story (16:19–23:55)

• In a dramatic re-telling, Brennan walks listeners through Michael’s fateful performance at Rock in Rio (1991), where he met Anselmo Feleppa, who became the love of his life.

  “He simply had to meet him...George Michael, however, had been enjoying the company of strangers since he was 16. And this sort of thing didn’t frighten him in the least. In fact, it turned him on. But there was something different about Anselmo.”
  — Jake Brennan [18:59]

• Anselmo becomes not just a secret lover, but a partner—though their relationship remained hidden under threat to Michael’s career.

• Anselmo’s diagnosis and eventual death from AIDS devastate Michael. His grief is channeled into moving tributes, including his powerful, secretly-dedicated performance of “Somebody to Love” at the Freddie Mercury tribute concert.

  "He secretly dedicated it to Anselmo. But no one could know this."
  — Jake Brennan [21:18]

Spinning Out: Depression, Drug Use, and Loss of Control (23:56–29:43)

• After Anselmo's death and his mother's passing, Michael enters a period marked by severe depression, drug use (marijuana, Prozac, later GHB), and withdrawal from touring.

• His life becomes defined by attempts to manage—or lose—control: solitary walks, regular cruising, and increasing recklessness.

• This culminates in the infamous April 7, 1998 arrest for a lewd act in a Beverly Hills public restroom—an incident Brenan describes in detail, critically examining the charge and the police’s tactics.

  "In George's eyes, this was entrapment, plain and simple. But whether or not George's version...was true didn't matter."
  — Jake Brennan [30:42]

Scandal, Outing, and Unexpected Liberation (29:44–34:09)

• The arrest leads to Michael’s public outing, immense tabloid ridicule, and professional embarrassment.

  "But as crushing as...it was for George Michael...the arrest and his subsequent outing had an unexpected result too. In many ways, it finally gave George the thing he'd sung so earnestly about years earlier. Freedom."
  — Jake Brennan [33:41]

• Michael responds not by retreating, but by embracing honesty—inviting journalists into his life and openly discussing the realities of his relationships, drug use, and cruising.

  “I’m a dirty, filthy fucker, and if you can’t deal with it, you can’t deal with it.”
  — Brennan quoting George Michael [34:07]

• Michael’s use of GHB and involvement in cruising become even more pronounced; the drug fuels his self-esteem and sexual confidence but entrenches his addiction.

Downward Spiral: Addiction, Crashes, and Prison (34:10–41:35)

• A montage of Michael’s repeated car crashes, arrests for possession and DUI, and escalating GHB use paints a picture of a superstar in self-destructive autopilot.

• Judges are lenient due to his tour commitments but warn him that consequences will become more severe.

• By 2010, after crashing into a photo shop and being arrested for the seventh time in 12 years, Michael is sentenced to prison at Pentonville and later transferred to a less severe facility:

  “Now, a judge is describing a new kind of penalty... You’re going to prison.”
  — Jake Brennan [39:56]

• Prison terrifies Michael and briefly sobers him up, but change is fleeting.

Epilogue: Sobriety, Relapse, and The Final Act (41:36–46:55)

• Post-release, Michael appears restored: an orchestral album, a new look, and a slew of creative projects.

• Brennan examines why short-term change doesn’t always become lasting transformation:

  "Sometimes there's something that takes hold, even stronger, whether it's a kink or a compulsion or an addiction...and obviously George Michael had the kind of demons you couldn't cast out by two weeks in a jail cell."
  — Jake Brennan [44:03]

• Michael relapses into GHB use. Ultimately, in 2016, he is found dead on Christmas Day, officially due to heart disease, but Brennan questions whether the death truly stemmed from physical illness or the weight of emotional pain.

  "It's entirely possible that it was a less medical and more emotional affliction of the heart that did end George Michael..."
  — Jake Brennan [46:29]

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Notable Quotes and Moments

• On Public Persona vs. Private Pain:

  "He was never able to feel as sexy as he was seen by others."
  — Jake Brennan [44:58]

• On the Consequences of Fame:

  "A sex icon for the ages, an icon for the gay community at large... With all of that, he was never able to feel as sexy as he was seen by others."
  — Jake Brennan [44:50]

• On the Legacy of Love and Loss:

  "No one could know that the power of his absolutely electrifying performance that night was in large part due to how he was mapping his own profound pain onto the song's painful lyric."
  — Jake Brennan [21:25]

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Important Timestamps

| Timestamp | Segment | |-----------|-----------------------------------------------| | 03:15 | Sex and imagery on MTV; George Michael's image| | 07:15 | Self-doubt, cruising, hiding sexuality | | 16:19 | Rio, Anselmo meets George | | 23:56 | Anselmo’s illness and death; spiral begins | | 29:44 | 1998 public restroom arrest | | 33:41 | Public outing and the “freedom” aftermath | | 34:10 | GHB use accelerates | | 35:40+ | Car crashes, court cases, ongoing spiral | | 39:56 | Sentencing to Pentonville Prison | | 41:36 | Post-prison, attempted sobriety | | 44:03 | Analysis of addiction and personal demons | | 46:29 | George Michael's death—interpretations |

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Tone and Analysis

Brennan’s storytelling is raw, irreverent, and sympathetic—never shying away from Michael's self-destruction, but always contextualizing it within the enormous pressures and internalized pain with which he grappled. There's deep empathy for his subject, especially in exploring the links between queerness, shame, compulsion, and the crushing demands of celebrity. The episode fluctuates between biting humor and genuine sadness, always underscoring the tragic cost of living a life in hiding—no matter how glamorous it may have appeared from the outside.

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For listeners and fans, this episode of DISGRACELAND offers a brutally candid, darkly entertaining, and ultimately poignant look at the man behind the icon—a reminder that some of music history’s most intoxicating stars burn brightest, and briefest, when no one can truly see them as they are.

Transcript

[Ryan Seacrest]

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[Jake Brennan]

This is Jacob Goldstein from what's yous Problem? When you buy business software from lots of vendors, the costs add up and it gets complicated and confusing. Odoo solves this. It's a single company that sells a suite of enterprise apps that handles everything from accounting to inventory to sales. Odoo is all connected on a single platform in a simple and affordable way. You can save money without missing out on the features you need. Check out Odoo at o d o o.com that's o d o o.com Disgraceland is a production of Double Elvis. This is the story about a pop star. A pop star with a rock and roll animal heart. It's about addiction and arrests, forbidden love, and an even more forbidden kink. It's about a man who defined sex, who was lusted after by millions but just couldn't find the confidence to see in himself what so many others saw. This is a story about George Michael, a man who made great music. Unlike that music I played for you at the top of the show. That wasn't great music. That was a preset loop for my melotron called Drive by Glory Hole MK2. I played you that loop because I can't afford the rights to all my life by KC and JoJo. And why would I play you that specific slice of silky slow jam cheese? Could I afford it? Because that was the number one song in America on April 7, 1998. And that was the day that George Michael walked into the public bathroom at the Will Rogers Memorial park in Beverly Hills a closeted man, and walked out in handcuffs. On this episode, lewd acts, undercover cops, liquid ecstasy, car crashes, notorious prisons, and George Michael. I'm Jake Brennan, and this is Disgrace Land. It's the 1980s. You're at home watching MTV, and every video by a major pop artist playing on your family's tiny television screen is just so horny. You've got Prince climbing out of a bathtub and dragging his naked body across the floor in When Doves Cry. And now here's Madonna in a white wedding dress being bedded by some Casanova for the very first time. Or so she claims in Like a Virgin. And what Gen Xer among us can forget? Michael Jackson grabbing his junk and screaming, oh. In Martin Scorsese's video for Bad. But as you watch the endless parade of innuendo pass before your eyes, you come to the realization that no artist on MTV right now in the late 1980s is hornier than George Michael. Sure, Prince, Madonna and MJ are all kinky in their own ways, but George Michael is the kinkiest of them all. He puts it all out there as clear as a bell in the title of his first single from faith, his incredible 1987 solo debut album. The song is called I Want yout Sex, which, you know, there's no subtext there at all. It's not she bop or Dancing with Myself. What it is is a horned up slice of stripped down synth pop heavily inspired by Prince's Kiss. And when the same churches and conservative watchdogs who came after Prince for darling Nicky come after George's tight fitting denim clad ass with their pitchforks, George counters with the explanation that the song I want your Sex is not about casual sex but monogamous sex, all while the AIDS epidemic rages on in the background. George's defense does him no favors. Neither does the song's music video, with all those body parts writhing on silk sheets and George himself, instantly iconic with his giant cross earring and impeccable stubble beard, seductively tying a blindfold around a woman's eyes. The BBC refuses to play the song before 9pm and many American radio stations ban it outright. But the more people talk about I want your sex, whether good or bad, the more it sells quickly, sending its album Faith to the number one spot on the Billboard album chart for 12 weeks and then going on to winning album of the year at the Grammys, thus making George Michael not only the horniest artist of 1988, but also the best selling artist of 1988. Only five years earlier, George Michael, or Georgios Ciago Penaldu as was his given name, was dead broke, still living with his parents and just beginning to embark on a whirlwind journey as a member of the pop band Wham alongside his friend Andrew Ridgely. Fame came fast for George and Andrew, but George quickly outgrew what he called the bright young thing image. He didn't want to sing cheeseball songs like Wake me up before you go go anymore. He couldn't pretend that everything was DayGlo colors, pearly white smiles and choose life T shirts. Life had its dark places. It was in those dark places that George found he was increasingly unable to escape, despite being one of the preeminent sex idols of his day, desired by hordes of fans who swooned over his Greek Elvis, smolder in that distinct and commanding Voice the things that George Michael desired. The real sex he wanted, he wasn't able to have. At least not in the public eye. His own personal kink, which he kept very secret, wasn't something he could put in a song, at least for now. He was 16 years old when he began cruising for sex with other men, or cottaging, as it's called back in George's home country of England. And it wasn't just the sex, but the pursuit of sex. The rush of strange, anonymous men sending their strange, anonymous glances. Carrying out these private fantasies in public places only added to the thrill. As did the ever existing chance that he'd get caught. Guilt, as George himself once said, was a massive turn on. Guilt got him off. Guilt was instilled early as a foundation of a very traditional culture in which, quote, unquote, gay was something you caught like a cold. The only thing George wanted to catch was the next kink. The more illicit, the better. But it was important that no one knew anything about this. He was terrified of being outed. Never mind what his own homophobic father would think. He was more concerned about what it would mean for his fame and his career. He worked tirelessly to keep it all a secret. And if you've ever had to hide who you really are from someone you know, it can be isolating for George Michael. He was hiding himself from millions of adoring fans. Add to that a corrosive lack of self esteem that stuck with him for life and well, it's like he said in his song Praying for Time. It's hard to love and there's so much to hate. Hate came easy to George where the press were involved. Are you gay? Was quickly becoming the first and only question that most so called journalists were interested in asking. It was none of their fucking business. He didn't tell them that he wasn't romantically involved with the women he strategically surrounded himself with, or that he wrote, I want your sex for an unrequited crush he had on a straight French playboy. And he certainly didn't tell them anything about who he'd met down in Rio and brought back with him to his house in Los Angeles. The papers had no clue that a man named Anselmo Felipa had finally allowed George Michael to want not just sex, but love. And George Michael didn't know that his love with Anselmo, while beautiful and life affirming in a way he'd never known, was also doomed. And that in the aftermath of that love, he would wind up deeper in the darkness where his old kinks would be waiting.

[Ryan Seacrest]

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[Public Investing Representative]

Support for the show comes from Public, the investing platform for those who take it seriously. On Public you can build a multi asset portfolio of stocks, bonds, options, crypto and now generated assets which allow you to turn any idea into an investable index with AI. It all starts with your prompt. From renewable energy companies with high free cash flow to semiconductor suppliers growing revenue over 20% year over year, you can literally type any prompt and put the AI to work. It screens thousands of stocks, builds a one of a kind index and lets you backtested against the S&P 500. Then you can invest in a few clicks. Generated assets are like ETFs with infinite possibilities, completely customizable and based on your thesis, not someone else's. Go to public.com podcast and earn an uncapped 1% bonus when you transfer your portfolio. That's public.com podcast paid for by Public Investing Brokerage Services by Open to the Public Investing Inc. Member FINRA and SIPC Advisory Services by Public Advisors llc. SEC Registered Advisor Generated Assets is an interactive analysis tool. Output is for informational purposes only and is not an investment recommendation or advice. Complete Disclosures available at public.comDisclosures Lets Talk

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[Jake Brennan]

For some, when you lose it, it costs a lot to get it back. For music festival promoter Roberto Medina, the cost to once again be in control was $5 million. Or rather, that's how much his family ponied up to guarantee his safe release. The armed men from Rio de Janeiro's criminal underworld who'd kidnapped him three weeks earlier kept their end of the bargain. They let Medina go and moved on to the next powerful Brazilian they could abduct and demand a heavy ransom for. In return, Medina got back to his life controlling what he could, which in his case meant planning the music festival Rock in Rio, a highly ambitious nine night affair with big corporate sponsorships and even bigger names that was scheduled to take place in January of 1991. Some artists turned tail when it became known that Medina's kidnapping ordeal was no isolated incident. Not George Michael. The $1.5 million he was getting paid to play two nights at the festival was one reason why the four armed bodyguards were four more. And then there were his other demands. To sweeten the pot, he had Medina pay for his friends to fly down to Rio too. Put them all up. And not just anywhere, but at the Royal Rio Palace. The same place Sinatra stayed when Medina brought Old Blue Eyes to Brazil for the first time some 10 years earlier. And then when the Royal Rio palace wasn't good enough for George, he had Medina move him to the even swankier Copacabana Palace. Specifically into the very suite where his friend Princess Diana had once stayed. What the hell else was Medina gonna do? He gave 5 million to armed thugs like it was nothing. And the least he could do was give a fraction of that to a guy who was royalty himself. Well, musical royalty. Even back in the Wham years, George was a star. The kind of star for whom demands were non negotiable. George expected the very best, even if that meant paying ten grand to fly his stylist sister across the Atlantic to fix his hair for a video shoot. George Michael, not Roberto Medina, was the one truly in control. Control of his image, his narrative, his closeted life. Only, he said, what photos of him could be used and what photos could not. For his second solo album, Listen Without Prejudice, Volume 1, a record intended to be a more mature artistic statement, he tore down his own iconography, literally torching the leather jacket from Faith in the music video for Freedom 90, a video which featured five of the hottest women in the world at the Linda Evangelista, Naomi Campbell, Cindy Crawford, AKA Cindy C, Tatiana Pattis and Christy Turlington, but most notably did not feature the man of the hour, George Michael in a video made by the soon to be famous film director David Fincher. An equal to George Michael when it came to artistic control. But I digress. The Freedom 90 video played on what felt like a non stop loop on mtv. Yet for all the sex oozing from the screen, George Michael was, like I said, conspicuously absent from it. He knew exactly what he was doing, just like he knew what he was doing back when Faith was released and his self described goal was to cross over not to the pop chart, as was typically the case, but to the soul in R and B charts. It was one thing to see his ballad One More Try top what was then called the hot Black Singles chart. But when he beat both Michael Jackson and Bobby Brown to win Best Sole RB Artist at the 1989American Music Awards. Singers like Dionne Warwick very publicly were like, uh, what the fuck? And Don Cornelius, host of Soul Train, said of that particular win, this being a quote unquote, free country people are entitled to call George Michael a soul artist and in effect change the meaning of the word soul. But at the Rock In Rio in January 1991, 27 year old George Michael's soul was very much alive and kicking out in the crowd. One of the locals, Anselmo Felipa, seven years George's senior, was staring directly into it. Anselmo's eyes burrowed deep into the pop star's sexually charged aura. He was smitten, he was struck by George Michael's beauty, his voice, the whole package. And this wasn't a fanboy thing. Anselmo was at the show for the experience and for some of the other performances, not George specifically. But right now, he felt a connection. He simply had to meet him. The next day, Anselmo tracked George down at the Copacabana palace and watched as he got into a taxi. He greased the palm of one of the cabbies at the hotel stand to give up George's destination, Buzios, a few hours away. And with the help of a well connected friend who owned a house in that resort town, Anselmo skipped work and made the two hour drive. He found George in a club, dancing and partying, walked over to him and told him straight up, I'm Anselmo Felipe and I followed you for 200 miles. Typically, a confession like this from a complete stranger would set off red flags for anyone. Not least of them being an international pop star with a legion of fans, some of them crazed. George Michael, however, had been enjoying the company of strangers since he was 16. And this sort of thing didn't frighten him in the least. In fact, it turned him on. But there was something different about Anselmo. He was more than a passing encounter in a public toilet. George could have sworn seeing him now, that he had actually first laid eyes on Anselmo way out in the crowd the night before from where he stood on stage. And that he too was feeling a strong connection, a connection that went beyond wanting just sex. This was fate. This was destiny. At least in the eyes of George Michael and Anselmo Felipe. The next stretch of time was more blissful than not. Or at least as blissful as it could be for a man who continued to live his life very much in secret. George flew Anselmo back to Los Angeles with him where they began living together in a lavish new home that George had built in Beverly Hills. The house was filled with orchids and also with love. Yet although George introduced Anselmo to his inner circle as his partner, their love was forbidden in public for fear that any public display would lead to George being outed. And if that happened, his career and everything that came with it. This house with giant glass walls, for instance, would be taken away. In the end, however, it was romantic bliss that was taken away. When Anselmo was diagnosed with aids, George continued to keep his sexuality in his private life a secret. And when he sang Queen Somebody to Love at a tribute concert for Freddie Mercury, who recently died from the same disease, he secretly dedicated it to Anselmo. But no one could know this, just like no one could know that the power of his absolutely electrifying performance that night was in large part due to to how he was mapping his own profound pain onto the song's painful lyric. No one could know any of it. Which is why George wouldn't visit Anselmo in the hospital when he got really sick, and also why he didn't fly down to Rio for the funeral. When Anselmo passed away in 1993 at the age of 36, George Michael fell into a deep depression. He was angry, angry at the press as they continued to pry. He was angry at his record label, too. He believed Sony had failed to properly promote Listen Without Prejudice and now had him shackled in what he called professional slavery. He sued and was told by a judge months later that his argument had no substance whatsoever. When his mother passed away, his depression intensified. He was taking Prozac daily and smoking marijuana at every waking moment, even though he was making new music, like his third studio album, Older, released in 1996. He wasn't touring the press. Those buzzards were unrelenting. They called him the Howard Hughes of pop music. But George Michael was no germaphobe recluse. He made sure he got out of the house regularly. He always went alone, leaving his new boyfriend, Kenny Goss, behind. They said long rock walks were therapeutic, and George supposed they were. But more therapeutic for him at this moment. More than the walk, the weed, the Prozac was the destination. Will Rogers Memorial park, about a mile from his house in Beverly Hills. There, he tried to blend in among the palm trees, his sunglasses and ball cap obscuring his face and thus his celebrity. He was just one, one of the guys searching, like they all were, for that furtive glance, that knowing look. He found one, just like he always did. Hanging around the yellow stucco public toilet. Six foot something, bright white teeth, T shirt and jeans. The two walked into the restroom together as strangers, but within minutes George Michael would find out that the man he thought was an anonymous trist was in fact an undercover officer The Beverly Hills Police Department. We'll be right back after this.

[Ryan Seacrest]

Word, word, word. Hey, it's Ryan Seacrest for Albertsons and Safeway. It's stock up Savings time now through March 31st. Spring in for storewide deals and earn four times the points. Look for in store tags to earn on eligible items from Lindor, Chips Ahoy, Gatorade, Host, Ziploc and Zoa. Then clip the offer in the app for automatic event long savings. Stack up those rewards to save even more. Enjoy savings on top of savings when you shop in store or online for easy drive up and go pick up or delivery restrictions apply. See website for full terms and conditions.

[Public Investing Representative]

Support for the show comes from Public, the investing platform for those who take it seriously. On Public you can build a multi asset portfolio of stocks, bonds, options, crypto and now generated assets which allow you to turn any idea into an investable index with AI. It all starts with your prompt. From renewable energy companies with high free cash flow to semiconductor suppliers growing revenue over 20% year over year, you can literally type any prompt and put the AI to work. It screens thousands of stocks, builds a one of a kind index and lets you back test it against the S&P 500. Then you can invest in a few clicks. Generated assets are like ETFs with infinite possibilities, completely customizable and based on your thesis, not someone else's. Go to public.com podcast and earn an uncapped 1% bonus when you transfer your portfolio. That's public.com podcast paid for by Public Investing Brokerage Services by Open to the Public Investing Inc. Member FINRA and SIPC Advisory Services by Public Advisors llc. SEC Registered Advisor. Generated Assets is an interactive analysis tool. Output is for informational purposes only and is not an investment recommendation or advice. Complete Disclosures available at public.comdisclosures

[Poshmark Spokesperson]

we all have different styles.

I may be into Levi's and you may be into Fendi or Miu Miu.

But we all should be into poshmark.com right?

Because we can all find exactly what we want to fit our style.

Poshmark has millions of new and pre

lived pieces, vintage, luxury, men's, women's, children's,

everything from Carhartt to coach.

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[Capella University Spokesperson]

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[Jake Brennan]

On April 7, 1998, at approximately 16:48 hours, that's 4:48pm Beverly Hills Police officers arrested the singer known as George Michaels. Mr. Michaels was arrested for a violation of 647A of the penal code, engaging

[Ryan Seacrest]

in a lewd act.

[Jake Brennan]

The arrest was made by members of the Crime Suppression Unit at Will Rogers park, located at Cannon and Lamitas in Beverly Hills. The undercover cop who slipped into the Will Rogers Memorial park restroom with George Michael on April 7, 1998, claimed that George went in first. George insisted it was the other way around. George also insisted that he unzipped his pants and began masturbating only after the other guy did this undercover cop dude. And that claim contradicted the police report that followed, which stated that the cop was not masturbating but rather simulating urination. And that was rich. George thought if he tried taking a leak while doing all the things that the guy was doing to himself in there, you'd get piss all over your hands. In George's eyes, this was entrapment, plain and simple. But whether or not George's version of what went down was true didn't matter. He knew that he'd never win a game of he said, he said against the Beverly Hills Police Department. Not when this was particular Task force. A Crime Suppression unit would do whatever it took to make arrests and thus justify their existence. After receiving numerous complaints about sexual activity in public toilets, George pled no contest. He was fined $910 and sentenced to therapy, community service, and two years probation. He was also forbidden from going back to Will Rogers Park. That part he could handle. There were other parks, other public toilets, many more fish in that proverbial sea of cruising subculture. But his reckless behavior, his complete disregard for the control he so carefully wielded when it came to his private life, had very nakedly revealed his secret to the entire world. And now the press was having a field day with that secret. Zip me up before you go go down and outed in Beverly Hills. These were actual headlines from actual publications at the time. But as crushing as I'm sure it was for George Michael to read all these things and to suddenly find himself the butt of every joke from every late night talk show host and as stupid. That's his word, by the way, as he felt over allowing himself to be well exposed in this particular way. The arrest and his subsequent outing had an unexpected result too. In many ways, it finally gave George the thing he'd sun so earnestly about years earlier. Freedom. I'm a dirty, filthy fucker, and if you can't deal with it, you can't deal with it. George Michael was taking the opposite approach that he once had when it came to journalists. Now he welcomed them into his house and told them everything. What do you want to know? His boyfriend, Kenny Goss. Open relationship tricks, Rent boys, escorts, whatever you want to call them. Of course, he's got a little black book and the wallet to match because sex ain't cheap. But you're not paying for the sex. Of course, that's not what the money's for. The money is to pay the trick to leave once the sex is over. Just like George was ready for this journalist to leave right now. The guy had gotten a good look at the bag of weeks and pills on his coffee table, of the Harlan Miller painting on his wall titled Incurable Romantic Seeks Dirty Filthy Whore. Now George's cell phone was blowing up. It was Paul. Paul made adult films and did dirty deeds, not so dirt cheap. But best of all, right now, Paul had the champagne. If George was willing and able. Champagne being the two's code word for ghb. B, AKA liquid ecstasy, an extremely potent drug capable of sending one into a heightened state of sexually charged euphoria. Shit, yeah. George was willing and George was able. Let's fuck. The journalists hit the bricks. And there was Paul, right on schedule, a travel sized shampoo bottle in his hand. George squeezed a few drops of GHB from the bottle into a glass of Cocoa Cola and drank it down. And the drug sent his libido into hyperdrive. Even better, it made him feel beautiful. On ghb, he didn't have to think about young George Michael, the overweight pimply reject, or so he'd always seen himself. He also didn't have to think about Anselmo and the others he'd lost, or that straight French playboy. And the others he never had in the first place. The drug made the music vibrate through his body. Each key he touched on the cigarette stained piano, the one previously owned by John Lennon, which George had won at auction for something like £1.5 million. Each key resonated inside of his fingertips and then his palms, his arms, his shoulders, his entire body. GHB supercharged his self esteem each time he left one of his many homes, like the one just north of London in Highgate. From there he took a path not unlike the one back in Beverly Hills. Down a curving hill and into Hampstead Heath, a big park full of bushes and trees where men just like him were looking for sex. The thrill of being caught, the guilt, it was all still there. But seeing as he'd been arrested once already, he was now far more cavalier than ever before. But the thing is, GHB is incredibly addictive. And when you overuse or abuse the drug, it can lead to what's known as a G hole, which is when someone high on GHB just slumps over and checks out, even when they're standing up. And for you, George Michael, you're about to fall into a G hole that won't let you go for the next four years. February 2006. Do some GHB, some marijuana, and then you hit a London club. You leave at 1am 30 minutes later you're found in your Mercedes, stalled out, knocked out, asleep at the wheel. The drugs are found on your person, as is allegedly a studded black leather fetish mask with a zipper on the mouth. So what you think? Live and let live. The cops Let you off with a warning. Two months later, it's April. More ghb, more weed. This time you're driving the Range Rover, trying to get back to your house in Highgate, and suddenly there's this fucking Ford Fiesta just parked there. Fuck. You put it in reverse and then in drive. And then. Shit. Where did that little Peugeot come from? Somehow you find your way home and the next morning the cops are at your door asking about the fucked up front end of your Rover parked in the driveway. Five months later, it's September. Your tour starts. Your first tour in 15 years. You're calling it 25 Live to celebrate your quarter century as one of the greatest to ever do it. The tour will stretch out for the next two years and will see you perform 106 shows in 41 countries and gross over $200 million. Every stage you step on, you kill it. You're a professional, which means you can compartmentalize. It also means that you work hard and you play hard too. On a day off, you tee up ghb, sleeping meds, antidepressant, chase it all with a joint. You can't see straight as your Mercedes tears ass into the night, weaving from one lane to the next, Hampstead Heath to get your rocks off. But you don't make it. You pass out. Your Mercedes rolls to a stop and once again the cops find you and your drugs. This time they charge you drug possession and driving under the influence. In December, the judge sentences you to community service and a small fine and she takes away your license for two years. But she doesn't want to interrupt your historic tour, the one that has become the most commercially successful European tour of the year. She knows that tomorrow you're playing the first of two sold out shows at Wembley. You show your gratitude, your capacity for change. I'm glad to put this behind me, you say. Now I'm off to do the biggest show of my life. Big shows and big plans aside, you don't put it behind you. It's still there, the addiction and the kink. You're no longer allowed to be in the front seat of your Mercedes or your your Range Rover. But guilt continues to drive your underlying compulsion. In September of 2008, police find you slinking around the public toilet at Hampstead Heath. You looked up and suspicious and, well, you are fucked up and suspicious. And your well documented reputation precedes you. They search you and find crack cocaine. Yet you swear to God they were tipped off, probably by someone who wants you to go to rehab. Jesus. Elton John should mind his own fucking business. You aren't in the market for salvation or for Elton John's pity. It's all self loathing and bad habits. Soon you can legally drive your car again. And much to no one's surprise, once again you crash it. Though this time not into a bunch of parked cars. This time you put your Rover through the facade of a one hour Photoshop in North London. The engine is still running when you're woken up by a police officer banging on the driver's side window. And a few days later someone writes wham. On the part of the storefront where you crashed your car. But you're not laughing. Because now on this, your seventh arrest in 12 years. Yes, years. Even though it's all been a blur and felt like mere months now, a judge is describing a new kind of penalty. Not just another fine and another loss of your license. There's something else. You're going to prison. By 2010, MTV was a shell of its former self. Gone were the days of non stop music video programming. Of Prince and Madonna and Michael Jackson, every hour on the hour and of MTV News, anchored for years by Kurt Loder. So there was no news coverage to be found on MTV on September 14th of that year, when 47 year old George Michael, Grammy winner, best selling artist of 1988, biggest grossing European tour headliner of 2006 and 2007, owner of multiple luxury homes throughout the world and one of the horniest MTV artists to ever live, was strip searched, given a nondescript inmate uniform and led down the dank and disgusting hallways of HM Prison Pentonville. Located in North London, Pentonville was no joke. The men's prison was infamous. It housed rapists, murderers and pedophiles. It was crawling with roaches and rodents. George was led by guards to the Vulnerable Prisoners Unit, which was for, quote, sex offenders and people who have committed serious crimes, unquote. His arrival was anticipated just as it had been years ago in places like Wembley and Rio. Only now, his audience was out. Not for his voice, his music or his sex, but out for his blood. The voices of incarcerated men, violent men, men at their absolute lowest, echoed through the prison halls. Where's George Michael? Bring us George Michael. George was terrified as he was led inside his cell. He kept his head down and kept to himself. Normally, the company of strange men loitering around toilets would have turned him on, but this, this was tough, different. The very thought of going to prison had been enough to scare him sober. He actually detoxed while awaiting sentencing. But now that he was on the inside. It was even worse than he could have ever imagined. Luckily, only the first three nights of his two week prison sentence would be here at Pentonville. The rest would be served two hours away in Suffolk at High Point Prison, where George slept in the good Behavior wing, played pool, received get well letters from Elton John and Paul McCartney, and on the day he left, signed autographs for every staff member and prisoner. A free and for now clean George Michael got to work on what was next, which was Symphonica, a live album documenting an orchestral tour of originals and covers he made in 2011 and 2012. Sober, George was all nice suits and button down shirts. His once trademark good hair had been buzzed down tight with a salt and pepper goatee to match even before he hit 50 years old. He was playing the elder statesman type. But a new lease on life, a new swell of creativity, a prison stint, detox therapy, a handwritten letter from a beetle. These are things that happen in hopes that they take hold and inspire not just change, but sustained change. And that doesn't always happen, because sometimes there's something that takes hold, even strong, whether it's a kink or a compulsion or an addiction, one driven by habit or by some deep seated psychological trauma. And look, I'm clearly not Sigmund Freud here, and I'm not kink or compulsion shaming either. We all have something, some more destructive than others, of course. And obviously George Michael had the kind of demons that you couldn't cast out by two weeks in a jail cell. A sex icon for the ages, an icon for the gay community at large. A man who owned numerous pieces of luxury property and lived the sort of life that most of us will only dream of. With all of that, he was never able to feel as sexy as he was seen by others. And so he was back to texting his friend Paul, back to asking for delivery of champagne, AKA ghb, back to a manufactured sense of sexiness, back in that G hole, unconscious this time, not behind the wheel, but in his bathtub, where an overdose sent him straight to the emergency room. Two years later, George Michael was dead at 53 years old, discovered by his latest boyfriend on Christmas Day. The official conclusion was natural causes stemming from a heart disease that makes it difficult for your body to pump blood. But considering that his family chose to withhold the toxicology report, and also considering that he died completely alone at some point on Christmas Eve or early Christmas morning, it's entirely possible that it was a less medical and more emotional affliction of the heart that did end George Michael, once one of the biggest stars on the planet. And that is a disgrace. I'm Jake Brennan and this is Disgrace Land. All right, thanks for getting kinky with me in this episode. This week's Question of the week is how many times have you had sex in a public toilet? No, that's obviously not the question of the week. The question is, which 1980s MTV era artist is your favorite? Is it Mr. George Michael or is it someone else who best defines the era for you and why? I want to know. Hit me up at 617-906-6638. Leave me a voicemail, send me a text. Hear your answer on the After Party bonus episode coming up right after this one and you can also send your answers to me. Disgracelandpod on Instagram X and Facebook. Leave a review for the show on Apple Podcasts or Spotify and win some free merch. Alright, here comes some credits. 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 [e-mail] 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 single episode of Disgraceland ad free. Plus you'll get one brand new exclusive 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 Disgracelandpod Rocka Rolla He's a bad bad man.

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[Jake Brennan]

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[Jake Brennan]

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