Pod Insights DISGRACELAND George Michael: Lewd Acts, Guilt, and Freedom About this episode Seven arrests in twelve years and more than a couple sleepless nights inside a London prison. This reads like the description of a stereotypical Sunset Strip metalhead, not that of pop prince George Michael. George’s criminal transgressions include a bust for a “lewd act” in a public place, a crack addiction, numerous car crashes. George Michael was on a collision course with an early death, but he died of a broken heart. Along the way he made great music. Here’s his story.
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Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:01 Speaker 00 This is Exactly Right.
0:10 Jake Brennan? Double Elvis.
0:13 Jake Brennan? I like a story with a twist as much as anyone, but some of the best traditions don't have one. They just started and kept going. That's something that's great about Chateau St. Michelle. They've been leading Washington wine since 1967 with wines that are balanced, expressive, and easy to enjoy. Choosing the right bottle shouldn't feel complicated. It should be something you open with confidence every time. So for once, here's a story with no twist, just a good bottle. Redefine your rituals with Chateau St. Michelle.
0:44 Speaker 02 This is Cheeky's from Soul Searching with Cheeky's. Have you ever ordered an ice cold Coca-Cola Zero Sugar and told yourself, "I'm just going to take one sip while I wait for my food," but somehow the first sip turns into a second? And then before you know it, your meal arrives and you're looking at an empty glass? Well, we've all been there. That's the thing about Coca-Cola Zero Sugar. It has a delicious Coca-Cola taste you love with zero sugar. Coca-Cola Zero Sugar, real Coke taste, zero sugar. It's too good to wait.
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1:42 Jake Brennan? Disgrace Land is a production of Double Elvis.
1:57 Jake Brennan? 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 from my Mellotron called "Drive-by Glory Hole MK2."
2:41 Jake Brennan? 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, nude acts, undercover cops, liquid ecstasy, car crashes, notorious prisons, and George Michael. I'm Jake Brennan, and this is DisgraceLand.
4:00 Jake Brennan? 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 X'er among us can forget? Michael Jackson grabbing his junk and screaming "Oooh!" in Martin Scorsese's video For Bad.
4:42 Jake Brennan? 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 Your Sex," which, you know, there's no subtext there at all. It's not "She Bop" or "Dancing With Myself."
5:22 Jake Brennan? 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 Nikki 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.
5:53 Jake Brennan? 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
6:36 Jake Brennan? not only the horniest artist of 1988, but also the best-selling artist of 1988. Only five years earlier, George Michael, or Georgios Kyogou Penaldou, 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 day-glow colors, pearly-white smiles, and "Choose
7:21 Jake Brennan? Life" t-shirts. Life had its dark places, and 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 swoomed over his Greek Elvis smolder and 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 sixteen years old when he began cruising for sex with other men, or "cottageing",
8:03 Jake Brennan? 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 "gay" was something you caught, like a cold. And the only thing George wanted to catch was the next kink. The more illicit, the better.
8:47 Jake Brennan? 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.
9:29 Jake Brennan? "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.
9:50 Jake Brennan? 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 Enselmo Felipe had finally allowed George Michael to want not just sex, but love. And George Michael didn't know that his love with Enselmo, 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.
10:49 Jake Brennan? I like a story with a twist as much as anyone, but some of the best traditions don't have one. They just started and kept going. That's something that's great about Chateau St. Michelle. They've been leading Washington wine since 1967 with wines that are balanced, expressive, and easy to enjoy. Choosing the right bottle shouldn't feel complicated. It should be something you open with confidence every time. So for once, here's a story with no twist, just a good bottle. Redefine your rituals with Chateau St. Michelle.
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11:51 Jake Brennan? Control. 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 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
12:36 Jake Brennan? 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 ten years earlier. And then, when the Royal Rio Palace wasn't good enough for George, he had Medina move him
13:20 Jake Brennan? to the even swankier Copacabana Palace, specifically, into the very suite where his friend, Princess Diana, had once stayed.
13:30 Jake Brennan? 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. Musical royalty.
13:44 Jake Brennan? 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 10 grand to fly his stylist's 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 One, a record intended to be a more mature artistic statement, he tore down his own iconography, literally torching the leather jacket from Faith
14:28 Jake Brennan? in the music video for Freedom 90. A video which featured five of the hottest women in the world at the time: Linda Evangelista, Naomi Campbell, Cindy Crawford, aka Cindy C., Tatiana Patyse and Kristy 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.
15:11 Jake Brennan? 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 and R&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 Soul/R&B Artist at the 1989 American Music Awards, singers like Dionne Warwick very publicly were like, "Uh, what the fuck?" Don Cornelius, host of Soul Train, said of that particular win, "This being a 'free country', people are entitled to call George Michael a soul artist" and, in effect, changed the meaning of the word "soul."
15:55 Jake Brennan? But at the Rockin' 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, Ensmo Felipe, seven years Georgia's senior, was staring directly into it.
16:12 Jake Brennan? Enselmo'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. Enselmo 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. And the next day, Enselmo 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, Buzyos, a few hours away. And with the help of a well-connected friend who owned a house in that resort town, Enselmo
16:55 Jake Brennan? 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 Enselmo 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 Enselmo. 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 Enselmo
17:40 Jake Brennan? 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 Enselmo 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 Enselmo 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 Enselmo to his inner circle as his partner, their love
18:25 Jake Brennan? 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.
18:40 Jake Brennan? In the end, however, it was romantic bliss that was taken away when Encelmo 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 Encelmo, 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 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 Encelmo in the hospital when he got really sick.
19:20 Jake Brennan? And also why he didn't fly down to Rio for the funeral when Encelmo 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,
20:06 Jake Brennan? he wasn't touring. The press was buzzards, were unrelenting. They called him the Howard Hughes of pop music.
20:15 Jake Brennan? 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 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 of the guys searching, like they all were, for that furtive glance, that knowing look.
20:58 Jake Brennan? He found one, just like he always did, hanging around the yellow-stucko public toilet.
21:05 Jake Brennan? Six foot something, bright white teeth, t-shirt and jeans. The two walked into the restaurant together as strangers. But within minutes, George Michael would find out that the man he thought was an anonymous tryst was in fact, an undercover officer, the Beverly Hills Police Department.
21:30 Jake Brennan? We'll be right back after this.
21:38 Jake Brennan? I like a story with a twist as much as anyone, but some of the best traditions don't have one. They just started and kept going. That's something that's great about Chateau St. Michelle. They've been leading Washington wine since 1967 with wines that are balanced, expressive, and easy to enjoy. Choosing the right bottle shouldn't feel complicated. It should be something you open with confidence every time. So for once, here's a story with no twist, just a good bottle. Redefine your rituals with Chateau St. Michelle.
22:09 Speaker 03 Cash flow crunch? OnDeck's small business line of credit gives your business immediate access to funds up to $200,000 right when you need it. Cover seasonal dips, manage payroll, restock inventory, or tackle unexpected expenses without missing a beat. With flexible draws, transparent pricing, and control over repayment, get funded quickly and confidently. Apply today at ondeck.com. Funds could be available as soon as tomorrow. Depending on certain loan attributes, your business loan may be issued by OnDeck or Celtic Bank. OnDeck does not lend in North Dakota. All loans and amounts subject to lender approval.
22:44 Speaker 04 On April 7th, 1998, at approximately 16:48 hours, that's 4:48 PM, 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 in a lewd act. The arrest was made by members of the Crime Suppression Unit at Will Rogers Park, located at Cannon and Lamedus in Beverly Hills.
23:18 Jake Brennan? 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.
24:01 Jake Brennan? He knew that he'd never won a game of he said he said against the Beverly Hills Police Department. Not when this 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. And 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
24:45 Jake Brennan? 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.
25:26 Jake Brennan? In many ways, it finally gave George the thing he'd sung so earnestly about years earlier: freedom.
25:36 Jake Brennan? I'm a dirty filthy fucker and if you can't deal with it, you can't deal with it.
25:42 Jake Brennan? 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 weed and pills on his coffee table, of the Harlan Miller painting on his wall titled, "Incurable Romantic Seeks Dirty Filthy Whore." Now, George's cellphone was blowing up.
26:28 Jake Brennan? It was Paul. Paul made adult films and did Dirty D's 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. 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 journalist 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 Coca-Cola and drank it down. And the drug sent his libido into hyperdrive. Even better,
27:12 Jake Brennan? 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 Ensalmo 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 pounds. 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
27:55 Jake Brennan? 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.
28:37 Jake Brennan? 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. You do some GHB, some marijuana, and then you hit a London club. You leave at 1 a.m. Thirty 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.
29:20 Jake Brennan? 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 we'll see you perform 106 shows in 41 countries
30:03 Jake Brennan? 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, antidepressants. 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. Destination 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.
30:45 Jake Brennan? 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 Range Rover, but guilt continues to drive your underlying compulsion.
31:27 Jake Brennan? In September of 2008, police find you slinking around the public toilet at Hampstead Heath. You look fucked up and suspicious and well, you are fucked up and suspicious. And your well-documented reputation precedes you. They search you and find cracked cocaine. And 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.
32:09 Jake Brennan? This time, you put your Rover through the facade of a one-hour photo shop 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 near 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.
33:10 Jake Brennan? 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, bestselling 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.
33:53 Jake Brennan? 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 "sex offenders and people who have committed serious crimes." 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."
34:38 Jake Brennan? 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 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 Behaviour Wake, played pool, received get-well letters from Elton John and Paul McCartney,
35:20 Jake Brennan? and on the day he left, signed autographs for every staff member in the prison.
35:28 Jake Brennan? 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'd made in 2011 and 2012. Sober George was all nice suits and button-down shirts. His once trademarked "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 Beatle... These are things that happen in hopes that they take hold and inspire not just change, but sustained change.
36:11 Jake Brennan? And that doesn't always happen. Because sometimes, there's something that takes hold even stronger. Whether it's a cank, 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 cank or compulsion shaming either. We all have something, some more destructive than others, of course. 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.
36:55 Jake Brennan? 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
37:40 Jake Brennan? 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 DisgraceLand.
38:17 Jake Brennan? 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 at @disgracelandpod on Instagram, X, and Facebook. Leave a review for the show on Apple Podcasts or Spotify and win some free merch. All right, here comes some credits.
38:58 Jake Brennan? 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 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,
39:42 Jake Brennan? @disgracelandpod, and on YouTube at youtube.com-at-disgracelandpod. Rockerola.
39:53 Speaker 00 He's a bad, bad man.
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40:58 Speaker 05 She's been thinking about this sleepover all week, but I think about her food allergies all the time. Fortunately, her doctor prescribed Zolair, omalizumab. It's proven to significantly reduce allergic reactions if a food allergy accident happens.
41:11 Speaker 06 Zolir 150mg is a prescription medication used to treat food allergy in people one year of age and older to reduce allergic reactions due to accidental exposure to one or more foods. While taking Zolir, you should continue to avoid all foods to which you are allergic. Don't use if you are allergic to Zolir. Zolir may cause a severe, life-threatening allergic reaction called anaphylaxis. Tell your doctor if you ever had anaphylaxis. Get help right away if you have trouble breathing or if you have swelling of your throat or tongue. Zolir should not be used for the emergency treatment of allergic reactions, including anaphylaxis. Zolir is for maintenance use to reduce allergic reactions, including anaphylaxis, while avoiding food allergens. Serious side effects such as cancer, fever, muscle aches and rash, parasitic infection, or heart and circulation problems have been reported. Please see zolir.com for full prescribing information. Ask an allergist about Zolir. This is an advertisement for Zolir,
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Previous Bonus Episode - Irish Artists, Def Leppard and Huey Lewis Next Bonus Episode - Video Directors, MTV stars, and Big News From Hollywood Page updated November 3, 2026 · transcript and summary are machine-generated