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Liberty Mutual Spokesperson
Neighbor Gable and Doug. There's nowhere I wouldn't go to help someone customize and save on car insurance with Liberty Mutual. Even if it means sitting front row at a comedy show.
Comedy Show Audience Member
Hey everyone, check out this guy and his bird. What is this, your first date?
Liberty Mutual Spokesperson
Oh no. We help people customize and save on car insurance with Liberty Mutual together. We're married. Me to a human, him to a bird.
Comedy Show Audience Member
Yeah, the bird looks out of your league anyways.
Liberty Mutual Spokesperson
Only pay for what you need@libertymutual.com Liberty, Liberty.
Comedy Show Audience Member
Liberty. Liberty.
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Jake Brennan
and ways to save Disgraceland is a production of Double Elvis. The stories about Bobby Brown are insane. He was arrested in the middle of a live performance for violating a Lewd act law. His Bad Boy influence may have been the reason Mike Tyson dramatically lost his heavyweight title. He lived in a haunted house in which he claims he had a sexual encounter with a ghost. He was shot in the knee, watched his best friend get stabbed to death, and discovered a secret of his mother's by mistakenly using cocaine as an ingredient. While making chicken. He thrust and gyrated his way to the top of the charts in the late 80s and early 90s, married to fellow pop star Whitney Houston and made great music. Unlike that loop I played for you at the top of the show, that wasn't great music. That was a preset loop from My Melotron called wristwatch overcoat mk2. I played you that loop because I can't afford the rights to Together Forever by Rick Astley. And why would I play you that specific slice of Rick roll? Slight return cheese? Could I afford it? Because that was the number one song in America on June 20, 1988. And that was the day that Bobby Brown released his second solo album, Don't Be Cruel, an album that became the biggest in the world at the time. A true sensation that changed music and Bobby Brown's life. Fore on this Lewd axe, horny ghosts, cocaine chicken, heavyweight champs Whitney Houston and Bobby Brown. I'm Jake Brennan and this is disgrace. When Bobby Brown was a kid, his Father, a construction worker, would tell Bobby and his siblings, a working man is everything. When you got work to do, you work hard, do your job and go home. Years later, in 1989, hard work paid for 20 year old Bobby Brown's new home, a 14,000 square foot Tudor mansion in Atlanta. Some said it was the largest house in America when it was built nearly two decades prior. A house once owned by Mike Thieves, AKA the Scarface of porn. And just like Bobby Brown, Mike Thievis was at the time he resided in this opulent mansion at the top of his game. Dirty magazines, dirty bookstores, dirty movie theaters. Mike Thievis owned them all. Not least of which were his bread and butter. The peep shows, those cramped, dirty little private rooms or a quarter bought you a few more seconds of flesh on celluloid. Pure depravity flickering on a tiny screen as your eyeballs bulged from their sockets. Just like your pants are bulging right now, you perverted little freak. But that's another story. The story I'm trying to tell is that all that smut, it made the Scarface of porn here, Mike Thievis, filthy, filthy rich. Hundreds of millions of dollars and counting. It was just like Bobby Brown's father said. You work hard, do your job. Mike Thieves had work to do. Hard work, necessary work. Like inviting his former business partner, a man who was now his rival, to his office, where, for the crimes of stealing his peep show technology, Mike Thevis put three bullets in the man's chest and then a fourth in his head. And now the Scarface of porn was doing life in prison. But back at his former residence, new homeowner Bobby Brown was making sure the party kept going. Bobby wasn't making his millions from porn, though the number of naked strippers making themselves comfortable in the place was enough to convince you otherwise. Many in America saw Bobby Brown as bordering on pornographic himself. Like those squares in Georgia who busted him for violating some lewd act law when all he was trying to do was dance. Bobby's trademark pelvic thrust put him in handcuffs right in the middle of his own show. But unlike Mike Davis, Bobby paid the $652 bail and was back on stage after the world's longest intermission, doing the same thing Elvis was doing three decades prior. But this wasn't 1959. This was 1989, the year of Bobby Brown. The year of his tight new Jack Fade, AKA the Gumby, his baggy pants, his shirts that flowed like blouses and which would soon be tossed to the wayside to make way for Bobby's cut chest and ab. The year of Don't Be Cruel, Bobby's sophomore solo album. A record that brought hood culture to the mainstream. And hip hop's hard knock sensibilities to RB music. The top selling album of the year, over 5 million copies. Released just before Bobby Brown's 20th birthday, making him the second teenager in history, behind Stevie Wonder to top the Billboard chart. Bobby Brown was a true sensation. As was his Atlanta Mitch portrait of Bobby made out of stained glass in the windows. A two story fish tank nestled beneath a golden staircase. Gold double doors that led into the bedroom. The place was always packed. The hottest women, the most loyal entourage, friends, family. And lots and lots of ghosts. These ghosts walked the hallways. They floated out of the walls. Spirits from Mike Thievis's porn empire, the peep show, hard bodies and magazine centerfolds. Maybe even scorned ex business partners back from the dead and looking to get revenge on ol Scarface. The place was definitely haunted. Nearly everyone who visited the mansion said so. But only Bobby Brown saw the ghost that came out of the mirror in his ceiling. Lying there in bed, naked, looking up at that handsome devil in the reflection above. When suddenly she appeared. Hovering in the air, long hair flowing. Her eyes locked on his. Transparent. A vision. And then more than a vision, a feeling as she descended right on top of him. Hard, willing, able. Feeling himself not so much pass through her as enter her. And the ghosts now, grinding him, riding him. And then. Hold up. I know what you're thinking. This is the craziest fucking thing that I've heard in my life. And you're probably right. But Bobby Brown swears that this actually happened. That he fucked a ghost. People. Okay? He delivers this story as 100% fact in his memoir. And here's the thing. Bobby Brown was a horny motherfucker back in the day. So it's not surprising that he tried to get with a ghost or vice versa. Bobby Brown got his fuck on people in a major way. Starlets, singers, dancers, groupies. Janet Jackson and Madonna. Allegedly. Allegedly as early as 14 years old, when he hooked up with an inmate at a woman's prison. And we'll get to that. Back to the Don't Be Cruel era. Touring behind Don't Be Cruel in Japan, Bobby's hotel suite was full of women. Nearly two dozen by his count. All of them desiring the very thing many women desired. When they watched Bobby hump the floor on stage, they were getting what they wanted. Not just for the star of the show, but with the heavyweight champion of the world as well, Bobby Brown's good friend, Mike Tyson. Two giants of pop culture at the time, so untouchable it seemed that the rules no longer applied to them. And they were rolling in so much money that you could light a pile of it on fire and tomorrow more would just magically appear in its place. There's Bobby and his Benz. Drove it to the airport, parked it, left it, never went back for it. Fuck it. But buy a new one, it didn't matter. Bobby Brown, like Mike Tyson, like Mike Divas, had money to burn. And he had a burning libido to match. Now getting his rocks off with a suite full of Japanese women, the undisputed champ, riding shotgun, wingman style, that is. The party didn't stop. Just like it didn't stop at Bobby's Atlanta mansion. But Mike Tyson had work to do. He had a title to defend, just hours away now in a fight against the latest challenger, Buster Douglas. Tyson had the WBC championship belt, the WBA and the ibf. And Buster Douglas just had a goofy name. And the odds were overwhelmingly in Mike Tyson's favor to win, just as they always were. Still right now, the night before the fight, it was something like 2 o', clock, 3 o' clock in the morning. Mike, Bobby was saying, man, you gotta quit. You gotta go to bed and rest up for tomorrow. Quit now. Let Bobby Brown have all the fun. Mike Tyson wasn't quitting shit. He could beat Buster Douglas with a raging hangover and a sore dick. Or so he thought. Mike Tyson thought wrong. Next day, Iron Mike went down to the 10th round when Buster Douglas delivered a whopping uppercut followed by four hard punches to the head. Mike Tyson was knocked down and knocked out for the first time in his career because he stayed up too late the night before partying with Bobby Brown, the biggest pop star in the world and also one of the world's baddest of bad influences. A true bad boy. This is what they called him. This is what they've been calling him his entire life.
Liberty Mutual Spokesperson
And Doug, there's nowhere I wouldn't go to help someone customize and save on car insurance with Liberty Mutual. Even if. If it means sitting front row at a comedy show.
Comedy Show Audience Member
Hey, everyone, check out this guy and his bird. What is this, your first date?
Liberty Mutual Spokesperson
Oh, no, we help people customize and save on car insurance with Liberty Mutual together. We're married. Me to a human, him to a bird.
Comedy Show Audience Member
Yeah, the bird looks out of your league anyways.
Liberty Mutual Spokesperson
Only pay for what you need@libertymutual.com Liberty.
Comedy Show Audience Member
Liberty. Liberty. Liberty
Jake Brennan
1983. Boston, Massachusetts. Bobby Brown felt that familiar sensation bubble up from his loins as he looked around the room. He was surrounded by women, all of them bad girls. And I'm talking really bad. You know, the kind, the ones you shouldn't be hanging around with, but you can't help it. The attraction was magnetic. It was primal. But here, attraction between Bobby Brown and most of these women was also illegal because Bobby was just a teenager and these women were, in many cases, much older. Besides, carnal desires were forbidden precisely because of where they were at the moment. Prison. Boston PD didn't dare stick young Bobby in lockup with adult men. Those hard timers would eat this kid alive. Instead, they put him in with the women, where he could sit and think about what he had done. Driving a moped without a license. A presentation he bought himself when he and the other guys in his R B group, New Edition scored their first hit with Candy Girl and each got $500 in return. But right now, he wasn't thinking about the moped or the arrest. Teenage Bobby Brown was just like Bobby Brown. At any age. He did what he wanted, when he wanted, and everyone else could just right the hell off. That was his. Well, you know. But right now, he was thinking about the women here in the joint. One in particular, a friend of his sister's who was staring him down from across the room. She was close to 20. At least she knew what he was thinking about. She could read his mind. She led him by the hand off to some dark corner where Bobby Brown had one of his earliest sexual experiences, again in prison with an older woman. In a way, Bobby was following his old man's advice. Working. Because sometimes the work you had to do was making the best out of a bad situation. Sometimes it meant working a room, and sometimes it meant work in the crowd. Work built. Core Memories had done so for years, 11 years earlier, in fact, watching James Brown on stage at the Sugar Shack over on Boylston, right off the common, some 20 minutes from the Orchard park projects in nearby Roxbury, where Bobby called home. Some people are baptized in the church, some are washed in the blood. Bobby Brown was baptized on a stage at just three years old next to soul brother number one, a man for whom work was practically his middle name. For years after, Bobby Brown continued to be motivated by the work that James Brown, no relation, put into his show. A show in which he invited kids like Bobby on stage to dance. Young Bobby Brown was now dancing on street corners for Pocket change. Before he hit publish puberty, he was hitting the weekend talent shows at the local clubs. He rolled up block parties and challenged anyone with two working legs to a dance battle. He had confidence on one shoulder and a chip on the other. Absolutely determined to prove anyone wrong who said he didn't have it. But he did have it. Just like his father had pride. Every time he gazed up at the Prudential building and marveled at his work. Or how his mother had that hustle, selling dinner plates on the side to folks in the neighborhood in order to make ends meet. But how many people could you sell plates to? Plates weren't going to feed six kids on the regular. So Bobby Brown's mother upped her hustle game. 10 year old Bobby assumed that the new metal door installed at their Orchard park project's apartment was to keep the Jehovah's Witnesses out. And he further assumed that the flower his mom kept in the kitchen was actually flourish. And it was getting late. His father was still at work and his mother was out with friends. Bobby was starving. He decided to make some fried chicken. He covered the chicken in the flour and then dropped pieces into a hot pan coated in oil. And when he finished cooking, he ate first one bite and then another. Soon a strange feeling came over him. His heart began to beat a little faster. He took another bite and the strangeness intensified. And his mind was moving fast, turning over on itself. And then his mother walked through the door and screamed. Bobby hadn't breaded the chicken with flour. He breaded it with his mother's cocaine. This was how Bobby Brown learned that his mother was dealing drugs in Roxbury by cooking chicken as a little kid and unintentionally using the drug as an ingredient. The hustle, the pride, the work. It wasn't without its dangers. Just like growing up black in Boston wasn't without its dangers. Boston PD came around to the Browns apartment looking for a couple of usual suspects. The kind that Bobby now understood associated with his mom. Bobby's mom didn't want the kids to hear anything, so she took the conversation outside. Bobby watched from the apartment window as his mom dramatically argued with the cops and then watched in horror as one of the cops lifted his billy club and hit his mom right in the face. For what? For knowing some other dudes she wasn't holding. She was clean. At least in this moment. The police would beat on anyone in Roxbury. Even the mother of six was fucked up. As was Bobby's mom right now, her eyes swelling up as the cops cuffed her and shoved her into the back of their cruiser. The danger, the violence, it crept closer. There was the night Bobby was out with his best friend Jimmy. Not in Roxbury, but in nearby Dorchester. Bored, looking for something to do. They spotted a couple of bikes leaned up against a building. No chains, no locks. Bobby grabbed one and Jimmy grabbed the other. And they rode them back to Roxbury, basking in the thrill of it, the thrill of their criminal prowess. Until that criminal prowess was challenged by a group of other kids looking to steal the two bikes that Bobby and Jimmy had just stolen. Bobby figured that he and Jimmy could take them. After all, they were scrappy, tough. These other kids, though, were vicious. Coming in hot with big swings, hard knuckle punches that hurt like hell. And then one of them pulled a knife. This. They could have the bikes. But it wasn't about the bikes anymore. These other kids wanted blood. And they got it too. When the one wielding the knife sliced Jimmy's arm open, Bobby tried to intervene. But the next thrust of the knife came too quick and the tip of the blade plunged straight into Jimmy's chest. Directly into his heart. Jimmy collapsed. The other kids bolted. Bobby was left watching the life drain out of his best friend friend's eyes and not being able to do anything about it. Losing his best friend at such a young age had a profound effect on Bobby. It motivated him to get out of Roxbury, out of Boston. But that meant more work. That meant traveling to New York City each weekend with New Addition playing shows from midnight to 4am Every Friday, Saturday and Sunday, and then scrambling back to Boston on an overnight bus to make it to school first thing Monday morning. And that hard work meant more hits. Cool it now, Mr. Telephone Man. Great songs and those hits and that attention meant growing up fast. Faster than most of the guys in New Edition were ready for. Bobby Brown was the odd man out, increasingly motivated by what he wanted, which was the spotlight. A solo career. An opportunity where he was only answering for himself. Or he didn't have bandmates concerned about his increasingly hypersexual dance moves on stage. Or he didn't have to get reamed out for showing up late or missing engagements entirely. No one was going to tell Bobby how to do his work. He was going to do it his way. Show up when he wanted, dance the way he wanted to dance, dance with whomever he wanted to dance with. Even girls who had other guys on the side. Those on again, off again, Romeos, they didn't scare Bobby Brown. He was Bobby Brown, for Christ's sakes. From Orchard Park. He had it since he was three years old. It was all his silly. Wasn't going to listen to this chick he was dancing with right now at a block party. The one who was a little bit older than him. She wasn't prison dangerous like his sister's friend back in lockup. She was still dangerous all the same. And she kept telling Bobby that this. This guy she was kind of sort of seeing was on his way over and that Bobby should probably split. But Bobby wasn't going anywhere. He kept dancing and he paid the other dude no mind. That is, until the other dude showed up. Or rather, his gun showed up first. As the first shots rang out, people scattered in every direction. Bobby saw him now, the tough guy, sometimes boyfriend, heading straight for him. Led by the the muzzle of his gun. Bobby hit the ground running. The boyfriend kept firing. Bobby's heart pounded in his throat. He gasped for air as he raced down a Roxbury sidewalk, every muscle in his legs burning. And then there was another burning sensation. He stopped running when he realized he was safe. And he looked down. His legs were shaking, his sweatpants were covered in blood, and there was a hole in his knee. The bullet had gone into in one side and exited cleanly out the other. He limped to a nearby hospital. Doctors sewed him up, sent him on his way. He didn't even tell his mother or his father. They had their own to worry about Bobby Brown. He had work to do. We'll be right back after this. Word. Word. Word.
Liberty Mutual Spokesperson
And Doug, there's nowhere I wouldn't go to help someone customize and save on car insurance with Liberty Mutual. Even if it means sitting front row at a comedy show.
Comedy Show Audience Member
Hey, everyone, check out this guy and his bird. What is this, your first date?
Liberty Mutual Spokesperson
Oh, no. We help people customize and save on car insurance with Liberty Mutual together. We're married. Me to a human, him to a bird.
Comedy Show Audience Member
Yeah, the bird looks out of your league anyways.
Liberty Mutual Spokesperson
Only pay for what you need, at least. LibertyMutual.com.
Jake Brennan
Getting shot, getting arrested, getting kicked out of New Edition, sleeping with any woman anywhere, including the one he knocked up and who had since given birth to his first child. All these things contributed to Bobby Brown's larger than life image. An image that defined who he was to the public as his solo career was just getting off the ground. He was a bad boy with a badass sophomore record, Don't Be Cruel. And that record was powered by the huge hit My Prerogative, a song that flipped A giant middle finger at everyone from his boys in New Edition to the naysayers who doubted he'd ever amount to anything. Not to mention a song that taught me and an entire generation of kids what the word prerogative meant. Bobby knew that not only was it his prerogative to do whatever the hell he wanted to do, but that the public and the people who tried to define you as this or that, that they didn't know what the fuck they were talking about. It was impossible for anyone but Bobby Brown to know the real Bobby Brown, at least in Bobby's mind. It was like that with Whitney, too. Whitney Houston living in that rarefied air, just like Bobby in the year 1989. Both nominees at the Soul Train Awards, where the two met for the first time. Megawatt superstars standing side by side. Bobby in his white silk suit and Whitney in a sparkling beaded dress. Although she'd had a run of seven number one singles leading up to this right now in 1989, Bobby Brown was it. Arguably the more dominant cultural and musical force at the moment. A moment in which Whitney Houston was on the receiving end of backlash from the black community for skewering Tupac. All that said, Whitney had her own public, publicly defined image, just like Bobby did. Unlike Bobby, that image was not dangerous. Whitney was America's sweetheart. She was apple pie. And Bobby knew better that beneath that polished facade and that perfect voice, Whitney Houston was as bad as he was. If he didn't know just how bad when they began dating, he quickly found out. On their wedding day, Bobby went looking for his bride to be be hours before the ceremony. His nerves were ramping up along with the sex drive. He wanted one last quickie before they were pronounced man and wife. And he found her behind a closed door snorting a huge line of cocaine. This story about Whitney Houston, America's sweetheart, blasting rails before her wedding day, like the story of the horny ghost, comes from Bobby's own memoir, which to some is going to run counter to the narrative that Bobby Brown, the so called bad boy in this relationship, was the bad influence on Whitney Houston, not the other way around. As Bobby tells it, it's been well established that over the years, Bobby Brown and Whitney Houston descended into an unhealthy life of hard drug use together, even in front of their own daughter. And for more on that, you can check out the episode we did here in Disgraceland on Whitney Houston. That said, there are plenty of other incidents that were weren't speculation. Incidents that were caught on tape and now exist online for all to see. Incidents that paint a very particular kind of picture of who Bobby Brown was at this very moment. 1994, Bobby Brown's 25th birthday party. Two years after Bobby and Whitney tied the knot. One year after their daughter Bobbi Kristina was born. As soon as the they step out of the limo, the cameras are flashing, paparazzi calling out Bobby and Whitney's names to try and get the best shot inside the party. The music's loud, the drinks are stiff, and reporters from MTV and other news outlets are pressing the flesh, all jockeying to interview what is now the most famous married couple in the world, the bad boy and the good girl. One reporter in particular puts a microphone in front of the couple. He says that he heard Bobby Bobby's mother was recently offered her own talk show. She's a riot, the reporter says. Bobby furrows his brow. Hold up. You want to call my mom a riot? Bobby forms his right hand like a gun, raising it to the reporter's head and pretending to shoot, and the reporter quickly clarifies she's a riot. As in she's funny, you know, She's a trip. Oh, she's a trip, bobby says, as if that clarifies it for him, as if that makes it better. But it doesn't. Bobby is clearly offended. This guy doesn't know his mom, doesn't know the first thing about her, and here he is with the fucking balls to stand in front of Bobby while the camera rolls and say that Mrs. Brown is a trip. In Bobby's mind, it's such condescending bullshit, and he lets the guy know. My mom is real, bobby says, and she's coming from the heart. And if you can't respect that, you shouldn't even be here. As Bobby goes off on the journalist, Whitney just smiles at the camera, looking equal parts embarrassed and wanting to get on with answering her questions because yes, this is Bobby's birthday party. But the reporter wants to talk with Whitney right now, and Bobby's not having it. He doesn't break the tension. He doesn't say he was just kidding around. Instead he walks away pissed, presumably, though to cool off, only to return moments later, interrupt his wife, put his face right in the camera with a dead serious get the fuck out of here look and shove the cameraman and announce the interview is over. That outsized sense of ego and danger. It's all there in Bobby Brown's body language, things that he had possessed since he was a little kid dancing on Roxbury street corners. Bobby had the fame, the money. And now add to that the most celebrated singer and one of the most beautiful women in the galaxy on his arm. Bobby Brown didn't want the world to see him as bad. He wanted to be seen as powerful. But when he returned from his honeymoon, a fresh scar visible on Whitney's face made people talk. And back in Boston, he was caught in the crossfire again, literally dodging bullets while witnessing yet another friend suffer a fatal wound on tour with a reunited new addition. A tour in which each member rode on his own bus. Buses loaded with guns and dope. Bobby was so high that he thought his own wife was trying to kill him. He couldn't point to a specific reason why. The thought just entered his head and it wouldn't leave. He made the bus driver pull over. He ran. Cocaine in one pocket and a handgun in the other. Hopping a fence and tearing ass through a huge field somewhere in the middle of America. Running fast and the wind blowing through his ears. His wife Whitney yelling from somewhere behind him. And the rest of his new edition boys yelling, bobby coming up on a house now, an oasis smack dab in the middle of this field. He made it up the stairs, the front stairs, in that house, where a man now opened the front door and stepped onto the porch, giant shotgun in his very capable hands. Get your ass off my property or I'll blow your head off. The shock of that moment, the aftermath of it, it didn't set Bobby straight. Neither did the stroke he suffered soon after freebasing so much cocaine. It wasn't until he was sent to jail again in the year 2000, this time in Florida, this time for violating conditions of parole stemming from a previous DUI that he was forced to clean up. Bobby thought the whole thing was just bullshit, the parole violation. The only reason he was being treated like this was because of who he was. Bobby Brown, the bad boy. But the judge's gavel came down and the cops stuffed Bobby in a cruiser to whisk him away for two and a half months. In the clink, sitting there in the back seat, he slowly slid his handcuffed hands down around his ass and under his legs and feet. The cops up front were clueless. He brought his cuffed hands to the zipper of his pants. They quietly undid his fly. And then Bobby Brown pissed all over the inside of the squad car. If a bad boy is what they wanted, a bad boy was what they were gonna get. December 2003. Bobby Brown and Whitney Houston were at home. Home. Bobby was sober. California sober, that is which means he was drunk, as was his wife. And they weren't alone. There was another man. Whitney Steeler. Things had been undeniably dark inside the brown Houston household as well as out of it. Like inside that limousine where Bobby and Whitney once smoked crack with their five year old daughter Bobbi Kristina sitting right next to them. But things were different now. Where at least. At least Bobby wanted them to be different. Mostly he just wanted this other guy out of his house. He didn't know why Whitney was bringing him around. She needed him for dope, sure. But why were they hanging around with this dude? Bobby was not his friend. And Whitney was not this guy's woman. She was Bobby Brown's girl. The number two to his number one. So Bobby grabbed the guy by his shirt and tossed him around all ragdoll style. A fucking you doing here, the you doing with my family. Bobby felt his rage bubble up. And then he felt his wife's hands on his back pulling him away before he did any real damage. But Bobby was out of control at this point. Shit faced, angry, he spun around, raised his hand and slapped Whitney Houston in the face. It wasn't long until Whitney filed for legal separation and then for divorce. That was her prerogative. Bobby left with a one way ticket to somewhere else and a little money in his pocket. No car, no house, no jewelry. Leaving it all behind like he left that white Mercedes Benz at the airport behind all those years ago. Such was the mindset of the all powerful and the untouchable. There would be other cars and there would be other houses and there was always more work to do and more money to be made. But you can't replace everything. Like his Grammy award, his People's Choice award, his American Music Awards. All of them according to Bobby Brown, either thrown out or sold by Whitney's family in the bitter wake of their split. The receipts as it were, the tangible things that proved he was the most popular entertainer in the world at one time, were now lost to time. And in time, Whitney would tell her side of the story. 2009, the Oprah Winfrey Show. Whitney Houston preparing to stage a triumphant comeback. America's sweetheart and the queen of daytime tv speaking candidly in a hotly anticipated conversation. Huge ratings, bigger revelations. Whitney laid it all out. That Bobby Brown was jealous of her success. That something happens to a man, a particular type of man, when a woman has that much control, that much fame. Fame on the grandest scale. Stoked by the enormous success of the soundtrack to the Bodyguard. Her soundtrack, the best selling soundtrack of all time, by the way, released the year that they were married and three years after, Bobby Brown's Don't Be Cruel was on top. But the Bodyguard outsold Don't Be cruel in spades. 18 times platinum. More than double the numbers that Bobby Brown put up. People would always love that record. Whitney's record, that is. People wouldn't always love Bobby Brown. A few years later, Whitney Houston was dead. Bobby and Whitney's daughter, Bobby Christina, she died three years after that. And then one of Bobby's sons, Bobby Brown Jr. Died shortly after. Bobby was distraught. It was one thing to lose a form former spouse, but to lose a child, two children, only 22 and 28 years old respectively, that was unthinkable. So Bobby kept busy. He wrote a memoir. He produced a TV series about his life. He worked hard to ensure that he had some hand in shaping his legacy. That was his job now. Because a working man is everything. And no man wants to work so hard only to find in the end, that he is a disgrace. 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@gracelandpod.com subscribe, follow, like, rate and review the Disgraceland podcast wherever you get your podcast, because the Disgraceland podcast is now available everywhere. If you love Disgraceland, tell someone. Tell everyone. Shout us out on social, Spread the word and follow us to find out how you can cop some free merch for spreading that word. Follow us on Instagram, TikTok, Twitter and Facebook DisgracelandPod, and on YouTube@YouTube.com DisgracelandPod Rock and roll. He's a bad, bad man.
Liberty Mutual Spokesperson
And Doug, there's nowhere I wouldn't go to help someone customize and save on car insurance with Liberty Mutual. Even if it means sitting front row at a comedy show.
Comedy Show Audience Member
Hey, everyone, check out this. This guy and his bird. What is this, your first date?
Liberty Mutual Spokesperson
Oh, no. We help people customize and save on car insurance with Liberty Mutual together. We're married. Me to a human, him to a bird.
Comedy Show Audience Member
Yeah, the bird looks out of your league.
Liberty Mutual Spokesperson
Anyways, only pay for what you need at libertymutual. Com.
Comedy Show Audience Member
Liberty. Liberty. Liberty. Liberty.
Host: Jake Brennan
Air Date: March 27, 2026
This edge-of-your-seat episode unpacks the notorious and complex life of Bobby Brown—pop icon, self-proclaimed bad boy, and a man inextricably linked with the chaos, crime, and spectacle behind the golden age of R&B. Host Jake Brennan guides listeners through a tour of Bobby Brown's meteoric rise, personal demons, headline-grabbing scandals, brushes with the law, and the high human cost of fame. Brennan’s storytelling is rich, irreverent, and packed with wild anecdotes, making this both a cautionary and entertaining exploration of fame, legacy, and self-destruction.
“The stories about Bobby Brown are insane. He was arrested in the middle of a live performance for violating a Lewd act law. His Bad Boy influence may have been the reason Mike Tyson dramatically lost his heavyweight title. He lived in a haunted house in which he claims he had a sexual encounter with a ghost…”
— Jake Brennan (00:58)
“Bobby Brown swears that this actually happened. That he fucked a ghost. People. Okay? He delivers this story as 100% fact in his memoir.”
— Jake Brennan (06:55)
“Mike, Bobby was saying, man, you gotta quit. You gotta go to bed and rest up for tomorrow. Quit now. Let Bobby Brown have all the fun. Mike Tyson wasn't quitting shit… Mike Tyson thought wrong.”
— Jake Brennan (10:05)
“He hadn’t breaded the chicken with flour. He breaded it with his mother's cocaine. This was how Bobby Brown learned that his mother was dealing drugs in Roxbury by cooking chicken as a little kid and unintentionally using the drug as an ingredient.”
— Jake Brennan (14:20)
“…his sweatpants were covered in blood, and there was a hole in his knee. The bullet had gone into in one side and exited cleanly out the other.”
— Jake Brennan (20:25)
“On their wedding day, Bobby went looking for his bride to be hours before the ceremony... And he found her behind a closed door snorting a huge line of cocaine.”
— Jake Brennan (26:40)
“A few years later, Whitney Houston was dead. Bobby and Whitney's daughter, Bobby Christina, she died three years after that. And then one of Bobby's sons, Bobby Brown Jr. Died shortly after. Bobby was distraught.”
— Jake Brennan (35:00)
“A working man is everything. And no man wants to work so hard only to find in the end, that he is a disgrace.”
— Jake Brennan (35:57)
| Timestamp | Segment Title/Topic | |-----------|----------------------------------------------------------------------------------------------------------------------| | 00:58 | Opening & Bobby’s wild reputation | | 04:15 | The haunted mansion & ghostly encounter | | 09:00 | Tokyo: Mike Tyson, Buster Douglas and the bad influence | | 12:18 | Bobby’s Boston youth, women’s jail, and “cocaine chicken” | | 15:48 | Death of Jimmy, the drive to escape Roxbury | | 19:30 | Getting shot, New Edition and rise to solo stardom | | 22:37 | “My Prerogative,” Whitney Houston, and R&B superstardom | | 26:40 | Whitney’s drug use revealed; bad boy vs. “America’s sweetheart” narrative | | 28:45 | Volatile public incident at Bobby’s birthday | | 31:45 | Tour bus meltdown, paranoia, stroke | | 33:00 | Florida parole violation, urinating in the cop car | | 34:30 | Domestic violence, divorce, professional and personal unraveling | | 35:18 | Aftermath: deaths of Whitney, Bobbi Kristina, and Bobby Brown Jr., attempts to reclaim legacy | | 35:57 | Closing reflection: work, disgrace, and legacy |
This episode of DISGRACELAND rips back the curtain on a flawed, fascinating, and deeply human pop icon. From supernatural sex stories to criminal misadventures, from love and loss to redemption and disgrace, Bobby Brown’s tale is rendered as both cautionary and compelling. Through Jake Brennan’s visceral narration, listeners are left with a nuanced image of an artist who was never merely the villain or the victim, but always the master of his own unruly story.