Pod Insights DISGRACELAND Aaliyah: Married Illegally at 15, Drugs, Corruption, and a Fiery Crash About this episode Married to R. Kelly at 15 years old and dead by the age of 22. Aaliyah was supposed to be as big as Beyonce, but drugs, corruption, and a fiery crash prevented that from happening.
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This episode contains themes that may be disturbing to some listeners, including sexual abuse of a minor.
This episode was originally published on November 12, 2024.
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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.
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1:11 Speaker 03 This episode contains content that may be disturbing to some listeners. Please check the show notes for more information.
1:19 Jake Brennan? Disgrace Land is a production of Double Elvis.
1:33 Jake Brennan? This is the story of a pop star, an incredible talent, Aaliyah. A talent whose creative fire burned from deep within. But it's also the story of R. Kelly and an illegal marriage. It's about drugs, corruption. It's about wild, A-list accusatory conspiracy theories. And it's a story about a fiery crash and about 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 Instant Theme Song, MK1. I played you that loop because I can't afford the rights to "Fallen" by Alicia Keys. And why would I play you that specific slice of Empire State of Mind cheese?
2:18 Jake Brennan? Could I afford it? Because that was the number one song in America on August 25th, 2001. And that was the day that a plane carrying Aaliyah and eight others crashed shortly after takeoff in the Bahamas, killing all onboard. On this episode, an illegal marriage, drugs, corruption, conspiracy theories, a fiery crash, and Aaliyah. I'm Jake Brennan, and this is Disgrace Man.
3:14 Jake Brennan? August 25th, 2001. If only the mind of 22-year-old Aaliyah Hutton was as clear as the blue skies here in the Bahamas. The sun, the sand, the weather, it was all perfect. Everything else was, well, it was complicated. Aaliyah didn't want to be here in the first place, which sounds crazy because here, specifically in the Apico Islands, was more than one person's idea of paradise. For Aaliyah, it was work. Leading a team of dancers on a catamaran out in the ocean, wrapping the video shoot for "Rock the Boat," the second single from her recently released self-titled album, her third album overall.
3:58 Jake Brennan? But though it was work, it wasn't Aaliyah's vision. The vision belonged to Hype Williams, arguably the most in-demand director when it came in music videos for the hottest hip-hop and R&B artists. When Hype insisted they leave Miami for the Bahamas, Aaliyah expressed her displeasure. She hated flying. She hated planes. She was the utmost professional. Despite her personal reservations, she wasn't going to rock the boat. Sorry, I had to do it. There were fights to fight and hills to die on, and Aaliyah knew that this wasn't one of them. So she got her nerves under control, got on the plane, and went to the Bahamas, all the while maintaining that quiet, reserved demeanor she was known for.
4:39 Jake Brennan? The same demeanor that simmered on low behind a pair of dark shades or her trademark peekaboo hairstyle, those long strands covering one of her eyes like Veronica Lake, her mother's favorite actress.
4:53 Jake Brennan? Under that quiet reserve, however, was the fire. Or so said Ed McMahon, one-time host of Star Search, a hugely popular TV talent show in the 1980s and 90s. When Aaliyah appeared on the show in 1990 to perform Rogers and Hearts: My Funny Valentine at just 10 years old, Ed McMahon, the longtime Tonight Show sidekick to Johnny Carson, saw the fire in Aaliyah before she even sang a note. "You weren't taught it. You didn't get it from your parents," McMahon said. The fire burned inside you, independent of outside influence. For Aaliyah Hotten, that fire burned bright and hot. Her parents knew this. They worked tirelessly to secure opportunities for their daughter to perform.
5:38 Jake Brennan? Her auntie Gladys knew this too. That's Gladys, as in Gladys Knight in The Pips, by the way. Aaliyah's aunt by marriage to her mom's brother. And it was that famous aunt who brought her 11-year-old niece up on stage to sing with her for all five of her sold-out shows at ballets in Las Vegas.
5:56 Jake Brennan? It sounds weird in 2024 to say that Aaliyah was groomed, but that's exactly what was happening throughout her childhood. She was a megawatt talent from a very young age who was groomed by everyone around her in order to make her a star. Of course, there are gross connotations with the word groomed in, for good reason. Because the next person to groom Aaliyah after Star Search and her parents and her auntie Gladys was R&B superstar R. Kelly, who, when Aaliyah was just 14 years old, a freshman at Detroit High School for the Fine and Performing Arts, majoring in dance, played the part of Predator Svankali as Aaliyah's professional career was just taking off.
6:41 Jake Brennan? R. Kelly wrote and produced Aaliyah's first record, which yes, bears the unfortunate title, "Age Ain't Nothing But A Number." Unfortunate because, again, Aaliyah was 14, and R. Kelly was 27. If the lyrical content R. Kelly was getting Aaliyah to sing wasn't troublesome enough, the fact that the teenager and the grown man were much more than a musical partnership absa fucking lutely was. Just a few months after the album's release in the summer of 1994, R. Kelly secretly married Aaliyah, who was then 15, just 15! And he did so by paying off a state employee to create a fake ID that showed that she was 18. But as our guy Kurt Loder pointed out when he broke the news on MTV, R. Kelly wasn't fooling anyone.
7:26 Jake Brennan? Because earlier that year, Aaliyah was dropped from the Budweiser Superfest tour precisely because she was a minor.
7:34 Jake Brennan? Based on what we now know about R. Kelly and his decades of sexual abuse and child pornography, one can only imagine that what went on between him and his child bride behind closed doors was, "I don't even want to go there." And if you're looking for a deeper dive into that whole saga, check out our episode on R. Kelly in the Disgraceant Archive, but I'm getting away from the story here.
7:54 Jake Brennan? At least one of R. Kelly's victims has claimed that he got Aaliyah pregnant and made her get an abortion during their time as husband and wife. But Aaliyah wasn't talking about it. Not then, and not ever. Once her parents stepped in to annul the marriage in February of 1995, whatever spell R. Kelly had cast over an innocent and impressionable Aaliyah was broken. She didn't just walk away. She denied the whole thing had ever happened. Not because it didn't happen for real, because she was moving on. She didn't wish death upon anyone but still keep that man away from her. Which was easier said than done.
8:30 Jake Brennan? R. Kelly's crimes were practically being perpetrated out in the open. But no one was calling him on it. Aaliyah's own uncle, Barry Hankerson, the one who was married to Gladys Knight, was a music business insider who continued to work with R. Kelly for years after his niece's illegal marriage. And then, there was Hype Williams, the director of Aaliyah's Rock the Boat music video here in the Bahamas. Hype worked with everyone in hip-hop and R&B, including R. Kelly, with whom Hype had made and was continuing to make a ton of content. Aaliyah was a force of nature, street but sweet, as she called herself. But her power wasn't to wipe R. Kelly from the face of the earth. It was to lift herself up. And she did this by following her own gut and by doing things her way.
9:14 Jake Brennan? Taking a chance on an unknown and unorthodox music production duo—more on that in a bit— performing all her own stunts in her movie debut Romeo Must Die. A month of training to learn one scene, she went the distance, literally all the way to Australia to film her next movie Queen of the Damned, while simultaneously recording tracks for her new album at night. She was creatively reborn as an inspired multi-hyphenate and she worked her ass off for it.
9:43 Jake Brennan? But right now, Aaliyah was done with work and she wanted to go home. She stood anxiously at the Marsh Harbour Airport there in the Bahamas, the island breeze blowing through her hair, and she stared down the Cessna twin-engine plane that was currently being loaded up with luggage that would soon bring her back to the mainland, back to normalcy, back to her boyfriend Damon Dash, co-founder with Jay-Z of Rockefeller Records. This fucking plane, though, it wasn't big like the one that had brought her out here. It was a puddle-jumping little piece of shit. It was supposed to carry her and her bodyguard and her makeup artist, two hairstylists, a Virgin Records executive, two employees of Blackground, her uncle's record label, and the pilot, plus all their stuff. She worried it was just too much, too heavy.
10:27 Jake Brennan? She called Dane and he told her to wait. He'd send a private jet tomorrow to bring her home. She wasn't sure. She just wanted to see him, and both of their schedules were crazy over the next few weeks. If she wanted some quality time with him, she had to go now. She was conflicted, exhausted. The baggage handlers packed in the plane heard her concerns over the way. They said they'd remove some of the stuff and lighten it up. That was helpful, but now she had a headache. She just needed to rest. Someone offered her a pill. Yes, please, anything, take the edge off. One of the baggage handlers, just a kid really, helping out with the family business, handed her a glass of water to wash the pill down. He was like 13, 14 years old, something like that.
11:09 Jake Brennan? Reminded her of when she was that age, figuring it all out, making mistakes, finding her way, street but sweet. And within minutes, she was out.
11:22 Jake Brennan? The dream she had was the same one she'd been having all week. It was dark, pitch black. She couldn't see anything, but she was scared. She was running. Something was after her, chasing her. Her heart was pounding, her legs ached, and then suddenly she took off. She was flying. She felt free, as weightless as that Cessna was loaded. She didn't want it to end here, asleep, dreaming, escaping, going to a place where no one could reach her. Aaliyah was untouchable.
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12:47 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.
13:18 Speaker 06 Hello, hello. I'm Malcolm Gladwell, host of Smart Talks with IBM. I spoke with IBM's Ana Paula Assis about what digital sovereignty actually means in the age of AI.
13:29 Speaker 07 AI now moves from somebody operating a system to the technology actually making decisions. So you have to have a much better visibility of what AI is touching, data it is accessing, and where.
13:45 Speaker 06 Hear the full conversation wherever you get your podcasts.
13:51 Jake Brennan? Life never plays out the way any of us want or expect it to. There's an old Yiddish saying that basically says, "Man plans, God laughs." Or as John Lennon put it in one of the last great songs that he ever wrote, "Life's what happens when you're busy making other plans."
14:12 Jake Brennan? For Aaliyah Hatton, life happened all the time, but never in order. Chronological order, that is. Her education at Detroit High School for the Fine and Performing Arts, where she trained as a dancer, was interrupted by her quick fame as a teenager. That meant juggling studies with stardom for four straight years. That meant working just as hard at maintaining a grounded, quote-unquote, "normal" teenage life as she did working to put out huge records atop the R&B and pop charts. By the time her senior year rolled around, in 1997, the desire for normalcy was so strong that she made the effort to show up in person to school events as much as she could. She even attended her senior prom, wearing a powder blue pantsuit, crop top,
14:54 Jake Brennan? a fashion statement that didn't just buck the expectations of what a prom outfit should look like, but one that played a riff on the kind of fashion that she was now modeling for Tommy Hilfiger. Her appearance in the industry giant's wildly successful campaign that year revitalized the Hilfiger name by aligning it with R&B and hip-hop culture, while simultaneously elevating Aaliyah in status at age 18. To repeat, when Aaliyah attended her high school prom, she did so while she was already a famous singer and a model on the come-up. She was everywhere: MTV, BET, The Tonight Show, Showtime at the Apollo, and now in Detroit at school, just trying to be normal.
15:36 Jake Brennan? But there was nothing normal about any of it, just like there was nothing normal about the music she was making. Her second album, One in a Million, released the year prior, in 1996, was unlike anything in the R&B world at that time. It wasn't diva music like Mariah, it wasn't baby-making music like Boys to Men, and it was purposefully divorced from the jailbait fantasy once propagated by her infamous ex. One in a Million was funky, trippy, a stew of R&B, hip-hop, and electronica that, for some, was actually a little too weird. Like, what were those sounds on that track? Were those crickets? A lot of radio stations hesitated to put the title track on air at first because it didn't fit in, which was exactly the point.
16:19 Jake Brennan? This new record was Aaliyah's chance to wipe the slate clean, to reintroduce herself to the public. And the first step in this new creative direction was to hire a new production duo out of the Dirty South. Aaliyah took a chance on Virginia natives Missy Elliott and Tim Mosley, aka Timbaland, where many others would not. And the chance paid off. The title track from One in a Million went to number one on the R&B chart, and to number five on the pop chart. More success followed, including Golden Globe and Oscar Award nominations in 1998 for her contribution to the Anastasia soundtrack. She couldn't beat Celine Dion in "My Heart Will Go On" from Titanic. Nobody could, but Aaliyah still made history, at age 19, by becoming the youngest artist ever to perform at the Academy Awards.
17:04 Jake Brennan? And soon, she wasn't just making history, she was making some of the most defining music of the era. Against all odds.
17:16 Jake Brennan? Timbaland got the call at one in the morning. It was Barry Hankerson, Aaliyah's uncle, Auntie Gladys's ex, owner of Black Ground Records, the label that had partnered with Atlantic Records to release Aaliyah's music. Tim was in LA, but Barry was back east in New York, where it was three hours later in the morning. But still, way too fucking early. Tim wanted to know what was so important they couldn't wait until tomorrow. Barry told Tim that a huge opportunity just presented itself. That Aaliyah had been offered the lead single on the soundtrack to Dr. Dolittle, the highly anticipated summer comedy starring Eddie Murphy. But there was a catch. The movie was weeks away from release. They had to produce the track now, tonight, and deliver it by 11 a.m.
18:00 Jake Brennan? Again, it was 1 a.m. out in Los Angeles, 4 a.m. in New York. The track was due at 11 a.m. Was that east coast or west coast time? Does it fucking matter? My point is that Timbaland and Aaliyah had hours to conceive and record this song, that Atlantic Records and 20th Century Fox, the studio putting out the movie, were betting on to be a huge hit and thus sell Boku soundtrack CDs. Timbaland's first reaction was to push back. He'd just come offstage in Los Angeles and he was exhausted. And now, he was expected to churn out a hit song. In what, 10 hours? Barney was out of his mind. They needed more time. But there was no more time. In fact, Barry had bluffed and told Atlantic that they already had a track in the can. There was, however, good money in it.
18:44 Jake Brennan? $400,000, which Timbaland and Aaliyah were welcome to split down the middle. And to sweeten the pot, the song was already written and ready to go. It was called "Are You That Somebody?" And it was the brainchild of Stephen Ellis Garrett, aka Static Major, a songwriter and producer who, unbeknownst to most, was currently in a secret relationship with Aaliyah. The promise of a pretty sweet payday lit a fire under Timbaland. He put up the bat signal and assembled Aaliyah, Static Major, and Tim's right-hand man and engineer Jimmy Douglas at Village Studios over on the west side of L.A. There, they get to work. Again, flexing the weirdo muscle, the one that Drew raised eyebrows and then earned
19:27 Jake Brennan? them a coveted number one slot with "One in a Million." Timbaland's stuttering beat, the clicks and the clacks and the off-kilter inverted funk of it all, inspired, and I'm not kidding here, by the Oompa Loompa song in the Willy Wonka and the Chocolate Factory film. That odd sonic place setting was then balanced out so delicately by Aaliyah's compelling vocal. So confident, so cool and collected. The genius of this track, and I remind you that it was created at the last minute in the wee hours of an early summer night turned morning, is how skillfully it balances avant-garde and mainstream sensibilities. Perhaps it was difficult to see at the time when it came out on the soundtrack for a silly Eddie Murphy comedy, but there is something so radical about this track that it's subversive. And I haven't even mentioned one of the song's most indelible
20:12 Jake Brennan? elements, which is the sampled sound of that baby cooing during the hook. A sound that Timbaland, in his delightfully strange and subversive way, had it at the last minute, right before they mixed The Master and Shift, "Argue That Somebody," to the label. That baby sound, by the way, comes from a 1964 album called Authentic Sound Effects, Volume 8. And if you think it sounds familiar, his row of badass prince had used the same exact sample some sixteen years prior at the very end of his song, "Delirious." But back to the story. The creative partnership between Aaliyah and Timbaland was a crystal ball of sorts, gazing into the future of R&B and hip-hop, who's coming down the pike at them. And that fact is a bit easier to see now in hindsight, but at the time, it
20:54 Jake Brennan? was just life happening. Calls in the middle of the night, songs whipped together under great pressure, necessity being the mother of invention, all of that. Three years later, in 2001, life was still happening, though still not in the way it's expected to happen. God laughing while we're busy making other plans and so on. Aaliyah and Blackground Records were now partnered with Virgin Records to release her third eponymous album. Timbaland, who was busy with other high-profile projects, barely had time to contribute, though Aaliyah was able to corner him to work on three of the album's tracks. The album was poised to level her up once again. The biggest tour of her career was on the horizon, with the goal being to make Aaliyah as much of a household
21:37 Jake Brennan? name as Madonna. That was the dream. But first, Aaliyah had to wake up from another dream, one she was having at an airport in the Bahamas while she was waiting to fly back home, and back to that long-lost sense of normalcy.
21:58 Speaker 05 Back after this word, word, word.
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22:32 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.
23:03 Speaker 06 I'm Malcolm Gladwell, host of Smart Talks with IBM. I spoke with Dr. Laura Jayhai of Cleveland Clinic about how advanced computing is helping shorten the path from medical discovery to treatment.
23:16 Speaker 05 The moment that there is a compound that someone in a lab thinks it would be effective to treat a certain disease, it takes about 10 to 13 years from that moment to when that drug is on a shelf for a patient. A big part of that gap could be computationally solved. Better simulation of compounds, designing drug trials that are more efficient, that would finish faster. That was the motivation to bring computational tools and technology closer to biomedical researchers.
23:51 Speaker 06 Learn more about how Cleveland Clinic and IBM are using AI and quantum computing to revolutionize biomedical research at ibm.com/smarttalks.
24:07 Jake Brennan? Aleah, a man never woke up from that dream.
24:13 Jake Brennan? That dream, by the way, the one I described earlier, in which he is running from something in the darkness, only to lift off, take flight, and escape. She described it as a dream that she kept having when she gave what would turn out to be one of her final interviews to a German reporter in Paris. This was just weeks before she traveled to the Bahamas to shoot the video for Rock the Boat with Hype Williams. Once again, according to the 13-year-old luggage carrier who was helping out with his family's business at the Marsh Harbour Airport, the one who saw someone give a pill to Aleah before she passed out. Once it was time to board the Cessna 402B twin-engine plane, traveling from the Bahamas back to Miami on August 25, 2001, Aleah was still asleep and had to be carried onto the plane.
24:56 Jake Brennan? Which leads to the obvious question: what was that pill? And who gave it to her? But I'm getting ahead of myself. Getting on the plane unconscious may have been the only way Aleah would have agreed to do it, seeing as how she had a lot of anxiety about boarding the aircraft in the first place. It was small, and she worried it was over the weight limit, directly preceding her being carried onto the plane. An argument took place among airport personnel about the total weight of the passengers and their luggage. The pilot was complaining to anyone that would listen, and the baggage handlers too. There was too much luggage onboard one minute, and there wasn't too much luggage onboard the next. It kept going back and forth. Aleah's team, that's her bodyguard, her makeup artist, two hairstylists, and three record label employees, were all getting restless.
25:41 Jake Brennan? The plane was scheduled to take off at 4:30 in the afternoon, but now it was almost 6, and they were still at a standstill. Tempers flared. The pilot threw up his hands and he conceded. He didn't even know what he was arguing about anymore. He just wanted to get his bird up in the air and get these irritated flatlanders back home.
26:01 Jake Brennan? It was 6:45 that evening when the Cessna finally boarded. Over two hours past its original departure time. The skies were blue, and the weather was calm. The plane's twin propellers began to squeak and twirl as the engine fired and then kicked into full speed. The sound like dual supersized lawnmowers burning hot and loud. The passengers settled in as the pilot taxied the aircraft to the top of the runway. And the call came in over the radio that they'd been cleared for takeoff. The pilot increased the throttle and the plane rumbled and sped forward, gaining speed as it traveled down the runway. More throttle, more rumbling, more speed, and they were airborne. The Cessna gradually making the climb from the ground to the clouds.
26:46 Jake Brennan? Steady, up a little higher, steady and higher still, steady. And then, after just sixty seconds, some one hundred feet in the air, the plane suddenly veered to the left, way off course. And as it did, the nose began to turn from ascent to descent, from skyward to earthbound, and the Cessna was in a free fall, straight down. The plane dropped like a stone within seconds, crashing into the marsh lined with bushes.
27:16 Jake Brennan? It exploded upon impact, and the wreckage was in flames.
27:21 Jake Brennan? First responders found an aircraft ripped to pieces. The bodies of all seven passengers as well as the pilot were strewn throughout the crash site. Someone was screaming. Three of the people on board, Aaliyah's bodyguard, her hairstylist, and one other unidentified person were found alive, though all three soon died either at the hospital or on the way. Everyone else was pronounced dead at the scene, including Aaliyah, who was discovered approximately twenty feet from the mangled, smoking twist of steel strapped into her seat. Curled up, head between her legs, covered in burns with signs of massive head trauma.
28:01 Jake Brennan? An investigation into the crash blamed it on engine failure, adding that, as Aaliyah herself suspected, the overloaded cargo and passengers onboard could have contributed to that failure.
28:14 Jake Brennan? But overloading and engine failure quickly took a backseat when new revelations came to light. Revelations about the pilot, the charter company, illegal drugs, and massive fraud. The kinds of things that make a plane go into a nosedive after takeoff. The kinds of things that ensure that life never plays out the way it's supposed to.
28:55 Jake Brennan? Two weeks before he flew the Cessna that crashed and killed Aaliyah, her team, and himself, the pilot Louis Morales III was in a Florida courtroom. He was facing four felonies, including one for possession of crack cocaine. He pleaded no contest. In exchange for that plea, Louis Morales was sentenced to three years probation.
29:18 Jake Brennan? Since he was technically not convicted of a crime, his pilot's license was not revoked. All the same, he wasn't supposed to be in the cockpit of that Cessna on August 25, 2001. We know this now because Louis Morales was not listed on the charter plane company's official certificate for the flight. This information was revealed days after the initial crash. It wasn't until close to a year later that an even bigger bombshell was revealed. That being an autopsy report which proved that there was cocaine and alcohol in Louis Morales's body at the time of the accident. Now, Louis Morales wasn't the only one involved in this tragedy who had a record. Blackhawk International Airways, the charter company in charge of the flight,
30:02 Jake Brennan? have been fined by the FAA four times in the last three years for violating safety standards, for failing to comply with maintenance standards, and for failing to test its employees for illegal drug use. Even more, Blackhawk's owner, Gilbert Chacon, had his own criminal record for fraud. And not some rinky-dink con job either. The guy was part of a huge $400 million insurance scam. His home address was listed as the address of another company called Sky Street, which was the owner of the Cessna 402B. As all of these facts were revealed to the public in the weeks following the crash, the FAA employee who had cleared the flight took his own life. It gets even more complicated from here.
30:44 Jake Brennan? It turns out that Blackhawk wasn't originally hired to charter the flight. That was supposed to have been the responsibility of another company called Skylimo, partnering with a shipment company called Profrate Cargo Service. Profrate had actually determined that the luggage was heavy enough to require multiple planes to get everyone and everything back to the mainland safely. But when the original flight time had to be rescheduled, someone used that blip in the plan to hastily replace Skylimo with Blackhawk. Someone. Who? We still don't know. And why? Was likely because Blackhawk was cheaper and cut more corners. Of course, there are other narratives out there about why Blackhawk, a cheap old company with a bad rep, was chosen last minute to bring Aaliyah home.
31:29 Jake Brennan? The R&B singer Mary J. Blige, for one, not a close friend of Aaliyah's but a known acquaintance, speaking on the BET Show 106 in Park, claimed that Aaliyah's death was not a simple accident, but rather, quote, "a murder, a spiritual murder," unquote. She went on to say, quote, "I could go a lot deeper. For a lot of people, I would have to bring proof," unquote.
31:52 Jake Brennan? More recently, there's Jaguar Wright, a singer-songwriter who was working with The Roots and Jay-Z around the same time that Aaliyah's star was on the rise. In the wake of the recent allegations against Sean "Diddy" Combs, Jaguar Wright has gone on the offensive publicly. In a series of impassioned interviews that have been circulating on social media, she lays out a conspiracy surrounding Aaliyah's death that lays the blame not on Diddy, but instead on Jay-Z, the one-time business partner of Damon Dash, the Rockefeller executive whom Aaliyah was dating at the time. And look, I'm not even gonna touch that one right now. You can go look it up for yourself and see what she has to say. It's wild. And then, there's Damon Dash, who in 2001 was the love of Aaliyah's life and the major
32:36 Jake Brennan? motivation for her to return back home on the day that she did. In an interview on Entertainment Tonight, Dame alleged that Lenny Kravitz offered to send a private jet to the Bahamas to pick up Aaliyah, but instead, Hype Williams took that jet, leaving Aaliyah stuck with the whole Blackhawk debacle. When asked if he'd ever confronted Hype Williams about this, Dame replied, "Fuck yeah." But when pressed to divulge the details of that confrontation, Dame only said, "Ask him." And just earlier this year, 2024, Dame Dash was talking again about his relationship with Aaliyah and how that immeasurable loss affected both his life and the music world. This time, he was speaking on the PBD Podcast. This time, Dame said, quote, "I know what happened, but I'm not gonna tell you what the truth is at this moment.
33:21 Jake Brennan? We're in public." Maybe that truth will come out in time, if there really is a hidden truth behind this great tragedy. Until then, we do know this. In 2002, one year after the accident, Aaliyah's family filed a lawsuit for wrongful death and negligence that named, among others, Blackhawk, its owner Gilbert Chacon, Skystream, Hype Williams, and Virgin Records. In addition to being accused by one attorney of, quote, "putting profits over people," Virgin also failed to honor a verbal promise to pay a Nassau mortuary to prepare the bodies of Aaliyah and other passengers. Ultimately, the R&B singer Maxwell stepped up to foot the bill for Aaliyah's funeral, but that's another story itself.
34:07 Jake Brennan? One year after the lawsuit was filed, the family settled with Blackhawk, Skystream, and Chacon for an undisclosed sum. The details of that settlement are confidential. But the incredible talent, the fire that burned deep in the heart and soul of Aaliyah, that's in the public record. The fact that that public record only lasted until 2001, now more than 20 years in the past, when Aaliyah Houghton was just getting started, that's a disgrace. I'm Jake Brennan, and this is Disgrace Land.
34:59 Jake Brennan? Disgrace Land was created by yours truly and is produced in partnership with Double Elvis, The Exactly Right Network, and iHeart Podcasts. Credits for this episode can be found on the show notes page at disgracelandpod.com. If you're listening as a Disgrace Land 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 Disgrace Land ad-free. Rate and review the show and follow us on Instagram, TikTok, Twitter, and Facebook @disgracelandpod and on YouTube at youtube.com-at-disgracelandpod. Rockerola.
35:44 Jake Brennan? He's a bad, bad man. 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.
36:20 Speaker 00 When the holidays start to feel a bit repetitive, reach for Sprite Winter Spice Cranberry and put your twist on tradition. A bold cranberry and winter spice flavors fusion, Sprite Winter Spice Cranberry is a refreshing way to shake things up this sipping season, and only for a limited time. Sprite, obey your thirst.
36:48 Jake Brennan? Hey guys, time to dust off your detective skills while unwinding in the Caribbean on Virgin Voyages' second true crime voyages. Back by popular demand, this five-night, adults-only escape sets sail March 20th, 2027 to Grand Turk in the Beach Club at Bimini. The difference between this year and last will be that I will be on the cruise this year, along with Zeph, and he and I will be taping a live version of DisgraceLand, along with podcast hosts from Exactly Right's Buried Bones, Podcast of the Year Award winners, Wyscrack, and other fan favorites. Get on this cruise with us, guys, and enjoy live podcast recordings, behind-the-scenes storytelling, exclusive meet-and-greets, and immersive true crime programming throughout this one-of-a-kind voyage.
37:32 Jake Brennan? Head over to www.virginvoyages.com/trucrime to secure your spot.
Next Bonus Episode - More Sports, Celebrity Politics, and Diddy's New Digs Page updated November 7, 2026 · transcript and summary are machine-generated