Pentagram: Demons, Curses, and Doom

In 1971, a teenage metalhead named Bobby Liebling flipped a five-pointed star upside-down, gave his band a cursed name, and summoned a sound so heavy it would echo for generations. But for Bobby and his bandmates, doom metal wasn’t just a genre – it was a prophecy. Drug addiction, jail time, sabotage, and strange hauntings followed, all as the myth of Pentagram grew louder underground. This is the story of the greatest band you’ve never heard – and the curse they could never shake. For a full list of contributors, visit ⁠⁠⁠⁠⁠⁠⁠disgracelandpod.com⁠⁠⁠⁠⁠⁠⁠ https://www.disgracelandpod.com/ To listen to Disgraceland ad free and hear an exclusive mini-episode about Bobby Liebling's wild night with the Rolling Stones, become a Disgraceland All Access member at ⁠⁠⁠⁠⁠⁠⁠disgracelandpod.com/membership⁠ disgracelandpod.com/membership⁠⁠⁠⁠⁠⁠. Sign up for our newsletter and get the inside dirt on events, merch and other awesomeness - ⁠⁠⁠⁠⁠⁠⁠GET THE NEWSLETTER⁠⁠⁠⁠⁠⁠⁠ https://mailchi.mp/doubleelvis/disgraceland-email-newsletter Follow Jake and DISGRACELAND: ⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠ https://www.instagram.com/disgracelandpod/ ⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠ https://www.youtube.com/@disgracelandpod ⁠⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠⁠ https://twitter.com/disgracelandpod (formerly Twitter) ⁠⁠⁠⁠⁠⁠⁠Facebook Fan Group⁠⁠⁠⁠⁠⁠⁠ https://www.facebook.com/groups/491024204626127/ ⁠⁠⁠⁠⁠⁠⁠TikTok https://tiktok.com/disgracelandpod To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices See omnystudio.com/listener https://omnystudio.com/listener for privacy information.

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

• 0:01Speaker 00

  This is exactly right.

• 0:13Speaker 01

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• 0:43Jake 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.

• 1:14Speaker 03

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• 1:28Speaker 04

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• 2:11Speaker 04

  This is an advertisement for Zolair, paid for by Genentech and Novartis. Disgrace Land is a production of Double Elvis.

• 2:29Jake Brennan?

  This is a story about inversion, about what happens when you take something ancient, something sacred, and you turn it upside down. It's about the sound of doom echoing from the basement of a suburban Virginia home. It's about mystery tapes and cheap pawn shop stereos. About the thin line between myth and memory. It's a story about drugs, demons, and deals that may or may not have ever gone down. And it's also a story about a curse, one which may have been cast the moment a certain name was spoken out loud. That name was Pentagram. A band that was supposed to be louder

• 3:14Jake Brennan?

  and heavier than anything else, but instead became a whisper on a worn-out cassette. Their music passed from one true believer to the next. 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 Haunted Star MK2. I played you that loop because I can't afford the rights to Maggie May by Rod Stewart. And why would I play you that specific slice of "Feels Like the First Time" cheese? Could I afford it? Because that was the number-one song in America on Halloween 1971. And that was the day that Bobby Liebling

• 3:58Jake Brennan?

  decided to form a band that he would call Pentagram and unknowingly unleash a curse he could never shake. On this episode, doom, demons, drugs, curses, Bobby Liebling, and the greatest band that never was: Pentagram. I'm Jake Brennan, and this is DisgraceLand.

• 4:44Jake Brennan?

  The guy in the back of the pawn shop, working on the stereo equipment. Was he a really young-looking old dude, or a really old-looking young dude? Was he white, black, Latino, Israeli? Was he either perpetually tanned, or just plain filthy? And what was with the perm? The Grecian yearning? The sinewy frame and piped wife beater? And was that a gold star of David, or a pentagram hanging around his neck? Most important, how did this dude look cool? So many questions. Rumors have persisted ever since he started working here. The pawn shop gig was the latest in a string of jobs out on the fringes.

• 5:28Jake Brennan?

  Bail bondsman, straight PI, off-the-book snatch-and-grab man. Word around town was that not only could he fix your turntable, he could play anything. Guitar, drums, sax. And most proficiently, the devil's instrument, the fiddle. The kids who came in the shop fucked with him. He was an easy target, part Soul Train, part porn star stand-in. But when he pulled an old cassette tape, and popped open the cheap plastic case with a flick of his thumb, and shook out the cream-colored cassette like he was shaking a Marlboro Red loose from the soft pack he kept in his shirt pocket, everything changed. At least it did for the two impressionable teenage headbangers who'd wound their way into the back of the pawn shop.

• 6:13Jake Brennan?

  Past the 30-8-6 and the velvet Elvis, and past the stuffed jackalope and the squire telecaster with the faded Steal Your Face sticker peeling from the pickguard, to where this dude was hiding in plain sight.

• 6:25Jake Brennan?

  He looked at them like he knew they were coming. And they looked at him like he had what they were looking for. And he did. They stood there with their Cliff Burton Peach Fuzz stashes and their torn Levi's jackets, ready to have their minds blown in a way that they knew the holier-than-thou 23-year-old down at the record store could never do. And they stared at the dude's stack of tapes with band names handwritten on the spines, names like Stone Bunny, Space Meat, Wicked Angel, and Virgin Death. They stared at the letters inked on the knuckles of this dude on his right and left hands. "Diaz Yre," "Day of Wrath." And they stared at the oily Chevron gas station work shirt that was chaotically tied around

• 7:10Jake Brennan?

  this dude's waist with a name patch over the left breast that read "Teddy." Teddy knew that these two headbangers weren't here for a busted watch or a faulty piece of stereo equipment. They were there for this. He popped the cassette inside a boombox that was sitting there on the counter. "It has to be a cassette," Teddy told them. "This shit doesn't sound right any other way. A CD is gonna give you too much clarity, too much definition. And vinyl, fuck vinyl. Vinyl's a pain in the balls." "Yeah, I see you nodding your head before you even had time to process it. But of course I'm right. Vinyl sucks."

• 7:52Jake Brennan?

  Teddy pressed play. The riff came storming from the speakers, heavy, thunderous, laying the tape hiss to waste. The boys instinctively slammed their heads up and down. "What the fuck was this? Motorhead? No, this is, it's more like Sabbath, but that definitely wasn't Ozzy on the mic. The guy sounded like an American."

• 8:17Jake Brennan?

  Teddy saw the excitement in their eyes. Saw that they were having that full-body chills reaction to hearing something for the first time that only kids of a certain age and suggestibility are capable of having. Teddy took in their reaction and breathed it in, really tried to absorb it in hopes that it would awaken some sort of long dormant feeling that he'd lost possession of years ago. And then, he exhaled. "Hear that? That's doom. And that hiss you're hearing too, that tape hiss? That's the tape breathing. That's, that's how you know it's alive. Never been pressed, never been released, buried for more than a decade.

• 9:01Jake Brennan?

  Only those who know, know about this." I know what you're about to ask me. "What's the name of the band, right?" Check it out. Teddy just pointed at the gold chain hanging around his neck. Teddy laughed, and as he did, he arched his head back, stretching out the leathery skin of his neck. And the boys could swear they saw his blue eyes turn red. "Nah, man," Teddy said. "This," he pointed at the gold chain again. And this time, the boys heard a sound like a thunderclap, an explosion. A billboard, all fiery red and blazing hot, seared into the back of their skulls. A billboard which read, "Teddy Pentagram." Teddy kept talking.

• 9:45Jake Brennan?

  "You haven't heard of the band Pentagram, have you? No one has, but they've been around for a while, just like their namesake, the pentagram, the five-pointed star. That's been around longer than Christ. The Egyptians carved it into their tombs. The Greeks used it as a secret handshake. One Greek in particular called it the mark of perfection. One line, five points. You learned about the golden ratio in school yet? Well, anyway, I'm talking about protection, order, virtue." From the tinny speakers, Pentagram's guitarist lit into a solo so fuzzed out, it sounded like the boombox was melting. Now, when you flip it upside down, the pentagram, all that order and virtue shit, it goes out

• 10:30Jake Brennan?

  the window. Teddy then took his gold chain between two nicotine-stained fingers and demonstrated what he was talking about. Just like that, you've got the devil's pitchfork, Satan's horns, not protection, damnation.

• 10:45Jake Brennan?

  He went on. Now Bobby Liebling didn't know all that back in 1971 on Halloween night when he was sitting in the basement of his parents' house in Alexandria, Virginia. He was just getting stoned out of his gourd, passing a joint back and forth with his friend Jeff, trying to ignore all the neighborhood kiddies as they went door to door with their pillowcases overflowing with that night's loot. But you two need to understand that Bobby Liebling was 18 years old, not much older than you guys, and just like you guys, he was chasing a heavy sound. He was sitting there on the pullout sofa, listening to his favorite band, Blue Cheer, at an ear blistering volume. You know summertime blues, I'm not talking about The Who, and I don't mean Eddie Cochran neither.

• 11:26Jake Brennan?

  Bobby and Jeff wanted to start their own band, and their one guiding principle was that they could be louder and heavier than Blue Cheer. Which wasn't exactly in the cards for Bobby, seeing as his father worked for Lyndon Johnson, Richard Nixon, and Gerald fucking Ford. They called Bobby Liebling's dad Little Kissinger. Swear to fucking god. But while his dad was stamping out his Winstons and ashtrays at the Pentagon, his son Bobby was dropping acid on his tongue. Actually, according to Bobby, he dropped acid directly onto his eyeballs. At the mention of this, the two metalheads shared a glance, somewhere between horror and fascination.

• 12:09Jake Brennan?

  Teddy brought his voice down to a whisper. This was back when LSD was legal. Back when a dropper full of that shit would blow the cobwebs out of your brain. Your mind would get so warped, you'd create people out of whole cloth and have conversations with them. And it wasn't long after that that Bobby got himself acquainted with the needle. My point is, Bobby Liebling was not his old man. Bobby Liebling wasn't born to be a conformist, suit and tie, shaking hands with the leaders of the free world, fuck that. Bobby was put on this earth to make a racket, to rattle the minds of others the way that his own mind had been rattled.

• 12:50Jake Brennan?

  Now, just exactly how do you do that in the late 1960s and early 70s? You know, you've read the books, you start a fucking rock and roll band, and I don't have to tell you this.

• 13:05Jake Brennan?

  But when Bobby Liebling started his band, it was faced with the same question that every guy who ever picked up guitars asked themselves. What am I gonna call my band? What do I choose? What name conveys how the music I'm going to make sounds?

• 13:19Jake Brennan?

  Well, for Bobby, the answer came to him very quickly.

• 13:23Jake Brennan?

  It was what all the suburban housewives were scared of at the time. Housewives like his own mother. They were haunted by images of Crazy Charlie Manson walking into court with those pinball eyes and with that big X carved into the flesh of his forehead.

• 13:38Jake Brennan?

  Suburban moms didn't just know about Manson. They listened to Sammy Davis Jr., man. They read The Enquirer. They knew about Anton LaVey and his book, The Satanic Bible. It was like their worst nightmares were coming true. In this symbol, the pentagram, the one right there on the cover of Anton LaVey's book, Bobby knew that that was the key that unlocked this other dimension. A dimension that the squares always thought never existed, but was now beginning to break through the fabric of reality as they knew it. This was what Bobby Liebling wanted his music to do. Pierce the veil. But again, just like the two of you, Bobby was young at the time he named his band Pentagram. And when you're young, you think you got the world by the balls.

• 14:23Jake Brennan?

  You think that any decision you make can somehow be unmade down the line if things get fucked.

• 14:30Jake Brennan?

  The thing about the pentagram, however, you draw that star one way, you keep the demons out. But you draw it the other way? Well, you let them in.

• 15:07Speaker 05

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• 15:35Jake 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.

• 16:06Speaker 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.

• 16:17Speaker 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.

• 16:33Speaker 06

  Hear the full conversation wherever you get your podcasts.

• 16:42Jake Brennan?

  As Teddy hit eject on the boombox and flipped over the tape, the two boys couldn't help but focus on his singular, long fingernail sticking out conspicuously from his pinky. And then there was the skull ring on the next finger over where some men would wear a wedding ring. But Teddy didn't strike them as the marrying type. Here, flanked on one side by a Sony receiver with a busted volume knob and on the other by a Morantz that no longer lit up powder blue when you flipped the power switch, Teddy was in his element. He pressed play, and once again, the sound of the greatest metal band the boys had never heard seemed to suck all the air from the room. Their feet felt like they were glued to the floor.

• 17:25Jake Brennan?

  And Teddy, Teddy almost appeared to be lit from below as he continued to tell the tragic tale of Bobby Liebling and Pentagram.

• 17:37Jake Brennan?

  There's always demons, man. And the demons were kept at bay for a while, but only briefly. You see, at first Bobby couldn't stick to the name. He probably knew deep down inside of himself that there was something wrong with it, that it would do him more harm than good in the long run.

• 17:55Jake Brennan?

  So for a short period of time, he called the band Macabre. And they released one single in 1972, this song called "Be Forewarned." What a title, right? It's almost like he was talking to himself, you know? But like most great artists, Bobby Liebling couldn't take his own advice. And the pentagram's pull, its power, it would not be denied. And so Bobby, with his friend Jeff on drums, Greg Mayne on bass, and Vincent McAllister on guitar, committed to that ancient symbol, and they committed to that cursed name. Pentagram, the band, was now a thing. And this is at the very same time that Bobby's hometown Alexandria, Virginia, that bedroom community just outside the nation's capital

• 18:37Jake Brennan?

  where his old man, Little Kissinger, was holed up doing god knows what with the Secretary of Defense. It was here that the demons began to make their playground. And it was here that the bodies began to pile up. The bodies of women specifically. A high school junior found in a ravine with an ice pick jammed in her skull. An English teacher who had been slashed with a knife well over 100 times. And an 18-year-old, a switchboard operator at the FBI, who was found murdered with a pair of scissors in her apartment. These are only a few of the many murders in Alexandria, Virginia, in the 1970s that are still unsolved to this day. Murders and cases that are as cold as the February wind whipping off the Potomac.

• 19:25Jake Brennan?

  Teddy paused to let this information sink in. The two metalheads just sat there, listening, waiting for more. And Teddy went on.

• 19:35Jake Brennan?

  And when Bobby decided to call his band Pentagram for good, the demons rounded the corner and zeroed in.

• 19:42Jake Brennan?

  The curse first struck in December of 1975. This is right around the time that the band Kiss was turning into this phenomenon. A bunch of clowns in makeup, right? Wrong. Kiss. K-I-S-S. Knights in Satan's Service. Sure, the band denied that that was even a thing, and they laughed at it. They said how stupid knights in Satan's service, but of course, that's what Satan's knights would say. They'd do anything to shield the very existence of their master. And before too long, Satan's knights came to Alexandria, just as the demons had before them. Only they came to make an unholy pact with Pentagram, right there in Bobby Liebling's parents' basement. Literally. Let me back up for a second.

• 20:28Jake Brennan?

  Pentagram's first manager, this guy named Gordon Fletcher, he was connected. And one of those connections was to Kiss. Now, look, I always thought that band was a fucking joke, but whatever. The point is, they were huge at the time, super big deal. And so Gordon Fletcher convinced Kiss's manager to send Gene Simmons and Paul Stanley over to Alexandria to hear Pentagram play. The idea was that Kiss would take Pentagram on the road and boost their profile, kinda like they did with Judas Priest later on.

• 21:00Jake Brennan?

  But from the jump, this whole meet and greet was fucked. Greg and Vincent, that's Pentagram's bassist and guitar player, they had these crummy jobs as janitors somewhere in town. And seeing that they were struggling musicians, starving artists, so to speak, they had no car, which meant that they hitchhiked to work every day. And this day was no exception. This most important of days for the career of their budding metal band. The day that two knights in the service of Satan, Gene and Paul, were gonna bring Pentagram into their army. Was this done via blood oath? Was there a sacrifice and offering to the Dark Lord? Greg and Vincent had no idea, but you can imagine, their minds fucking wandered, man.

• 21:42Jake Brennan?

  Just like they themselves wandered down the side of the road after they got out of work that day. Just drifting along, their thumbs out, their pride the bitterest of fucking pills to swallow, waiting for someone to take pity and stop to give them a ride. And when they finally arrived at Bobby's place, they were a sweaty mess. And even worse, Gene Simmons and Paul Stanley had been waiting for close to an hour, getting more annoyed by the minute. But Pentagram's private performance for two of the biggest rock stars on the planet, it seemed to put everything right. At least for the brief time while it was happening. They ran through songs like "Forever My Queen," "When The Screams Come," and "Living in a Ram's Head." But Bobby did his best possessed lead singer shtick, and when they were finished, they felt triumphant.

• 22:27Jake Brennan?

  It was only then that they felt the sting of the curse. Paul Stanley was polite enough, tried to let them down easy, but Gene, well, you guys know Gene. He didn't hold back. He said, "You guys call yourselves Pentagram, and yet there's only four of you? You can't make a pentagram with four points? That's just a fucking square." Which is what Bobby, Jeff, Greg, and Vincent were, to Gene Simmons at least. Square. And so Satan's army packed up and left. And there was no blood oath, no deal with the devil. I'm not talking about demons, because unlike the devil, demons didn't make a deal. A curse is not the byproduct of a deal.

• 23:11Jake Brennan?

  And how does one go about lifting a curse when you're unaware of its existence? The two metalheads looked at each other, confused. Teddy didn't care. He went on. So as all of this is happening, Columbia Records comes calling by way of Murray Krugman. Murray Krugman at the time was one of Blue Oyster Cult's managers and producers. And Murray Krugman ponied up cash to bring Pentagram to New York City so that they could record a demo. Murray Krugman brought them to the precipice. These four guys from a basement in Alexandria, Virginia, were now balancing on the edge of the big time. And right then, right there, right then, at that pivotal moment, what did Bobby Liebling do? He tanked the session. He insulted Murray.

• 23:56Jake Brennan?

  He acted like they were making pet sounds or some shit, and he just had to get his vocal perfect just right.

• 24:03Jake Brennan?

  But to Murray, to Columbia, it was just a fucking demo, man. Fast, cheap, but Bobby couldn't let it be. Because something wasn't letting him let it be. Do you understand what I'm saying to you? This story kept playing like a broken record. Pentagram's name was inked on the ledgers of seven different managers in five years' time. Every bridge Bobby crossed went up in flames as quickly as his feet got across it. Now, back in the Middle Ages, way the fuck back. Chivalrous knights would display the pentagram on their shield. Sir Gawain, for one, had it on both his shawl and his shield. Five points for five virtues: courage, honor, kindness, truth, loyalty.

• 24:47Jake Brennan?

  It was meant as protection against demons. But Pentagram, the band? Protection was never in the cards. The only thing Bobby Liebling or anyone else could count on was the always-present sound of doom.

• 25:10Speaker 04

  We'll be right back after this.

• 25:14Speaker 01

  OnDeck is built to back small businesses like yours. Whether you're buying equipment, expanding your team, or bridging cash flow gaps, OnDeck's loans up to $400,000 help make it happen fast. Rated A+ by the Better Business Bureau and earning thousands of five-star TrustPilot reviews, OnDeck delivers funding you can count on. Apply in minutes at ondeck.com. 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.

• 25:44Jake 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.

• 26:15Speaker 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.

• 26:28Speaker 08

  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.

• 27:02Speaker 06

  Learn more about how Cleveland Clinic and IBM are using AI and quantum computing to revolutionize biomedical research at ibm.com/smarttalks.

• 27:17Jake Brennan?

  Back in the back of the pawn shop, Teddy stared at the two metalheads. And he said, "Close your eyes. I want you to imagine something."

• 27:27Jake Brennan?

  The two boys did as Teddy instructed. Each of them was conscious that they were still standing in the same place in front of the fix-it counter at the far end of the local pawn shop. And they were aware that they had been standing there for far longer than they had ever intended. And it was because Teddy wanted them to do so. There was no denying it. Pentagram was some of the best shit they'd ever heard. But they couldn't leave even if they wanted to. What had begun as this weird guy playing an obscure metal band for them had turned into something else. Now Teddy's obvious enjoyment of their enjoyment, simply listening to his cassette tape, was kind of creepy, to be honest. It was like he was getting off on it or something. And so when he told them to close their eyes and imagine something,

• 28:12Jake Brennan?

  every fiber of their being said it probably wasn't the best idea. But they were powerless to deny it. So they closed their eyes. And Teddy put another pentagram tape in the boombox and hit play. And then he went on, "Now, I want the two of you to imagine you stepping into the cockpit of a single-engine Cessna for the first time. You've only ever been on a plane once in your life, a big commercial jetliner when you went to visit your Aunt Rhonda in San Diego that one time. But now you're behind the wheel of this little Cessna and you're expected to fly it from Virginia all the way to Bogota, Colombia. What is that, 2,000 miles at least?

• 28:53Jake Brennan?

  Yeah, you're good at following instructions, aren't you? But here's the thing, first, you gotta get this big bird up into the sky and then you have to keep it down low, so low, that you stay off everyone's radar. Because your maiden voyage here isn't exactly on the up and up. And that's putting it mildly. Because you, my friend, are headed to Bogota, where you'll load up with kilo upon kilo of the finest Colombian cocaine and then smuggle it back into the United States. And you never met Escobar in person, but from what you've been told, that's a good thing. If you ever did meet him, it would probably be for all the wrong reasons and you'd never walk away alive. The only people you meet down there

• 29:36Jake Brennan?

  are a couple of guys with no names and sunburnt faces standing next to a badly rusted pickup on the side of a windswept cliff, high in the hills. This remote field where a makeshift landing strip waits for you. You land the Cessna somehow, by the grace of God. You literally have no clue how you managed not to run out of gas and drop into the ocean and then you load up quickly before the sun falls below the horizon. The next day, you're handing over the stacks of coke to a distributor in Virginia, and he's handing you stacks of cash in return. I'm talking millions of dollars. Money which you then proceed to burn through. Women, cars, houses, diamond rings and chinchilla coats. Shit,

• 30:18Jake Brennan?

  man, you could have literally set it all on fire and it would have lasted longer. Then, just like that, you go back to your life as the leader of a metal band that no one's ever heard of. But actually, the band isn't there anymore because, you know, dynamics, you're difficult to work with. A band is like being married to three or four people at the same time. There ain't even juice for the squeeze. Pick your reason, it's over. So you, a guy who just ran drugs for Pablo fucking Escobar and lived to tell about it, you are back in your parents' basement, dreaming up Pentagram Mark II.

• 30:53Jake Brennan?

  Now tell me, do you believe that story?

• 30:57Jake Brennan?

  Hey! Open your eyes. The two boys did as Teddy commanded. He looked beyond excited to see them again. Almost as if they'd gone away while their eyes were squeezed tight, and now here they were again, at Teddy's behest. So Teddy went on.

• 31:16Jake Brennan?

  Bobby Liebling said that all that really happened to him. That he piloted a Cessna with Colombian coke in the hold. But this is the same guy who said he dropped acid in his eyeballs. Maybe it was another hallucination in his parents' basement. Remember what I was talking about earlier? Creating people out of whole cloth? Maybe Bobby thought he was staring at a briefcase full of millions, when in reality, he was looking at a shoebox full of Roche clips. But that's not the only explanation. It's all this careless handling of the pentagram business. You invert it, even by accident. Now we're talking corruption of perception. The Wiccans, well, some of them at least, will tell you that the upright star in the pentagram keeps the spirit on the top.

• 32:00Jake Brennan?

  And the five points of the star being air, fire, water, earth, and spirit. But if you flip it upside down, now you've got two points on top. And it doesn't matter which two points or elements they are. You get two different points up top, and that means the spirit has been suppressed below. The beast rises, the spirit sinks. So all this could have led to Bobby seeing Escobar's product at his feet, and also, as he later claimed, to finding himself at a party at George Harrison's house in Maryland, where John Lennon's guitar pick somehow ended up inside his pocket. Now, did Bobby steal that pick? Or was it gifted? Even more important, did George even own a home in Maryland? I don't think so, dude. Fucking Maryland, George Harrison, he's a Beatle.

• 32:46Jake Brennan?

  This is a delusion, okay? But somehow, Bobby Liebling managed to remain in some part of reality long enough to restart Pentagram after the initial few lineups had fallen apart. And fourteen years after the band was formed, Pentagram self-released their debut album in 1985.

• 33:08Jake Brennan?

  But at this point, the doom metal sound that they'd helped define had fallen out of fashion. Quote-unquote "metal," at least to the mall-going, record-buying public, was rats round and round in Motley Crue's Home Sweet Home, not hulking slabs of riff and songs about desecrated bones and maggot-infested flesh. The fucking curse, okay? Back to the curse. The curse was in control. It buried the spirit, and the beast took over, just like when the pentagram flipped. Now, look, it's right here in the album's artwork. Teddy reached down below and pulled out another cassette, this one being the self-titled

• 33:52Jake Brennan?

  Pentagram album from 1985. The two boys looked at it like they'd been staring at a TV screen for hours, like their brains had been sucked out through their noses, almost like the image wasn't registering at all. Teddy pointed to the band's logo, which was, of course, an inverted pentagram. And then he said, "See? The balance has been tipped, and that was Bobby. That was the band. The spirit got buried, and the beast took over."

• 34:40Jake Brennan?

  Hey, guys. Earlier in the episode, our narrator here, Teddy Pentagram, mentioned Bobby Liebling's story about running drugs for Pablo Escobar and the cartels back in the day, and then another one about a party at George Harrison's house and John Lennon's guitar pick. Bobby was a bit of an unreliable narrator, to say the least, and his wild stories don't stop there. In fact, he's got a particularly crazy one about going on a bender with the Rolling Stones in their limo for hours. And we just didn't have time to cover that story here in the full episode, but you can hear it. If you listen to this week's brand-new mini-episode of Disgraceland, which is available only to All-Access members, to become a member, just go to disgracelandpod.com/membership to sign up. All right, now, back to this story about doom metal godfathers, Pentagram.

• 35:28Jake Brennan?

  Teddy rooted around in the pocket of his black jeans, clearly not finding what he was looking for. He pulled his hand out and dropped a couple of quarters on the counter, along with a guitar pick he'd made by cutting a triangle out of a Land O' Lakes butter tub. "Fuck is it?" "Oh yeah, here we go." His hand was back in his pocket, and this time he got it. A tiny metal vial with an even tinier metal chain attached. He unscrewed the cap and carefully tapped on the vial, knocking some white powder out onto that long, pinky fingernail. Then he brought the fingernail up to his nose and inhaled sharply. The boys could see the blue veins in his biceps. His eyes bulged as the nasal pick-me-up took effect.

• 36:13Jake Brennan?

  And he fumbled with another cassette tape, plunked it into the boombox and hit play.

• 36:20Jake Brennan?

  This one definitely sounded like it was Pentagram circa the 1980s. And Teddy was right. It did sound way better on this shitty cassette. Inspired by the music, Teddy continued his story. "Those old Pentagram tapes finally surfaced around the turn of the century. Now, this metal label out of Pennsylvania, Relapse Records, reissued them as a new compilation. Suddenly, a-all the Doom kids were lapping it up. They called Pentagram proto-legends. They called Bobby Liebling the American Ozzy Osbourne. And before long, you even had guys like Hank III, Hank Williams's grandson, playing Pentagram songs as part of his live set. This is where it's supposed to pay off for Bobby Liebling, right?

• 37:04Jake Brennan?

  Where all the years of struggling in the shadows, all the lineup changes, the missed opportunities with Kiss and major labels, all of it worth it because now suddenly everyone wants a piece? But you guys know better than that. You know that a curse doesn't just up and quit. The beast doesn't just let go. And like those demons down in Alexandria, they never went anywhere. All those cold cases there in Bobby's hometown, they're still unsolved. And the air there is still unsettled. And for Bobby, his life continued to be just as unsettled." Only a few years back, in 2017, he was kicked out of his own band. Some say he was admitted to a hospital, when in fact, he had been arrested,

• 37:49Jake Brennan?

  charged with first-degree assault and physical abuse of a vulnerable adult. Word was he pushed his 87-year-old mother down the stairs, and that got Bobby 18 months in prison and three years probation. And then, earlier this year, 2025, with Bobby back in the lineup, back in the saddle at 7 fucking something years old, Pentagram, incredibly, was once again riding a wave of delayed goodwill and opportunity. They were getting ready to embark on their very first tour of Australia and New Zealand. But just weeks before, the promoter pulled the plug. On the entire tour, Sydney, Melbourne, Perth, Auckland, all of it, this whole thing was suddenly on hiatus.

• 38:32Jake Brennan?

  Pentagram was being denied the world stage some 50 years after they first began. And why? Quote-unquote "current allegations." So you gotta assume they're talking about the thing with Bobby and his mom, I guess, I don't know. Though, why would a conviction from years earlier for which he'd already done his time, one would presume? Why, why would that be described as a "current allegation"?

• 38:54Jake Brennan?

  Could the "current allegation" be the very thing I've been talking to you guys about this entire time? The allegation of Bobby Liebling's associations with that upside-down star? The curse? The beast?

• 39:09Jake Brennan?

  Teddy suddenly hits stop on the boombox, and a shocking silence replaced the music. But there, seeping in ever so slightly, was the tape hiss.

• 39:22Jake Brennan?

  The sound slowly grew louder, even though the tape was no longer playing. And the boys... Wait. Wait. Where were those two teenage boys? The boys who had been here the whole time? The ones who couldn't leave? Who had been held captive by Teddy's otherworldly pull?

• 39:43Jake Brennan?

  Hey, you. Yeah, you, the one listening to me talk right now. What teenage boys do you think you're referring to? There's no one else here. It's just you and me. You're the one who's been standing here the whole time. You nodded your head when I said that vinyl sucked. You closed your eyes and then opened them back up when I told you to. You remember, right? I'm dead fucking serious. You thought you were listening to a story? You thought you were one step removed? Like you could eavesdrop from the safety of your car or your kitchen or wherever it is you're listening to this right now? Nah, man. You weren't listening to a story. You've been listening to the tape.

• 40:29Jake Brennan?

  And once you hear it, you can't unhear it. It's inside you, just like it's inside Bobby. Just like it's inside me. You can call it a curse. You can call it the beast. You could even call it a disgrace.

• 40:48Jake Brennan?

  I'm Jake Brennan and this is DisgraceLand.

• 41:09Jake Brennan?

  All right, thanks for hanging out with us and our very trusty narrator here, Teddy Pentagram, for our pentagram story. Question of the week. You know, we all had a Teddy Pentagram in our lives. Someone who shepherded us to the great music. Who was that for you? Was it an older sibling, an uncle? Was it someone at a record store, some cool dude in a band? You know, your older sister? Who, who, let me know. Who, who was your musical sherpa who opened up the world of great rock and roll, punk rock, jazz, whatever it was who turned you on? 617-906-6638, voicemail and text, and you might hear your answer on the after-party bonus episode coming up right after this. Hit me up at DisgraceLandPod on the socials. All right, here comes some credits.

• 41:55Jake Brennan?

  Disgrace Land 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 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. Rate and review the show and follow us on Instagram, TikTok, Twitter, and Facebook @disgracelandpod and on YouTube at youtube.com/atdisgracelandpod. Rockerola.

• 42:32Speaker 06

  He's a bad, bad man.

• 42:35Jake Brennan?

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• 43:05Speaker 09

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• 43:36Speaker 10

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