DISGRACELAND: Pentagram – Demons, Curses, and Doom

Host: Jake Brennan
Date: October 7, 2025
Episode Theme:
A dark, myth-soaked journey into the legend of Bobby Liebling and his band Pentagram—the “greatest metal band that never was.” Through the lens of a mysterious narrator, the episode explores curses, doomed creativity, suburban malevolence, and the thin line between heavy music, mayhem, and hallucination.

Overview

This episode of DISGRACELAND dives into the shadowy world of Pentagram, offering both oral history and narrative drama. It paints Pentagram as a foundational doom metal band cursed from inception, hamstrung by missed opportunities, addiction, and Bobby Liebling’s spectral personal demons. Melding true(ish) events, urban legends, and sinister local crime, Jake Brennan (as both host and narrator, "Teddy Pentagram") immerses you in a fog of nostalgia, myth, and plausible hallucination—ultimately reflecting on how obsession, mythmaking, and music history become indistinguishable from one another.

Key Discussion Points & Insights

1. The Pentagram: Symbol and Omen

[02:31 – 05:30]

• Inversion and myth: The story starts with a pawn shop scene, where a mysterious character named Teddy introduces two teenage metalheads to a special, unlabeled cassette tape. The pentagram as a symbol is examined: upright as protection, inverted as damnation.
• Quote:

  "The pentagram, the five pointed star that’s been around longer than Christ. ... When you flip it upside down ... you got the devil’s pitchfork, Satan’s horns. Not protection—damnation."
  (Teddy, 06:14)

2. The Birth of Pentagram & the Underworld of Alexandria, Virginia

[07:00 – 13:00]

• Bobby Liebling’s origins: Raised in a politically connected family, Bobby rebels through drugs and heavy music. Band name inspired by suburban fears of Satanism, pentagrams, and pop culture panic.
• The curse is set: Drawing the pentagram one way protects you; invert it, and “you let [the demons] in.”
• Dark local history: Pentagram’s rise is juxtaposed with a surge in brutal, unsolved murders in ‘70s Alexandria, suggesting a malevolent synergy.

3. Near-Fame Encounters and the Curse in Action

[17:23 – 23:30]

• KISS connection: Pentagram nearly signs a deal following an audition for Gene Simmons and Paul Stanley, but are dismissed for only having four members (“You can’t make a pentagram with four points. That’s just a fucking square.” – Gene Simmons, paraphrased by Teddy, 20:47).
• Missed opportunity with Columbia Records: Bobby tanks a crucial demo session in New York, derailing another chance at success.

4. Bobby Liebling’s Myth-Making & Drug-Fueled Delusions

[27:12 – 33:00]

• Drug smuggling stories: Teddy recounts Liebling's claim of piloting a Cessna full of cocaine for Pablo Escobar—a likely hallucinated or mythologized event.

• Reliability of memory: Reflects the blurred line between Bobby’s hallucinations, legendary claims (e.g., John Lennon’s guitar pick, a party at George Harrison’s house), and sad reality.

• Quote:

  “Maybe Bobby thought he was staring at a briefcase full of millions, when in reality he was looking at a shoebox full of roach clips. … This is a delusion. Okay?”
  (Teddy, 31:30)

5. The Doom Metal Legacy and the Triumph of the Curse

[33:01 – 39:00]

• Later years: Pentagram self-releases a doom metal album in 1985, years too late for commercial impact, yet they become underground legends (“proto legends,” “American Ozzy Osbourne”).
• Relapse Records reissue: A new generation discovers Pentagram decades after their prime, but Bobby's troubles continue.
• The curse persists: Even as recognition finally comes, Bobby is kicked out of his own band, imprisoned for assaulting his elderly mother, and a comeback tour is canceled due to “current allegations.”
• Quote:

  “The curse was in control. It buried the spirit and the beast took over—just like when the pentagram flipped.”
  (Teddy, 36:44)

6. Meta-Narrative Twist—The Listener as Participant

[39:12 – 41:30]

• In a final meta turn, the narrator turns directly to the listener, implying that listening to the tale itself invokes the same pentagram curse, drawing you in as complicit—a story that sticks to you.

• Quote:

  “You thought you were listening to a story. ... but nah, man, you weren’t listening to a story. You’ve been listening to the tape. 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.”
  (Teddy/Jake Brennan, 40:43)

Notable Quotes & Memorable Moments

• On the legend:

  “There’s always demons, man. And the demons were kept at bay for a while, but only briefly.” (Teddy, 17:30)

• On Pentagram’s curse:

  “Every bridge Bobby crossed went up in flames as quickly as his feet got across it.” (Teddy, 22:43)

• On the significance of the name:

  “Housewives like his own mother. ... They were haunted by images of crazy Charlie Manson ... 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.” (Teddy, approx. 11:34)

• Meta-narrative closer:

  “What teenage boy do you think you’re referring to? There’s no one else here. It’s just you and me. ... You thought you were listening to a story. ... You’ve been listening to the tape.” (Teddy/Jake Brennan, 40:43)

Timestamps for Key Segments

• [02:31] – Introduction to the pentagram and pawnshop scene
• [06:14] – Symbolism: upright vs. inverted pentagram
• [13:00] – Bobby Liebling’s origins and early rebellion
• [17:23] – The rise of Pentagram, murders in Alexandria
• [20:47] – Rebuffed by Gene Simmons and KISS
• [22:43] – Bobby’s demo sabotage and mounting career calamities
• [27:12] – Bobby’s tall drug tales and hallucinated memories
• [31:30] – Commentary on hallucination/reality
• [36:44] – Pentagram's curse and its persistence
• [39:12] – Listener drawn into the story/cursed
• [40:43] – Episode's meta-narrative conclusion

Tone & Style

The episode is dense, atmospheric, and tinged with the melodrama of heavy metal, blending fiction and fact. Jake Brennan channels a gravelly, conspiratorial narrator (“Teddy Pentagram”), shifting between sardonic, mythic, and deeply sympathetic tones.

Takeaways for New Listeners

• Myth vs. reality: The history of Pentagram and Bobby Liebling is a tangle of verifiable events, unreliable narration, and urban legend—mirroring both the band’s musical legacy and the genre’s occult reputation.
• The curse as metaphor: The “curse” dogging Pentagram is an amalgam of societal paranoia, addiction, and the repetitive cycles that doom marginalized genius to obscurity.
• Immersive storytelling: DISGRACELAND uses sound design, direct address, and script to pull listeners into the myth—ultimately blurring the line between observer and participant.

For more stories and references, visit disgracelandpod.com or join Disgraceland All Access for expanded material, including the Bobby Liebling/Rolling Stones limo story teased in this episode.