DISGRACELAND Bonus Episode: Musical Sherpas and Spooky Sounds

Podcast: DISGRACELAND
Date: October 9, 2025
Host: Jake Brennan (Double Elvis Productions)

Overview

In this interactive "afterparty" bonus episode, Jake Brennan explores the theme of musical discovery—paying tribute to the “musical sherpas” who turn young fans on to life-changing music, and bemoaning the shift from analog, word-of-mouth recommendations to AI-generated playlists. The episode is filled with listener stories about their own musical mentors, deep dives into Halloween-appropriate tracks, a critique of Rolling Stone’s “most terrifying” songs list, and a call for spooky music recommendations just in time for the season. Listeners are encouraged to participate in the ongoing conversation through calls, texts, and emails.

Main Segments & Highlights

1. The Death of the Musical Sherpa (02:01–09:50)

• Jake’s Reflection: Jake laments the cultural shift from learning about music via older siblings, “cool dudes at the record store,” or friends, to receiving recommendations from algorithms and AI-powered apps like Spotify x ChatGPT.
  • “My, how far we have come from those days of searching out the cool dude at the record store to turn you on to the music that you needed to know about. Instead of stoned record store clerks... we now have artificial intelligence BOT turning us on to new music. It was always gonna come to this... All that will soon be completely gone. Dead ritual from the past…” (04:12)
• He sets up the episode’s “Question of the Week”: Who turned you on to music as a kid? Listener responses follow in the show.

2. Halloween Playlist: Deep Cuts & Vibes (09:51–14:50)

• Jake’s Mix: Jake shares his carefully curated Halloween/fall party playlist, emphasizing Donnie Darko dinner party vibes, not haunted house kitsch.
  • Playlist includes: “Diamonds and Rust” (Judas Priest), “The Killing Moon” (Echo & The Bunnymen), “Gimme Danger” (The Stooges), “Don’t Fear the Reaper” (Blue Öyster Cult), “Fascination Street” (The Cure), “My Girlfriend is a Witch” (October Country), “Murder in the Red Barn” (Tom Waits), “Werewolves of London” (Warren Zevon), "Evil Woman" (Black Sabbath), and more.
  • “I want to look at this great Halloween music from the perspective of a list that I found on Rolling Stone... and line it up against my mix.” (12:14)

3. Rolling Stone’s 25 Terrifying Songs – A Critical Look (14:51–21:23)

• Jake vs. Rolling Stone:
  • Critiques and discusses selections from Rolling Stone’s "25 Songs That Are Truly Terrifying" (2019), offering both praise and pushback.
  • Examples:
    • “Murder of the Lawson Family” (Carolina Buddies)—subject appropriately ‘Halloweeny’, but not sonically spooky.
    • “Knoxville Girl” (The Louvin Brothers)—his definitive murder ballad.
      • “If someone asked me what’s a murder ballad, this is the song I’m playing for them.” (17:38)
    • “The End” (The Doors)—thinks “Riders on the Storm” would fit Halloween better.
    • “Avalanche” (Leonard Cohen), “Frankie Teardrop” (Suicide), "Nebraska" (Bruce Springsteen), “Down By the Water” (PJ Harvey), “Farmer in the City” (Scott Walker), “Song of Joy” (Nick Cave & The Bad Seeds), “What’s He Building in There?” (Tom Waits).
      • “Oh, Leonard was on a heater with that one. Great tune. Love it. Can't wait to put it on my list.” (18:52)
  • Invitations for listeners to recommend more “spooky music” and fill any gaps in his or Rolling Stone’s lists.

4. Listener Segment: Musical Sherpas & Discovery Stories (23:26–32:41)

Voicemails, Texts, and Emails

• Caller 816: Big brother as first musical sherpa; skate videos in the ’90s as a portal to punk, hip hop, and obscure artists.
  • “We heard about tons of punk and hip hop acts… Just so much great music and stuff you don’t just stumble upon in your day-to-day life… Skate videos… are a great source to this day.” (23:26)
• Jake’s Response: Nostalgic story about ‘borrowing’ Circle Jerks and Bad Brains records from older skater Dan Thomas, who recently tracked Jake down to get them back. Notes the undeniable music curation power of skate culture.
  • “Dan was, of course, a skater… Very eclectic, those skate videos from the ’90s… Great taste.” (24:14)
• Caller 619 (Jeremy): Shoutout to Cliff Cunningham of Social Spit—local record store clerk who turned punks onto great music.
  • “That guy used to basically turn every local punk rocker onto some great, great music… letting them know what to buy.” (25:42)
• Caller 781 (Kelly): Emotional tribute to her late brother, Francis, who got her into Metallica, Led Zeppelin, “all that” through constant jamming and big speakers.
  • “He was a guitarist and so he had like two Marshall half stacks in his room… I just distinctly remember hearing Metallica ‘One,’ that’s the first time I ever heard it from him…” (27:07)
• Text 530: Friend Derek, who “solely responsible” for punk/hardcore exposure, later died under mysterious circumstances.
  • “He also mysteriously disappeared and was found dead in a California desert… His spirit remains close.”
• Text 416: Using “Bop” by Miles Davis as the soundtrack to an Instagram reel after a Jamaica trip, thanks to podcast recommendations.
• Email (Paulie McCracken): Cool Aunt Judy as the family Deadhead and musical confidante.
  • “She was my mom’s little sister, the fun aunt, my favorite person ever. We got along so well because she was so cool and let me do things my mom would not and I could talk to her about anything.”

5. Sports Rant (35:15–35:23)

(Fast segment for sports fans and New Englanders; can be skipped by music heads.)

• Jake’s mea culpa: Admits being wrong about Drake May’s potential and gushes about the New England Patriots’ future.
  • “Listen, it takes a real man to admit when he’s wrong… But I’m here today to tell you flat out that I was wrong… We have a real coach and a real quarterback who can ball out.” (35:15–35:23)

6. Hollywoodland Segment Preview (36:23–38:32)

• Dr. Zeth Lundy teases “Wrap Party” segment on Hollywoodland: the eternal question “Are movies dead?” and Ridley Scott’s claim that only 5% of movies are any good.
  • Zeth’s quick-and-dirty research shows it’s always been thus—the ratio of good-to-bad films historically has remained about the same.
    • “I quickly identified at least about 20 that I thought were great [from 1989], which was a 3% rate… it’s still about the same.” (37:32)
  • Jake encourages listeners to subscribe to Hollywoodland for deep-dive film content.

7. Wrap-up, Next Episodes & Final Call for Spooky Recommendations

(43:02–End)

• Upcoming Episodes:
  • Pentagram full episode (out now)
  • Rewind episodes: The Cramps and Brandon Lee/The Crow
  • Next week: Houdini, featuring the Red Hot Chili Peppers
• Call to Action: Share “spooky, evil, dark” music for Halloween playlist.
  • “Which evil, spooky, dark… musical madness are you digging into in October? I want to know. I want to update my playlist with your recommendations.” (42:40)
• Community Vibe: DISGRACELAND is more than a podcast—it's “a community of the obsessed.” Jake thanks listeners and reiterates that listener participation is what makes the show work.

Notable Quotes

• “The thrill of discovery, that sense of danger, that feeling of being special… All that will soon be completely gone. Dead ritual from the past…” – Jake Brennan (04:12)
• “If someone asked me what’s a murder ballad, this is the song I’m playing for them.” (re: The Louvin Brothers’ “Knoxville Girl”) – Jake Brennan (17:38)
• “He was a guitarist and so he had like two Marshall half stacks in his room ... I just distinctly remember hearing Metallica ‘One,’ that’s the first time I ever heard it from him…” – Kelly (Caller, 27:07)
• “We heard about tons of punk and hip hop acts… Just so much great music and stuff you don’t just stumble upon in your day-to-day life… Skate videos… are a great source to this day.” – Caller 816 (23:26)
• “She was my mom’s little sister, the fun aunt… and I could talk to her about anything.” – Paulie McCracken (via email)

Timestamps for Key Segments

• 02:01 – Show intro & theme: AI vs. “vinyl sherpas”
• 09:51 – Halloween party playlist rundown
• 14:51 – Rolling Stone's most “terrifying” songs (and critique)
• 23:26 – Listener stories: musical mentors (voicemails, texts, emails)
• 35:15 – Sports rant (Patriots, Drake May)
• 36:23 – Hollywoodland preview with Dr. Zeth Lundy
• 42:40 – Final call for listener participation, community wrap-up

Tone & Style

True to DISGRACELAND’s signature style, this bonus episode is fast-talking, witty, referential, and casual—but deeply reverent for both music history and the “weirdos” who keep its secret threads alive. Jake’s banter is self-deprecating (“I’m a dick. I admit it.”), engaging, and always laced with nostalgia for the tactile, social rituals of music fandom. The show radiates communal energy, with listeners and host forming a virtual family of music obsessives.

Takeaways

• Jake Brennan and his audience treasure the lost art of the “musical sherpa.”
• Halloween is more than horror sound effects—it's full of mood, nuance, and playlists that blend deep cuts, classics, and personal vibes.
• Listener participation is central—DISGRACELAND thrives on stories about discovery, loss, and the music that links them all together.
• More spooky music is always welcome. Call or text (617-906-6638) to share what’s haunting your speakers this October.

Find show notes and sources at: www.disgracelandpod.com
To submit, email: disgracelandpod@gmail.com or call/text 617-906-6638
All Access content & exclusive convos: www.disgracelandpod.com/membership