Political Beats – Episode 151: Damon Linker / Tom Waits [Part 2]

Date: September 29, 2025
Hosts: Scott Bertram & Jeff Blehar
Guest: Damon Linker (UPenn, Notes from the Middle Ground Substack)
Topic: The second phase of Tom Waits’s career (1983–2011)

Overview

In the second installment of their exhaustive two-part exploration of Tom Waits, Scott, Jeff, and returning guest Damon Linker traverse the avant-garde breakthrough and relentless reinvention that marked Waits’s post-1983 career. Picking up with the transformative Swordfishtrombones, the discussion blends biographical insight (including the profound influence of Kathleen Brennan), detailed musical analysis, and debates over the merits of Waits’s most celebrated—and divisive—late-era works. Favorite albums and songs are chosen, critical themes are unpacked, and the hosts repeatedly underscore both the accessibility and strangeness of what became Waits's defining artistic era.

Key Discussion Points & Insights

Kathleen Brennan and the Artistic Transformation (03:31–09:52)

• Kathleen Brennan’s Influence: Brennan, whom Waits met working on the One from the Heart soundtrack, catalyzed his transformation from genre pastiche (jazz, blues) to genuinely idiosyncratic outsider-art.
• Jeff: “I officially designate Kathleen Brennan to be the anti-Yoko Ono...here’s the opposite. Here’s a person who actually finally becomes what they were always. Now in retrospect, it feels like they were destined to be. And it was just because he found a person who could focus him and maybe challenge him, elevate his work and take him to a new level.” (07:45)

The "Sea Change": Swordfishtrombones (09:52–36:31)

• The formal content finally matches the hobo-outcast aesthetic: “What you hear on Swordfishtrombones and going forward is the form totally matches the content in a way that it never did before.” – Damon (11:47)
• Voice as percussion: Waits’s vocal style becomes integral, near-instrumental.
• Standouts: Underground, Shore Leave, Johnsburg, Illinois, 16 Shells from a Thirty-Ought Six, In the Neighborhood.
• “In the Neighborhood” proffers small-town empathy and a Salvation Army brass feel. – Scott (26:15)
• Album is front-loaded with classics; side two seen as weaker.

The Masterpiece Consensus: Rain Dogs (36:26–56:47)

• Argued as Waits’s apogee; a “dense,” “band” album, global in its textures.
• Mark Ribot’s angular guitar noted as a crucial new color.
• Ballads “Hang Down Your Head,” “Time,” and “Downtown Train” vector toward accessibility without sacrificing artful abrasion.
• “This is a really dense album and I feel like I could have spent another four weeks with it and still not explored or appreciated all the corners that lay inside.” – Scott (44:58)
• Radiohead’s Kid A and Amnesiac take open inspiration ("they all went to heaven in a little rowboat" from “Clap Hands” prefigures "Pyramid Song,” harmonium textures on “Hang Down Your Head”).

Closing the “Trilogy”: Frank’s Wild Years (58:06–74:42)

• A mix of praise and disappointment: “about half a great album...half spinning his wheels.” – Damon (60:15), echoed by Jeff.
• Noteworthy tracks: “Hang On St. Christopher,” “Temptation” (Diana Krall cover cited), “Way Down in the Hole” (immortalized by The Wire), “Cold Cold Ground.”
• Too many fragmentary or undercooked tracks; indulgence with repeated songs/effects.

The Industrial/Avant-Garde Shift: Bone Machine (75:32–96:41)

• Highly rhythmic, abrasive, sometimes unmelodic; critically praised but divisive among hosts.
• “Earth Died Screaming” cited as uniquely terrifying – Damon: “It scares the crap out of me.” (79:07)
• “Dirt in the Ground,” “Who Are You,” “A Little Rain,” and “That Feel” (co-written with Keith Richards) as key ballads within the clangor.
• Noted for cinematic, radio-theater-like use of sound effects and novel instruments (e.g., the self-invented “conundrum” on "In the Coliseum").

The Theatrical/Opera Era: The Black Rider, Alice, Blood Money (97:27–141:50)

• Hosts divided: All agree The Black Rider is the weakest; Alice earns Damon's praise for its ballads, while Scott prefers the earthiness of Blood Money.
• Stage constraints seen as inhibiting Waits’s songwriting vitality. Damon: "Alice is an incredible collection of ballads...but all of the kind of vitality artistically of this second half of his career is gone." (136:45)

The Late-Career Miracle: Mule Variations (103:30–129:54)

• A summative, “warm,” Americana-heavy album marking Waits’s songwriting and arranging at an exceptional late peak.
• “The Mule Variations may well be one of the two best Tom Waits albums ever released.” – Jeff (105:55)
• “Hold On,” “Georgia Lee” (based on a true story), “House Where Nobody Lives,” “Picture in a Frame,” “Take it With Me,” and “Come On Up to the House” highlighted for their emotional clarity and craft.

The Outtakes Collection: Orphans: Brawlers, Bawlers & Bastards (157:26–162:14)

• Compared favorably to Dylan’s Bootleg Series; surprising strength and variety, especially Ballers disc (“shut up and eat your ballads”).
• Many outtakes as good as official album tracks; “Sea of Love” a particular highlight.

The Final Chapter: Real Gone and Bad As Me (142:41–181:21)

• Real Gone: Piano-less, percussive, sometimes grating and overlong; “charismatic in their ugliness.” (147:48–149:45)
• Bad As Me: A return to focused songcraft; brevity helps; aptly sums up Waits’s career if it becomes his swansong.
• “There’s some joy here that is not always evident on Tom Waits record...Get Lost is more joyful than funny though.” – Scott (171:06)
• “Last Leaf” (feat. Keith Richards), “New Year’s Eve” seen as especially moving sign-offs.

Notable Quotes & Memorable Moments

• On Waits’s Transformation:
  “It’s like all of a sudden he becomes the man he was always supposed to be, maybe was searching for, but now he’s finally found his place. And his place is as weird and outsider a place as has ever existed in American rock and roll.” – Jeff (05:25)

• On “In the Neighborhood”:
  “Under different circumstances, you could see this being a Billy Joel song like ‘Allentown’ or a Randy Newman song...instead of Tom Waits doing it in a very different way musically, in a very different arrangement, with that same sort of empathy toward the people he’s describing.” – Scott (26:15)

• On Rain Dogs:
  “If I had to make a list of my top 10 or 20 albums of all time, this would be in very serious contention to make that list.” – Damon (41:56)

• On Waits’s Legacy:
  “He can write songs that you feel were, you know, were made a hundred years ago, a thousand years ago that you kind of unearthed in some archive of primordial music.” – Damon (114:49)

• On the Late-Career “Warmth”:
  “This, in some ways, to me, is almost like the climax of Tom Waits’s career. There are many albums that come further, and a lot of really good ones. But this, to me, was a shock to have come out when I was a kid...wow, well, this guy from 1973 has still got it.” – Jeff (129:24)

• On Waits & Cultural Obliquity:
  “As I. I said right back at the beginning of the first episode...when I encountered him, it was like having a door kicked open in my mind. I just didn’t know that there were worlds like this. There was music like this. That weirdness could be made to work, could be harnessed.” – Jeff (181:24)

Timestamps for Important Album Discussions

• Kathleen Brennan’s Influence: 03:31–09:52
• Swordfishtrombones: 09:52–36:31
• Rain Dogs: 36:26–56:47
• Frank’s Wild Years: 58:06–74:42
• Bone Machine: 75:32–96:41
• The Black Rider, Alice, Blood Money: 97:27–141:50
• Mule Variations: 103:30–129:54
• Orphans Box Set: 157:26–164:41
• Real Gone, Bad As Me: 142:41–181:21

Final Consensus — Albums & Essential Songs (184:27–189:25)

Albums to Own:

• Rain Dogs
• Mule Variations

Songs to Hear (Selections from All Three):

• “In the Neighborhood”
• “Clap Hands”
• “Jockey Full of Bourbon”
• “Time”
• “A Little Rain”
• “Georgia Lee”
• “Picture in a Frame”
• “Last Leaf”
• “16 Shells from a Thirty-Ought Six”
• “Sea of Love” (from Orphans)
• “I’m Still Here” (from Alice)

Summary Tone & Style

The dialogue is lively, deeply affectionate toward Waits’s art, and rich with both musical and biographical context. The hosts blend dry humor, moments of critical disagreement, and a shared awe for Waits’s capacity to innovate without losing emotional resonance. Their reverence never dulls the discussion’s energy—a welcoming window into a daunting but rewarding catalog.

For Newcomers

This episode provides an expert’s immersion into Tom Waits’s post-1983 work, arguing for the accessibility, strangeness, and emotional depth of his “weird years.” The recommended albums (Rain Dogs, Mule Variations) and songs make a perfect entry point; deep cuts and box set gems offer rewards for further exploration.

[“You gotta help me keep the devil way down in the hole...” (68:04)]