Political Beats – Episode 150: Damon Linker / Tom Waits [Part 1]

Release Date: September 4, 2025
Host(s): Scott Bertram and Jeff Blehar
Guest: Damon Linker (Senior Lecturer, University of Pennsylvania, author of Notes from the Middle Ground)

Main Theme & Purpose

This episode of Political Beats delves deep into the early career of the singular, gravel-voiced songwriter Tom Waits, exploring his evolution from jazzy, piano-based troubadour to the literary, enigmatic outsiders’ poet of the American underbelly. Hosts Scott Bertram and Jeff Blehar, alongside guest Damon Linker, discuss why Waits matters, how his artistry and persona developed, and which albums and songs define the first phase of his prolific career (1973–1982). The conversation combines music commentary and personal anecdotes with sharp humor and critical engagement, aiming both to enlighten longtime fans and create accessible entry points for Tom Waits newcomers.

Episode Structure & Key Segments

Intro & Housekeeping
[00:07-03:38]
The hosts discuss the podcast's reach, Patreon supporters, and introduce their guest, Damon Linker. Linker describes his political and philosophical journey and introduces his Substack, "Notes from the Middle Ground."

I. Discovering Tom Waits: Personal Histories

[05:12-24:28]

• Damon Linker’s Origin Story

  • Exposed to Waits as a child by his father—Small Change became a formative influence.
  • Captivated by Waits’ intensely charismatic blend of “ugliness with great beauty and pathos.”
  • “It sounded like you could hear him bleeding from an open wound coming from the speakers. And this combination of ugliness with great beauty and pathos, even to my seven year old ears, I just found incredibly charismatic.” —Damon [07:18]

• Jeff Blehar’s Entry Point

  • Discovered Waits starting with the avant-garde era (Rain Dogs).
  • Initially repelled by the jarring differences from more mainstream artists, but eventually hooked by the persona and art-rock inventiveness.
  • “It was a baptism, just a cold baptism...I became an art rocker...Tom Waits was the guy who really explained to me musically that there was a world going on underground.” —Jeff [14:16]

• Scott Bertram’s Perspective as a Newcomer

  • Unfamiliar with Waits beyond the reputation and a couple covers, Bertram approaches the discography with curiosity and skepticism.
  • Compares Waits in his mind with Nick Cave and John Hiatt: “Both guys who ended up writing a ton of great songs that ended up being covered by other artists through the years.” —Scott [20:29]
  • Finds Waits a challenging yet intriguing listen—some songs “brilliant,” others “I can’t rush to skip even after three or four or five full spins...” [20:29]

II. Tom Waits the Performer, Persona, and Outsider Poet

[24:28-28:59]

• Jeff emphasizes Waits’ role as a stage actor and adopter of personae, likening him to David Bowie for the way he “decided to make a break” and reconstruct his musical identity.
• Waits as an “engine of creativity” who connects to the “weird left corners and back channels in popular music.”
• “He brings stage props to his shows because he loves making it a production. He's always been about a certain performance in his music.” —Jeff [43:28]

III. Early Jazz-Lounge Years: Album-by-Album Breakdown

1. Closing Time (1973)

[28:59-43:28]

• Waits’ debut, an outlier among the Laurel Canyon Asylum set.
• Damon: Celebrates the “incredibly beautiful ballads,” especially “Old 55,” “Martha,” “Grapefruit Moon," and the wordless title track.
  • “I have a mix on Spotify with 43 ballads from Waits's entire career…almost every album has a few…that I think are some of the most beautiful songs ever written.” —Damon [29:48]
• Scott: Highlights the shifting influences—Gordon Lightfoot, Dylan, country rock. Praises cuts like “Rosie” and “Ice Cream Man.”
• Jeff: Notes Waits’ early attempts to “try on new skins” and predicts his lean into what will become his artistic strengths.
  • “He can sing, but he cannot be pretty. He's always going to have that sort of gutty kind of bluesy authenticity.” —Jeff [43:28]

2. The Heart of Saturday Night (1974)

[45:28-57:17]

• More picaresque, literary; Waits’ persona moves further toward boozy, late-night chronicler.
• Jeff: “The watchword…is piano-based lounge jazz…songs get a little more detailed about all these picaresque details.”
• Scott: Responds positively to much of the album, especially ballads (“Please Call Me Baby”), while disliking the more overtly talk-sung tracks like “Diamonds on My Windshield.”
  • Notable quote: “If I exercise my devils, my angels might leave too. And when they leave, they’re so hard to find.” —Scott [51:55]
• Damon: Praises the “classic” “San Diego Serenade” and “Shiver Me Timbers” but calls the record “a recapitulation” that doesn’t match the debut’s freshness.

3. Nighthawks at the Diner (1975)

[59:04-68:42]

• A studio/live hybrid, heavy on beat poetry and stage patter.
• Jeff defends its “phenomenon of sound” and party atmosphere; adores Waits’ patter and “Better Off Without a Wife.”
• Damon and Scott (fiercely) disagree—Scott: “I am allergic to the very concept of this record…the beat poetry performing, the speaking, not singing...”
  • “If you like someone just sort of reading ‘Stratocasters slung over Burgermeister beer guts and swizzle stick legs jackknife over naugahide stools’ over a baseline, then Nighthawks…is the album for you.” —Scott [65:40]

4. Small Change (1976)

[74:18-96:56]

• An artistic pivotal point: Waits debuts his infamous, ruined croak.
• Damon’s sentimental favorite (“close to me...managed to invoke a line from Tom Traubert's Blues in my father's obituary").
  • “It is truly shocking the way he sings... It's as if they did a movie musical of Eugene O’Neill’s The Iceman Cometh.” —Damon [76:21]
• Jeff: Sees Waits as an actor playing a broken man at the end of his rope. “Step Right Up” is lauded as comedic genius.
• Scott: Unreservedly loves “Step Right Up” but finds the hobo persona off-putting overall, craving more musicality or narrative distance.

5. Foreign Affairs (1977)

[97:51-107:09]

• More cinematic, jazz-noir, story-songs.
• Scott: Prefers this new direction, especially “I Never Talk to Strangers” (duet with Bette Midler) and “Sight for Sore Eyes.”
• Damon: Feels it’s Waits “spinning his wheels,” beginning to succumb to self-parody.

6. Blue Valentine (1978)

[109:13-124:25]

• Raymond Chandler via song—grittier, with blues influences and richer stories.
• Jeff: Praises “Somewhere” and “Christmas Card from a Hooker in Minneapolis.”
• Damon: Points to “Kentucky Avenue” as a rare, moving twist song: “a trap door falling out from under you.”
• Scott: Declares this his favorite Waits album so far, connecting emotionally with its cinematic, noir storytelling, especially on “Red Shoes by the Drugstore,” “Sweet Little Bullet,” and the closing “Blue Valentines.”

7. One from the Heart (1982)

[129:01-134:52]

• Soundtrack for Coppola’s Las Vegas romance, featuring Crystal Gale.
• Damon: “He was starting to feel like he was in a rut and that he wanted to do something different…But the honest truth is he did a pretty good job of it.”
• Scott: Highlights "Old Boyfriends" for its detail: “Why do you keep turning them into old boyfriends?”

8. Heartattack and Vine (1980)

[135:50-154:22]

• Last of the “Asylum” era; embraces guitar-driven, blues-inflected sound.
• Jeff: “I love Heartattack and Vine. I love the sense of sentimentality, I love the obvious Bruce Springsteen tribute (Jersey Girl).”
• Damon: “Very much better than the last two…It is not surface, it’s not anywhere like [what comes next].” Praises “Saving All My Love for You,” “On the Nickel," and especially “Ruby’s Arms" (inspiring a scene in Ishiguro’s The Remains of the Day).
  • “Hearing that character admit that his heart is breaking inspired Ishiguro to say, ‘You know, I have to have a scene in this novel where we see the facade crack.’” —Damon [147:36]
• Scott: Endorses the album’s more dynamic, funky elements, especially the title track and “Mr. Siegal.” Marvels at Waits’ ability to create vivid snapshots of seedy bohemia: “The song fades out because the stories never end.” [150:49]

IV. Reflections, Picks, and Teasers for Part 2

Two Albums and Five Essential Songs [156:23-161:49]

Damon Linker’s Picks:

• Albums: Small Change, Closing Time
• Songs:
  • “Grapefruit Moon” (Closing Time)
  • “San Diego Serenade” (Heart of Saturday Night)
  • “Tom Traubert’s Blues” (Small Change)
  • “Kentucky Avenue” (Blue Valentine)
  • “Ruby’s Arms” (Heartattack and Vine)

Scott Bertram’s Picks:

• Albums: Blue Valentine, Heart of Saturday Night
• Songs:
  • “Martha” (Closing Time)
  • “Please Call Me, Baby” (Heart of Saturday Night)
  • “Christmas Card from a Hooker in Minneapolis” (Blue Valentine)
  • “Sweet Little Bullet from a Pretty Blue Gun” (Blue Valentine)
  • “Heartattack and Vine” (Heartattack and Vine)

Jeff Blehar’s Picks:

• Albums: Small Change, Heartattack and Vine
• Songs:
  • “Closing Time” (instrumental)
  • “Better Off Without a Wife” (Nighthawks at the Diner)
  • “Christmas Card from a Hooker in Minneapolis” (Blue Valentine)
  • “Heartattack and Vine” (title track)
  • “Jersey Girl” (Heartattack and Vine)

Notable Quotes & Memorable Moments

• “Tom Waits was as much an actor and an adopter of personae...as David Bowie was. He was more consistent...but when he decided to make a break, he made similarly an intellectual decision to change up his music.” —Jeff [16:51]

• “It is truly shocking the way he sings...It is, I want to erase, not almost. It is truly shocking...No one with a voice like this would ever choose to sing.” —Damon on “Tom Traubert’s Blues” [76:21]

• “If you like someone just sort of reading...over a baseline, then Nighthawks at the Diner is the album for you.” —Scott [65:40]

• “Maybe that's why you have to break your voice like that. It's a great observation.” —Jeff (on Waits’s style permitting sentimentality) [117:39]

• “Hearing that character admit that his heart is breaking inspired Ishiguro to...have a scene in [Remains of the Day]...where we see the facade crack. And he wrote the novel inspired by that [Waits song].” —Damon [147:36]

Timestamps for Essential Segments

• 05:12 – Damon’s first exposure to Tom Waits and “Small Change”
• 14:16 – Jeff’s “baptism” into avant-garde Waits with Rain Dogs
• 20:29 – Scott’s initial reactions as a Tom Waits novice
• 28:59 – Start of Close Read: Closing Time
• 43:28 – Discussion of Waits’ “performance” and affectation
• 59:04 – Nighthawks at the Diner & the great debate
• 74:18 – Small Change and the signature “hobo croak”
• 109:13 – Blue Valentine and the maturing of Waits’ cinematic, lyrical storytelling
• 135:50 – Heartattack and Vine as the end of an era and sign of transition
• 156:41 – Each panelist’s pick for two essential albums and five must-hear sings

Overall Tone & Language

The conversation is highly engaged, witty, and often passionate—especially in dissecting the merits and flaws of Waits’s “beat poet” personae and the live storytelling approach. Each participant maintains the spirit of deep music fandom, with critical disagreements handled in an amused, good-natured manner, all set against a backdrop of personal reminiscence and erudition.

Conclusion & What’s Next

The episode wraps by hinting at major transitions awaiting Tom Waits in the next era—new love, a new city, a radical sonic shift ("gonna get weirder"), with the promise that what comes in Part 2 will challenge both expectations and ears. Damon Linker is expected to return as guest. Listeners interested in the strange and inspiring left corners of American songcraft are encouraged to stay tuned.

For new listeners & seasoned fans alike:
This episode is an expertly guided, honest, and entertaining journey through Tom Waits’s first decade—a capsule of American music where the night never ends, hearts are always breaking, and “everybody’s a winner.”

[End of Part 1: Tom Waits]
Stay tuned for Part 2—Tom Waits in the wilder years.