Bill Callahan, photo by Bill McCullough
Bill Callahan has shared “Lonely City,” the second preview single from My Days of 58. Set to arrive on Feb. 27 via Drag City, the venerable singer-songwriter’s ninth solo studio album under his own name – and 20th including his releases as Smog – is billed as a “living room record,” and the latest advance captures that casual, off-the-cuff feeling with a naturally unfurling acoustic ramble. It’s matched with a music video from street photographer Daniel Arnold, who assembled a testament to the collective character of cityscapes from 15 years of his New York portraits.
Where lead single “The Man I’m Supposed to Be” was a hard-fought affirmation on striving to live as a higher self, “Lonely City” is less apprehensive and more observational. Callahan talks and offers understanding to his home city like an old friend, with oblique verses rolling impulsively over meandering guitar and saxophone and snares that snap and fizzle. Beyond his band of guitarist Matt Kinsey, tenor saxophonist Dustin Laurenzi and drummer Jim White, who proved “that they could handle anything I threw at them” on his 2024 live album Resucitate!, the song is embodied by backing vocals and tambourine from Eve Searls and Jerry David DeCicca.
“‘Lonely City’ is a song I’ve been meaning to write for decades,” Callahan shared:
“It has been inside me that long. I tend to focus my writing on humans and the spirit within. So writing about concrete and steel felt like a no go. Like I’m going to write a song about a car next?
But of course cities are made by humans so they are human, too.
You have a relationship with them, like friends.
You get mad at them when you get a parking ticket, you love them when they offer you a nice meal.
It’s a song acknowledging all this.”
Callahan cut the basic songs of My Days of 58 with just White, then individually tracked the other players, including fiddle from Richard Bowden, piano from Pat Thrasher, bass from Chris Vreeland, trombone from Mike St. Clair and pedal steel from Bill McCullough. This process brings a knowing closeness to his lived-in storytelling, toward that “living room” angle.
“I’m not talking about fidelity at all here,” Callahan detailed. “Living room attitude. Living room vibe. Not too loud, not otherworldly. I asked for the horns to be relaxed like someone on the couch playing, not a blast from heaven or hell.”
My Days of 58 is available to pre-order and pre-save now. Watch the music video for “Lonely City” below, and read on for the album’s full tracklist.
My Days of 58 – Bill Callahan:
01 “Why Do Men Sing”
02 “The Man I’m Suppoised To Be”
03 “Pathol O.G.”
04 “Stepping Out For Air”
05 “Lonely City”
06 “Empathy”
07 “West Texas”
08 “Computer”
09 “Lake Winnebago”
10 “Highway Born”
11 “And Dream Land”
12 “The World is Still”

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