This level of self-interrogation is unusual for Callahan—what once might have been suggested poetically is now stated plainly, though with some slightly goofy humor—and it’s disarming at first to hear such diaristic writing from him. “As time wore on I found myself increasingly turning to my guitar instead of other people in times of loneliness and sorrow and confusion,” a spoken passage from “Pathol O.G.,” is not a line you’d expect to hear from the author of “Cold Blooded Old Times.” But familiarity with the full sweep of Callahan’s catalog gives his uncharacteristically direct expression power. It feels like he’s earned it.
“Empathy,” a song addressed to his father, goes even further in this direction, and given the subject matter the risk of artless oversharing is even higher. Callahan has admitted in interviews that he never would have written the song if his dad were still alive. But his lines are clear and focused as he strikes just the right balance between anger, puzzlement, and the titular emotion. He describes a conversation with his father where his dad unapologetically shares why he was never there for his son, and another exchange in which Callahan recounts the sad fact that he only earned his father’s respect once he showed him a $3,000 check he’d received for a gig. “Dad, I’m just like you,” he sings, and then, in a funny and touching turn, breaks the fourth wall and adds: “Although they’re in the middle/I added these lines last/I don’t know if they’re true.”
The second half of My Days of 58 is more closely connected to Callahan’s past few releases, with songs about the therapeutic benefits of travel and the restless life of touring. He’s in an uncharacteristically playful mood on several of these tracks, and the sonic character of the recording takes on some of the emotional work. The bone-dry clarity and close-miked intimacy of his vocals on “West Texas” suggests Voice-of-God authority, but he undercuts his bucolic reverie with jokey asides like “And the starry starry starry nights/Make me say Dude.” “Lake Winnebago,” a deceptively light and warm tune about revisiting a vacation spot where Callahan buried his parents, is one of several tracks with perfect backing vocals by Eve Searls, an Emmylou Harris to his Gram Parsons. On the road-dog anthem “Highway Born,” he even allows himself to whistle a cheerful refrain over a country shuffle. The arrangements throughout are a marvel, with each instrument—strummed acoustic, pedal steel, fuzzy sax—captured honestly and laid into place with care.
The first hints of Callahan’s new openness were found on his 2019 album Shepherd in a Sheepskin Vest, but the most noticeable shift in his work since 2013’s Dream River has been musical, as he embraced noisy jams and woolly textures (the aesthetic reached its apogee with his 2024 live album Resuscitate!, which has a nearly 13-minute song that earns its length). Here, it feels as if something in the songwriter’s process has been jarred loose, and his willingness to talk about his life so directly is leading him somewhere unfamiliar. My Days of 58 is a weird Bill Callahan album, and a good one.
