In the 1990s and early ’00s, Bill Callahan was an enigma. He wrote about guys who wandered dark neighborhoods alone and yearned to escape the world in submersibles that had been lowered to the ocean floor. The kind of guy who swipes his girlfriend’s list of people to invite to a party and angrily scratches the word “Enemies” at the top of the page. A guy who, after his girlfriend inevitably moves on, takes her bras and underwear from his dresser drawer and lays them out in human-shaped piles on the floor so he can admire them. Creepy, sure, but his profound alienation was rendered poetically, and it wasn’t hard to map the disturbing details from his tales onto the most awkward and painful moments of your own life. You never knew if his alternately horrifying and hilarious songs were based on his experiences, and his media shyness and lack of interest in explaining his work meant you had to take them at face value.

With 2005’s A River Ain’t Too Much to Love—Callahan’s final album as Smog, though he wanted to release it under his own name—his music began to change. It grew quieter and more curious; what once repelled him began to make him wonder. The record was so important to his development as an artist that he sat for a long and illuminating podcast to go over it in detail (a must-listen for any fan of his songwriting). On later LPs like Sometimes I Wish We Were an Eagle (2009) and Apocalypse (2011), he wrote about the natural world, searching for clues about humanity in the motion of birds and the rawness of the land. He got married and had children and wrote about the comfort of human connection and the shattering joy of bringing a new life into existence. Instead of leaving us wondering what was real, he happily explained where it all came from.

This is where we find Callahan on his latest album, My Days of 58, which is easily the most autobiographical record he’s made. Here, he sings about being a father and husband as well as the how and why of his winding career as a songwriter and performer. He approaches the material with an older man’s earned wisdom and a clarifying distance, as if he’s watching his life from afar while simultaneously living inside it. With the opening “Why Do Men Sing,” he even writes what for him is rare—a true anthem that invites listeners to join him on a chorus hook, complete with horns, that repeats over and over and somehow leaves you wanting more. It starts with some slowly plucked guitar and gathers energy, guiding us through a grim backstage scene and a surreal dream involving fear of death and a comforting word from Lou Reed. (“Baby, you just got to let it ride,” which actually sounds like something the VU frontman might say).

The set’s first half continues to grapple with the “Why?” of it all, with Callahan musing about fatherhood, his mortality, and the creative impulse. On “The Man I’m Supposed to Be,” he realizes that death could be coming for him at any moment, and his current way of moving through the universe isn’t cutting it. “I’ve been living too long in my head,” he sings, a statement that will be unsurprising to anyone who has followed his work. “Pathol O.G.” goes deeper, dissecting his compulsive desire to write songs as a way of understanding his surroundings and himself. He begins speaking, explaining his attraction to songwriting over pinging guitar harmonics—“I don’t want to say that it saved my life but it gave me a life”—and admits that immersing himself in his music became a way to avoid people.

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.

Bill Callahan: My Days of 58

$39.99 at Rough Trade