My relationship to Bill Callahan goes back to 1992, when he released the album Forgotten Foundation under his longtime moniker Smog. It marked the beginning of a relationship that has only deepened over the 30-plus years since – he’s become one of those rare artists who seem to grow in tandem with your own life.

Now 59, Callahan has matured profoundly as a singer and songwriter, evolving from his homemade, fuzzy, lo-fi beginnings into a bandleader with a more eclectic, full-bodied sound. His forthcoming 2026 album, My Days of 58, offers the first glimpse of where he’s heading.

The somber, acoustic opening of its first single, “The Man I’m Supposed to Be,” gradually blossoms into richer, more exploratory textures reminiscent of his 2022 album YTI⅃AƎЯ. Here, he deals with adulthood, reflections on the past and the future, life and mortality, and being the best version of yourself. As the master of mundane observations and personal struggles, his poetry cuts through as always with clarity, stark realism and vivid imagery.

And now my biggest fear is not the dying
My biggest fear is that I’ll stop trying
To be the man I am supposed to be

There’s something deeply human about Bill Callahan. And in the end, can we ever ask for more from an artist? It’s been a remarkable ride together and still is. Here’s to our next thirty together.