Bill Callahan Beautifully Explores the Limitless Expanse of Being Alive on Shepherd in a Sheepskin Vest

by Carter Delloro

I’ve got a lot going my way right now. I’m starting a new day job that’s a big professional step forward. I’m finally moving in with the woman I love after living long distance for too long. In many ways, I’m really happy.

But I’ve also been thinking about death a lot. And the enormity of time and the meaning of existence, and it’s all causing me a lot of anxiety. The people in my life don’t really understand why such stressful thoughts are manifesting right when I’m on the precipice of being my most content. I don’t really understand it either.

Bill Callahan, however, understands it.

On his latest record, Shepherd in a Sheepskin Vest, Callahan has found contentment and death all at the same time. Unlike me, though, he faces it all with a sense of peace.

These days, I’m not really into sitting down and parsing oblique lyrics (I suppose I’ve never really been into that). Callahan’s record can undoubtedly be a challenge. The first time I put it on, it floated by me while I did other things. As usual, he doesn’t rely on expected chord changes. His arrangements are loose but intricate. His tone is (mostly) warm even when he litters in unexpected minor chords. The upright bass that often accompanies him reminded me of Van Morrison’s Astral Weeks while some songs’ folk aesthetics had me feeling more Blood on the Tracks. With Callahan’s rich baritone complementing the lightness of the music, it was easy to let the album pass me by.

When I stopped, though, and confronted the lyrics, it was a meditative experience. Callahan has constructed a song cycle that brings the listener through his entire process of falling in love, settling down and becoming a father. All the while, he embraces the moments of quiet and self-reflection that help him appreciate the joy in his present.

The track that made me give in and fall in love with Shepherd was “747.” In under three and a half minutes, Callahan uses a light motif to connect birth, death and the human condition. Saying that human beings “Walked on the moon/Like flies on a mule” really helps put things in perspective. Not every song on Shepherd covers such vast existential ground, but they cover this kind of material.

Yet, it’s inevitably juxtaposed with family matters. Towards the end of the album, Callahan covers the Carter Family’s meditation on death called, “Lonesome Valley.” He then immediately follows it with “Tugboats and Tumbleweeds,” a letter of advice for his newborn son. Thematically, it’s like a somber version of Sturgill Simpson’s “Keep It Between the Lines.”

Callahan concludes with “The Beast,” which repeats the word “love” eleven times and compares he and his new wife to the sky and the sea, “fill[ing] one another’s needs.” It’s a beautiful moment on a beautiful record that explores both the limits and the limitless expanse of being alive.

There are always albums or songs that reach you right when you need them, if you’re paying attention. I didn’t think I would like Shepherd in a Sheepskin Vest and I still don’t necessarily enjoy it. But I sit in awe of it. It’s exactly what my soul needed at this moment in time. And if you’re also holding conflicting emotions in your soul, and you’re ready to dive in, it might be just what you need too.