Bill Callahan has unveiled “The Man I’m Supposed to Be”, the latest single and accompanying visualizer from his newly announced album, My Days of 58. The album, which marks Callahan’s eighth solo record and his first new collection of songs since 2022, is set for release on February 27, 2026 via Drag City.
The new single offers a glimpse into the “uncanny depths” of the forthcoming twelve-track album. For My Days of 58, Callahan focused on applying the “living, breathing energies” of his live performances to the studio process. The result, as described in the album’s announcement, sharpens his “slice-of-life portraiture to cut deeper than ever before”.
The album’s sound is built around the core synergy of his recent touring band: guitarist Matt Kinsey, saxophonist Dustin Laurenzi, and drummer Jim White. Callahan shared this about the album’s creative process:
“I usually just sing a melody to a horn player or let them try a few takes and go from there. This time I thought, why not get some of the record charted out. There’s always room for spontaneity on top of that. And we did indeed throw some off the cuff stuff on top of the charted horns in a couple cases where they weren’t fully doing what I wanted.
“With this record I kept thinking of it as a ‘living room record.’ I’m not talking about fidelity at all here. 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.”
This pursuit of an organic, human feel was central to the recording, which prioritised “improv/unpredictability/the unknown”. Callahan, who prepared songs with each player separately and recorded most basic tracks as a duo with drummer Jim White, explains his philosophy: “A lot of the best parts of a recording are the mistakes-making them into strengths, using them as springboards into something human”.
My Days of 58 also features contributions from several other players, including Richard Bowden on fiddle, pianist Pat Thrasher, and pedal steel player Bill McCullough, who also shot the album’s front and back cover photography.

My Days of 58 Tracklist
- Why Do Men Sing
- The Man I’m Supposed To Be
- Pathol O.G.
- Stepping Out For Air
- Lonely City
- Empathy
- West Texas
- Computer
- Lake Winnebago
- Highway Born
- And Dream Land
- The World is Still
My Days of 58 (2xLP, CD, CS, and Digital formats) February 27, 2026 via Drag City.
Pre-Order/Save: https://billcallahan.lnk.to/mydaysof58
